Thank you @deanwinchestersgirl8734 for the request 🫶
I was wondering if you can do a crossover where the reader is dating dean and they take a case in Vegas where the reader is Gil Grissom's daughter and the boys meet him.
This one was fun. I loved making Dean squirm. Hope you like it lovely.
Warnings: Talks of death, Talks of werewolf attack (chest open, missing heart)
Thank you @copperboom82 for being my beta bae!
"So, you're telling me you just happened to find a case in Vegas?" Sam snarked, shutting the passenger door of the Impala.
"We got dead bodies and missing hearts, missing hearts and you are questioning this?"
"Dean, there is a dead body and one missing heart."
"Screams werewolf to me."
"Ya know, if you wanted to see her-"
"I found a case that happens to be in Vegas, end of story." Sam's dimples caved in as smirk danced across his lips, making Dean roll his eyes, "What?"
"You love her." Sam mocked as he drew out the o sound in love.
"Shut up, Sam" Dean reached into his chest pocket as they approached the yellow tape, unfolding the holder he flashed his fake FBI badge. "Hi, I'm agent Bonham, this is agent Copeland, FBI."
The blonde man's eyebrows furrowed at the fake names. "Let me see those badges again."
Dean cleared his throat as he pulled out the badge holder for the second time. "Is this the only body you have found so far."
The man adjusted his glasses as his eyes started to scan over the fake ID. "You think there will be more?"
"Um, we have reason to believe there might be another attack." Sam stammered
"And just want would those reasons be?"
Sam shook his head and Dean looked over to him in panic, silently hoping the older man wouldn't notice. "Sorry, can't say. The case is confidential."
"Yes…" Dean agreed, pointing a finger at Sam. "Confidential, FBI."
The man's eyebrows furrowed deeper as Dean's words.
"Gil, we might have something." A younger brunette walked up.
"Agents, why don't you join us." Gil raised the yellow tape for them, "Sara can give you the run down, while we walk."
"There she is." You heard his voice before you saw him walking into the forensics building.
You chuckled. "Bat those eyelashes at someone else, Nick." He started walking with you quickening his pace to keep up. "Taken remember?"
"Oh that's right. The guys that is always out of town." He mocked bending his fingers with the lat part of his sentence.
You rolled you eyes "As a matter of fact-"
"Hey y/n." Your attention snapped to Sara as she said your name. "Did you know the FBI was coming in on this on?" She asked handing you a file containing the files from the newest case.
A groan pushed past your lips "Seriously?"
"I'll take that as a no. By the way he is in the lab with them right now."
"Thanks." you waved your hand as she sipped her coffee, continuing on her way.
"That doesn't make sense." you voiced looking over the case.
"Wanna share?" Nick asked.
"FBI over one dead body?" he leaned in as you turned the pages in his direction.
"I don't know, maybe they have had similar cases."
"Well let's go see." you said, closing the file you started for the lab.
"Hey sweetheart." Gil said looking up from the microscope. your eyes roamed the room, not finding anyone with him.
"Hiya Dad."
"Dad?!" You heard his voice and then there he was peaking around the pillar he was standing behind. Dean freaking Winchester, eyebrows quirked, jaw hanging open, and eyes wide. Sam nudged him as Gil shot him a wondering gaze. "Uh… It's just your so young sir. I would have never guessed you would have a daughter so…" you eyes narrowed at his fumbled words, making Dean swallow the lump in his throat hard.
"Mature." Sam spoke up.
"Yes, mature." Dean agreed.
You bit your lips, trying to fight the smile that was spreading across your face. "So, these must be the FBI agents Sara told me about…"
"Yes," your father answered "They are in town for the missing heart."
"Yea I got it." you held up the manila file folder in your hand. "Over one dead body though?" you challenged with a smirk.
"Well.. there was a case down in Austin-"
"And in Phoenix." Sam chimed in
"Yes and Phoenix. Same M.O, young dead girl, chest open, missing heart."
"Hmm. I haven't heard anything about them…" you quipped, pushing your lips into a straight line as Gil looked up from the microscope again.
"Wh-why would you?" Dean blurted out. "I mean, they aren't close to around here."
"y/n has a… friend that keeps her keen on big cases." Dean's eyebrows raised at your dad's word.
"A friend?" He probed. "What's his name? Maybe we knew him. "Dean crossed his arms over his chest with a wink.
"Winchester." you challenged with a brow raise.
"Like the gun?"
"Yep."
"Ya know, I can't say I've heard of his."
"Aw, that's too bad," you said returning his wink. "He's pretty freaking awesome."
I remember watching CSI late at night when I lived with my grandparents growing up so I think this is so funny, especially with the references to the show within SPN.
pairing: dean x (gender neutral) reader
genre: fluff
warnings: slightly suggestive but nothing explicit
word count: 1.6k
a/n: i've also published this little drabble on ao3. i’m just craving fall weather and the halloween mood.
He had to do a double take.
Dean had not gotten much sleep tonight – hence the decision to slip out of the motel room and grab coffee to go so early in the morning –, so who really knew, if he wasn’t still dreaming? The sight before him sure could have been straight out of his imagination.
Actually, he was sure he had a dream just similar to this before. Some time ago. Or maybe not too long ago. Kinda hard to tell with how often you haunted the three to four hours of shut-eye he was able to catch each night.
When he had left, you were curled up in your blanket, looking like a little burrito wrap. He could barely see your face, a tuft of hair sticking out the only indication of your presence. He figured you were fast asleep and since there was a coffee shop just around the corner, it shouldn’t take too long for him to get back; and it didn’t. Except in the twenty minutes he’d been gone, you had already gotten out of bed, having exchanged the blanket for something else to wrap yourself into.
Not even the soft creaking of the old door to your shared motel room was enough to startle you. Dean’s eyes scanned you up and down, admiring the look of his leather jacket on you. The material hung loosely around your frame, several sizes too big on you. Hell, it was too big on him, but it seemed to swallow you whole, practically dwarfing you.
The leather was loosely crinkled at the joints of your elbows, as if you had attempted to roll up the sleeves a little, but soft, hugging your frame as you rummaged through the kitchenette‘s cabinets.
“Not even any damn tea here,” you sighed to yourself, bottom lip jutting out into a grumpy pout. Your mission to get at least somewhat warm and cozy failed miserably. You weren’t much of a morning person to begin with, but the busted heater in the motel room was your last straw.
October nights in Minneapolis were freezing, according to you at least. “Do we really need to go hunting a werewolf here? He‘ll probably turn into an icicle once the sun sets anyway,” you had grumbled during the car ride.
“Will a pumpkin spice latte do?”
Dean‘s voice startled you at last. He watched you visibly flinch, spin your head around and stare at him with wide eyes. You blinked at him first, then at the disposable cups in his hands and he could practically see your eyes light up with anticipatory sparkles.
You had teased him about his quote-unquote fragile masculinity before, but watching your lips curl up into a giddy smile was worth the feeling of self-consciousness at the coffee shop‘s counter. Somehow asking for extra sweetener and added vanilla went against his principles.
You never understood his aversion to coffee with milk and sugar and how it wasn’t as tough as Dean’s usual americano order. Either way; maybe those syrupy sweet beverages weren‘t too bad after all if they made you happy. And maybe instead of caffeine, he just needed the adrenaline rush of your fingers brushing against his. You took the cup he held out for you – or rather snatched it away.
“Easy, sweetheart,” Dean chuckled. “You’ve got plenty of time to practice the goblin thing for Halloween.”
His teasing remark earned him no more than a roll of your eyes. You were much more occupied with the brew in your grasp, clearly savoring the warmth on your hands and the sweetness on your tongue as you took a sip. The pleased hum that left your lips bordered on a moan and thus sent a shiver down Dean’s spine.
“Whatever witch blessed Minnesota with pumpkins in these weather conditions, may no hunter find them,” you hummed happily.
“I‘m pretty sure the artificial flavor is not from any local pumpkin patch,” Dean snorted softly.
“Shut up and let me enjoy the magic.”
“Magic, huh?,” he grinned, before he gestured downwards to your… attire. “That your wizard‘s robe then?”
You nearly choked on your beloved pumpkin spice latte, realizing the state you were in. After having woken up pretty much abandoned and freezing, you had grabbed whatever clothing item was nearest. It just so happened to be Dean‘s leather jacket, which now made you feel absolutely silly. You had simply thrown it on without thinking, not even bothering to change out of your pajamas beforehand.
At least that was what you were telling yourself and what you were set on convincing Dean with too.
“I was cold,” you shrugged defensively, but there was no way Dean would fail to pick up on the way your ears turned slightly red.
Noticing the tell-tale sign of your flustered state, his lips curled up and he huffed out a bemused chuckle. Emerald eyes wandered down your body once again with that shameless spark in them that he never bothered to conceal. “Didn’t say I was complaining.”
Far from it.
He was itching to reach out to you, pull you closer, let his hands wander all over you. To slip his fingers under that jacket, under that cozy pajama–
“Let me get changed so we can visit the witness.” Your suggestion interrupted those thoughts of his and left him scoffing. Of course you’d divert the topic to the case. Surely, if he were to point it out, you’d blame it on your desire to abandon this nightmare of a motel.
But Dean wasn’t quite ready to get to work just yet.
“Wouldn’t dream of it,” he spoke, his tone as rich as the cinnamon in your coffee, and stole the pumpkin spice latte from your hands again, setting it on the small kitchen table. “What’s the rush? At least finish your coffee first.”
“It’s called a to go cup for a reason,” you half-chuckled half-sighed, but joined him as he took a seat regardless.
The two of you shared your coffee over idle conversation, your inner morning grouch more and more satiated with each sip. Despite your previous nagging about freezing, you definitely didn’t mind the coziness of lazier mornings like this.
Sure, the heater in this cheap motel wasn’t working properly and you forgot to pack an extra sweater to shield yourself from the crisp October air — but some aspects of fall did make you feel warm. Namely pumpkin spice lattes. Or the fact that Dean remembered you liked them with two pumps of vanilla.
Once having finished your coffee, you disappeared into the bathroom to get ready for the day. A quick shower later and having changed into your daily attire, you went back to Dean.
And you caught him red handed. He was eyeing your coffee tumbler, giving it an experimental sniff, before downing the very last bit of it. You snorted softly as he grimaced and tossed the empty thing into the waste bin.
He looked about as flustered as you did when he caught you wearing his jacket earlier. To each their own guilty pleasures, huh?
“Yummy?”
Christ, that smug smirk of yours was dizzying. Or maybe it was the sugar rush, from just a singular sip.
“Not for me,” Dean grumbled, tone more defensive than necessary. “Just wanted to try and..”
As he trailed off, he averted his gaze away from your eyes towards the leather jacket in your hands. A hint of irritation flickered across his expression.
You raised an eyebrow at him, your smirk not fading whatsoever. As you made your way towards the door, you stopped in front of him and held out the neatly folded jacket. “And?” You asked.
“And, uh… confirm that I prefer more subtle flavors,” he mumbled, his eyes wandering back up, but stopping at the curve of your lips. The second he saw them part slightly, some witty remark likely already on the tip of your tongue, he leaned in to place his own atop.
The kiss was chaste, but he was still able to taste it — behind the freshness of toothpaste, the mixture of cinnamon and nutmeg still lingered.
Subtle, just the way he preferred it. Or maybe it was just his imagination; or some of that autumnal magic you had mentioned earlier.
As Dean broke the kiss, he grinned watching your eyes flutter back open. He’d never get tired of that sight. Just like he’d never get tired of seeing you wearing his clothes. Placing one hand on top of the jacket, he nudged it back towards you.
“Keep it for today,” he said, his words neither an offer nor a suggestion, but rather a request. “Don’t want you complaining about being cold the whole day.”
You blushed and you pouted, but you didn’t protest and swiftly slipped it back on.
Dean gave an approving nod, adjusting the collar of it and smoothing the material over your shoulders. It was definitely too big on you, your hands weren’t even visible under the long sleeves anymore.
“You know you could’ve just asked if you wanted to borrow my clothes, sweetheart,” he teased, which earned him a playful smack on the chest.
“You weren’t complaining earlier,” you puffed. “And while we’re on the topic: You could’ve just asked if you wanted to try the pumpkin spice latte.”
Dean gave a short laugh and stole yet another kiss to savor the taste. You shivered as you felt his tongue slip past your lips and his fingers underneath the leather, settling on your waist. Even through the remaining layer of your shirt his touch seemed to leave a trail of fire down your sides.
“You weren’t complaining either,” he whispered, his warm breath on your flushed skin still the best remedy against cold weather.
credit & links: dean icons ──〃★ dividers ──〃★ request heretaglist: there's no taglist yet, but feel free to hmu if you want to be added <3
As we go into the second part of the year, I can't help but look forward to my favorite season and all the cozy vibes it brings. This so encapsulates that feeling; I can practically smell the pumpkin spice and feel the leather jacket.
This exchange, I think, was my favorite:
“You know you could’ve just asked if you wanted to borrow my clothes, sweetheart,” he teased, which earned him a playful smack on the chest.
“You weren’t complaining earlier,” you puffed. “And while we’re on the topic: You could’ve just asked if you wanted to try the pumpkin spice latte.”
Tags/Warnings: Smut, choking, rough sex, threat/talk of a gangbang, sex in a public bathroom, no aftercare, face fucking, deepthroating, cunnilingus, fingering, dry humping/thigh humping, hair pulling, degradation, dirty talk, spanking, slapping, unprotected sex, cream pie, squirting, pussy slapping, finger sucking, edging, orgasm denial, overstimulation, multiple orgasms, Sir kink if you squint, masochistic reader, brat reader, no use of Y/N, reader has no descriptors other than being slightly shorter than Dean and has enough hair to pull.
Summary: It's been six months since you struck the deal with Dean, and true to his word, he comes back like clockwork—even when you're not at home.
Word Count: 7.7k
Author's Note: Title from the song Animal by Chase Holfelder
A part two to this post from 2025 Kinktober was requested, so here it is!!
This counts for the Mirror Sex square for @j3bingo
Thank you to @gappyswife for beta-reading this for me!
Dividers: Line Divider 1 by @olenvasynyt Line Divider 2 by @omi-resources SPN Divider by @talesmaniac89
Tag List: @copperboom82 @sleepycues @xpurdyglambertx @flanneledfae
Neon paints your body in hues of red and blue as you cross the dance floor. The dive bar has little by way of illumination beyond the signs on the wall depicting beer and food, half-naked cowgirls, and the name of the joint. A few yellowed lights hang from the ceiling, joining the bright colors to shine down on the crowd below.
You wind your way through the throng of sweaty bodies, their boisterous conversations meld with the thrum of music soaking into the atmosphere. Cold glass bites into your palm as you carry your fresh beer back to the edge of the dance floor.
It’s standing room only— a regular occurrence on Thursday nights where ladies drink free— and since your friends have long since returned home, you don’t see the point in trying to snag a high-top for yourself.
No, half drunk on the music and the cheap beer, you don’t want to sit–you want to dance.
Between line dances, you down long-necks and tall glasses of water alike, feeling like you’re sweating it out faster than you can consume; the last thing you want is to wake up in the morning with a splitting headache, even if your freelance job awarded you a day off.
After being contained to your apartment by the threat of being ripped to shreds at the razor-sharp claws of a pack of supernatural beasts, you want to spend your new lease on life as you pleased, and right now, you are doing just that.
You’ve lost count of how many dances you’ve finished by the time your bladder begs you to vacate the floor and empty it. Reluctantly, you shuffle off the dance floor, having to only wait behind three other girls before you snag an open stall.
The bathroom itself leaves something to be desired. Dingy tile line the floors; you aren’t sure if the patterns were actually design choices or were poorly cleaned stains. Raunchy love notes cozy up to random phone numbers with instructions to ‘call for a good time’ with crude pictures of dicks on the cheap stall walls and door.
Noting the bathroom was empty, you finish up and wash your hands, smiling at the additional graffiti etched into the edges of the dirty mirrors. Most of it is hazy anyway, the blanket of alcohol warming you at the edges. You pull your tube of lipstick from the pocket of your miniskirt, the denim barely covering you enough to avoid a public indecency charge.
You don’t think much of it when the music grows louder, too busy shoving the lipstick back into your pocket. The door to the bathroom creaks open before it shuts hard with a thud, muting the sounds once more.
It isn’t until you hear the snick of the lock sliding into place that you look up to see a figure standing behind you in the reflection of the mirror. Your heart drops to your stomach in the same second your pussy throbs violently when you whirl around to familiar green eyes that blink black before returning to their alluring jade.
“Hiya, Sweetheart,” Dean purrs, stepping closer so that there’s less than a foot of space between your bodies. “Forget what day it is?”
Your boots have a bit of a heel, so there’s less of a height difference than the first time he visited you. Usually, you’re at home. Most of the time you’re already in bed when he arrives, sometimes in the shower, sometimes making food.
“No. Just lost track of time.” Somewhere between the dancing and the drinks and your phone being tucked away in the purse you’d brought, the time had slipped away.
His head cocks to the side, the move more animalistic than human. “That so?”
“I wanted a night out with my friends. Sue me.”
His eyebrows raise but he says nothing.
Not right away at least.
Instead his attention drifts from your face, slipping down your body.
You can see his eyes catch on your strappy tank top where the halter neckline plunges to near obscene levels, showing off the scalloped lace of your bra. The green in his gaze goes dark in a different way than you are used to the further down it travels, down all the way to the bare expanse of your legs and where your boots sit upon your feet.
“Must’a had every guy in here tonight drooling over you,” Dean says appreciatively, eyes flicking back up to yours.
You brace your hands on the sink behind you and lean back with a shrug, trying to act casual and not like your pussy isn’t growing wetter by the second. The heat that rises to your cheeks is in humiliation. He hasn’t even touched you yet and here you are like a bitch in heat.
You’d noticed the heated stares, the way some of the men in the bar’s eyes would pop out of their skull like some cartoon, and you’d be lying to him and to yourself if you said you didn’t revel in it.
He leans in, and you’re not sure when he got this close to you but you’re assaulted with the intoxicating smell of him. Something masculine and dark that makes you want to bury your face in the crook of his neck.
You jump a little when the warmth of his palm spreads along the inside of your thigh, too entranced by his gaze, heavy and focused, to notice his arm slipping between your bodies until it’s there. His fingers tease along the soft skin, the tips just inches from the throbbing need between your thighs.
“Too bad your pussy’s already got someone takin’ care a’her, right?” He croons, slipping his hand up.
Words escape you as he slides your panties to the side, not that the lacy scrap of fabric was covering much to begin with.
Your mouth gapes open at the first teasing touch, the calloused tips of his fingers sliding through your slick, bumping against your clit. Hands gripping the edge of the sink so hard you’re sure the porcelain will crack any second, your hips buck up against his hand, seeking the stimulation.
The sense of euphoria is short lived when his other hand shoots out, wrapping around your neck. A gasp gets stuck in your throat and your eyes flare wide. His fingerprints dent your skin.
“Right?” He asks again with a darker edge this time.
The bathroom around you narrows to the tightness of his grip on your neck and the pleasure derived from his fingers still working over your soaking core. Every inch of your body erupts in tingles, and you would have nodded if his hold allowed it.
“Yes,” is all you manage to choke out.
It is a funny feeling. Dean quite literally has your life in his hand. By all accounts you should be pissing-yourself-terrified. But you’re not. Instead, all you can focus on is the dark whorls of lust eddying in the depths of his eyes, the green heightened with his enjoyment, and how his middle finger is circling your clit with precision.
That was, until it retreats and you nearly whine at the loss of contact.
You sense where his hand is going milliseconds before his open palm makes contact with the side of your face. It’s not hard enough to do any damage beyond a buzzing beneath your skin that will last probably as long as this encounter, but it’s hard enough for tears to sting at your eyes.
“Yes,” you wheeze, his grip on your throat just loose enough for the words to squeeze out. “My pussy’s yours.”
Another slap, this one no less gentle than the first. “Say it again.”
Your hand slips up, wrapping around his wrist. “My pussy’s yours.”
His pulse is even under your frantic grip. If it weren’t for the desire written in his gaze and the sizable bulge straining against the front of his jeans, you wouldn’t have guessed he was enjoying this. You’re painfully aware of arousal dripping down your inner thigh, your core clenching around nothing.
Dean’s hand connects with the side of your face one last time then returns between your thighs. The edges of your vision start to go fuzzy, and the moan he pulls from your lips when his fingers press harshly against your clit comes out more like a high pitched keen.
He leans in, keeping steady pressure on your neck. “You’re gonna cum for me before I let you go. Can you do that for me, whore? Not like you need to breathe, anyway.”
“Yes,” you choke out, voice a little louder than a whisper.
“Yes what?” Dean asks teasingly, his fingers moving across your core in a way that makes it really hard to formulate words.
“Yes, sir.” Your words are slurred, but they seem to suffice anyway as his hand picks up the pace.
Your hips grind against his palm, matching the rhythm he’d created. You feel dazed when his hand slips lower, two fingers shoving inside you while the heel of his palm acts as the perfect surface to grind your clit on.
He doesn’t seem to notice or care when your nails dig into the inside of his wrist, your other clawing at his shoulder to brace yourself against the rapidly growing wave of pleasure stemming from between your thighs.
His muscles shift under your grip as he angles his arm better so he can send his middle and ring finger even deeper into you, curling them up towards your belly. Your hips grind down against his hand, the rough surface providing the most divine friction against your needy clit.
An amused chuckle from Dean vibrates through your body. “I can feel your pussy clenching around my fingers. Fuck, I can’t wait to feel ‘er around my cock.”
A strangled whine is all you can muster as he curls his fingers inside you, stroking that soft spot within you that darkens your vision even further. Arching your back, you press your chest into Dean’s, his preternatural warmth soaking into you.
You’re sure he can feel the way your nipples are hardened, even through both your shirts. The bralette underneath is little more than decorative lace with a paper thin backing there to not irritate your skin.
His blood-red button down is immaculate, tucked into a pair of dark wash jeans; it’s similar to the outfit he wore the first time you met him.
Well, he’s nothing if not consistent, you think before stars burst behind your eyes, which you squeeze shut as the tightness in your belly gives way.
You cum harder than the first time he fucked you. Harder than you ever have in your life.
Your body goes rigid, trembling from head to toe as electric shocks spark through you all down your spine. The ache of pleasure pulses through your body as he works you through the throes of your climax.
Head lolling to the side as Dean’s grip on your neck lessens, you gasp in air. The room around you spins as you gulp down oxygen the best you can through your unabashed moans.
Dean’s lips slot over yours, drowning out your sounds of ecstasy and you can taste the whiskey on his tongue when it sweeps into your mouth. Your hand slides up his shoulder to the back of his neck, fingers tangling in the shaggy ends as you kiss him back with matching intensity. A low rumble of satisfaction emanates from his chest.
As you slowly come back into your body, Dean’s hand slows, his fingers leisurely dragging out of you and stroking your oversensitive clit on their way out from between your trembling legs. He grips your chin none too gently, breaking the kiss.
There isn’t enough time for you to miss the feeling of his lips on yours, to savor the tingling he left behind, before his fingers are in your mouth.
The calloused tips press down your tongue and instinctively you wrap your lips around the second knuckle. You can taste yourself as you work them over with your tongue, your whimper turning into a gag when Dean shoves his fingers deeper into your mouth.
“That’s right,” Dean all but purrs, looking on with a lust-drunk expression. “How are you gonna take my cock if you can’t take two little fingers?”
He’s right, you think, but I wouldn’t call his fingers small, either.
His grip on your chin relaxes just enough for you to work your jaw open more. Viscous saliva floods your mouth as Dean moves his fingers in and out of your mouth. Every time he bottoms them out, you cough and gag as the tips wiggle against the back of your throat.
Tears sting your eyes, spilling down your cheeks in fat droplets when you blink up at him. There’s a hungry edge to the way he gazes down at you, obsession bleeding in as he fixates on how your spit collects on his knuckles and rolls down his hand.
Another rush of want crashes over you at the way he’s looking at you and in response, your thighs clench together unconsciously. The miniscule movement isn’t missed by Dean, not that you were really trying to hide your insatiable need anyway.
“God, you’re such a greedy slut,” he groans. “I just got you off and you’re already wanting more, aren’t ‘cha, Sweetheart?”
With his fingers shoved into your mouth, all you can do is hum in agreement.
Dean hums his approval, and with the slightest nod his fingers slip from your mouth, the hand on your jaw following suit. You suck air in greedily, the strings of drool starting to cool on your chin.
With eyes half-lidded out of pure lust, you watch him raise the hand pulled from your mouth up to his own. A particularly strong pulse of arousal nearly sends you to the floor as his tongue darts out from between his lips. The sounds that come from him slurping your spit from his hand are purely pornographic, all while he keeps his eyes locked on yours.
“Knees. Now,” he commands, wiping the mix of your spit on his jeans.
With how shaky your knees have become in the aftermath of his display— as well as the leg-shaking orgasm he gave you— you’re tempted to comply. A glance down to the bulge in his pants is enough for saliva to pool under your tongue, but the alcohol in your system has made you bold.
“And if I don’t want to?”
His head cocks to the side, eyebrows quirked up. “No?”
A shake of your head as you look up at him through your lashes. “No.”
“You don’t want me?” He asks, his hand curling around your wrist, bringing your palm to rest on the evidence of his arousal. “You don’t want my cock?”
His grip disappears, but you press the heel of your palm against him, dragging your hand along the length of him. “No, I don’t.”
Dean gives you a knowing smirk, and the moment stretches wide between you before he finally speaks.
“Liar.”
His hand moves too fast for you to react, fingers tangling painfully in your hair as he grabs a fistful.
You cry out softly, half from the pain and half out of shock. He leans forward and the sound dies out into a quiet gasp. Your eyes dart from the depths of his gaze to his lips, which are still tugged upwards in a satisfied grin, and back again.
“You want me. I’ve been inside you. Tasted you.” His thumb traces the plush of your bottom lip, smearing your lipstick even further. “I know just how desperate you are for my cock, whore. You can’t ever pretend otherwise.”
Your knees make contact with the grimy bathroom floor and you can feel yourself tremble with anticipation as Dean angles your head to look up at him.
“Keep your eyes on me,” he says, undoing his belt with his free hand.
“And if I don’t?” You ask before you can think better of it.
Dean doesn’t even bother to shove his jeans and boxers down his muscular thighs. They barely make it down past his balls before he’s languidly stroking himself, the tip red and already leaking.
Your throat bobs and you barely flinch when he grips himself at the base and slaps his heavy cock against your cheek.
“Oh, Sweetheart. Don’t make me ask twice,” he says.
Heart beating a million miles a minute, you barely feel the small sting of contact nor the dull ache of the tight grip he has on your hair. Your world is narrowed to the throbbing need in your pussy and Dean’s hard cock bobbing in front of you.
“Now don’t be difficult and open your fucking mouth,” he growls, shoving his cock towards your mouth.
You have the good sense this time to obey, your lips parting without hesitation. Tongue lolling out, you barely have enough time to situate yourself before his cock is halfway down your throat.
Instantly, your throat is on fire and you gag at the sudden intrusion. Hands flying up to brace against his denim clad thighs, you brace yourself as Dean holds your head in place.
“Fuuuck,” he rasps, dragging his hips back and briefly allowing you to breathe. “I missed this. Had a lotta girls, but none of their mouths feel half as good as yours does.”
It takes a second for you to adjust to how he’s stuffed into your mouth. Drool has already started to leak out of the sides of your mouth with every thrust of his hips. The stretch of your lips, the taste of him is just right. He smells warm, like sweat and skin and some clean, masculine soap.
And it’s pathetic the way you silently enjoy him pressing your face further onto his cock until your nose is buried in the thick, curly hair at his pubic bone. Your throat spasms as he holds you there, unable to breathe and frozen with sensory overload.
Hot tears crawl down your cheeks, blending with your drool on your chin. Just when the edges of your vision start to blur, Dean yanks you off his cock by your hair. You cough and sputter, replenishing the void of oxygen in your lungs.
Thick strings of drool stick to your chin and neck, and you just know your mascara is running down your cheeks, half-dried to your skin with your tears.
“Such a messy girl,” he coos, honey-laced words dripping with condescension. “See, all you needed was a good dick in that brat mouth.”
You welcome the sting as his hand leaves another hot print on your cheek and you have to resist from leaning into his palm when it caresses the hurt. It slips away just as quickly, and in turn you wrap a hand around the spick-slick shaft of him.
“Gonna keep fucking my face, or do you want me to make it actually feel good?” You ask, locked on his eyes as your mouth closes around the head of him.
The groan Dean utters when your cheeks cave around him, when your tongue slides along the sensitive underside of his cock, is all the answer you really need.
You’d learned early enough on that you really had to squeeze your hand around his cock when stroking him. “Harder, bitch,” he’d growled. “Don’t be fucking scared. You’re not gonna break it.”
His fingers still threaded themselves in your hair, the tips gliding across your scalp as you descended back down upon him. His head falls back, and the red ambient lighting in the bathroom gleams along the column of his throat, skin dewy with sweat.
You’d like nothing more than to stand and lick the salt from his skin.
Tongue pressed to the underside and cheeks hollowed, you slide his cock all the way to the back of your throat. Your gag reflex balks, but you ignore it, pulling back barely half way before bobbing your head back down. The small whimpers and moans that you make no attempt to stifle travel along his cock.
Dean’s hand curls further into your hair, leaving your head littered with sharp pinpricks. All it does is add to the slickness between your thighs. Thighs that you press together seeking any kind of friction; you can feel your arousal roll down the insides. Your skirt is still hiked up around your hips, leaving your dripping pussy exposed to the cool air.
A dull ache makes itself known in your knees, the bathroom tile extremely unforgiving on the joints. You do your best to ignore it, hand sticky with spit abandoning his shaft in favor of cupping his balls.
Dean’s hips buck into your mouth at the additional touch, seeking the wet heat.
“Oh fuck,” he grunts. “Keep doing that.”
So you do, fondling him there while maintaining your rhythm; push your head down on him until you can feel him in your throat— until you gag harshly— then pull back enough to breathe through the spasm. Rinse and repeat all the while your free hand inches closer to your throbbing pussy. The wet, sloppy sounds from your mouth meld with his decadent grunts and groans, filling the bathroom.
The system works, up until the point it doesn’t.
You come up for air only for Dean’s hand to press against the back of your head, pushing you back down onto his cock. Your eyes screw shut as your nose is mashed into the mess of curls at his pubic bone.
A sound of displeasure vibrates from your lips up the length of him, and after a second you try and pull your head back. It ends fruitlessly, though, as Dean only presses harder.
“Shut up. Just a little longer,” he growls. “Fucking take this cock. Fucking choke on it like the whore you are.”
Your tear-filled eyes screw shut as your throat spasms hard. Bracing a hand on his muscular thigh, your fingernails dig into the denim. Dean’s cock moves, barely pulling out an inch before it’s back, harshly slamming into your throat. A soreness grows in your jaw for how long you’ve kept it open.
“Fuck, that’s it,” he moans, his chest heaving. “Gonna fucking cum, baby.”
That fuzzy, floaty feeling returns as you struggle against the need to breathe, against the intrusion of cock in your throat. He starts to twitch against your tongue, and the pistoning of his hips grows sloppy and uneven. Pushing through the haze, you swallow around him, earning yourself a string of curses from above you.
The crass words are cut off by a garbled moan. You hear your name somewhere in there, but you’re too busy swallowing down Dean’s cum to pay much attention to what he’s saying. He holds you there, cock pumping his seed down your throat until he stops twitching and his length softens a bit.
Lines of spit connect your lips to his cock once he finally wrenches himself from your mouth, and they snap back against your chin when he takes a step back. Your body is wracked with wet coughs as you gasp for air. Heart beating what seems like a million beats a second, you lean back on your heels and wipe the spit from your face.
Out of the corner of your eye you see Dean tuck his half-flaccid cock back into his boxers, leaving the jeans unbuttoned.
“Up,” he rasps, still breathing hard from his climax.
On shaky legs, you rise up, wincing at the stiffness in your knees. You brace a hand on the sink behind you as the feeling returns to your lower extremities.
Dean’s hand slips around to the nape of your neck, drawing you in. His lips capture yours before your brain can catch up. He licks into your mouth and you whimper when his leg slots between yours. The top of his thigh bumps against your neglected core and you nearly cry at the sensation.
“I can fucking feel you soaking through my jeans, baby,” he says, sliding both hands to your hips. “Soaked just from sucking cock, just like a proper whore.”
Your brain buffers, overloaded with the repeated deprivation of oxygen and the way the roughness of denim feels against your needy clit, your panties still pulled to the side. All that leaks out of you is a pathetic whimper that’s mostly intelligible.
Dean laughs cruelly, kissing a line of fire down your jawline. “So dumb, baby, and you haven’t even had my cock yet.”
He bounces his thigh against you and you cry out, hands scrambling to find purchase on his broad shoulders.
“Please,” you manage to whine.
“Please what?” His teeth graze the line where your jaw meets your neck.
“Need’a cum. Please.”
“You think you deserve it?”
“Mhmm,” you nod vigorously. “Please, Dean.”
You can feel the wet spot your soaked pussy has made, now. The dampness of the fabric allows you to slide easier along the rigidness, your movements barely a fraction of what you need.
“You think you can make yourself cum on just my thigh?” He pulls back from your neck, an amused tilt to his lips. “Gonna hump my leg like the dog you are?”
“Please,” you say barely above a whisper, legs trembling again.
“I’m not gonna help you. Gonna have to be a big girl and do it all yourself.”
“That’s okay, it’s okay. I can do it. Please, please,” you babble nonsensically now, much to his sadistic satisfaction.
“Better get on with it then,” he says.
No sooner are the words spoken into existence are your hips grinding down against his thigh. You feel him flex his quad beneath you, creating a ridge that feels mind-numbingly good against your clit.
You cling to his shoulders for stability, wanton moans spilling from your lips unimpeded. It takes less than a minute for a tightness to grow low in your belly. The heat from his body, the smell of him, it all wraps around you and soaks into your veins like an aphrodisiac.
There’s no sane part of you left to care how humiliating this is, how desperate you are to dry hump his thigh just from having a dick down your throat. Everything in you is narrowed down to how good dragging your pussy along his thigh feels. How with every shift of your hips, sparks of pleasure threaten to set you alight.
“Such a dirty girl,” Dean croons in your ear as you puff out breathy moans. “So goddamn pathetic it’s almost sad.”
Your pussy clenches on nothing at the words, at the names he’s calling you. You bury your face in the crook of his neck, hiding the way your cheeks warm. The scent of him is stronger here, and you inhale deeply.
Dean’s hands have moved to the sink directly behind you, his body effectively caging you between the solidness of his torso and the cool porcelain. It’s that fact alone that keeps you mostly upright, your legs shaking. It grows worse with each drag of your pussy along his thigh, pressure building between your legs.
“I can feel you shaking, you close?” Dean’s words rumble through you.
You nod against his neck, moaning into his skin like you can imbue your need to cum into his system. You squirm and hump against him, mouth falling open as you rapidly approach the edge of your orgasm. It’s so close, the final build up making your movements erratic as you push yourself just that little bit further.
But just as you are about to tip over the edge, Dean pulls his thigh from between your legs and steps back enough you have to reach behind you to keep yourself from collapsing to the ground.
“No!” You cry out, very nearly at the verge of tears. “Wha—what the fuck?!”
Dean chuckles darkly, meeting your frustrated gaze. “Did you really think it was going to be that easy? God, you’re dumb.”
“Fuck you,” you spit at him.
“All in good time, baby. Now turn around, put your hands on the sink.”
You scowl and instead you reach down, tugging your skirt back over what little it covers before crossing your arms over your chest. “No.”
Dean’s head tilts and he pouts his lip mockingly. “No? Gonna throw a little tantrum now?”
“Fuck. You.” You say again.
“You’re really gonna try this with me?”
He’s stepped closer again, so if you really did want to go anywhere, you’d have to push past him.
But you don’t, and he knows it.
It’s all part of the game. You play it up, act like you don’t want him, just so that he’ll snap and manhandle you into whatever way he wants you. The best part about it is, he wants to fuck you just as much, so no matter how much you brat, how much you pretend, you’ll end up with his cock shoved into you anyway.
It’s a welcome change to all the hook-ups you’d had before. Men— boys, really— who would give up at the slightest bit of pushback, who’d pussy out at the level of roughness you so desperately craved.
And that’s why, even though Dean popped up once a month to rock your world and leave you sated, you never felt the need to indulge the men like the ones who’d been at the bar tonight. They could never satisfy you in the same way.
“Turn around, and put your hands on the sink,” he instructs again, both of you knowing you won’t before the words even leave his mouth.
You stand taller, looking him straight on. “Make me.”
You can see the instant his resolve snaps. Something in his face twitches and his expression darks the millisecond before his hands grasp onto your hips roughly. A gasp makes its way out of you when you’re spun around and shoved roughly into the sink.
The edge digs into your stomach, but that’s the last thing you’re paying attention to when Dean kicks your legs apart with his boot. His hand presses into the middle of your spine, pressing your upper half forward so you are half laying across the sink.
Looking up, you are met with your reflection for the first time since Dean walked into the bathroom.
You were right to assume you looked absolutely wrecked. Mascara is streaked down your face, your red lipstick smeared across your kiss-swollen lips. Then your eyes cant up and you catch Dean staring, but not at your face. His eyes, pupils blown so wide you can barely see his green irises, are trained lower.
Bent over like this, your skirt rides up an obscene amount, baring your panty-clad pussy to him. His lower lip is caught in between his teeth, and he almost looks contemplative in his admiration.
“Gonna keep staring or are you gonna do something?” You snark, watching his eyes snap up to yours in the mirror.
“And what are you gonna do if I don’t?” He asks in turn. “What if I just make you stand like this and let all those guys out there who were eye-fucking you come in here and take their turn?”
Your pussy clenches at the thought, and even though Dean no doubt caught the motion, he makes no comment.
“You wouldn’t. You’re too fucking possessive,” you respond, calling his bluff with not a bit of confidence in your statement.
Dean smiles, and it’s not a kind expression.
Warm skin against the backs of your thighs makes you flinch a bit, even though you can see him take a step forward. His hands slide your skirt back over the swell of your ass, bunching the fabric around your waist.
“Maybe, maybe not,” he muses, slipping his fingers beneath the waistband of your panties. “Maybe when I’m all done with you here they can fuck you while my cum’s still leaking out of you.”
Cool air meets your soaked core as Dean drags your panties down your thighs, down your legs. His fingertips skate your skin as he lifts your feet, removing the scrap of fabric completely. Your mouth twists in a fleeting moment of disappointment when he shoves them into his back pocket.
Those were my favorite pair.
“Either way, I still get to cum,” you finally say.
You yelp as his hand comes down hard on your ass. Once, twice, three times in rapid succession. It stings, leaving your skin tingling. The sensation shoots right between your thighs, reinvigorating the swelling need inside you.
“You really wanna cum that bad you’d let strangers fuck you?” He says with a condescending incredulousness. “God, you’re more pathetic than I thought.”
Another slap, this time to your other asscheek. Your fingers grip the edge of the sink as you resist the urge to rock back towards him. Your cheeks burn from the sting of his words, but he’s not finished.
“Do you think of me when you fuck yourself?”
You didn’t think your cheeks could grow any hotter in embarrassment, but he never fails to surprise you.
“What the fuck kind of question is that?” You squeak.
“The kind I expect answered,” he says with another slap to your ass.
His hand smooths over the warm skin and you nearly moan when it slides inward, his thumb ghosting across your pussy.
“Why does it matter?”
“Because I wanna know if I make you scream my name even when I’m not here to fuck you senseless.”
Your mouth opens and closes as you try to formulate a sentence, but it’s hard to focus with his thumb stroking the slickness of your core. It’s teasing, not enough for the sensations to build, just enough to keep you on edge.
You cry out, flinching forward only to be stopped by the sink, when Dean’s hand makes contact with your exposed pussy this time. It hurts more than your ass, but the pleasure that it turns into isn’t diminished.
“Answer me, slut.”
His hand comes down on your core again and you can’t contain the moan that comes with it.
“Yes, I think of you,” you relent, gripping tighter to the sink.
His thumb presses against your clit and your breath catches in your lungs. The pad rubs circles around the nub and you could cry from the direct stimulation.
“Good.” Is all he says before you lose sight of him in the mirror when he sinks to his knees behind you.
Your head drops forward at the first puff of his hot breath against your core. His tongue follows, licking a hot stripe up your pussy. A soft moan leaves your lips as he does it again, the tip of his tongue swirling around your clit as he uses both hands to grope your asscheeks.
His stubble scrapes against your inner thighs, the combination of sensations making your head spin. You rock back against his face, and surprisingly he lets you. His tongue and lips lick and suck at your core, and nothing about the way he’s eating you out is quiet.
Your hips buck when his teeth close around your clit, not ready for the sudden second of pain. His tongue is right there following, licking away the immediate hurt. His thumb takes over, his tongue dipping inside you.
“Don’t stop, please,” you moan, grinding back on his face.
“Wasn’t planning on it,” he says, pulling away from your pussy just long enough to say as such before going right back.
The pressure of your climax rushes up and you barely have enough strength in your legs to keep yourself upright. The orgasm roars through you in one giant wave. Your mouth falls open as his mouth works you over through it.
In the mirror, you see him stand, and then you’re being flipped around so that you're leaning back against the sink again.
His lips connect with yours and you can taste yourself on his mouth as he kisses you. It’s not gentle, his teeth clash with yours, your tongues dancing and somewhere in the way he licks into your mouth you feel his hand slide between your bodies to your pussy.
You’ve barely recovered from the orgasm he just brought you to, and now his middle and ring finger are slipping inside you.
Carding your fingers through his hair, you kiss Dean hard, letting his mouth swallow your desperate moans. Stars spark behind your eyes as he curls his fingers up towards your belly. Quickly, he finds that soft spot that makes your legs feel like jelly, threatening to send you to the floor.
“De-Dean! Oh fuck,” you cry out.
His mouth has migrated to your neck, sucking hard on your pulse point. You clench hard around his fingers, a different kind of pressure building low in your belly. Another orgasm builds slowly, especially as the heel of his palm presses against your clit.
“That's right, bitch. Scream my name. Scream it loud so everybody out there knows who you belong to.”
He shoves his fingers further into your sloppy pussy, wet and obscene sounds reaching your ears. Your head lolls to the side, allowing him better access to kiss and nibble on your neck. You’ll have to wear make up to cover up the hickies that he’s undoubtedly placing along your skin like a sign to say you’re his. He punches his digits in and out of you, petting that fucking spot.
Your thighs are trembling so hard now— so is the entirety of your body. The pressure just keeps building and building. He’s everywhere, between your legs, other hand groping your body, his mouth on your neck. Nowhere is left unattended and it is so much.
“Feel you clenching so fucking tight on my fingers, baby. Gonna cum again for me?” Dean says against your neck, leaning up to nip at your ear.
All you can do is nod. Words don’t feel real to you right now and no amount of anything could change that.
Your nonverbal confirmation seems to satisfy him well enough. Then, he does something, something so good and he keeps doing it. Everything around you fades to just his ministrations and the feel of his body caging yours, and you feel the pressure snap.
Everything goes white and your body seizes up with the intensity of which your orgasm slams into you. But Dean’s fingers don’t stop. They continue to pump into you, curling into you. You don’t even feel in control of your body as you feel yourself gush all over his hand.
Dean curses under his breath and you just barely acknowledge it as you gasp for air, clinging to his shoulders with all your might.
Dean draws his fingers from you and a perverted sense of deja vu hits you as he licks you from his fingers. He keeps you upright with his other arm snaked around your waist, and for that you are grateful.
“Did— did I just…?” You pant, slowly realizing what’d happened.
“You just squirted all over my fucking hand,” Dean affirms, wiping his hand on his jeans. “Wish I would’a just stayed down there. Drank it right from the source.”
You groan at his obscene words, unable to stand the way his verbal filth immediately makes your overstimulated body respond in kind.
He taps your cheek none too gently. “Don’t go tapping out on me now. We’re not done yet.”
You’re putty in his hands as he spins you around, bracing your hands on the edge of the sink. He let’s go, and on shaky legs you stand there watching him shove his jeans and boxers back down his thighs.
“You’re so wet, not gonna have any issue getting in,” Dean mutters quietly.
You moan softly at the drag of his cock through your arousal. The spongy head of him bumps against your clit and you whimper, the overstimulation becoming borderline painful.
“What’s a’matter?” Dean asks. “Too much?”
“Uh huh,” you nod.
“Too fucking bad.”
You moan weakly as Dean presses forward, shoving the blunt tip of his cock inside you. Involuntarily, your hips sway forward, away from the stretch. With how wet you are, there’s not much pain, but his fingers can only prepare you for the girth of his cock so far.
Dean’s hands grab fast to your hips, pulling you back to him, the motion sinking you down onto him almost to the hilt. You gasp a moan, feeling unbelievably full to the point it knocks the air from your lungs.
“Where you goin’?” he grunts, working his hips forward and back. “I know you’re not running from my cock after crying for it.”
“So big,” you gasp, inner walls clenching around him as you try to adjust to the sudden stretch.
Dean leans forward, rutting his cock into you. “Stop your fucking whining and take it, pathetic slut. I can feel you dripping down my balls.”
Tears prick at the corners of your eyes as his words hit their mark. It’s all so much; you can practically feel every vein and contour of him inside you. As he drags himself out, the bulge of his head catches on that sensitive spot, immediately making your legs shake.
“Oh, baby, cry all you fucking want,” Dean lays a sloppy kiss to your bare shoulder. “All it’s gonna do is make me harder.”
As if in emphasis, he snaps his hips into yours. You are thrust forward, the unforgiving edge of the sink digging into your lower stomach. Blinking, the tears leak down your cheeks, rewetting the paths from the ones that had fallen earlier.
His arm snakes around to your front, pulling you back against his chest. A big hand pulls your shirt and bra to the side, enveloping a breast. He rolls the hardened nipple between his fingers, every movement made with expert precision.
You swear you can feel his cock in your stomach with every grinding thrust into you. His hips barely break contact with your ass like he can’t be bothered to pull out for even a second. The outcome is his cock stimulating that sensitive spot; the pressure is helped by the way the sink edge ensures he slides along it with each and every movement.
“So fucking tight, baby,” Dean moans in your ear, still fondling your breast. “Always a perfect fuckin’ cumslut for me.”
Your hand reaches behind you both, sinking your fingers into the hair at the nape of his neck. His balls slap against your skin as his thrusts grow longer, his hand sliding up from your tit to your neck. He doesn’t squeeze this time, but just the feel of his calloused palm and fingers circling your throat makes you clench around his cock.
“Fucking me…so good,” you moan out, holding a hand to his wrist.
“Say my name, bitch. Who’s fucking you so good?” He growls, nipping at your shoulder.
“You are, Dean,” you babble.
The hand not on your throat dips between your legs, finding your thoroughly abused clit. A whine crawls its way up your throat and you feel his hand tighten almost imperceptibly around your neck.
“Shut up. I don’t wanna hear it,” he snaps. “Just take it. Fucking take it.”
“But—”
“I don’t care. Not my fucking problem.”
And he doesn’t, his fingers speeding up their motions on your clit. Sharp pangs stab at you with each brush of his callouses over your swollen nub. It all melts into pleasure and all you can do is push your ass back against him, meeting his thrusts.
Dean moans his approval. “See, that’s a good whore. Feels fucking good, don’t it.”
“Yes,” you keen, slamming yourself back on his cock.
His thrusts don’t let up. Instead, they become more forceful, sending you into the sink hard enough you’re sure you are gonna have bruises on your hips tomorrow morning. His cock throbbing against your inner walls, and his panting moans in your ear have become ragged. His fingers on your clit are unrelenting, pushing you towards the brink of yet another orgasm.
He’s all but draped over your back at this point, snapping his hips into yours erratically. Just when you think you can’t take any more, Dean groans into your ear.
“Gonna fucking paint this pussy white, and you’re gonna take it all. Y’hear me?”
Your pussy pulses in response. “Yes, please cum in me.”
Dean moans and it’s one of the sexiest things you’ve ever heard. “That’s fucking right. Beg for my cum, bitch.”
His hand slides from your neck to your shoulder, bracing you and himself as he thrusts harder, balls slapping harshly against you. The grip is bruising, but you’re too far gone to care.
“Please, cum in me, Dean. Need’a feel you fill me,” you whimper.
“Oh fuck, baby.”
You feel hips stutter then, his cock throbs as his orgasm hits him. He’s not quiet, moaning your name loudly.
You can feel his cum filling you, thick ropes spurting into your pussy, and that alone sends you over the edge, yet another orgasm crashing into you. This time, your violently shaking legs give out.
Instantly, Dean's arm wraps around your waist, holding you there as he gives a few more rutting thrusts into your pussy, milking his cock. You both stay there for a second, heavy breathing filling the room as you gasp for air.
He breaks the silence first. “Can you stand?”
You take a second, assessing your still trembling body. Finally, you nod.
Taking you at your word, Dean relinquishes his hold on you, leaving you to brace yourself on the sink as he walks over to the paper towel dispenser. He snags a few, using them to clean his cock off before tucking himself away.
He doesn’t offer you any, instead he turns and unlocks the door.
Sparing a glance over his shoulder, he gives you that sharp grin. “So, same time next month?”
You tug your clothes back into place. “Fuck you.”
“Darlin’, you just did,” is all he says before he disappears out the door.
Please like, reblog, and/or comment if you enjoyed. Feedback is appreciated and encouraged!
Summary: Dean attends your daughter’s play—and meets your ex-boyfriend for the first time. The only real commitment Dean Winchester has ever had is to his work. Is he really a man you can rely on?
AN: We had some office spice. Ready for some fluff and family feels?
Posted on Patreon: June 26, 2026 | Word Count: 2.5K
Tags & Warnings: Single mother!reader, ft. a deadbeat dad, jealousy, fluff and feels
Series Masterlist ➤ Dean Winchester Masterlist
Dean finds a guest spot in front of the school. The old Impala rumbles to a stop there, and he climbs out, grabbing the bouquet resting in his passenger seat.
His keys jangle in his other hand as he makes his way to the front office to check in, just like you told him to in your texted instructions. The nice ladies there give him a guest badge that he slaps on his chest, over his dress shirt, and they tell him how to get to the theater.
He feels awkward and out of place walking down the halls of this school alone, but you had to take Emma over there early before the show.
The hell am I doing here?
He has to fucking wonder.
But he promised you. He promised the kid. So he’s here.
He’s relieved to see you standing off to the side of the theater’s large double doors, waiting for him, by the look of you. And in that little black dress and heels, perfect for every curve, he more than appreciates the view.
His smile is almost involuntary when you notice him, your eyes brightening.
“Hey,” you say, “I um, wasn’t sure you would come.”
Dean kisses your cheek, lingering there at the scent of your perfume.
“Mmm, you smell nice,” he whispers.
You try to temper your smile, but it’s no use.
“Behave,” you warn. Though you notice the bouquet of red roses he’s holding, and you soften. He plucks one of the stems out of the bunch and presents you with a single rose.
“Gotta save the rest of these for the star of the show, but don’t think I forgot about you, sweetheart,” he says.
That crooked grin of his should come with a warning label.
You take the rose, biting your lower lip. Your mouth opens, even though you don’t know what’s about to come out. But any reply you could’ve made is completely derailed—by the voice of your ex-boyfriend.
He greets you by name, and you turn around on reflex. While you’d been a bit uncertain about Dean, you thought could’ve banked on the fact that Nick wouldn’t be here. He certainly takes note of Dean when he approaches, holding out his hand in greeting.
“Nick Vaught,” he supplies.
Dean glances at you briefly. He knew who this man was before he spoke, just by the more guarded look on your face.
“Dean Winchester,” he offers, along with his hand to shake.
Nick quirks a brow and points at Dean in recognition.
“Winchester. HunterCorp. You took over for your father, right? I remember reading the press release, after Ashland broke into the Fortune 500,” Nick says. His arrogance shines through in his tone and the subtle raise of his chin.
“Yeah, we almost worked with an F500 company, Roman Enterprises,” Dean says, sharing a knowing look with you. “They tried to sell me a gun that would take your hand off on the reload. So as far as I’m concerned, being a top seller doesn’t always mean quality. But congrats. I’m sure you guys earned it.”
One thing Dean also has down is a fake ass grin. You cover a smile with your fingers. His hand slips to the small of your back.
“Should we go in, find our seats?” he asks you. You start to nod, but—
“Wait a minute,” Nick says. He watches the closeness between you and Dean shrewdly, but focuses on you. “I get that you work for HunterCorp, but why does the CEO care about my kid’s play?”
You almost sigh. This was why you almost didn’t tell Nick about tonight, but you knew Emma deserved at least the attempt to have her father see her.
“We’re seeing each other,” you say, matter of fact, and without the embarrassment you thought you might have, despite the judgy raise of his brows. You decide not to tack on the whole executive assistant part.
“Right, right. So you’re fucking,” Nick says flatly.
It earns him a frowning look from another parent walking into the theater.
You gape at him, until a glower overtakes your face. “Jesus Christ, Nick.”
Dean’s expression hardens, but he doesn’t let go of you. If anything, his guiding hand becomes more protective and he presses you toward the door.
“Come on. You don’t owe him an explanation,” he says in your ear.
“I don’t need one. It’s fucking obvious,” Nick says, gesturing at you two. He snorts in amusement. “Though I shouldn’t be too surprised. Guess you just have a type for authoritative men.”
“Watch your mouth,” Dean snaps. His voice is quiet, but deep enough to be a real warning.
Nick’s lips press together in annoyance.
You’re already close to seething, but unlike him, you have some fucking decorum. You look around to make sure no one’s watching you all too closely before you speak.
“There’s actual parents around, and this is your daughter’s school, if you haven’t noticed,” you hiss. “Which to be fair, you probably haven’t, since you’ve never actually been here before. Hope you enjoy the fucking show.”
You pivot on your heel, and Dean follows after you. Though he glances over his shoulder, finding Nick standing there testily with one hand in his pocket and a tonight’s playbill in the other.
“I’m sorry,” you whisper, as you lead Dean down the row to the seats you reserved. Your dad is already sitting in one of them.
“We were bound to meet sooner or later,” Dean replies wryly. “Grade A asshat.”
“You have no idea,” you say. Though you pause and give your dad a small wave when he sees you. “By the way, you’re meeting my dad too.”
Dean pauses. “Wait, what?”
“Please,” you say. You grab his hand for solidarity, and because you want to, offering him a slightly nervous smile.
Amused, he can’t help but humor you. He steels himself a little as you two shuffle down the second row. He shakes hands with your father and exchanges pleasantries. Though when you stumble slightly on how to introduce Dean, your father is the one who actually helps you fill in the gap.
“Are you the brave soul who’s been dating my daughter?” he asks.
Dean shakes his hand firmly. “That would be me.”
The other man eyes him for a moment, seizing him up. After a moment, he nods.
“Good. You know you’ve got a gem on your hands.”
Dean gives you a sly smile. “Oh, I know very well.”
A blush blooms warmth in your cheeks. You take your seat between them and help Dean situate the bouquet on the floor. The rose he gave you rests in your lap.
It’s just in time for Nick to take his seat at the end of the opposite row. He glances over at you two, but soon ignores you to take a look at the program.
You heave a long breath through your nose. Dean takes possession of your left hand, earning your attention. He presses a kiss to your knuckles. You smile, though doubt begins to creep in regardless. You lean in closer to him.
“You sure about this?” you ask softly. “You know this can’t be the thing where you get bored after a week and send me a Tiffany bracelet as a consolation prize. You can’t do it to Emma—”
“Hey,” Dean says, stopping you quietly, but firm. “I already told you…this is more than that.”
You stare back at him with a measure of surprise. He understands it, considering his track record, but he knows he’ll just have to convince you. When he thinks of you and the kid, he sees the life his father used to trade for long hours at the office and a heart attack at 52. Dean’s come to realize that if he’s not careful, he’ll end up just like his old man.
So he smiles and leans in to steal a kiss. You can’t help but melt into it, and into him.
Your father watches out of the corner of his eye with a smile of his own.
While Emma isn’t Matilda herself, she plays a very adorable Lavender, one of Matilda’s best friends—complete with a purple dress and glasses you found at Target. Through a lot of motherly pride and shedding a few tears, you’re able to get a few discreet pictures of her on your phone.
After the play, you’re half dreading and half looking forward to the moment she runs out from the backstage area with her teacher (who hilariously played Miss Trunchbull) and the rest of her class. Emma’s back in her normal clothes, and most of the makeup was cleaned off with wipes, but she still somehow has glitter in her hair when she attacks you with a hug.
“Baby you did so good!” you say. You’re smiling from ear to ear as you two sway back and forth.
“Good job, kiddo,” your father says, ruffling her hair. Emma gives her grandpa a big hug next.
“I remembered all my lines. And I held the lizard, but he was slimy!” she exclaims.
You laugh, though you still can’t believe they used a real newt to drop into Miss Trunchbull’s drink.
“Well, you’ve got some more people who came to see you—”
“Hey, Em,” Nick says. He makes a subtle point to step into his daughter’s line of vision before Dean, who just waits behind.
He knows what Nick is doing, but it’s also kind of fair that he sees his daughter first. Dean is…what, a family friend? He doubts you’ve told her more than what Emma already knows him to be: Mommy’s work friend.
Emma’s face brightens. “Daddy!”
She hugs his waist. He holds her back, petting her hair.
“You saw me?” she asks hopefully.
“Of course, honey. You did a great job.”
“What was your favorite part?” she asks.
Nick stumbles there slightly. Your lips quirk. Before intermission, you happened to look over and saw him scrolling through his phone. You suppose you can give him partial credit for sitting through the whole thing.
“Uh, well, it’s hard to pick. Everything was so good,” he says. “Hey, would you want to come over to hang out with me tonight?”
“Nick,” you cut in sternly. He gives you some side-eye, but he’s focused on Emma. She looks a little unsure though.
“What? She’s never stayed over with me before. Tonight’s a special night,” he says.
“That’s because,” you say, but you stop yourself short with an annoyed frown. You don’t want to say in front of your daughter that the reason why she’s never slept over at his apartment is because it goes against your full custody agreement, what he wanted to begin with.
“Well, you know very well why,” you say, holding Emma by her shoulders. “I think it’s time for us to say goodnight.”
Nick is about to protest, when his cell rings in his pocket. His jaw clenching, he checks his phone and swears under his breath.
He looks down at his daughter and gives her an apologetic look.
“This is an important work call that I need to take, but I love you, and it was good to see you, honey.”
“You’re leaving?” she asks, her eyes filling with disappointment. Nick hesitates, but glancing up at your unyielding face, then back to hers, he just strokes her on the head.
“I’m sorry, Em. I’ll see you again soon,” he says. He answers the call right before it stops ringing. “Hey, no, cancel that. I want to see the new reports first. Get it to me within the hour.”
His voice drifts down the hall as he walks away. It leaves a crestfallen little girl in his wake.
But she finally notices Dean. He’s been standing off to the side with a dozen roses behind his back. When he smiles at her gently, she’s able to smile again too.
“Hey, sweetheart. Finally get to move up the line to say hi to you. Looks like I’m in the presence of a little celebrity,” he says. He takes a knee so that he can be eye-level with her when he gives her the bouquet.
Her eyes go wide as she accepts them. “Whoa, there’s so many.”
You smile, sharing a look with your dad while you blink past a telltale sting in your eyes.
You squeeze Emma’s shoulders. “What do you say?”
“Thank you,” Emma says, swaying a little with her pretty roses.
Dean laughs and playfully thumbs at her cheek. “You’re welcome.”
She giggles.
Dean glances up at you and your dad as he gets back up to his feet. “So, can I take you guys out to celebrate? I know a nice place not too far.”
“Food sounds good to me,” your father says.
“How nice are you talking?” you ask. Unlike Dean, you don’t come from money. Your family’s idea of a night out consisted of Red Lobster, Outback, or the Dairy Queen around the corner.
“How about the Ruth’s Chris down the street,” Dean offers. He sees the look of reservation on your face and takes your hand in reassurance. “Come on, it’s on me.”
You bite your lip. “You sure?”
“The man’s sure, sweetheart. Let’s get moving,” your father says, rubbing his hands together before he steers Emma toward the exit. “God knows I haven’t had a good steak in the last decade.”
He helps Emma hold her flowers on the way to the parking lot, allowing Dean to keep his hold on your hand as you followed behind.
“This is dangerous you know,” you say in amusement. “You’re gonna give my dad a taste of the high life. He’ll think it’s free steak and bourbon forever.”
“Hey, if that’s what the guy wants, I’m not above bribery,” Dean remarks.
You laugh and lean into his side, wrapping your arm around his. He presses a kiss to the side of your head, smiling all the while.
Two Years Later
Dean scans the very detailed document on his laptop with a critical eye.
“Okay, Yale graduate. MBA. Internships, the works. Strong start.”
Kevin Tran, the latest candidate, pushes up his glasses.
“I also maintained a 4.56 GPA weighted average, 4.78 cumulative,” he says. “Um, I can tell you more about how my roles in finance have intersected with business and sales, or first I can give you the highlights from my internships. Would you like that in chronological order or in order of relevance?”
Dean clears his throat and takes another sip of iced tea. Kevin watches him do it with some nervous energy as he tries not to fidget in his seat.
“What do you think, sweetheart?” Dean asks.
He glances over at you, where you sit in your own leather chair. This may be Dean’s office, but yours is now down the hall. As Operations Manager, you oversee HunterCorp’s logistics, budgets and resources, quality assurance, and office management. You’re literally the connective piece between Sam and Dean, and every department in the company. But you’ve been spread a little too thin for the past few months, juggling your new responsibilities with the old. Now, Dean needs your replacement.
You peruse Kevin’s resume again and flip the page. Your engagement ring catches the light.
“Let’s start with internships.”
AN: How'd you like Dean stepping up? You think he'd make a good stepdad? 😘
I am working on a longer Dean AU series at the moment. I'll be telling you guys more about it next week, but until then, please let me know what you thought about this little mini series!
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I loved the way this wrapped up!! I was looking forward to reading it after seeing you post it on your Patreon.
“Behave,” you warn. Though you notice the bouquet of red roses he’s holding, and you soften. He plucks one of the stems out of the bunch and presents you with a single rose.
“Gotta save the rest of these for the star of the show, but don’t think I forgot about you, sweetheart,” he says.
The whole thing was very sweet, but I really liked this part. I love when, in media (and irl), the men get flowers for both the mom and the daughter. My dad and I do daddy-daughter nights whenever my mom is out of town and I'm home from school. He doesn't as much anymore, but he used to get me flowers and leave a bouquet for my mom when she got home.
I know its a common theme in my comment reblogs, but I can't stress enough how relatable your stories are.
While Emma isn’t Matilda herself, she plays a very adorable Lavender, one of Matilda’s best friends—complete with a purple dress and glasses you found at Target. Through a lot of motherly pride and shedding a few tears, you’re able to get a few discreet pictures of her on your phone.
So I thought I mentioned this in my comment reblog of part two, but maybe not, but love Matilda. I've never seen it in play format, but I've watched the movie more times than I can count and I have a copy of the book, so seeing this was the play was a treat!
“How about the Ruth’s Chris down the street,” Dean offers. He sees the look of reservation on your face and takes your hand in reassurance. “Come on, it’s on me.”
Not gonna lie, I had to look up what Ruth's Chris is because my family also does not/did not go out to fancy restaurants except for major special events (weddings, graduations, ect)
This was super sweet, and I definitely think Dean as you write him would be a wonderful stepdad to Emma. I also cannot wait to hear more about this AU you have cooking up!
Tags/Warnings: Smut, choking, rough sex, threat/talk of a gangbang, sex in a public bathroom, no aftercare, face fucking, deepthroating, cunnilingus, fingering, dry humping/thigh humping, hair pulling, degradation, dirty talk, spanking, slapping, unprotected sex, cream pie, squirting, pussy slapping, finger sucking, edging, orgasm denial, overstimulation, multiple orgasms, Sir kink if you squint, masochistic reader, brat reader, no use of Y/N, reader has no descriptors other than being slightly shorter than Dean and has enough hair to pull.
Summary: It's been six months since you struck the deal with Dean, and true to his word, he comes back like clockwork—even when you're not at home.
Word Count: 7.7k
Author's Note: Title from the song Animal by Chase Holfelder
A part two to this post from 2025 Kinktober was requested, so here it is!!
This counts for the Mirror Sex square for @j3bingo
Thank you to @gappyswife for beta-reading this for me!
Dividers: Line Divider 1 by @olenvasynyt Line Divider 2 by @omi-resources SPN Divider by @talesmaniac89
Tag List: @copperboom82 @sleepycues @xpurdyglambertx @flanneledfae
Neon paints your body in hues of red and blue as you cross the dance floor. The dive bar has little by way of illumination beyond the signs on the wall depicting beer and food, half-naked cowgirls, and the name of the joint. A few yellowed lights hang from the ceiling, joining the bright colors to shine down on the crowd below.
You wind your way through the throng of sweaty bodies, their boisterous conversations meld with the thrum of music soaking into the atmosphere. Cold glass bites into your palm as you carry your fresh beer back to the edge of the dance floor.
It’s standing room only— a regular occurrence on Thursday nights where ladies drink free— and since your friends have long since returned home, you don’t see the point in trying to snag a high-top for yourself.
No, half drunk on the music and the cheap beer, you don’t want to sit–you want to dance.
Between line dances, you down long-necks and tall glasses of water alike, feeling like you’re sweating it out faster than you can consume; the last thing you want is to wake up in the morning with a splitting headache, even if your freelance job awarded you a day off.
After being contained to your apartment by the threat of being ripped to shreds at the razor-sharp claws of a pack of supernatural beasts, you want to spend your new lease on life as you pleased, and right now, you are doing just that.
You’ve lost count of how many dances you’ve finished by the time your bladder begs you to vacate the floor and empty it. Reluctantly, you shuffle off the dance floor, having to only wait behind three other girls before you snag an open stall.
The bathroom itself leaves something to be desired. Dingy tile line the floors; you aren’t sure if the patterns were actually design choices or were poorly cleaned stains. Raunchy love notes cozy up to random phone numbers with instructions to ‘call for a good time’ with crude pictures of dicks on the cheap stall walls and door.
Noting the bathroom was empty, you finish up and wash your hands, smiling at the additional graffiti etched into the edges of the dirty mirrors. Most of it is hazy anyway, the blanket of alcohol warming you at the edges. You pull your tube of lipstick from the pocket of your miniskirt, the denim barely covering you enough to avoid a public indecency charge.
You don’t think much of it when the music grows louder, too busy shoving the lipstick back into your pocket. The door to the bathroom creaks open before it shuts hard with a thud, muting the sounds once more.
It isn’t until you hear the snick of the lock sliding into place that you look up to see a figure standing behind you in the reflection of the mirror. Your heart drops to your stomach in the same second your pussy throbs violently when you whirl around to familiar green eyes that blink black before returning to their alluring jade.
“Hiya, Sweetheart,” Dean purrs, stepping closer so that there’s less than a foot of space between your bodies. “Forget what day it is?”
Your boots have a bit of a heel, so there’s less of a height difference than the first time he visited you. Usually, you’re at home. Most of the time you’re already in bed when he arrives, sometimes in the shower, sometimes making food.
“No. Just lost track of time.” Somewhere between the dancing and the drinks and your phone being tucked away in the purse you’d brought, the time had slipped away.
His head cocks to the side, the move more animalistic than human. “That so?”
“I wanted a night out with my friends. Sue me.”
His eyebrows raise but he says nothing.
Not right away at least.
Instead his attention drifts from your face, slipping down your body.
You can see his eyes catch on your strappy tank top where the halter neckline plunges to near obscene levels, showing off the scalloped lace of your bra. The green in his gaze goes dark in a different way than you are used to the further down it travels, down all the way to the bare expanse of your legs and where your boots sit upon your feet.
“Must’a had every guy in here tonight drooling over you,” Dean says appreciatively, eyes flicking back up to yours.
You brace your hands on the sink behind you and lean back with a shrug, trying to act casual and not like your pussy isn’t growing wetter by the second. The heat that rises to your cheeks is in humiliation. He hasn’t even touched you yet and here you are like a bitch in heat.
You’d noticed the heated stares, the way some of the men in the bar’s eyes would pop out of their skull like some cartoon, and you’d be lying to him and to yourself if you said you didn’t revel in it.
He leans in, and you’re not sure when he got this close to you but you’re assaulted with the intoxicating smell of him. Something masculine and dark that makes you want to bury your face in the crook of his neck.
You jump a little when the warmth of his palm spreads along the inside of your thigh, too entranced by his gaze, heavy and focused, to notice his arm slipping between your bodies until it’s there. His fingers tease along the soft skin, the tips just inches from the throbbing need between your thighs.
“Too bad your pussy’s already got someone takin’ care a’her, right?” He croons, slipping his hand up.
Words escape you as he slides your panties to the side, not that the lacy scrap of fabric was covering much to begin with.
Your mouth gapes open at the first teasing touch, the calloused tips of his fingers sliding through your slick, bumping against your clit. Hands gripping the edge of the sink so hard you’re sure the porcelain will crack any second, your hips buck up against his hand, seeking the stimulation.
The sense of euphoria is short lived when his other hand shoots out, wrapping around your neck. A gasp gets stuck in your throat and your eyes flare wide. His fingerprints dent your skin.
“Right?” He asks again with a darker edge this time.
The bathroom around you narrows to the tightness of his grip on your neck and the pleasure derived from his fingers still working over your soaking core. Every inch of your body erupts in tingles, and you would have nodded if his hold allowed it.
“Yes,” is all you manage to choke out.
It is a funny feeling. Dean quite literally has your life in his hand. By all accounts you should be pissing-yourself-terrified. But you’re not. Instead, all you can focus on is the dark whorls of lust eddying in the depths of his eyes, the green heightened with his enjoyment, and how his middle finger is circling your clit with precision.
That was, until it retreats and you nearly whine at the loss of contact.
You sense where his hand is going milliseconds before his open palm makes contact with the side of your face. It’s not hard enough to do any damage beyond a buzzing beneath your skin that will last probably as long as this encounter, but it’s hard enough for tears to sting at your eyes.
“Yes,” you wheeze, his grip on your throat just loose enough for the words to squeeze out. “My pussy’s yours.”
Another slap, this one no less gentle than the first. “Say it again.”
Your hand slips up, wrapping around his wrist. “My pussy’s yours.”
His pulse is even under your frantic grip. If it weren’t for the desire written in his gaze and the sizable bulge straining against the front of his jeans, you wouldn’t have guessed he was enjoying this. You’re painfully aware of arousal dripping down your inner thigh, your core clenching around nothing.
Dean’s hand connects with the side of your face one last time then returns between your thighs. The edges of your vision start to go fuzzy, and the moan he pulls from your lips when his fingers press harshly against your clit comes out more like a high pitched keen.
He leans in, keeping steady pressure on your neck. “You’re gonna cum for me before I let you go. Can you do that for me, whore? Not like you need to breathe, anyway.”
“Yes,” you choke out, voice a little louder than a whisper.
“Yes what?” Dean asks teasingly, his fingers moving across your core in a way that makes it really hard to formulate words.
“Yes, sir.” Your words are slurred, but they seem to suffice anyway as his hand picks up the pace.
Your hips grind against his palm, matching the rhythm he’d created. You feel dazed when his hand slips lower, two fingers shoving inside you while the heel of his palm acts as the perfect surface to grind your clit on.
He doesn’t seem to notice or care when your nails dig into the inside of his wrist, your other clawing at his shoulder to brace yourself against the rapidly growing wave of pleasure stemming from between your thighs.
His muscles shift under your grip as he angles his arm better so he can send his middle and ring finger even deeper into you, curling them up towards your belly. Your hips grind down against his hand, the rough surface providing the most divine friction against your needy clit.
An amused chuckle from Dean vibrates through your body. “I can feel your pussy clenching around my fingers. Fuck, I can’t wait to feel ‘er around my cock.”
A strangled whine is all you can muster as he curls his fingers inside you, stroking that soft spot within you that darkens your vision even further. Arching your back, you press your chest into Dean’s, his preternatural warmth soaking into you.
You’re sure he can feel the way your nipples are hardened, even through both your shirts. The bralette underneath is little more than decorative lace with a paper thin backing there to not irritate your skin.
His blood-red button down is immaculate, tucked into a pair of dark wash jeans; it’s similar to the outfit he wore the first time you met him.
Well, he’s nothing if not consistent, you think before stars burst behind your eyes, which you squeeze shut as the tightness in your belly gives way.
You cum harder than the first time he fucked you. Harder than you ever have in your life.
Your body goes rigid, trembling from head to toe as electric shocks spark through you all down your spine. The ache of pleasure pulses through your body as he works you through the throes of your climax.
Head lolling to the side as Dean’s grip on your neck lessens, you gasp in air. The room around you spins as you gulp down oxygen the best you can through your unabashed moans.
Dean’s lips slot over yours, drowning out your sounds of ecstasy and you can taste the whiskey on his tongue when it sweeps into your mouth. Your hand slides up his shoulder to the back of his neck, fingers tangling in the shaggy ends as you kiss him back with matching intensity. A low rumble of satisfaction emanates from his chest.
As you slowly come back into your body, Dean’s hand slows, his fingers leisurely dragging out of you and stroking your oversensitive clit on their way out from between your trembling legs. He grips your chin none too gently, breaking the kiss.
There isn’t enough time for you to miss the feeling of his lips on yours, to savor the tingling he left behind, before his fingers are in your mouth.
The calloused tips press down your tongue and instinctively you wrap your lips around the second knuckle. You can taste yourself as you work them over with your tongue, your whimper turning into a gag when Dean shoves his fingers deeper into your mouth.
“That’s right,” Dean all but purrs, looking on with a lust-drunk expression. “How are you gonna take my cock if you can’t take two little fingers?”
He’s right, you think, but I wouldn’t call his fingers small, either.
His grip on your chin relaxes just enough for you to work your jaw open more. Viscous saliva floods your mouth as Dean moves his fingers in and out of your mouth. Every time he bottoms them out, you cough and gag as the tips wiggle against the back of your throat.
Tears sting your eyes, spilling down your cheeks in fat droplets when you blink up at him. There’s a hungry edge to the way he gazes down at you, obsession bleeding in as he fixates on how your spit collects on his knuckles and rolls down his hand.
Another rush of want crashes over you at the way he’s looking at you and in response, your thighs clench together unconsciously. The miniscule movement isn’t missed by Dean, not that you were really trying to hide your insatiable need anyway.
“God, you’re such a greedy slut,” he groans. “I just got you off and you’re already wanting more, aren’t ‘cha, Sweetheart?”
With his fingers shoved into your mouth, all you can do is hum in agreement.
Dean hums his approval, and with the slightest nod his fingers slip from your mouth, the hand on your jaw following suit. You suck air in greedily, the strings of drool starting to cool on your chin.
With eyes half-lidded out of pure lust, you watch him raise the hand pulled from your mouth up to his own. A particularly strong pulse of arousal nearly sends you to the floor as his tongue darts out from between his lips. The sounds that come from him slurping your spit from his hand are purely pornographic, all while he keeps his eyes locked on yours.
“Knees. Now,” he commands, wiping the mix of your spit on his jeans.
With how shaky your knees have become in the aftermath of his display— as well as the leg-shaking orgasm he gave you— you’re tempted to comply. A glance down to the bulge in his pants is enough for saliva to pool under your tongue, but the alcohol in your system has made you bold.
“And if I don’t want to?”
His head cocks to the side, eyebrows quirked up. “No?”
A shake of your head as you look up at him through your lashes. “No.”
“You don’t want me?” He asks, his hand curling around your wrist, bringing your palm to rest on the evidence of his arousal. “You don’t want my cock?”
His grip disappears, but you press the heel of your palm against him, dragging your hand along the length of him. “No, I don’t.”
Dean gives you a knowing smirk, and the moment stretches wide between you before he finally speaks.
“Liar.”
His hand moves too fast for you to react, fingers tangling painfully in your hair as he grabs a fistful.
You cry out softly, half from the pain and half out of shock. He leans forward and the sound dies out into a quiet gasp. Your eyes dart from the depths of his gaze to his lips, which are still tugged upwards in a satisfied grin, and back again.
“You want me. I’ve been inside you. Tasted you.” His thumb traces the plush of your bottom lip, smearing your lipstick even further. “I know just how desperate you are for my cock, whore. You can’t ever pretend otherwise.”
Your knees make contact with the grimy bathroom floor and you can feel yourself tremble with anticipation as Dean angles your head to look up at him.
“Keep your eyes on me,” he says, undoing his belt with his free hand.
“And if I don’t?” You ask before you can think better of it.
Dean doesn’t even bother to shove his jeans and boxers down his muscular thighs. They barely make it down past his balls before he’s languidly stroking himself, the tip red and already leaking.
Your throat bobs and you barely flinch when he grips himself at the base and slaps his heavy cock against your cheek.
“Oh, Sweetheart. Don’t make me ask twice,” he says.
Heart beating a million miles a minute, you barely feel the small sting of contact nor the dull ache of the tight grip he has on your hair. Your world is narrowed to the throbbing need in your pussy and Dean’s hard cock bobbing in front of you.
“Now don’t be difficult and open your fucking mouth,” he growls, shoving his cock towards your mouth.
You have the good sense this time to obey, your lips parting without hesitation. Tongue lolling out, you barely have enough time to situate yourself before his cock is halfway down your throat.
Instantly, your throat is on fire and you gag at the sudden intrusion. Hands flying up to brace against his denim clad thighs, you brace yourself as Dean holds your head in place.
“Fuuuck,” he rasps, dragging his hips back and briefly allowing you to breathe. “I missed this. Had a lotta girls, but none of their mouths feel half as good as yours does.”
It takes a second for you to adjust to how he’s stuffed into your mouth. Drool has already started to leak out of the sides of your mouth with every thrust of his hips. The stretch of your lips, the taste of him is just right. He smells warm, like sweat and skin and some clean, masculine soap.
And it’s pathetic the way you silently enjoy him pressing your face further onto his cock until your nose is buried in the thick, curly hair at his pubic bone. Your throat spasms as he holds you there, unable to breathe and frozen with sensory overload.
Hot tears crawl down your cheeks, blending with your drool on your chin. Just when the edges of your vision start to blur, Dean yanks you off his cock by your hair. You cough and sputter, replenishing the void of oxygen in your lungs.
Thick strings of drool stick to your chin and neck, and you just know your mascara is running down your cheeks, half-dried to your skin with your tears.
“Such a messy girl,” he coos, honey-laced words dripping with condescension. “See, all you needed was a good dick in that brat mouth.”
You welcome the sting as his hand leaves another hot print on your cheek and you have to resist from leaning into his palm when it caresses the hurt. It slips away just as quickly, and in turn you wrap a hand around the spick-slick shaft of him.
“Gonna keep fucking my face, or do you want me to make it actually feel good?” You ask, locked on his eyes as your mouth closes around the head of him.
The groan Dean utters when your cheeks cave around him, when your tongue slides along the sensitive underside of his cock, is all the answer you really need.
You’d learned early enough on that you really had to squeeze your hand around his cock when stroking him. “Harder, bitch,” he’d growled. “Don’t be fucking scared. You’re not gonna break it.”
His fingers still threaded themselves in your hair, the tips gliding across your scalp as you descended back down upon him. His head falls back, and the red ambient lighting in the bathroom gleams along the column of his throat, skin dewy with sweat.
You’d like nothing more than to stand and lick the salt from his skin.
Tongue pressed to the underside and cheeks hollowed, you slide his cock all the way to the back of your throat. Your gag reflex balks, but you ignore it, pulling back barely half way before bobbing your head back down. The small whimpers and moans that you make no attempt to stifle travel along his cock.
Dean’s hand curls further into your hair, leaving your head littered with sharp pinpricks. All it does is add to the slickness between your thighs. Thighs that you press together seeking any kind of friction; you can feel your arousal roll down the insides. Your skirt is still hiked up around your hips, leaving your dripping pussy exposed to the cool air.
A dull ache makes itself known in your knees, the bathroom tile extremely unforgiving on the joints. You do your best to ignore it, hand sticky with spit abandoning his shaft in favor of cupping his balls.
Dean’s hips buck into your mouth at the additional touch, seeking the wet heat.
“Oh fuck,” he grunts. “Keep doing that.”
So you do, fondling him there while maintaining your rhythm; push your head down on him until you can feel him in your throat— until you gag harshly— then pull back enough to breathe through the spasm. Rinse and repeat all the while your free hand inches closer to your throbbing pussy. The wet, sloppy sounds from your mouth meld with his decadent grunts and groans, filling the bathroom.
The system works, up until the point it doesn’t.
You come up for air only for Dean’s hand to press against the back of your head, pushing you back down onto his cock. Your eyes screw shut as your nose is mashed into the mess of curls at his pubic bone.
A sound of displeasure vibrates from your lips up the length of him, and after a second you try and pull your head back. It ends fruitlessly, though, as Dean only presses harder.
“Shut up. Just a little longer,” he growls. “Fucking take this cock. Fucking choke on it like the whore you are.”
Your tear-filled eyes screw shut as your throat spasms hard. Bracing a hand on his muscular thigh, your fingernails dig into the denim. Dean’s cock moves, barely pulling out an inch before it’s back, harshly slamming into your throat. A soreness grows in your jaw for how long you’ve kept it open.
“Fuck, that’s it,” he moans, his chest heaving. “Gonna fucking cum, baby.”
That fuzzy, floaty feeling returns as you struggle against the need to breathe, against the intrusion of cock in your throat. He starts to twitch against your tongue, and the pistoning of his hips grows sloppy and uneven. Pushing through the haze, you swallow around him, earning yourself a string of curses from above you.
The crass words are cut off by a garbled moan. You hear your name somewhere in there, but you’re too busy swallowing down Dean’s cum to pay much attention to what he’s saying. He holds you there, cock pumping his seed down your throat until he stops twitching and his length softens a bit.
Lines of spit connect your lips to his cock once he finally wrenches himself from your mouth, and they snap back against your chin when he takes a step back. Your body is wracked with wet coughs as you gasp for air. Heart beating what seems like a million beats a second, you lean back on your heels and wipe the spit from your face.
Out of the corner of your eye you see Dean tuck his half-flaccid cock back into his boxers, leaving the jeans unbuttoned.
“Up,” he rasps, still breathing hard from his climax.
On shaky legs, you rise up, wincing at the stiffness in your knees. You brace a hand on the sink behind you as the feeling returns to your lower extremities.
Dean’s hand slips around to the nape of your neck, drawing you in. His lips capture yours before your brain can catch up. He licks into your mouth and you whimper when his leg slots between yours. The top of his thigh bumps against your neglected core and you nearly cry at the sensation.
“I can fucking feel you soaking through my jeans, baby,” he says, sliding both hands to your hips. “Soaked just from sucking cock, just like a proper whore.”
Your brain buffers, overloaded with the repeated deprivation of oxygen and the way the roughness of denim feels against your needy clit, your panties still pulled to the side. All that leaks out of you is a pathetic whimper that’s mostly intelligible.
Dean laughs cruelly, kissing a line of fire down your jawline. “So dumb, baby, and you haven’t even had my cock yet.”
He bounces his thigh against you and you cry out, hands scrambling to find purchase on his broad shoulders.
“Please,” you manage to whine.
“Please what?” His teeth graze the line where your jaw meets your neck.
“Need’a cum. Please.”
“You think you deserve it?”
“Mhmm,” you nod vigorously. “Please, Dean.”
You can feel the wet spot your soaked pussy has made, now. The dampness of the fabric allows you to slide easier along the rigidness, your movements barely a fraction of what you need.
“You think you can make yourself cum on just my thigh?” He pulls back from your neck, an amused tilt to his lips. “Gonna hump my leg like the dog you are?”
“Please,” you say barely above a whisper, legs trembling again.
“I’m not gonna help you. Gonna have to be a big girl and do it all yourself.”
“That’s okay, it’s okay. I can do it. Please, please,” you babble nonsensically now, much to his sadistic satisfaction.
“Better get on with it then,” he says.
No sooner are the words spoken into existence are your hips grinding down against his thigh. You feel him flex his quad beneath you, creating a ridge that feels mind-numbingly good against your clit.
You cling to his shoulders for stability, wanton moans spilling from your lips unimpeded. It takes less than a minute for a tightness to grow low in your belly. The heat from his body, the smell of him, it all wraps around you and soaks into your veins like an aphrodisiac.
There’s no sane part of you left to care how humiliating this is, how desperate you are to dry hump his thigh just from having a dick down your throat. Everything in you is narrowed down to how good dragging your pussy along his thigh feels. How with every shift of your hips, sparks of pleasure threaten to set you alight.
“Such a dirty girl,” Dean croons in your ear as you puff out breathy moans. “So goddamn pathetic it’s almost sad.”
Your pussy clenches on nothing at the words, at the names he’s calling you. You bury your face in the crook of his neck, hiding the way your cheeks warm. The scent of him is stronger here, and you inhale deeply.
Dean’s hands have moved to the sink directly behind you, his body effectively caging you between the solidness of his torso and the cool porcelain. It’s that fact alone that keeps you mostly upright, your legs shaking. It grows worse with each drag of your pussy along his thigh, pressure building between your legs.
“I can feel you shaking, you close?” Dean’s words rumble through you.
You nod against his neck, moaning into his skin like you can imbue your need to cum into his system. You squirm and hump against him, mouth falling open as you rapidly approach the edge of your orgasm. It’s so close, the final build up making your movements erratic as you push yourself just that little bit further.
But just as you are about to tip over the edge, Dean pulls his thigh from between your legs and steps back enough you have to reach behind you to keep yourself from collapsing to the ground.
“No!” You cry out, very nearly at the verge of tears. “Wha—what the fuck?!”
Dean chuckles darkly, meeting your frustrated gaze. “Did you really think it was going to be that easy? God, you’re dumb.”
“Fuck you,” you spit at him.
“All in good time, baby. Now turn around, put your hands on the sink.”
You scowl and instead you reach down, tugging your skirt back over what little it covers before crossing your arms over your chest. “No.”
Dean’s head tilts and he pouts his lip mockingly. “No? Gonna throw a little tantrum now?”
“Fuck. You.” You say again.
“You’re really gonna try this with me?”
He’s stepped closer again, so if you really did want to go anywhere, you’d have to push past him.
But you don’t, and he knows it.
It’s all part of the game. You play it up, act like you don’t want him, just so that he’ll snap and manhandle you into whatever way he wants you. The best part about it is, he wants to fuck you just as much, so no matter how much you brat, how much you pretend, you’ll end up with his cock shoved into you anyway.
It’s a welcome change to all the hook-ups you’d had before. Men— boys, really— who would give up at the slightest bit of pushback, who’d pussy out at the level of roughness you so desperately craved.
And that’s why, even though Dean popped up once a month to rock your world and leave you sated, you never felt the need to indulge the men like the ones who’d been at the bar tonight. They could never satisfy you in the same way.
“Turn around, and put your hands on the sink,” he instructs again, both of you knowing you won’t before the words even leave his mouth.
You stand taller, looking him straight on. “Make me.”
You can see the instant his resolve snaps. Something in his face twitches and his expression darks the millisecond before his hands grasp onto your hips roughly. A gasp makes its way out of you when you’re spun around and shoved roughly into the sink.
The edge digs into your stomach, but that’s the last thing you’re paying attention to when Dean kicks your legs apart with his boot. His hand presses into the middle of your spine, pressing your upper half forward so you are half laying across the sink.
Looking up, you are met with your reflection for the first time since Dean walked into the bathroom.
You were right to assume you looked absolutely wrecked. Mascara is streaked down your face, your red lipstick smeared across your kiss-swollen lips. Then your eyes cant up and you catch Dean staring, but not at your face. His eyes, pupils blown so wide you can barely see his green irises, are trained lower.
Bent over like this, your skirt rides up an obscene amount, baring your panty-clad pussy to him. His lower lip is caught in between his teeth, and he almost looks contemplative in his admiration.
“Gonna keep staring or are you gonna do something?” You snark, watching his eyes snap up to yours in the mirror.
“And what are you gonna do if I don’t?” He asks in turn. “What if I just make you stand like this and let all those guys out there who were eye-fucking you come in here and take their turn?”
Your pussy clenches at the thought, and even though Dean no doubt caught the motion, he makes no comment.
“You wouldn’t. You’re too fucking possessive,” you respond, calling his bluff with not a bit of confidence in your statement.
Dean smiles, and it’s not a kind expression.
Warm skin against the backs of your thighs makes you flinch a bit, even though you can see him take a step forward. His hands slide your skirt back over the swell of your ass, bunching the fabric around your waist.
“Maybe, maybe not,” he muses, slipping his fingers beneath the waistband of your panties. “Maybe when I’m all done with you here they can fuck you while my cum’s still leaking out of you.”
Cool air meets your soaked core as Dean drags your panties down your thighs, down your legs. His fingertips skate your skin as he lifts your feet, removing the scrap of fabric completely. Your mouth twists in a fleeting moment of disappointment when he shoves them into his back pocket.
Those were my favorite pair.
“Either way, I still get to cum,” you finally say.
You yelp as his hand comes down hard on your ass. Once, twice, three times in rapid succession. It stings, leaving your skin tingling. The sensation shoots right between your thighs, reinvigorating the swelling need inside you.
“You really wanna cum that bad you’d let strangers fuck you?” He says with a condescending incredulousness. “God, you’re more pathetic than I thought.”
Another slap, this time to your other asscheek. Your fingers grip the edge of the sink as you resist the urge to rock back towards him. Your cheeks burn from the sting of his words, but he’s not finished.
“Do you think of me when you fuck yourself?”
You didn’t think your cheeks could grow any hotter in embarrassment, but he never fails to surprise you.
“What the fuck kind of question is that?” You squeak.
“The kind I expect answered,” he says with another slap to your ass.
His hand smooths over the warm skin and you nearly moan when it slides inward, his thumb ghosting across your pussy.
“Why does it matter?”
“Because I wanna know if I make you scream my name even when I’m not here to fuck you senseless.”
Your mouth opens and closes as you try to formulate a sentence, but it’s hard to focus with his thumb stroking the slickness of your core. It’s teasing, not enough for the sensations to build, just enough to keep you on edge.
You cry out, flinching forward only to be stopped by the sink, when Dean’s hand makes contact with your exposed pussy this time. It hurts more than your ass, but the pleasure that it turns into isn’t diminished.
“Answer me, slut.”
His hand comes down on your core again and you can’t contain the moan that comes with it.
“Yes, I think of you,” you relent, gripping tighter to the sink.
His thumb presses against your clit and your breath catches in your lungs. The pad rubs circles around the nub and you could cry from the direct stimulation.
“Good.” Is all he says before you lose sight of him in the mirror when he sinks to his knees behind you.
Your head drops forward at the first puff of his hot breath against your core. His tongue follows, licking a hot stripe up your pussy. A soft moan leaves your lips as he does it again, the tip of his tongue swirling around your clit as he uses both hands to grope your asscheeks.
His stubble scrapes against your inner thighs, the combination of sensations making your head spin. You rock back against his face, and surprisingly he lets you. His tongue and lips lick and suck at your core, and nothing about the way he’s eating you out is quiet.
Your hips buck when his teeth close around your clit, not ready for the sudden second of pain. His tongue is right there following, licking away the immediate hurt. His thumb takes over, his tongue dipping inside you.
“Don’t stop, please,” you moan, grinding back on his face.
“Wasn’t planning on it,” he says, pulling away from your pussy just long enough to say as such before going right back.
The pressure of your climax rushes up and you barely have enough strength in your legs to keep yourself upright. The orgasm roars through you in one giant wave. Your mouth falls open as his mouth works you over through it.
In the mirror, you see him stand, and then you’re being flipped around so that you're leaning back against the sink again.
His lips connect with yours and you can taste yourself on his mouth as he kisses you. It’s not gentle, his teeth clash with yours, your tongues dancing and somewhere in the way he licks into your mouth you feel his hand slide between your bodies to your pussy.
You’ve barely recovered from the orgasm he just brought you to, and now his middle and ring finger are slipping inside you.
Carding your fingers through his hair, you kiss Dean hard, letting his mouth swallow your desperate moans. Stars spark behind your eyes as he curls his fingers up towards your belly. Quickly, he finds that soft spot that makes your legs feel like jelly, threatening to send you to the floor.
“De-Dean! Oh fuck,” you cry out.
His mouth has migrated to your neck, sucking hard on your pulse point. You clench hard around his fingers, a different kind of pressure building low in your belly. Another orgasm builds slowly, especially as the heel of his palm presses against your clit.
“That's right, bitch. Scream my name. Scream it loud so everybody out there knows who you belong to.”
He shoves his fingers further into your sloppy pussy, wet and obscene sounds reaching your ears. Your head lolls to the side, allowing him better access to kiss and nibble on your neck. You’ll have to wear make up to cover up the hickies that he’s undoubtedly placing along your skin like a sign to say you’re his. He punches his digits in and out of you, petting that fucking spot.
Your thighs are trembling so hard now— so is the entirety of your body. The pressure just keeps building and building. He’s everywhere, between your legs, other hand groping your body, his mouth on your neck. Nowhere is left unattended and it is so much.
“Feel you clenching so fucking tight on my fingers, baby. Gonna cum again for me?” Dean says against your neck, leaning up to nip at your ear.
All you can do is nod. Words don’t feel real to you right now and no amount of anything could change that.
Your nonverbal confirmation seems to satisfy him well enough. Then, he does something, something so good and he keeps doing it. Everything around you fades to just his ministrations and the feel of his body caging yours, and you feel the pressure snap.
Everything goes white and your body seizes up with the intensity of which your orgasm slams into you. But Dean’s fingers don’t stop. They continue to pump into you, curling into you. You don’t even feel in control of your body as you feel yourself gush all over his hand.
Dean curses under his breath and you just barely acknowledge it as you gasp for air, clinging to his shoulders with all your might.
Dean draws his fingers from you and a perverted sense of deja vu hits you as he licks you from his fingers. He keeps you upright with his other arm snaked around your waist, and for that you are grateful.
“Did— did I just…?” You pant, slowly realizing what’d happened.
“You just squirted all over my fucking hand,” Dean affirms, wiping his hand on his jeans. “Wish I would’a just stayed down there. Drank it right from the source.”
You groan at his obscene words, unable to stand the way his verbal filth immediately makes your overstimulated body respond in kind.
He taps your cheek none too gently. “Don’t go tapping out on me now. We’re not done yet.”
You’re putty in his hands as he spins you around, bracing your hands on the edge of the sink. He let’s go, and on shaky legs you stand there watching him shove his jeans and boxers back down his thighs.
“You’re so wet, not gonna have any issue getting in,” Dean mutters quietly.
You moan softly at the drag of his cock through your arousal. The spongy head of him bumps against your clit and you whimper, the overstimulation becoming borderline painful.
“What’s a’matter?” Dean asks. “Too much?”
“Uh huh,” you nod.
“Too fucking bad.”
You moan weakly as Dean presses forward, shoving the blunt tip of his cock inside you. Involuntarily, your hips sway forward, away from the stretch. With how wet you are, there’s not much pain, but his fingers can only prepare you for the girth of his cock so far.
Dean’s hands grab fast to your hips, pulling you back to him, the motion sinking you down onto him almost to the hilt. You gasp a moan, feeling unbelievably full to the point it knocks the air from your lungs.
“Where you goin’?” he grunts, working his hips forward and back. “I know you’re not running from my cock after crying for it.”
“So big,” you gasp, inner walls clenching around him as you try to adjust to the sudden stretch.
Dean leans forward, rutting his cock into you. “Stop your fucking whining and take it, pathetic slut. I can feel you dripping down my balls.”
Tears prick at the corners of your eyes as his words hit their mark. It’s all so much; you can practically feel every vein and contour of him inside you. As he drags himself out, the bulge of his head catches on that sensitive spot, immediately making your legs shake.
“Oh, baby, cry all you fucking want,” Dean lays a sloppy kiss to your bare shoulder. “All it’s gonna do is make me harder.”
As if in emphasis, he snaps his hips into yours. You are thrust forward, the unforgiving edge of the sink digging into your lower stomach. Blinking, the tears leak down your cheeks, rewetting the paths from the ones that had fallen earlier.
His arm snakes around to your front, pulling you back against his chest. A big hand pulls your shirt and bra to the side, enveloping a breast. He rolls the hardened nipple between his fingers, every movement made with expert precision.
You swear you can feel his cock in your stomach with every grinding thrust into you. His hips barely break contact with your ass like he can’t be bothered to pull out for even a second. The outcome is his cock stimulating that sensitive spot; the pressure is helped by the way the sink edge ensures he slides along it with each and every movement.
“So fucking tight, baby,” Dean moans in your ear, still fondling your breast. “Always a perfect fuckin’ cumslut for me.”
Your hand reaches behind you both, sinking your fingers into the hair at the nape of his neck. His balls slap against your skin as his thrusts grow longer, his hand sliding up from your tit to your neck. He doesn’t squeeze this time, but just the feel of his calloused palm and fingers circling your throat makes you clench around his cock.
“Fucking me…so good,” you moan out, holding a hand to his wrist.
“Say my name, bitch. Who’s fucking you so good?” He growls, nipping at your shoulder.
“You are, Dean,” you babble.
The hand not on your throat dips between your legs, finding your thoroughly abused clit. A whine crawls its way up your throat and you feel his hand tighten almost imperceptibly around your neck.
“Shut up. I don’t wanna hear it,” he snaps. “Just take it. Fucking take it.”
“But—”
“I don’t care. Not my fucking problem.”
And he doesn’t, his fingers speeding up their motions on your clit. Sharp pangs stab at you with each brush of his callouses over your swollen nub. It all melts into pleasure and all you can do is push your ass back against him, meeting his thrusts.
Dean moans his approval. “See, that’s a good whore. Feels fucking good, don’t it.”
“Yes,” you keen, slamming yourself back on his cock.
His thrusts don’t let up. Instead, they become more forceful, sending you into the sink hard enough you’re sure you are gonna have bruises on your hips tomorrow morning. His cock throbbing against your inner walls, and his panting moans in your ear have become ragged. His fingers on your clit are unrelenting, pushing you towards the brink of yet another orgasm.
He’s all but draped over your back at this point, snapping his hips into yours erratically. Just when you think you can’t take any more, Dean groans into your ear.
“Gonna fucking paint this pussy white, and you’re gonna take it all. Y’hear me?”
Your pussy pulses in response. “Yes, please cum in me.”
Dean moans and it’s one of the sexiest things you’ve ever heard. “That’s fucking right. Beg for my cum, bitch.”
His hand slides from your neck to your shoulder, bracing you and himself as he thrusts harder, balls slapping harshly against you. The grip is bruising, but you’re too far gone to care.
“Please, cum in me, Dean. Need’a feel you fill me,” you whimper.
“Oh fuck, baby.”
You feel hips stutter then, his cock throbs as his orgasm hits him. He’s not quiet, moaning your name loudly.
You can feel his cum filling you, thick ropes spurting into your pussy, and that alone sends you over the edge, yet another orgasm crashing into you. This time, your violently shaking legs give out.
Instantly, Dean's arm wraps around your waist, holding you there as he gives a few more rutting thrusts into your pussy, milking his cock. You both stay there for a second, heavy breathing filling the room as you gasp for air.
He breaks the silence first. “Can you stand?”
You take a second, assessing your still trembling body. Finally, you nod.
Taking you at your word, Dean relinquishes his hold on you, leaving you to brace yourself on the sink as he walks over to the paper towel dispenser. He snags a few, using them to clean his cock off before tucking himself away.
He doesn’t offer you any, instead he turns and unlocks the door.
Sparing a glance over his shoulder, he gives you that sharp grin. “So, same time next month?”
You tug your clothes back into place. “Fuck you.”
“Darlin’, you just did,” is all he says before he disappears out the door.
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Chapter Tags/Warnings: Angst, graphic descriptions of gore/violence, graphic descriptions of injuries, near-death experience/perilous situation(s), explicit description of self-harm scars, pain utilized to stop a panic attack (fingernails cutting into palms), first-aid on self including stitches, Crowley being Crowley, mental health struggles, language
Chapter Summary: As yet another diversion, Crowley forces Tori to hunt down Juliet's pup while the boys continue their search
Word Count: 8.9k
Author's Note: Title from Take Me Back to Eden by Sleep Token
Tag List: @copperboom82 @zepskies @immastealurkneecaps
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Tori slid on the slick cobblestone floor, her hip smarting and chest heaving in oxygen as she scrambled behind a wall.
A golden shield lay discarded at her side, an inhuman growl echoing on the stone. It was followed by the muted thud of steps prowling closer. Sweat clung to her skin and blood leaked through her cargo pants from slowly healing cuts on her legs. More trickled slowly down her arms.
She scrambled to grab the shield, and within her silent and desperate pleas to whoever was out there, all she could think was:
If I get out of here, I am going to burn them alive
12 Hours Earlier
“We still haven’t heard from Cas, right?” Sam asked Dean.
Dean looked up from his place at one of the tables in the Bunker’s library. “Nada. It would be nice for the guy to check in every once in a while.”
Sam huffed a laugh. “Yeah, it’s probably hard to do that if you aren’t on this plane of existence.”
He looked around, “Where’s Tori? Thought she’d be out here.”
“Shower, I think,” Dean answered, flipping to the next page of the newspaper he had been looking through for new cases when Sam came in. “She should be out here soon.”
“Find anything?” Sam took the chair across from his brother, setting his laptop in front of him.
“Nothing’s jumpin’ out at me. We may have better luck lookin’ stuff up online.”
Sam shrugged. “I mean, it’s only been two weeks since we got back from taking care of the kelpie. We don’t need to jump right back out there. Especially if it’s not our thing.”
“Don’t let Tori hear you say that.” Dean half joked.
When she wasn’t scouring the news for cases, the huntress had taken it upon herself to work on the Fury. He’d ordered parts for it to the P.O. box they had set up in town, but one of them was on backorder and wouldn’t be here for at least a few more weeks, which meant downtime.
Dean sighed contentedly into his coffee. It wasn’t often they got slow mornings like this. Growing up, there was no such thing, but with finding the Bunker, it was easier to slow things down and relax. To enjoy a slice of normalcy.
No check out times—not that they ever really adhered too strictly to those anyway—and no room fees or loud neighbors fucking or fighting on the other side of paper thin walls at all hours.
“Squirrel, Moose. Just the denim wrapped nightmares I was looking for.”
It was peaceful, except for the demons who tended to show up out of nowhere demanding things, that is.
“Fuck off, Crowley,” Dean groaned. “No, we don’t have any leads, and yes we’ve been trying.”
The demon slipped his hands into the pocket of his black slacks. “Squirrel, you wound me. I can’t just show up to have a chat?”
“No,” Sam and Dean said in unison.
“Radio silence for weeks and you just decide to show up and chat?” Dean said. “Nothing’s ever that simple with you.”
Crowley shrugged as if saying ‘fair enough’. “Well, as you said, I was checking to see if you’ve made any progress on our mutual problem, but it seems you both have started to lose your touch.”
Every word out of the demon’s mouth was like nails on a chalkboard to Dean’s ears. The very fact that they were in league with the fucker made his blood pressure skyrocket more than he would like to think about.
His knuckles ached to crack across Crowley’s face; the knowledge that he’d probably be killed in an instant if he did was the only thing keeping him from doing so.
“Well, it’d be a lot easier if you gave us something to work with,” Sam interjected.
“What, preserving human life isn’t enough motivation, Moose? When’d you’d get so heartless?”
“Not what I meant,” Sam grumbled.
“Besides,” Crowley continued, ignoring Sam. “I did give you something to work with. I sent you on that vampire hunt, didn’t I?”
Dean went still at that. A blink. Then another. Blood rushed in his ears and he could barely hear himself when he finally spoke.
“You…you knew? That she was going to be there?”
A serpentine smile painted itself on Crowley’s face, equal parts smug and self-assured. It’s all the answer Dean needed, but as per usual, the demon can’t keep his mouth shut.
“Of course I knew. Despite all your righteous indignation, a little tail is all that takes to get you going. From what I hear, she’s pretty easy to get into.”
Red flooded his vision, and Dean was on his feet before he could stop to think rationally about what he was doing.
His fingers dug into the sides of Crowley’s neck, feeling the steady beat of the demon’s pulse beneath his fingers, warm and taunting.
“Don’t you dare talk about her that way,” Dean snarled, sinking his fingers in deeper.
The sound of wood scraping against wood rang out in the library as Sam shot to his feet. “Dean! Don't!"
“Get the knife, Sam,” Dean called out to him, an enraged expression leveled at the demon in his grasp.
Crowley’s face had grown into a deeper red, but his arrogance remained. “Listen to your brother, Squirrel. Remember, I can snap her pretty little neck from across the bunker. I can clap my hands, and all innocent lives you saved will be snuffed out..."
A raspy breath, and Crowley lifted his hand shakily. “Just…like…”
With a frustrated yell Dean shoved him away, hands instantly curling into fists to replace the conduit of anger. The demon coughed, rubbing the front of his neck where a red handprint had already started to make itself known.
“Knew you couldn’t do it,” Crowley wheezed. “You Winchesters. So soft.”
“What the Hell?”
Dean felt his heart drop into his stomach as Tori’s voice came from the direction of the hall. Her brows had pulled together in confusion, glancing between the three of them.
No, no, no. Why couldn’t you have stayed away just a little longer?
“Were your ears burning, love?” Crowley asked with all the suaveness of a serpent. “We were just talking about you.”
Tori made a sound of disgust as she stalked forward, the dutch braid down the center of her head swinging with each step. “I don’t want to know.”
“Tori, go back to your room,” Dean said harshly, perhaps a bit more so than he had meant.
She cocked her head in his direction. “Since when do you give me orders?”
“Tori, please,” he tried again, putting everything into the words, trying to convey just how desperate he was for her to listen.
It must have worked at least a little bit, her stride shortening halfway to the tables where they were.
“On the contrary, Squirrel,” Crowley cut in, stepping towards her. “It was our sweet T-bird here I was looking for.”
“Oh no,” Tori huffed, coming to a halt. “Absolutely not, you creepy fuck. You keep me out of whatever shady-ass dealings you’ve got going on.”
She was putting up a good front, but even Dean could tell she was scared. The blink-and-you-miss-it waver in her voice, how her hand hovered around her hip where she would normally have her knife holstered.
Only, this morning it was noticeably absent; no sheath was buckled into the loops of her black cargo pants. A black spaghetti strapped tank clung to her upper half like she couldn’t decide if she wanted to be comfortable or practical.
“Unfortunately my dear, I am in need of services only you can provide.” Crowley gestured to Dean and then to Sam. “And these two are a bit busy looking for our mutual enemy.”
Dean felt stuck in place. With Crowley between them, he stood no chance of getting her away from the demon. One wrong move and she could be dead before he even made it one step. He looked sidelong at Sam to find his brother already looking at him.
Get her outta here, Sammy. I’ll take care of the rest.
It was a split second silent interaction, but Dean knew Sam got the message. His brother’s expression hardened, looking away to Tori, assessing just how fast he could get to her before all Hell broke loose.
Everyone moved at once.
Sam shot forward towards Tori, arm outstretched aiming to drag her away. Tori, face twisted in defiance, aimed herself at Crowley, moving fast. Dean forged forward, cocking his arm out with every intention to slam his fist into Crowley’s face.
The demon was faster, though, vanishing and reappearing besides Tori.
“No!” Dean shouted as Crowley gripped her bicep.
“I’ll bring her back, don’t you worry,” Crowley gave a small wave with his other hand.
Then they were both gone, leaving the sound of silence in their wake.
Tori felt like she was falling.
Her stomach lurched in the way it does when gravity takes hold. If she didn’t know better, she would have said she’d gone blind. Nothing but darkness surrounded her as she fell, the phantom wind whipping past her strangely hot like she was plummeting into a volcano.
A hand, presumably Crowley’s, still gripped her right bicep, though the man’s hand barely made it half way around the muscle. When she looked, she couldn’t even see her own body, let alone the disembodied grip on her.
This is not how I expected to die, she thought. Not the way I would have chosen, either.
She didn’t have the slightest idea of how long she felt like they’d been falling when solid ground reappeared under her feet. Dizziness kicked in as she opened her eyes.
Stone bit into her knees as she fell forward onto her hands, swallowing back the nausea that came with the spinning of her surroundings.
“What…the…fuck?” Tori panted, trying to regain control over her body again.
“Welcome to Hell,” Crowley said, ignoring her question.
She felt him walk past her, and once she felt the room stop spinning around her, she glanced up. They’d landed in what looked to be some kind of throne room. Or, rather, he’d deposited them here.
“This? This…is Hell?” She asked skeptically, sitting back on her heels.
Crowley slumped into a throne positioned on a slightly raised dais, the frosted panes of glass in the windows above his head revealing nothing of what was beyond the room.
“A small part of it,” he answered, though it left her with more questions than it clarified.
His eyes fell upon her, and a shiver of disgust slithered down her spine as she realized the position she was in. She stood up faster than she had probably her entire life, resisting the urge to dust her knees off.
“Where’s the rest of it?” Tori asked, looking around the room at the carved pillars and candle stands casting a flickery glow into the room, the fireplace on the far end of the room providing warmth.
Hell must not have electricity. I don’t really know why I was expecting there to be, really.
“You mean the torture racks, the firey pits, the screams of the damned?” He said, amused.
She was about to say something snarky back, but she hadn’t realized until he said something that there were no screams. It was quiet, save for the subtle creaks and groans just like a normal structure would have. The sticks and logs in the fireplace crackled and popped as they burned to ash.
“Yeah,” she said slowly, the word drawn out as she looked back at the demon lounging on the throne. “That.”
“Well, Dante had to get the idea of there being 9 circles from somewhere,” he answered, speaking like it was obvious. “But it’s more like 5-ish.”
“Right,” Tori nodded like it made sense. Nothing about hunting really did if she thought long enough about it, but she’d been able to avoid the existential crisis thus far. “So why did you bring me here? And don’t tell me you were practicing your method acting for a retelling of Hades and Persephone.”
Crowley stared at her for a second longer than Tori would have liked. Something was turning in that vicious head of his, and Tori knew she wouldn’t like whatever came out on the other side of it.
He propped an elbow on the arm rest, crossing ankle over knee. “You know, I’m starting to see why Squirrel likes you.”
Tori’s face crinkled. “What? Who the hell is Squirrel?”
Crowley waved a dismissive hand. “That’s inconsequential at the moment. You asked why you were here and I have better things to be doing.”
A snarl so deep it rattled her bones emanated from behind her, followed by the click of nails on stone. Every hair on her body stood on end as it prowled closer, and Tori had to keep her hand from jerking away as fur brushed her hand.
It snuffled at her pants, its snout pressing into the outside of her thigh with curiosity.
Slowly, and without moving her head, Tori looked down. She could have sworn her heart stopped beating when she made eye contact with the hound.
It was somewhere between a pit bull and a German shepherd; taller than any dog had a right to be, its back parallel with her hip. Luscious fur that looked just as soft as it felt covered its body, but its muzzle was shorter and wider.
Better bite force, she realized with a shiver.
It huffed, then sneezed, then continued forward, its tail wagging all the way. Tori’s hand drifted to her chest, fingers tracing the barely healed scar on her sternum from the last time she came that close to a dog-like beast.
“This is Juliet,” Crowley explained, petting the hounds head.
The growling turned softer, something more affectionate as the beast nuzzled into her master's palm.
“Uh huh,” Tori said. “Cute.”
“She is, isn’t she? She’s also a mother.”
Tori nodded, growing more impatient by the second. “Mhm. Still not seeing your point.”
His hand stilled on the hounds head, and Juliet, as if sensing her master's slight displeasure, whined quietly.
“Didn’t your mother ever teach you patience?” Crowley asked with a raised brow.
She knew she should stop, that she should take the glint in his eye as a warning, not a challenge. But being wise nor suppressing her pride had ever been easy. It was a fond memory, her mother trying to get her to ‘act right’.
Clearly, it never stuck.
But it was bigger, deeper, than pride. That bravado, the posturing, it was all she could do to shove down every bit of fear that was flooding her nerves like a toxin.
She was sure it seeped through her pores anyway, the sour scent no doubt being picked up by Juliet who was looking more pup than beast at the moment.
The even more terrifying thought that Crowley could see, or god forbid smell it on her too? Well, she didn’t entertain it any longer than it took for it to crop up in her brain. Instead, she pushed past it, fortifying the walls of swagger she tended to up around most.
“Oh, she did,” Tori shrugged flippantly, with hope it was convincing enough. “I just didn’t listen.”
A pause as Crowley considered her rebuttal. Tori tensed, waiting for agony or death to follow.
It never came, though. He resumed stroking Juliet’s silken fur.
“Well, we can’t all be saints, can we?” He mused. “In any way, Juliet’s pup is no saint either. It seems the little bastard has gotten himself lost on one of the other Levels. The demons at my behest are cowards on their good days, which leaves you, my dear.”
The dots connected. Her mouth fell open a bit and she glanced between the demon perched on his throne and the hound at his side. Juliet had started to pant a little, and in doing so, Tori could see fangs larger than any dog should have in its mouth.
“You..want me…to hunt down and capture a Hellhound puppy?” Tori asked slowly.
“You weren’t joking when you said you don’t listen.”
“Just how do you expect me to capture it? My specialty is killing those kinds of things, let alone the fact that I am human! How am I to fare any better than your cronies?”
Crowley scoffed quietly, like the answer to her questions were obvious and she was a moron for even posing them. He adjusted the cuffs on his suit jacket, Juliet letting out a huff of displeasure at the loss of his touch.
“You know your Greek mythology, yes?” He asked, referencing her mention of Hades and Persephone. “Then you know the myth of the Labors of Heracles, and how he captures the mighty Cerberus?”
Tori nodded. English Lit had been one of her favorite classes in high school alongside shop and autos. All A’s, even into college Gen Ed’s. She never could have guessed how useful it would become.
A second passed, then Crowley snapped his fingers. An oval, golden shield appeared on the floor in front of her, a snarling lion’s head depicted on the front.
“It’s no Nemean lion hide, but it will give you strength and invulnerability, to a point,” he explained.
“To a point?” Tori repeated, eyeing the shield. “The fuck does that mean?”
“I can’t have things too easy for you, can I?” Crowley shrugged. “You’ve got a reputation to uphold after all. And I cannot have you running around Hell unchecked.”
So I’m capturing a fucking Hellhound with nothing but my bare hands. By myself. In Hell. What the absolute fuck has my life come to?
Her life hadn’t felt like her own in a while, and this? It wasn’t helping the existential crisis.
“I’ll be around, so once you’ve got him, just give a shout.”
Tori crouched down, slipping her arm through the straps of the shield. She was expecting some rush or tingling. Something that would confirm what Crowley said was the truth.
But there was nothing.
Just as she stood straight and looked up at Crowley, her mouth open with questions, that stomach dropping sensation of falling started again.
The last thing she saw before she started to fall into darkness, was the smug look on the demon's face as he waggled his fingers at her in parting.
Wherever Crowley had whisked her away to, it didn’t look much different from the throne room she had just been in. She was dropped in what looked like a foyer, three hallways spanning out around her; two entryways on her left and right, and one in front of her.
Sconces were lit down each hallway and in the room which she currently stood, casting a buttery-soft glow onto the crude stonework. It was nearly identical to the masonry in the throne room.
Surely he hadn’t whisked her away simply to another part of, well, wherever it was Crowley lived.
The shield was at least still strapped to her arm. It was lighter than she expected it to be, though maybe, hopefully, Crowley wasn’t full of shit and it did have some supernatural ability. She twisted her arm, the golden metal catching the light on every detail.
A solid, slow, dripping emanated from somewhere, echoing hollowly against the walls in the otherwise deafening silence.
Drip…drip…drip…failure…failure…failure…
It was maddening, crawling under her skin. A familiar sense of hopelessness opened up a yawning pit in her stomach and Tori contemplated her surroundings and—by extension—her options.
She blew a breath out her mouth, swiveling to either side and peering down each hallway, hands on her hips. The paths curved out of sight not far past their entryways, save for the one that lay in front of her. That one at least continued on straight for longer before turning harshly.
In reality, it wasn’t much different from where she and the Winchesters sat with their problems. A goal with nowhere to go, no honing into what path they should take and sorely underprepared for what lay ahead. There was no such light at the end of the tunnel for her, not that she could see anyway, in either situation.
Faintly, she recognized her heart racing, her breath coming in shallow pants.
Hell. She was in Hell all by herself with a shield that would maybe be her saving grace.
The hallways around her started to fade, leaving nothing but the squeezing in her chest and the trembling in her body.
Move, I need to move. I need to move before—
She was walking down the left hall before she could even finish the thought, fingernails dug so deep into her palm it was a wonder there wasn’t blood trickling down onto her fingers.
The goosebumps on her arms were equal parts nerve and chill, the dampness oozing from the stones soaking into her body. It all came back in to focus slowly, like colors bleeding into a black and white film. Any forward momentum was better than inertia, no matter how blindly she stumbled forth into the unknown.
Presuming this is even the level the dog is lost on, I’ve got to run into it eventually, right? It can’t be that big.
Oh how wrong she was.
Her watch had stopped working the moment Crowley had stolen her away to Hell, but she checked it anyway. It’d felt like she’d been walking for an eternity down the same hallway to the point she’d started to seriously consider that maybe this whole ordeal was simply a fever dream when the wailing started.
At first it was soft and mournful, hauntingly drifting down the hallway, but the further she advanced, the screaming grew demonic, the voices drenched in agony and ire.
Turning yet another corner, the shrieks pierced her ears, and Tori could see their origin. Cells with wrought iron doors replaced solid brick walls she’d started to become accustomed to. Some were open, their cells empty. Others, though, had ghoulish hands wrapped around the bars and as she crept closer, faces came into view.
Features sunken into their skulls, their faces were twisted in eternal wrath. Darkness sat in the pits where their eyes should be, skin pale and wrinkled. Mouths with missing teeth snarled at her as Tori picked up her pace, braving the corridor. What teeth still sat in their jaws were black and rotted, dark liquid spilling from the empty spaces and down their chins.
This…this was the Hell she had been expecting. Tortured souls in cages, screams of the damned. All that was missing was the firey pits and the racks.
She’d always known she’d end up here, in Hell, even before everything that had happened with Alice. Weekly trips to Mass on Sundays and, more often than not, on another night during the week if things were particularly rough had her realizing early on no matter how pious her mother wanted her to be, she wouldn’t be seeing those pearly gates when she punched her ticket.
More than once as a child she’d woken up from dreams of flames licking at her skin to wet sheets. She’d outgrown the bedwetting, but the dreams had stayed, varied in their visions.
A panicked yelp slipped past her lip when a gnarled and bony hand shot between the bars. The soul’s spindly fingers, paper thin skin pulled taut across the knuckles, wrapped around her forearm. For what little muscle remained, the soul’s grip was surprisingly bruising.
Klaxon bells peeled loudly through her and Tori tried to pull her arm back from its grasp. The soul howled, the sound worse than a banshee’s, and pain blossomed from the inside of her wrist. Another harsh yank, putting a little more effort in the swing of her body and the soul lost purchase on her limb.
The action wasn’t without consequence, however.
Tori cried out as its yellowed nails left angry cuts in their wake. Distracted by the pain, she didn’t realize the momentum needed to pull herself free was maybe a little too overzealous until she was falling backwards, the uneven floor sending her careening backwards into the waiting clutches of the souls on the other side of the hallway.
Her back hit the unforgiving metal of a cage and almost immediately multiple sets of hands sunk into her body.
Adrenaline was pumping harder through her veins now, blotting out the sharp stabs of nails into her shoulders and biceps.
Wide-eyed, Tori lashed out violently. Her blows were uncoordinated and messy, but effective nonetheless.
Only once she was shaking and out of breath with no hands on her skin did she scramble back to the very center of the hallway, too far out of reach from either side.
The screeching was nearly unbearable now, and Tori wondered if some of the blood splashed onto her face was from her ears. Using her shoulder, she wiped the droplets from her cheek, eyes scanning for any other potential threats.
They stopped on one of the cell doors and disbelief rattled through her.
A huge dent had been smashed into the metal, the concavity just about the size of her body. Slowly, she looked down at the shield on her arm. Maybe it was just the light, but the brass seemed to dully glow like it was waking up from a long slumber.
Huh…how about that, Tori laughed to herself and she wasn’t deaf to how unhinged it was. It was a sound steeped in exhaustion that ran deeper than what lay in her body.
Crimson leaked from cuts on her arm, and it itched from where it spilled from punctures and scratches on her shoulders and back, dampening her tank top along with her sweat. It gathered along her skin, beads catching in the baby hairs along her forehead.
Hidden within the anger, Tori could pick out the distinctive notes of grief in the souls’ cries, and they reverberated a little too far into her chest like a full metal round through flesh and bone.
They had been human, and they weren’t far enough gone to be demons yet; suspended in limbo, and she wondered if they knew what awaited them at the end of that journey.
Sticking to the center of the hallway this time, far from the souls’ reach, she avoided any further incidents the rest of the way.
She didn’t stop moving, stop walking. Just feet to stone over and over not really thinking while navigating the twisting hallways. Not one part of her even knew how to look for the Hellhound, and she supposed the Winchesters were rubbing off on her more than she would like because she was going into this with less than half a plan.
Not that she really had a choice for that in the first place.
She counted her blessings, though, that at least in Hell she could see them. The beasts being invisible to the human eye on the Earthly plane was void here.
It made sense; this was their home plane, and every soul here was damned including their own. There was no biological or strategic reason to hide, and as far as she knew, they were an apex predator with no natural predators of their own.
Not that it made them any less terrifying. Juliet in all her glory had her nearly shitting her pants when the beast snuffled at her. It didn’t really help that she’d nearly been gored by a distant cousin of the Hellhound not that long ago and was still reeling from that experience.
To her surprise, the wounds that had been leaking droplets of blood like little rubies were nearly healed. It wasn’t quite the invulnerability she’d been promised, but she’d take anything.
After one too many dead ends, she’d wandered her way into an open room, larger torches mounted on the walls to fill the space with light. More hallways shot off from the room like legs on a spider, their lengths unknown.
A particularly strong gust of wind tore at her, the air warm and dry, and Tori looked up. Her lips parted in shock as the walls that should have reached up had crumbled away, leaving no ceiling above her head and exposed what she could only assume was the sky.
Muted red and green mottled clouds roiled angrily, joined by the occasional flash of dulled yellow light like lightning, though no sound of thunder followed. It was like the colors had been drained of their vibrance, sucked dry by the oppressive nature of the atmosphere.
It was kind of beautiful, Tori decided, in the kind of fucked up way one might find beauty in violence; You know you aren’t supposed to, but you do anyway. Keep it a dirty little secret and only indulge when you are well and truly alone.
Her fingers itched for her sketchbook and the set of oil pastels she rarely broke out of the storage locker because she never knew when she’d have the money to replace them once she used them up. She knew she’d never truly capture its likeness, but shit, she wanted to try.
It’d been a hot minute since she’d touched the book with anything, let alone pastels. Whatever she tried to create would no doubt look like hot shit, but in time it’d get better. It always did. She just had to knock off the rust and everything would be right as rain.
But she didn’t have her art supplies.
All she had was a shield on her arm and what little determination borne of generational stubbornness.
Usually the latter was enough, but when a deep growl—deeper than the Snarly Yow— resounded from the hallway to her left, Tori lost faith that even that could save her now.
The hound was huge. Tori wasn’t even sure how it managed to squeeze its way through the halls.
Puppy my ass, she scoffed to herself, turning to face the beast, its back nearly level with her waist. It was bigger than Juliet, but not quite as large as the Snarly Yow.
For that one, at least, she’d had a gun.
How the fuck am I supposed to subdue this bastard? What am I gonna do, sing it a lullaby and hope it rolls over for me to scratch its belly?!
Its eyes glowed red and they were honed in directly on her. There was a time Tori was convinced she could fight anything, could kill anything, but not anymore. Not after what she’d seen, and especially not now.
Holding up her hand, she tried to keep her voice from shaking. “I don’t suppose you’re gonna make this easy for me, huh?”
An even angrier snarl was her only response, and all Tori could do was nod. I suppose I deserve that.
Her eyes darted around, looking for anything that could be useful. And okay, maybe plotting some kind of escape route because shit was definitely going to go sideways here in the next few minutes if she couldn’t come up with something.
The shield worked, that much she did know. But the fucking thing didn’t keep her from being hurt, and while it healed her faster, something told her it wouldn’t even extend to the point of saving her life. And it wouldn’t take much for the fucking Fido standing across from her licking it’s chops to do so.
Tori bent her legs at the knees slightly, taking a deep breath. It was clear she wasn’t equipped to face this thing head on, so she needed to figure out some other way of getting her arms around the hounds neck.
An idea struck, and while every fiber of her being balked like a horse in a storm at it, nothing better was popping up.
“Hey, fucker!” Tori called to the hound, watching it cock its head at her. “Follow me!”
And without a second thought, Tori turned on her heel and ran.
Everything was a blur around her.
There’s nothing conscious about the way Tori sprinted down the hallways, the lights passing by what felt like too fast to be normal. Deciding to chalk it up to the adrenaline high, Tori let her body guide her.
The thundering of massive paws was way too close for comfort, but she could tell she was already pushing herself to her limit.
The first corner nearly took her out. There wasn’t enough time between her recognizing the obstacle and having to actually execute the actions necessary to pass said obstacle.
Too late she tried to slow down and instead nearly collided face first into the wall. There was no doubt in her mind that if she somehow managed to get out of this alive, that no part of her would be anything less than black and blue.
Building up the momentum again, nothing felt dislocated in her shoulder, but there wasn’t much she could do at this point if it was.
Tori ducked her head as everything around her shuddered. She couldn’t help but laugh to herself, assuming the Hellhound made the same exact miscalculation she did. It would slow the beast down a little, but she didn’t count on it giving her that much of a lead, not with its too-long legs.
Instinct drove her forward, the burn in her lungs barely on the radar, neither was the tightness towards the tops of her thighs with every step propelling her down the hallway at what seemed like breakneck speeds.
Running as a hobby really only came about when she started hunting. Sports in general were a staple in her school years, but that really only extended to soccer. Similar, but sprinting for her life really had its own kind of special kick. And sprinting while trying to remember in which direction she came from was its own kind of Olympic level event.
Every fixture on the wall looked the same, every winding turn a near carbon copy of the one before. Nothing about any part of this entire ordeal was anything she could put stock in, and the fact that she’d lasted this long was a surprise to her core. It was not a welcome feeling.
It was only when the wailing started up again did she allow a little bit of relief slip through. The high pitched screams never sounded so sweet, and Tori willed herself to go even faster.
The entire plan was batshit crazy, and there was little faith that she wouldn’t get ripped to shreds like she nearly had been an hour ago in the process.
Crowley had forbade her from hurting the beast, but he’d said nothing about anything else hurting it along the way. Yet another assumption she felt less than sure on: the souls could maim the Hellhound in the first place.
But if Tori was a betting woman—and she was—she would bet that they could do something, and that something would weaken it just enough for her to disable it and get Crowley to bring his creepy ass down here to retrieve them both.
Their arms were already stretching through the bars of their cells when Tori whipped around the corner that would lead her to the corridor of tortured souls. The screams were somehow worse now than they had been the first time she blew through here.
Riled up by all your racket, probably, she thought to herself as she listened for the Hellhound bounding after her. Well, Mamma always said I was too loud.
For its size, the hound was nimble. It’d kept up with her with relative ease, and it wasn’t more than a few seconds before the rumbling of its clamoring met her feet.
“That’s right. Right this way,” Tori murmured to herself, hopping back a few steps before whirling around and dashing down the hall.
The first hallway was a breeze. Their arms weren’t quite long enough to reach her, and the small break had provided a bit of air back into her seizing lungs. But the pause had also lost her valuable distance. The stench from the hounds' breath wafted after her and the heat from its maw nipped at her heels.
A pang of guilt struck her in the heart when she heard a yip from behind her followed by the faint sound of flesh tearing, the pup not as lucky as she’d been in avoiding the souls claws.
She didn’t slow. She doubted that the first hallway would do much damage, but it did prove her sketchy theory correct: It could be hurt.
The second hallway narrowed in width, and that was where the problems started.
Distracted by how close the beast had managed to get despite being injured, Tori failed to stick to the very center of the hallway. Maybe the particular soul had long, gangly arms. Either way, a hand shot out between the iron bars and landed solidly on her shoulder.
Not even adrenaline could mask the agony that sliced through her skin. Without stopping, Tori knew between her speed and the state of the nails on the soul’s hand, the gashes were deep. Maybe deeper than the ones she’d received earlier.
Blood spurted from her arm, spreading warmly down to her hand. She didn’t even have time to cry out nor correct the path she’d been shoved on. Balance thoroughly thrown off, she careened to the other side and into the waiting clutches of the souls there.
Unlike last time, she was able to keep moving albeit with little coordination. Red hot knives slashed across her thigh and the edges of Tori’s vision darkened with agony. A guttural howl ripped its way out of her lungs, anger and pain weighing down each of her steps.
Cazzo! Cavolo, che male che fa!
She wasn’t fully hobbled, but every step forward sent spikes of pain through her leg. It was nearly unbearable.
Gritting her teeth, and a few tears leaking down her cheeks, Tori forced herself onward. She had half a mind to simply toss the shield away; clearly it wasn’t doing much for her. But, what it was doing, aka, keeping her from bleeding out from the deep gashes, was enough.
One more hallway. One more and then we’ll see. It was a small comfort, but any goal would suffice. Otherwise Tori was sure she’d drop to the floor and let the hound devour her. Anything would be better than this.
The hallway thinned again and more cuts joined the ones on her arm and leg. More yelps and whines followed closely behind her. Tori blinked, the edges of her vision going fuzzy as blood continued to pour out of the slashes on her arm.
It wasn’t healing fast enough.
Preoccupied with trying to keep herself upright as she cleared the last hallway with souls and onto the next, she was caught completely off guard when her foot landed wrong on a loose stone in the floor.
Her entire body pitched forward as her ankle gave out. The impact rattled through her knees and her elbows, pain singing up her limbs like a tuning fork. She groaned, scrambling on her hands and knees to hide behind the curve of the hallway.
Blood and sweat covered her arms like a second skin and from the rip in her pants Tori could see more blood seeping into the dark fabric. How much, she didn’t know, the black masking the spread of the flow.
With the force of her fall, the shield had been yanked from her arm and lay beside her. There was barely enough strength in her shaky arms to grab it and secure it back onto her forearm. It weighed a ton, now, no longer feeling like it was made of cardboard.
Between yelps, the Hellhound snarled after her. Like hers, its gait had slowed down significantly; Barely a walk, now.
Heart thudding wildly, Tori dared to peek her head around the corner. The Hellhounds fur was matted down in places, dark with blood. With what little coherence was left in her blood-loss-addled brain, a soft and satisfied smile made its way onto her face.
It had worked. Her bat-shit crazy plan had worked. Maybe she’d gone a little insane in the process, but god knew there wasn’t much sanity to lose to begin with.
Rallying what was left of her strength, Tori pushed herself to her feet. Hissing through the pain, she stumbled forward, readjusting the shield on her arm.
The hound snapped at her, but the resounding growl was significantly weaker. She pulled in a deep breath, much to her probably broken ribs’ dismay. Whatever she was about to do next, it wasn’t going to be pretty.
Eyeing the razor sharp claws on the hounds' paws and the matching set of teeth covered in drool, Tori sent out a silent prayer to whatever beings were out there that could decide to take pity on her.
Realistically, she wasn’t sure if that could even work in Hell. It’d never really worked on Earth, so why would it work in possibly the most damned place in the universe? Out of habit, and maybe a bit of superstition, she did it anyway.
Please, don’t let me die like this. And don’t make me kill somethings’ child.
The Hellhound’s massive body shuddered, its sides rising and falling raggedly, but it made no move towards her.
Tori’s eyes narrowed, and she dared to inch forward.
It watched her intently, and as she took another step forward, it finally moved. Not towards her, though, but downwards. The pup lowered itself to a sit, and then with a heavy sigh, it plopped down onto its side with enough force to shake the foundation.
She could have wept. Exhaustion and relief that she didn’t have to try and wrestle the dog washed over her like a much needed shower. A real shower sounded nice right about now.
And a strong drink or 5.
“You’re just a big ‘ol baby when you’re not murderous, huh?” Tori crooned as she knelt by the Hellhounds head.
Already she could see its cuts starting to heal, the skin beneath the heavy layers of fur stitching itself back together. Blood matted into the dark fur, but when Tori reached out to stroke the spot between the hounds’ ears and it was as soft as Juliet’s had been.
Tori shook her head, trying to rid herself of the dizziness making the room spin. The hound let out a small whine, nudging her knee. Black spots dotted the edge of her vision, but she patted its head, savoring the warmth radiating from underneath her bloodsoaked palm. Cringing, Tori slid to the floor, sitting with her back against the wall, the cold stones making her shiver.
“I’m alright, fuzzball. I just need a second,” Tori said aloud. “Crowley, you better get your conniving ass down here before I bleed to death.”
The distant wailing of souls was all there was, their screams harmonizing with the irregular whooshing of her pulse. The pup whined again, nudging her leg harder this time. The wounds on her arms were starting to itch, a sign that they were healing, however slowly. Being Hell-born, the hound seemed to have a higher regeneration.
Fair enough, I am just a measly human after all.
“Crowley!” Tori yelled, this time. “Come fucking get us, you brutto figlio di puttana.”
“You sure do have a mouth on you,”
Tori blinked and she was back in the throne room, still sitting with the hound's head in her lap. She didn’t dignify him with a verbal reply. Instead, she lifted an unsteady arm up, flipping him off.
The demon simply smiled, amused at her action. “Sure you don’t want to stick around? Seems like Cerberus is attached to you.”
“Maybe we can schedule playdates,” she jibbed back with a less than amused expression. “Just take me the fuck home.”
She didn’t have to ask twice.
Crowley must have used whatever decency he had because when the falling feeling came over her again, she ended up right next to the table in the War Room. The demon in question was thankfully absent, but the room wasn’t empty.
Dean and Sam stood at the table, stacks upon stacks of books piled high on wood. The Demon Blade and an Angel Blade lay within the mess, and Tori could see the glint of Dean’s 1911 peeking out of the back of his jeans.
They looked like they were ready to go to war, but surely it wasn’t for her, right?
Their stoic expressions melded into ones of shock as Tori wavered, then collapsed back into one of the chairs at the table.
“Hello boys. I’m baaack,” Tori said, slightly delirious and channeling her inner Randy Quaid from Independence Day.
She glanced down, shocked to see the Nemean Lion shield still on her arm. Her shoulder itched like crazy now as the deep part of the wounds knitted back together. A wave of nausea hit her, the vertigo making her feel like she was standing on a sailboat in a storm.
“Holy shit,” one of them—Dean—exclaimed. “Sam, get the med kit.”
The shield slowly pulled away from her arm, and warm hands pressed to her arms. Tori damn near hissed in delight at the heat.
It was short lived comfort, though, as the hand migrated up to her shoulder. A whimper slipped out of her before Tori cut it off, digging her teeth into her lip as the hand put pressure on the wound.
Tori pried her eyes open to see Dean face to face with her. His hand encompassed her shoulder, and the warmth from his body was deliciously enticing.
She shook her head, trying to ignore that fact, which turned out to be a mistake as another wave of vertigo hit her like a truck. With a groan she leaned forward with the intent to brace her elbows on her knees.
“Woah, woah, woah. Tori, hey, stay with me,” Dean said, catching her before she could go too far.
She shoved at him, overcome by the swell of her pride. “‘m fine.”
Dean scoffed. “No, you’re not. You look like Hell, Tor.”
Tori batted his hands away, pleased when he finally backed off a little, shuffling back.
She needed to get to her room. Everything about him seeing her like this repulsed her. She didn’t need their help. It was one more thing to be in their debt for. One more reason for her to stay at the end of all of it.
“That’s cause I was in Hell, Dean.”
“I’m well fucking aware,” he waved his hand in front of her face. “How many fingers am I holding up?”
She looked at his hands—at the three fingers he held up—then at his face, then at his hand, then his face. “You cannot be fucking serious right now?”
“Yes I am fucking serious, Tori!” Dean half shouted at her. “Answer the fucking question.”
Too much. Too much care, too much attention on her. The concern in his face was overwhelming, and Tori couldn’t stand seeing her battered reflection in those green eyes of his.
He was right, she looked bad. Worse than she had after the Snarly Yow. The shield had mitigated most of the damage, keeping her from bleeding out, but that’s all she needed from it. The rest she’d do on her own.
“All I fucking see, is a mother hen who needs to get the fuck out of my way,” she snapped, shooting up from the chair and pushing past Dean.
“Hey!” Dean’s hand wrapped around her bicep, stopping her before she could walk past him. His grip was firm but mindful of the gashes on her shoulder.
He was close, or rather, she was close to him. Close enough she could smell his decadent aftershave and the tang of whiskey on his breath. Close enough to count the freckles on his cheeks and see every fleck of green in his irises.
Close enough to fear the authenticity of the worry told in the lines of his face. To fear what that meant. To hate it, with nearly every part of her being.
“Let go of me,” Tori said, her voice low. She wasn’t sure Dean knew just how close she was to snapping.
“I got the…” Sam trailed off, slowing to a halt at the entrance to the War Room, holding up the med kit in his hand.
It was enough of a distraction for Tori to wrench her arm from his grasp, breathing sharply through the pain the movement caused. She wouldn’t give him the satisfaction of acknowledging it, nor the way her gait was uneven from the sharp pain still lingering at her thigh.
“Thanks Sam,” Tori said, taking the med box from his hand on her way past him.
In her other hand, she snatched one of the bottles of Jameson from the cart where Dean stored all his liquor. No glass, no ice. She didn’t need that shit. Just the burn and the blankness of the alcohol.
“I’ll get you more eventually,” Tori called out over her shoulder, lifting the half full bottle.
In her underwear, Tori sat in front of the full-length mirror set up in her room, digging into the med kit. Thankfully, the damage was localized to her arm, shoulder, and her legs, though she was mostly sure a rib or two had broken or were fractured from her fall.
Her entire body felt like one gigantic bruise, a problem soon to be solved with the bottle of whiskey on the floor next to her.
Dousing a cotton ball in alcohol—and downing a few good swigs of whiskey—Tori took a deep breath and pressed the ball to her shoulder.
The stinging was somehow worse than the initial pain, but she kept it there, swiping away at the puffy skin. She was good and clean from the shower she'd taken as soon as she grabbed her clothes, but the little nagging voice in the back of her head told her to do it just in case.
Twisting in the mirror, a hint of regret for not accepting Dean’s help inched in as she tried to angle herself in a way she could properly see the wounds.
4 long cuts, their edges jagged, were carved into the upper part of her bicep, curving around to her back over her shoulder. She’d determined in the shower they weren’t deep enough to need stitching, but placing that large of a piece of gauze was going to be just as difficult.
Burning gulps of whiskey punctuated every scissor snip as Tori cut the medical tape down to size. It took another good couple of swallows, but in the end, the tape held the gauze in place long enough for her to wrap the elastic bandage she’d found coiled up at the bottom of the box, around her upper body, securing the whole MacGyver looking mess in place for now.
Maybe in the morning she would swallow her pride and ask one of the boys to rewrap it for her.
Probably not, though.
Tori grimaced, knowing the cuts on her legs were worse. Those ones needed stitching—the edges gaping and angry looking. She repeated the process, prepping the area with another cotton bud soaked in alcohol.
Her mouth twisted in quiet contemplation. The newest gashes were deep and red, the edges warm to the touch as she ran her thumb over them. Running her hand up her thigh, the motion was more soothing than observation.
Her fingers grazed neatly raised lines along the way, some white and thin or dark and thick and fully healed. Some were still scabbing over. No supernatural monster had put them there, just the sharp edge of a blade in her hand and too many sins to atone for.
Adorning both thighs, the scars were high up enough she could, in theory, wear shorts. Most of the time, though, she didn’t risk it. All it would take was a moment of forgetfulness, of not paying attention to the hem of the pants and she’d be bombarded with questions and worry.
She had lots of scars on her body, but those were the ones she was least proud of.
The needle and thread were familiar in her hand, as were the motions of pushing the needle through her skin, measuring the tension and knotting the sutures off, clipping the material neatly with the trauma shears from the box.
It took less time to sew her leg back together then it had to place the stupid bandage on her shoulder. And she’d been sober for that.
More too-white gauze and elastic wrap went around her thigh, and Tori shut the med box. She’d replenish the stuff she’d used eventually. Probably on her next run into town for cigarettes.
If her knees weren’t stiff, all of her motions shallow and halting as she walked across her room to deposit the first aid box onto her desk for the morning, she would have taken her happy ass outside and smoked the rest in the carton. But the bed was calling her name, and who was she to deny its siren song.
Leaning back against the pillows, the rest of the whiskey went down smooth. It tingled along her skin, warming her belly while dulling every sharp edge of pain and misery.
She’d probably regret it in the morning, but that was a problem for the version of her that at that point would be a little more put together.
But for tonight, none of that mattered. Just sleep and the hope that tomorrow would be a better day.
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Summary: Let’s take it back to Day 1. Here's how you got the job at HunterCorp as Dean Winchester’s Executive Assistant, how you kept it, and the day your professionalism with him finally broke.
AN: Ready for more Boss Man Dean? insert Chandler Bing gif (Friends fans will know lol) This of course is in the same world as Pratt Fall, but it spans the year building up to that moment.
Posted on Patreon: June 19, 2026 | Word Count: 9.6K
Tags & Warnings: 18+ | Single mother!reader, ft. a deadbeat dad, mutual pining, Dean’s dirty thoughts, office shenanigans and smut (v. fingering, penetrative sex – yes, on the desk)
Series Masterlist ➤ Dean Winchester Masterlist
“No,” Sam says, snatching the resume out of his brother’s hand.
“Aw, come on,” Dean says. He swivels in his leather chair but doesn’t bother getting out of it.
Sam levees him with an exasperated look. “This girl spelled ‘assistant’ with three Cs and a Y.”
“She’s funny,” Dean shrugs, once again taking a look at the applicant’s profile on his computer. In his opinion, her pouty lips and dewy young face speak for themselves. “And smokin’ fucking hot.”
“She’s illiterate,” Sam deadpans. He sorts through the resumes he printed off and hands his brother three strong candidates that he picked himself.
Dean glances down at each packet. He snorts and tosses the first one into the metal garbage bin beside his desk. Sam frowns.
“What was wrong with that one?”
“He’s a dude. Don’t you think we’ve got enough of a sausage fest going on around here?” Dean says, gesturing wide at the multi-floor building that makes up HunterCorp. His father’s enterprise, distilled down to two sons who, on their best day, have very different opinions on what makes for a good executive assistant.
Sam utters a longsuffering sigh.
“Man or woman, you need a real assistant, Dean. Someone competent enough to deal with your demanding schedule and…personality.”
“What’s wrong with my personality?”
“And I need you to have an assistant so I can focus on my real job. You know, running the entire Legal department.”
Dean rolls his eyes. “I know how to do my job, okay? I think I’ve picked up the slack pretty damn well since Dad died.”
Sam pauses, acknowledging that with a nod, and a heavier note.
“Yeah. You have.”
“So while I’m throwing money away hiring for a wholly unnecessary assistant, who I’m gonna have to tolerate looking at every day, I might as well be looking at somebody hot,” Dean says.
Another exhale leaves Sam’s body, along with the brief buoyant feeling of admiration for his brother.
And now we’re back where the neanderthals live.
Sam gets a text from Reception that has his pocket buzzing. After he checks the message, he nods to himself. Here we go.
“All right. The first one is on her way up now, so do me a favor and get yourself together,” he says. “For example, it’s a little early for the booze, don’t you think? It’s 10:00 a.m.”
Dean pauses. The crystal decanter in his hand is halfway to pouring his first fifth of whiskey.
Second breakfast, if you will.
He gives his brother a flat look, one that’s accusing him of being an eternal wet blanket. But he begrudgingly concedes the point and puts both the decanter and the tumbler in a cabinet under his desk.
Classy. Sam rolls his eyes.
A knock at the door stops him from commenting out loud.
Clearing his throat, he walks over to let you in.
“Hi, Sam…and Mr. Winchester,” you say, shaking hands with the slightly taller brother. Then you turn to Dean Winchester, CEO of HunterCorp. He stands and leaves his desk to greet you.
In the time it takes him to cross the room, he takes you in within the breadth of a few seconds. More than the professional pantsuit and your pretty face, he notices your bright smile, the slight bout of nerves in the way you shake his hand. He finds himself smiling back.
“Uh, hi,” he says eloquently. “Call me Dean. Can we get ya some water, coffee, iced tea…”
He doesn’t even think they have iced tea, but he’s willing to make Sam go and find some.
“No, thank you. I’m fine,” you reply.
“Okay, then. Just, uh, take a seat.” He gestures to the open seat in front of his desk before he returns to his own plush leather chair. It squeaks as he swivels back in place. He shares a nod with Sam, who heads out of the office. The door closes behind him.
Dean glances down at the list of questions Sam prepared for him to ask each candidate, a sheet of paper that lies over your resume. He brushes the questions aside and focuses on the information printed under your name.
His brows raise in interest. “You graduated from Stanford University like my brainiac brother?”
The sound of your light laugh draws his gaze from the page, up to your face.
“Yeah, we were actually friends. It’s just been…a while,” you say, clearing your throat a little.
Dean inclines his head. His understanding grows along with his suspicion as he reads.
“Look at that, a Marketing major. Looks like you had a couple of promising internships too.”
“In college, yes.”
“And you were a Communications Specialist at Ashland for…eight months in 2021?”
“Yes, that’s right.” Again, you nod, smoothing a non-existent wrinkle in your pants. Your gaze falls away from his.
This time, Dean thinks you know full well what he’s getting at when he sets down your resume.
“That was five years ago,” he says. “You haven’t worked in five years since getting out of college?”
“It’s a bit complicated,” you admit, though you sit a little straighter. “I gave birth to my daughter, Emma, in November of 2021. My ex…was not supportive. My mother was also having some heath issues, so I moved back home to help my father take care of her. They took care of me too.”
Your fingers flex and interlace together in your lap. Dean notices the subtle fidget, but otherwise you’re calm and professional as you admit to something so personal. He can respect that you didn’t try to bullshit him.
“Hmm. Complicated,” he nods, then hesitates. “How’s your mom doing now?”
Your lips tug, but not at a smile. “She passed away a few weeks ago.”
Dean dims further as he inhales deeply. “I’m sorry.”
You give a tight nod, your throat swallowing.
“Look, since you’ve been honest with me, I’m gonna be real with you,” he says. “I run a company of 300 employees, 20 departments, 10 floors. I work 60-hour weeks minimum. I meet with department heads, shareholders, business partners and prospective clients on the daily—the kind of schedule that would make your head spin. I know you’ve done what you had to do, but I’m not sure you’re ready for a job like this. And that’s besides the fact that I’m not convinced I even need an assistant who’s probably just going to slow me down by sticking her nose into my process and asking questions I don’t have the damn time to answer.”
You tighten up at that, understandably taken aback. Your lips purse, but instead of tossing him a fuck you then and walking out, like he half expects, you sit with his words. You think it through, and you give him exactly what he doesn’t expect.
“I may not have been clocking into an office for the past few years, but I haven’t been a stranger to hard work, Mr. Winchester. I’ve done nothing but fulfill the role of an assistant,” you say, and your gaze never leaves his when you say it. “Appointments, calls, messages, emails, paperwork, finances, data reports, coffee, power lunches, drycleaning—whatever you need, however quickly you need it, I can get it and I can make it happen. If there’s someone you can rely on, it’s a single mother who knows how to get shit done.”
Dean understands now. He understands the pain hidden in your eyes, and the too-tight set of your shoulders that hold the weight of responsibility. Urgency. A hint of desperation.
You need this job, maybe a little too much.
He should let you down gently. You’re not the kind of girl he’s looking for.
But whenever his mind and his gut are in conflict, he usually heeds his gut. That’s worked out well for him so far.
So he shrugs, and he stands up, holding out his hand to you across the desk.
“Like I said, call me Dean.”
Two Weeks
He groans into the ceramic mug at the first sip. Jesus Christ, you make a good fucking cup of coffee. That’s not even in the top five of the talents you possess, as it pertains to his business and your ability to learn quickly, talk minimally, and begin to anticipate his needs.
You dress nice, you’re always on time, and hell, you smell good too. Like body lotion and just the right amount of perfume. Obviously he can’t comment on any of these things, unless he wants a visit from Meg in HR. But it doesn’t stop him from noticing you, his heart thumping whenever you come in close to show him a document or ask him a question about a report.
Instead of rolling his eyes or snapping that you should have someone who’s not running this entire company explain it to you—like he did the last assistant who didn’t even survive three days—Dean finds an ounce of patience to spare for you.
He sits there and explains the difference between an M1911 handgun and a shotgun, and why the background checks take two months for one model and a few weeks for the other one is just a difference of state law, not HunterCorp’s manufacturing techniques.
Sam is rather fucking gloaty about it too—mainly at the fact that his top candidate made it through Dean’s initial hiring plans.
“Admit it, she’s good,” Sam says later in the day, while the two of them eat lunch together in his office. You just had it delivered ten minutes ago, still piping hot.
“She’s all right, for being your little college friend.” Dean slurps his lo mien and casts his brother some side-eye. “Is that all she was, or did you two occasionally sneak off for a little rec room break on the side?”
Sam gives him a flat look. “No, I was with Jess by then.”
“Just asking.” Dean shrugs. Secretly, he’s pleased. “You know anything about the ex-boyfriend, Father of the Year?”
Sam snorts in derision. “Some asshole in Sales while she was at Ashland. From what I heard, they were dating for six months or so, and she got pregnant. He, uh, tried to get her to end it.”
Dean frowns, and actually pauses eating to raise his head.
“She told you that?” he asks.
Sam holds back on answering for a suspicious moment, his eyes shifting down at his food.
“Made a couple calls to some contacts I have over there,” he says.
Spies, in other words. Dean nods in understanding. His brother’s always been the smart one. That’s what everyone used to say, including their father.
Two Months
You’re not sure if you should do it.
You have a sensitive report in your hand, fresh off the printer. You really think Dean should see it before he gets any deeper into his negotiations with Roman Enterprises, but he’s meeting with them right now in the big conference room, with Dick Roman himself, as well as the rest of his sales and legal representatives.
This isn’t the first meeting Sam and Dean have undergone with the company; Roman Enterprises been courting HunterCorp into a partnership on a new product, but this could be the day that makes the big swinging dicks in the room shake hands (even if that little visual almost makes you snort).
Dean’s never expressly warned you about entering a meeting uninvited, but it’s still nerve wracking as you stand outside the door. You can hear familiar voices, including the nasally tone of Alastair, the one who gives you the creeps whenever he slithers through the office and gives you a “charming” once-over.
But you also hear Dean. His voice is deep and smooth and confident. It gives you the little confidence boost you need to twist the knob and push the door open.
Just as you predicted, with a sinking feeling, all eyes turn to you when you enter the conference room. Sam and Dean and their lead sales manager, Cas, look over at you in varying degrees of surprise (Cas with disapproval). Dick Roman remains impassive, if slightly amused when you squeak out an, “I’m sorry.”
It’s Alastair’s gaze you feel on your profile when you quickly make your way around the large conference room table and over to Dean. You lean over to hand him the paperwork.
His lips purse when he notices the line of Alistair’s gaze—on your ass.
Dean then frowns at you, and your express delivery.
“What’s this? You think it could’ve waited?” he asks in a low whisper.
“Look,” you whisper back, pointing to the section you starred. It’s a report that Roman Enterprises failed to disclose about their product, a double-chambered gun that can store silver rounds and witch-killing bullets as well as salt rounds: the perfect gun for a hunter.
The problem is the safety and performance report. The one Dean has up on his laptop doesn’t match the one now physically in his hands—the one that says two out of three units of this gun fail to chamber correctly on reloading, resulting in a backfire on the user.
Dean’s brows furrow. “Where did you get this?”
“Is something wrong?” Dick asks. He straightens in his seat, his demeanor a fraction sharper.
Dean glances up at him, then at Sam and Cas, who wear similar looks of confusion. Sam raises his brows expectantly.
“Sorry, one moment,” Dean says to the room, before redirecting his attention to you.
You’re all too aware of being the rabbit caught in the proverbial trap in this room of nearly all men, but you rest a hand on the table and lean in near his ear.
“Their weapons analyst sent this to me,” you explain. “He almost got his hand blown off. Said they didn’t want to go back to the drawing board and waste time when they had us as a prospective distributor.”
Dean blinks in surprise. A fucking whistleblower just outed his own company, but he supposes he can’t blame the guy. If he had half a hand, he’d sue everybody.
“Okay, thank you,” Dean tells you.
It sounds like a dismissal, and truth be told, you’re ready to get the hell of this room. You make a quick escape and shut the door carefully behind you.
Dean watches you leave, but then he collects the report you gave him and passes it along to Sam, with a pointed look that says read it now. Sam doesn’t need the prompting. He shares it with Cas, and they both eventually come to the same frowning conclusions as Dean.
“You gonna fill us in on what that little skirt just gave you that has all of you so fucking sour?” Alastair remarks.
It makes Dean bristle. “That’s my assistant. Have some fucking respect.”
Dick shoots his associate a warning look, as well as a placating hand before he folds both of his on the table.
“Apologies. I’d like to move forward here. How about we discuss oversees shipping—”
“No, I don’t think that’s necessary,” Dean says. He shares a look with Sam. He’s disappointed, but he nods in agreement all the same.
Dick’s head tilts. His fake-ass smile twitches at the corners. “Excuse me?”
Dean closes his laptop and slides your report across the table.
“We deal with all kinds, but there’s nothing I hate more than a liar,” he says. “Cas will see you guys out to your line of Teslas out front.”
You’re sitting at your desk, stress-eating with a snack bag of popcorn while you answer emails, even though your mind is racing as you imagine what might be going on in that conference room.
You perk up in your seat when the door swings open, and the entire team of Roman Enterprises files out with steam practically coming out of Dick’s ears. You’re more than happy to see the back of Alastair. Cas follows them closely, while Sam and Dean are the last ones lingering outside the door.
They speak for a moment there in the hall, though you’re too far to hear what they’re saying. Dean eventually rubs a hand over his stubble-covered cheeks and jawline as he heads toward his office, and toward you. He gives you a wry look when he steps through the glass doors of the reception area, squeezing your shoulder as he passes by.
“Good job, sweetheart.”
That’s all he says as he disappears back into his office. You can’t help the warm blush blooming across your cheeks, but you do get up to follow him.
“Um, Dean…”
He turns to you as the door of his office closes behind you. You fold your hands in front of you, an almost contrite expression across your face.
“I’m sorry. That just cost you a lot of money, didn’t it?” you ask.
Dean shakes his head. “Don’t be sorry. What you saved me is one bitch of a headache, and probably millions in legal fees. So thank you.”
You smile, making him smile in return.
“Okay, um, would you mind if I leave just a few minutes early today?” you ask. “My father usually picks up my daughter after school, but he has a doctor’s appointment. I can come back after she’s settled.”
Dean frowns. “What time does she usually get out of school?”
“Three. She’s in kindergarten.”
He considers it for a moment. “You know, we have a daycare. Cas brings his kids here too.”
You do know that, all too well. Cas is married to Meg in HR, and they have two, very odd twin daughters. You think they’re stealing ink from the printer and using it for “ink blot tests.” You didn’t know that eight-year-olds knew what those were.
“We do. But I, uh…I can’t afford it,” you admit, with some embarrassment. You’re still helping your dad pay off your mom’s medical bills, and even her funeral. It’s not easy to afford to live and provide for a child, but it seems like it’s almost as expensive to die.
Dean taps his fingers on his desk. He shrugs and rounds his desk to sit down in his comfortable chair.
“How much does it cost?” he asks.
“$500 a month. I’m already trying to get her into a private school…”
Dean does the math in his head, easy. Then he sends a quick text to Meg in HR.
“Well, now you can afford it. I’m gonna raise your annual salary by $10K,” he says. “That should cover the tax deductions and extra gas mileage.”
Your mouth falls open in shock. It closes, then opens again before you’re able to make words pass through them.
“Um, w…what?” you ask.
Dean leans back in his chair and smiles. It isn’t often he gets you flustered.
“Consider it an early Christmas bonus,” he says.
You laugh, slightly breathless still in wonder. “It’s the middle of July.”
Again, Dean shrugs. “Just say thank you.”
You bite your lip in amusement, but you nod. Your gaze on him is sincere, and a little shiny with emotion. Your daughter’s definitely getting into private school now.
“Thank you,” you say.
Dean watches you walk out of his office, along with that brief look over your shoulder before you close the door. His smile fades.
“Fuck,” he mutters.
He sits up in his chair and goes for that stash of whiskey under his desk. If he wasn’t already an alcoholic, you sure were on your way to making him one.
Three Months
Dean blows out a sigh, then rubs his eyes at the strain of just how long he’s stared at a screen and tried to make these goddamn numbers work.
The building is probably empty by now. Even his brother left two hours ago to go home and have dinner with Jess. Dean’s reluctant to go home to his empty apartment. So here he sits, the workaholic that he is, as the sun fades behind other buildings and casts his apartment into darker shades. He switches on the desk lamp.
A knock on the door kicks his thoughts out of alignment, like an old engine sparking out, into crispy defeat.
“Yeah,” he calls out without looking up. He does though, when you come into view.
“Hey, I’m heading out,” you say.
He can see you’re ready to go, packed up and on your way downstairs to pick Emma up from daycare. He still hasn’t met the kid. He’s surprised himself with the idea that he wants to, though he’s never asked. Never wanted to intrude on your life outside of work. Never wanted to get too close to it.
You’re a single mother living with your father, and that’s complicated enough. You don’t need a man like Dean upsetting the delicate balance. And he doesn’t think he can give a woman like you what you need…besides the fact that you’re his employee.
“All right. Make sure Benny keeps an eye on you heading to your car. It’s getting late,” he says.
“Not that late,” you say with a smile. Though you’re a bit concerned when you step further into his office. “When do you typically head home?”
“Uh, around eight or nine, usually.”
“That’s pretty late. You don’t have anyone waiting on you?”
“Not unless you count the beers in the fridge,” he remarks, sending off another email to a sales rep to get his ass in gear if they’re going to make quota for Quarter 3.
By the time Dean looks up, he sees your small frown. Concern.
It rubs him the wrong way (or maybe the right one), so he clears his throat and waves you over to his computer, opening up a tab he was looking at earlier.
“Hey, do me a favor. Tell me what you think of these. I have to go to some tech expo this weekend with Sam,” he says.
You look over his shoulder at the rows of ties on the screen.
“Well, first of all, don’t get them off Amazon. Go to a men’s store,” you say with a short laugh. “Second, what color is the suit?”
“Uh, just black,” he says in amusement.
You hum in contemplation. The man does look good in his usual slacks and nice buttoned-down shirts, but picturing him in a full suit and tie is an enticing image.
“This burgundy one looks nice. Or the blue one with the pattern,” you suggest.
“You don’t think it’s too loud?”
“No, I think it would look nice with a black dress shirt. Or hey, a black vest with a white dress shirt underneath.”
“A vest?” Dean intones.
“Yeah, with your shoulders, you’ll look really sharp when you pair it with the suit jacket,” you say.
“My shoulders, huh? What about ‘em?” he asks in amusement, verging on the edge of flirtatious, before he realizes what he’s doing.
You both pause then.
You eventually find something approaching a respectable response, if not really a professional one.
“Just…you have a strong frame for a suit. I’m sure whatever you pick will look good,” you say. Though you turn away to grab your purse from where you left it leaning against his desk on the floor. Your face is blushing hot all the while. “Um, have a good night. I’ll see you tomorrow.”
“Yeah, you too,” he nods, clearing his throat. He tries not to watch you leave, but he can’t help himself. The natural sway of your hips is too hard to ignore, as is the way you walk away from him on those heels.
Once the door is firmly shut, he tips his head back against his chair and groans. He hates himself for hoping, even fantasizing, that one day you’ll come back and straddle him on this goddamn chair and fuck him with those heels still on.
He bangs the back of his head repeatedly against the chair, as if that could rid him of his pig-like thoughts.
Fuck. Me.
Four Months
Dean steps into his office after four hours of solid back-to-back meetings. If he had to sit through even five more minutes of Crowley’s condescending ass explain 15 subsections of a contract, as if Dean didn’t know how to fucking read, then he was going to throw his laptop into the nearest window.
He expects to find the quiet refuge of his office, and very quickly his stash of Angel’s Envy. What he gets is a kid sitting in his chair, eating his Doritos. She doesn’t look older than five or six, swinging her little legs as she swivels in his nice leather chair.
The sight is so dumbfounding that Dean stops not two steps through the doorway, his hand still lingering on the doorknob. He frowns.
“Hey,” he says. Not in a nice way. In a who the hell are you way.
“Hi!” The kid smiles and waves at him with fingers coated in Cool Ranch Dorito dust.
Dean’s head tilts. “Uh, hi.”
“You said that,” she says.
His lips twitch upward. He points at her, and the chair she’s sitting in.
“That’s my seat,” he says, with some censure in his voice. “You wanna get down?”
She blinks and pauses, realizing she might be in trouble.
“Sorry.” She slides down carefully without letting go of her snack. She wears a private school uniform: a plaid skirt, navy polo, and a matching headband. Her pink Peppa Pig sneakers give away her personality though. It matches her backpack, which boasts a Minnie Mouse keychain and a princess sticker of Belle in her yellow ballgown.
“What’s your name?” he asks.
“Emma,” she replies.
Dean’s brows raise high in recognition, then they furrow.
“Interesting. Where’s your mom?”
“She had to talk to Miss Nancy, so she told me to stay here.”
Miss Nancy. Gotta be the daycare lady, Dean thinks.
“Here? As in, my office?” he asks in suspicion. “Or did your mom tell you to hang out at her desk?”
Emma guiltily glances down at her feet instead of at him, like Sammy did when he was four, and didn’t want to admit he broke their dad’s watch.
Here, it looks like Emma got bored and wanted to go into the big mysterious room. She continues eating her Doritos.
Dean can’t help but smile. “Did you find those in my desk drawer?”
She blinks up at him with the face. Like when Sam got caught looking through their dad’s old collection of baseball cards with peanut butter and jelly stains on his hands. That puppy dog look had Dean taking the fall—and the week-long grounding.
Emma tentatively offers him her snack. “Want one?”
The look on her face tells him that she’d rather not share, but it’s a clever little manipulation with those big doe eyes. Girls learn quick, don’t they?
Dean shakes his head and pulls out a nearby guest chair after setting down his laptop on the desk.
“It’s okay. You can sit here if you want,” he says.
The chair is a little high, so she reaches for the edge of his desk to help her. Dean offers her his hand instead. She’s happy to settle her little Dorito grime-covered hand in his and have him help her into the chair.
“Thank you,” she says, with that cute little voice. He almost laughs.
“You’re welcome,” he says. You’re definitely going to owe him for this one.
Dean sits at his desk and contemplates just what the hell he’s going to do with this kid for the next few minutes. At least, he hopes it’s just a few minutes. Does he need reinforcements? Should he call Sam up here? Cas?
“Are you and Mommy friends?” Emma asks.
Dean considers her question with a quirk of his head.
“Yeah, I guess you could say that. I work with your mom.”
“She said you’re her boss.”
“You know who I am?”
“Yeah. Your face is on her phone when you call,” Emma says. When she finishes the chips, he can tell she’s looking for a garbage can. He takes the empty bag from her and tosses it in the small bin under his desk. He wishes he could pour himself a much needed adult drink, but he thinks you’d have something to say about that later.
He settles on the bottles of water you keep putting in his other drawer. He grabs one for the kid, and even opens the cap for her, like he used to do for Sam when they were little.
“Uh, how was school?” Dean asks. Because what else do you ask a kindergartner?
She shrugs. “Okay.”
Fair enough, he thinks. He never liked school much, but he has to keep this conversation going somehow.
“Just okay?” he asks.
“Yeah. I don’t like math, but Music was fun. We’re learning how to play the recorder. Oh! And I drew Peppa after school. Wanna see?” she says, pointing at her backpack.
Dean raises a brow, but he grabs her backpack off the floor and hands it to her. She unzips it and rifles through her notebooks and her modest collection of crayons. She then pulls out her prized drawing to show him. It looks more like a ball of pink squiggles to him. But he looks harder, and he can see the eyes and the mouth and the nose are close enough to the character on her sneakers.
“Hey, that’s pretty good,” he indulges her, earning her shy smile.
“Thank you,” she says. But her face soon falls. “I wanted to draw her yellow crown, but a boy took my crayon and broke it.”
“Aw, that sucks,” Dean says. Though a smile threatens his lips at the little angry pout on her face. “What did you do when he wouldn’t give it back?”
“I just pushed his arm and he fell and cried,” she says.
Dean blinks in surprise. “Oh.”
Yikes. No wonder you had to go back and talk to Miss Nancy.
“But I didn’t mean to! He was mean to me first,” Emma argues.
Dean shakes his head in amusement, once again tempted to laugh.
“Well, you know, you should never put your hands on somebody. You wouldn’t want him to hit you, right?” he reasons.
The girl considers it, still with that little pout, but she nods begrudgingly.
“See? But if that kid messes with you again, you come tell me, okay? I’ll set him straight, man to man,” Dean says.
She starts to smile again. “Promise?”
“I promise. Let’s shake on it,” he says, giving her his hand. She puts her much smaller one in his, and they shake on it like adults.
“Emma?” your voice calls from outside the office in worry. The door is still open, so you catch sight of your daughter just as Dean tells you to come over. Your eyes grow wide with embarrassment as you realize where Emma ended up. You hasten inside his office.
“What are you doing in here?” you ask her sternly, taking her hand and leading her off the chair. “You were supposed to be doing your homework at my desk. Dean, I’m so sorry. I didn’t think it would take so long.”
“It’s all right,” he says.
You still look a bit mortified and apologetic.
“Seriously, it’s okay. She’s a good kid,” Dean says. You smile, if a bit wryly as you caress her head.
“Well, she wasn’t on her best behavior today, so we’re going to sort that out tonight. But thank you for watching her.”
Dean sends you off with a raised hand, though it turns into a small wave when Emma looks back at him with a sneaking smile.
He chuckles and shakes his head. Kids. Jesus.
She looks just like you.
Five Months
The insistent ring and vibration of your cell phone disturbs your deeply rooted slumber. You slap at the device charging on your nightstand and nearly yank out the cord in attempt to bring the screen to your eyeballs.
Once your bleary vision adjusts to the brightness, you growl in annoyance.
Still, you answer the call.
“Dean. Jesus Christ, it’s three in the morning.”
“I just need your opinion on the new crossbow flame throwers.”
Your sigh can probably be heard across the Atlantic Ocean.
“It’s fine, but it would make more sense on a gun, right? Half gun, half flame thrower.”
“That’s what I said! But Cas says we need to diversify—”
“Dean. Three. In the morning. Go to sleep and let me get back to dreaming about Pedro Pascal as a gladiator, feeding me grapes as his queen.”
“…You like Latin guys, huh?”
You groan and turn your face fully into your pillow.
“Sleeping now. I’ll see you in five hours.”
Six Months
“Look! Emma got first place in the Spelling Bee.”
You pass Dean your phone while he scrapes the pickled onions off his burger and onto your plate. In turn, you give him the pickle wedge off your plate. By now you know that he’s a veritable bottomless pit when it comes to food in general, except for the fact that he doesn’t like pickled onions, and doesn’t trust sushi.
He smiles as he scrolls through the pictures of your daughter’s kindergarten class.
“Clearly taking after her mom in the smarts department. Though you didn’t have to do her like that with those Pippi Longstocking braids,” he remarks.
You scoff in amusement. “Oh, come on, they’re not that bad. It’s not like she’s got a wire hanger in there. She’s just going through a frizzy phase. No matter what products I use, I can’t seem to tame that hair.”
Dean chomps his burger. You’ve reminded him at least 30 times, but he still talks with his mouth full.
“Looks like she’s trying to land a plane,” he says.
You snort, shaking your head. You shove his arm lightly and go back to eating, while Dean takes another look at the pictures.
He sees a lot of you in that little girl. She’s got your eyes, your smile, but she probably has her dad’s hair, his chin. Dean hopes that’s all the girl’s going to get from that fucking deadbeat, biologically speaking. From what you’ve told Dean, all that guy is good for is sending monthly wire payments. After you got your raise, he even tried taking you to court to get his child support reduced.
“Did you want kids—you know, before? Was that even on your radar?” Dean asks.
He doesn’t know what possesses him, but he asks.
You hum in contemplation. “Honestly, it wasn’t. I was focused on my career.”
You wipe your mouth as the thought settles in.
“I thought I’d do it right, you know? Work hard, achieve my goals, find a husband who wanted the same things I did, then build a life, and a family. I always thought I was smarter than a broken condom in the back of his goddamn Lexus,” you say, your tone bordering on disgust at the end. You shake your head and sip your iced tea.
Dean quirks his head. “Well, we’ve all been thrown a few curveballs in life. What matters is how you take it. And I’d say you’ve got the better end of the deal. You get Emma, a good job, the best boss in the world…”
You shoot him a knowing smile.
Dean smirks, but he’s still serious.
“And that guy, all he gets is a life without his kid, and without the woman who could’ve given him a family,” he says. “Sounds like a fucking chump to me.”
He continues eating, but you’re not sure if he realizes how that just tilted your entire axis. It makes you look at him differently, the warmth of admiration in your chest, and something deeper coiling in your belly, stirring up something unexpected.
You stare at him long enough that his brows furrow.
“What? Got something in my teeth?” he asks.
Your face relaxes, your lips tugging at a smile.
“Yeah, ground beef. Can you please swallow before you talk?”
“This is how I am, sweetheart. Don’t try to change me,” Dean says, taking another massive bite. Oily ketchup dangles from the bun and threatens to stain one of his nicer buttoned-down shirts.
You roll your eyes. “Wouldn’t dream of it.”
You stick a napkin in his collar, just in time for the ketchup drip.
Seven Months
You and Sam have lunch together every Wednesday. It started out as a way to reconnect with your old friend, but it’s often devolved into an hourly venting session about his brother’s many idiosyncrasies, how he’s driving you both fucking crazy, and how to best manage the man’s schedule, as well as steer him away from any half-cocked decisions that could cause a PR disaster.
Like the time he accidentally asked a reporter at a charity benefit why albacore tuna was becoming an endangered species.
“I mean, come on. They’ve literally got fish on the menu tonight. Maybe if you people stopped eating so much damn sushi with your avocado toast, we wouldn’t need this bougie dinner party. $5,000 a plate? Give me a fucking break.”
The fact that he slept with her that night still didn’t save him from the article she published later that week, complete with direct quotes. She had a good goddamn memory.
Today though, your weekly lunch with Sam is less about quasi-therapy, and more about celebrating the fact that Jess is pregnant. You’re even helping her and her sister plan the baby shower.
“Any advice? Just, you know, about parenting in general,” Sam asks. For once, he seems less his normal confident self, and a little more sheepish. It’s sweet, even endearing.
You smile. “God, I don’t know. I’ve been winging it from the beginning. Just…be present, as much as you can. Jess is going to need you to show the hell up, without being asked, without being nagged. You’re the rock she’ll need to lean on, even when she thinks she can do it all while you’re here trying to show up for the job. Especially when the baby’s born. If you’re not covered in three layers of bodily fluids, then you’re not doing it right.”
He laughs a little. “Noted.”
Your mind veers into other directions as you finish up your sandwich and crumple up the foil wrapper. Most predictably, along the road that leads back to Dean.
“Dean doesn’t seem to be the family man type,” you remark. “More married to his work, but…he’s been really good with Emma every time I’ve brought her up to visit the office.”
“Doesn’t surprise me. He basically half raised me after Mom died. More than half, actually. Dad was always working,” Sam says.
“What about relationships?” you ask.
It earns you a certain look from Sam. You’ve come to learn that both Winchester brothers are incredibly sharp, just in different ways. Dean knows how to read people. He’s a good judge of character, and it makes him a shark in the board room, the kind of man that can take in the information his department heads serve him and make swift decisions that often pan out well for HunterCorp.
Sam is perceptive in an almost clinical way, analytical and methodical. He’s the one who can read the data and find the one thing that’s missing. He can anticipate problems before they start, and when it comes to people, Sam often catches the little things, tells and underlying motivations. It gives you away before you’ve even realized it.
“Well, Dean’s been pretty predictable when it comes to women, even before Dad passed,” Sam says.
And it’s true. Dean’s never seen the same woman more than a week at a time. You know this, because you’ve seen the “consolation gifts” he sends them. A Tiffany bracelet. An Apple Watch. Gucci sunglasses. The perfect gift that tells a girl she won’t need to stick around for breakfast.
“But to his credit, he’s up front with them,” Sam says, drawing your gaze. “They know what not to expect.”
Your lips quirk. “Sounds so transactional…and lonely.”
“Yeah,” Sam nods, “but I get it. He took a lot onto his shoulders when Dad died. Right now, Dean’s more focused on making sure we survive than on what he might want. To be honest, I doubt he’s even thought about what that is.”
For some reason, that hits you behind the ribs in a quiet, sharp strike. In your mind, you can’t help but see the familiar tense set of Dean’s shoulders hunched at his desk, eyes glued to his computer while an evening sun sets behind his head.
Even in that big office overlooking the entire city scape, he never has time to admire the view.
Eight Months
It’s your mistake.
Your fingers brush Dean’s for half a second too long when you give him a stack of purchase orders to sign. His eyes meet yours. You point out the new way you’ve color-coded the departments for each PO.
Your heel wobbles on your pivot, an uneven floorboard. Suddenly it’s his hand closing around your wrist and the other wrapping around your waist, giving you stability. Your eyes meet his, heated breaths in between.
A thank you falls from your lips, drawing Dean’s attention there.
But he lets you go.
You walk away, pretending you don’t know his eyes are following you.
You bite your lip against a smile.
One Year
“Seriously, which one?”
“Jesus, Dean. Green! I already told you.”
“No need to get snippy. I just want your opinion.”
“You always want my opinion. That’s why I already laid out the green one for you.”
“But I like the black one.”
“You always wear the black one. The black one says politician. The green one says you’re the boss, but you’re approachable.”
“I don’t want to be approachable. That’s how I get stuck in a 45-minute fucking conversation in the break room with Garth about his side hustle YouTube sock puppet show. That shit was deeply uncomfortable. I just wanted my damn coffee.”
“You know, you could also cut back on the caffeine and the booze while we’re on the subject.”
“Oh, what are you, my mother?”
“You tell me. I’m the one dressing you right now.”
You work the collar dark green suit jacket over his shoulder and smooth down the wrinkles. You firmly ignore how his gaze roams your face, and lower still. You want to pretend you haven’t noticed these signs, all while you try to stop yourself from giving any yourself.
“There, looks good,” you say. Though you make the mistake of meeting his eyes.
He grins. One of those grins that makes you want to grab his face, either mushing it into his seventeen mugs of coffee, or kissing him fucking stupid. You’ve been restraining the latter urge by a tenuous thread for several months now, mostly because you sicken yourself.
He’s your fucking boss. It’s unprofessional. You’ve already been down this road once in your life, and—
“You okay?” he asks.
Suddenly you realize how close he is. You can feel the warmth of his body, you can smell his cologne, and he sounds so sincere in his concern, briefly touching your arm.
You nod, knowing you should create some distance between you and him. Somehow you can’t force yourself to take that one small step back.
Instead, you reach for his tie. “Remember, you’re meeting Frank Devereau and his wife tonight, and Charlie Bradbury. She’s the brains behind the project, so you’ll want to talk to her about the details, how the program works, and how we can incorporate it into our existing tech.”
Dean hums in agreement, but in truth, his attention is on your nimble hands as you work on his tie. You slide the knot up to settle snugly, but not too tight against his throat. You allow your hands to slide down his chest while you admire your handiwork with satisfaction, but your small smile fades. Your mouth goes dry as your gaze travels back up to his, lingering on his parted mouth.
His hands slowly come to hold you by your arms, making your heart tap a syncopated beat.
“Does that look mean you want me to kiss you, or am I just seeing things?” he says at last.
Your eyes widen. You bite the inside of your lip, nervous energy fluttering through you, even as everything within you would like to scream a resounding yes.
“We can’t…shouldn’t,” you say, in a quieter voice. His office door is closed, but it’s not locked. There are far better reasons than that though, and you struggle to remind yourself of each and every one of them.
Dean steals your focus, however. His eyes seem greener than usual, probably because of the jacket. You picked it with that in mind.
“In this case, shouldn’t isn’t a moral argument,” he says. “It’s society’s rules. I don’t know about you, sweetheart, but I’ve never much cared about what people who don’t matter think about me.”
Your brows begin to knit together. “Who matters to you? Because my daughter and my father. They matter to me.”
“Being with me doesn’t hurt them,” he argues, a little peeved at the implication that it would; that he would hurt them, or you.
“Being with you?” you ask in shock.
Dean’s mouth opens, but he hesitates, like what he just said surprises even himself. His lips quirk at a smile.
“I know you, uh, probably think I’m not capable of something like that,” he asks.
“I mean, it is surprising,” you admit airily. Your cheeks warm in a blush. “You could have anyone, Dean…and you have.”
He chuckles dryly. “All right, fair enough. But other than Sam, who gets me better than you? Who else is gonna handle this, the pressure of my life and everything that goes with it…better than you?”
Your eyes widen. A softer smile threatens your lips, because you realize then that he’s actually serious.
About you?
Of course, that’s when your very real, rational doubt creeps in.
“People are going to talk,” you point out. “That’s why shouldn’t always matters. And you and me? Jesus, Dean, this is the oldest cliché in the fucking book.”
His hands move down to your waist, squeezing gently. Enticingly.
“Then we’ll be discreet,” he says, with one of his crooked grins. You shake your head, but you start to smile too. You allow him to pull you back in, figuratively and literally as he bows his head closer to yours.
“You really think you can pull that off?” you ask.
“Sweetheart, with the right motivation, we can pull off anything,” he says, half whispering them on your lips as he captures them with his own.
It’s slow and laced with a curling heat that licks tingles down your spine, just like his hand moving to the small of your back, pressing you into him. Your body betrays you then, with a moan in your throat and your own hands traveling up his arms, over his shoulders, cupping the back of his neck.
The graze of your nails at his nape makes him shiver and groan as he licks into your mouth, holds you tighter. You feel the press of his growing arousal against your belly.
Your good sense knocks at the door of lust and yearning, reminding you that you’re making all the same mistakes again. This isn’t a man you can trust—not with this. But Dean’s lips are hard to ignore, covered in the remnants of your lipstick as he kisses his way along your jaw and down your neck, where he sucks and nips just hard enough to make you gasp his name and writhe against him. He squeezes your ass and smiles against your skin.
“So fucking beautiful, you know that? Even the little sounds you make when I touch you. I wanna find out what that pretty voice sounds like when you come,” he says, in a voice dripped in whiskey and wicked promises.
Jesus. Your heart flutters. You haven’t been touched like this in so very long. You haven’t felt desired like this in…
“How long have you been thinking about that?” you ask, a little breathlessly. He continues his exploration, his lips blazing a sensuous trail down the column of your throat, along the line of your collar bone, and between the rise and fall your breasts. He slides open the buttons of your blouse with a practiced hand, his eyes drinking in the sight of your lace bra.
“Since the day you started wearing these sexy fucking heels,” he says, dragging his hand up your thigh, over your skirt, in a way that raises goosebumps on your arms. But he hesitates. His eyes ask a question as they meet yours.
“You need to tell me what you want though,” Dean says, more seriously than you expected. “You want me to touch you?”
Your heart feels like it’s beating in your throat, but you nod, biting your lip.
“Kiss me, touch me, make me fucking come,” you say. “But first, you need to lock that door.”
A crooked grin spreads across Dean’s face. He steals another kiss before he does exactly that—he crosses the room and locks that fucking door. You lean against his desk for a breather, but you realize that half this shit needs to go. You move stacks of files to the side, the coasters you put for his mugs of coffee along with the empty cups themselves. You push his double-screen monitors forward, giving Dean just the angle he needs to hold you from behind and start laying more tantalizing kisses along your neck.
You sigh and help him with the zipper of your skirt while he works on the bra clasp. The straps loosen down your arms, and he flings the bra away so he can get a handful each of your breasts. You moan and rest your head against his as he begins to squeeze and tease, gently twisting your nipples between his fingers. He leaves open-mouthed kisses against your jaw, sucking at your pulse point.
When his hand moves further down and slips behind the waistband of your skirt and panties, he feels your pulse flutter and trip along with your gasp. His fingers dip between your folds and find the slick mess of your arousal.
“Goddamn, baby. Soaked for me already,” he teases.
You don’t need to see his face to know that smug smirk is plastered across it. You reach back and tug sharply on his hair.
“You can gloat, or you can fuck me,” you retort.
He chuckles and kisses your temple. “Don’t you worry. You’re gonna have to bite down on my belt to keep from screaming in a minute.”
His hand that never left your breast begins to strum the hardened, sensitive nub, at the same time his other hand finds your clit. You shudder against him at that first touch, that perfect moment when you realize he knows exactly what he’s doing as he learns your body. He circles your clit slowly, but with a delicious pressure until it swells under his fingertips.
Then his long fingers dip down into your needy channel, making you whimper as you hold onto him and the desk for stability. His fingers pump smooth strokes inside you, almost as deep as he plans to fuck you with his cock.
He knows he has you when his fingers curl and brush deliberately against that perfect spot inside your inner walls. Your thighs begin to shake, your breaths labored, your hips bucking against his hand in a quiet plea.
Your orgasm rolls swift and steady against his fingers. Your pussy flutters around his hand, and he groans along with you.
“Good girl. Can’t wait to feel that squeeze around my cock,” he says, a filthy whisper in your ear.
You laugh a little, nodding in agreement. You turn around to help him with his belt.
“Yeah, right now. Want you inside me before we run out of time. You have to meet Sam downstairs soon.”
It’s another work event Dean can’t get himself out of, even if the networking opportunities are good for the company.
“You should come with me,” he says, grinning at the way you slide his jacket off his shoulders, but you toss it as carefully as you can across the nearest chair. You just had it drycleaned this morning.
“What?” you laugh. “Dean, you don’t need me there. I’m just an assistant—”
“No,” Dean says, stilling your movements when his hand cups your cheek. Your lashes raise as you look up at him, finding him serious again. His gaze roams your face, his thumb brushing your lower lip. “If it ain’t fucking obvious, you’re more.”
Your mouth falls open, but you’re not sure what’s going to spill out. Dean doesn’t give you time to figure it out, or even let himself settle into his own admission.
He just kisses you, hard and thorough, knocking any more doubts out of your mind, and any deeper thoughts out of his.
He grabs you up by your hips and seats you on his desk, rattling the surface. Your arms wrap around his shoulders on reflex. You feel the muscles flexing under his dress shirt—a crisp black. You help him yank up your skirt and kick off your panties, though they get tangled around your ankle. His slacks and boxer briefs end up coiled around his knees, just far enough to give him room and leverage to slide into your heat.
You both moan at the feeling of him settling snug inside, bottoming out, his almost bruising grip on your ass. Your thighs are wrapped almost as tightly around his waist as he lays you out more fully on the desk. It’s probably harder to do it this way, instead of him just bending you over the hard mahogany. But you’re glad you get to see his face, get to run your fingers through his hair and share his breaths while he fucks you in a slow-rolling rhythm.
It’s more intimate. It feels like it means something, especially when he once again cradles your cheek and brushes wild strands of hair away from your face. Especially when he kisses you deep enough to taste the Almond Joy you snacked on earlier.
You kiss him back just as fervently, as if this will be the first and the last time. You have no idea what happens after today, and you know that probably makes you a fucking idiot. It could lead to the end of your second chance at a career, but you want to trust this. You want to trust the steadiness in Dean’s hands and the look in his eyes.
So you give into what you want, sitting up to lay nipping kissing along his prickly cheek and neck, sucking your own marks against his skin. The way he groans and shudders and fucks you harder—it makes you feel powerful.
“Lean back, sweetheart,” he grits out. “Touch yourself for me.”
You manage to follow his lead, shakily laying back down and letting your hand drift back down your body, finding your clit. Dean watches you play with yourself, his fingers flexing against your hip. You feel him so deep, so good, that the coil of pleasure in your lower belly begins to tighten in earnest.
He’s only satisfied when you have to smother your own mouth against a cry, your hips snapping up to meet his as your release finally hits. Another few ragged strokes, and he spills into you as well.
“Fuck,” he groans into your neck, catching his breath. That was awesome.
But then, his eyes widen. “Christ, forgot a condom.”
“I’m on birth control.” You breathe out a laugh as you soothe him, caressing his shoulders.
He blinks, then he relaxes, chuckling faintly.
“Guess you just make me lose my head,” he says.
“It’s okay. I’ve gotten used to doing the thinking for you,” you tease, biting your lip.
Dean stares down at you, brows raised, yet amused at your cheek.
“Hmm, I’m gonna remember that one. Might have to punish you tomorrow,” he remarks.
You smirk, though a blush burns down your neck at the idea, and the depths of his voice.
He withdraws from you with a quiet moan, then helps you up with a steading grip on your arms when he feels that you’re still a bit shaky. After pulling up his pants, he finds the paper towels you keep handy in one of his desk drawers for the cleanup.
“Seriously, come with me tonight. I’m sure you’ve got a nice dress. If not, I’ll buy you one on the way,” he says, as you two start to pull your clothes back on. And in your case, find your bra.
“Dean, I need to take Emma home,” you say.
You pause with your fingers poised on his dark green jacket, ready to smooth down any wrinkles. The color matches his slacks perfectly. His hair is a bit messy, but overall, he looks edible and professional at the same time. He’s ready to shmooze with the heads of conglomerates and Silicon Valley tycoons and the politicians they own.
But you know you’re not a part of that world.
“Maybe next time,” you say, though you don’t really mean it. Your hand falls.
Dean nods, but he catches your hand before you walk away from him. He slowly winds you back in and kisses you thoroughly enough to make your knees buckle, just a little.
You’re still not sure if he meant what he said about wanting to be with you, or if this is just something he’ll change his mind about in the morning after a few glasses of whiskey.
You definitely think about more than just the road ahead while on your way home, Emma’s chatter filling the car. For once, you can’t say you’re fully paying attention.
Your fingers keep touching the memory lingering on your lips.
AN: 😘❤️🔥 How'd you like the slow build? lol Did Dean's earnest appeal surprise you there at the end? He's been a pretty successful play boy up until now, but he's really going to prove himself in Part 3 of our adventure, set shortly after Pratt Fall.
Next Time in Nothing by Halves:
Dean finds a guest spot in front of the school. The old Impala rumbles to a stop there, and he climbs out, grabbing the bouquet resting in his passenger seat.
His keys jangle in his other hand as he makes his way to the front office to check in, just like you told him to in your texted instructions. The nice ladies there give him a guest badge that he slaps on his chest, over his dress shirt, and they tell him how to get to the theater. He feels awkward and out of place walking down the halls of this school alone, but you had to take Emma over there early before the show.
The hell am I doing here?
He has to fucking wonder.
But he promised you. He promised the kid. So he’s here.
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I always appreciate how you open your fics. It starts right in the action and grounds the reader in the story/world/setting so well.
Immediately I am attracted to the fire in the reader, how she’s not brazen, but firm with Dean after he gives her shit. I also like how Dean recognizes that in her as well, and recognizes that stubbornness and fire can work in his favor.
You really think Dean should see it before he gets any deeper into his negotiations with Roman Enterprises, but he’s meeting with them right now in the big conference room, with Dick Roman himself, as well as the rest of his sales and legal representatives.
One thing I cannot get enough of in AU’s, your’s in particular, is how well you weave canon characters/dynamics into the new setting
Just as you predicted, with a sinking feeling, all eyes turn to you when you enter the conference room. Sam and Dean and their lead sales manager, Cas, look over at you in varying degrees of surprise (Cas with disapproval).
Oh absolutely not. I think I’d shit myself if I did this and ended up with everyone staring at me.
“You gonna fill us in on what that little skirt just gave you that has all of you so fucking sour?” Alastair remarks.
It makes Dean bristle. “That’s my assistant. Have some fucking respect.”
Yesss! Gotta give the respect regardless of if the lady is in the room or not. Good boy, Dean.
You think they’re stealing ink from the printer and using it for “ink blot tests.” You didn’t know that eight-year-olds knew what those were.
Oh gosh this made me laugh so hard!!!
He bangs the back of his head repeatedly against the chair, as if that could rid him of his pig-like thoughts.
The way I can soooo imagine this so vividly in my head lmao.
Oh good lord, Dean meeting Emma was so fucking adorable, and so fucking hilarious at the same time. Him starting out so standoff-ish and then dissolving into entertaining her was so fun to read.
“See? But if that kid messes with you again, you come tell me, okay? I’ll set him straight, man to man,” Dean says.
She starts to smile again. “Promise?”
“I promise. Let’s shake on it,” he says, giving her his hand. She puts her much smaller one in his, and they shake on it like adults.
So cute!!!
“Dean. Three. In the morning. Go to sleep and let me get back to dreaming about Pedro Pascal as a gladiator, feeding me grapes as his queen.”
This is an original experience, but man do I wish I dreamt of Pedro as a gladiator feeding me grapes too
Dean knows how to read people. He’s a good judge of character…Sam is perceptive in an almost clinical way, analytical and methodical. He’s the one who can read the data and find the one thing that’s missing.
The characterization here is spot on. Most don’t think to compare and contrast just how different they boys are in the way that they tackle problems. On the surface? Sure, but not to this depth.
And then the ending smut was smoking hot!!! I can’t wait to see what you’ve got in store for part 3!!
Summary: Behind every powerful man is a resourceful woman. He doesn’t realize how much he relies on you, until he realizes how much he wants you.
AN: This was originally requested as a birthday fic for a lovely Patreon member, @redhoodieone! It's my first attempt at an office AU with Dean, but I know it's a popular trope for a reason lol. Hope you guys enjoy this little snack of office smut ❤️🔥
Word Count: 1.7K
Posted on Patreon: Feb. 7, 2026
Tags & Warnings: (18+) Office politics, power imbalance (but not really), hint of angst, but mostly smut (v. fingering, oral – female receiving)
“Dean, you’re driving me crazy!” you snap. “Just read the speech as written. Sam and I worked on it for two weeks. It’s perfect.”
“Yeah, but it doesn’t even sound like me,” he grumbles. “What the hell does ‘solidarity’ mean?”
You utter a sigh as you follow him into his office, shutting the door behind you with your ass. Your hands are full—with a large binder of purchase orders that still need to be approved by the very man who can’t seem to take anything seriously.
He has the notecards Sam gave him in one hand, a glass tumbler with a generous pour of whiskey in the other. He’s meant to address the entire company in twenty minutes, and he still hasn’t put on his suit jacket or picked out his tie. You laid two options over the arm of his desk chair: black and white pinstripe or burgundy with a tiny triangle pattern.
“Cohesion. Harmony. Camaraderie. All the things you want to inspire in your employees after another million-dollar deal that’s going to make their workloads triple over the next six months,” you say, heaving the binder onto Dean’s large desk. The rest, you mutter under your breath. “And something severely lacking between you and I.”
Dean looks up from the small print on the index card, aiming his furrowed brows your way.
“What’re you talking about?” he asks, drawing closer. He sets his glass with a heavy clink down on polished wood. He glances down at his still unbuttoned collar and starts closing buttons. “You and I are one of the most well-oiled machines in this place. By the way, which—”
You hold up the burgundy tie for his inspection. Dean’s lips twitch at a grin. It’s like you’re in his goddamn head.
“See? You already know what I want before I gotta ask,” he says. A small sigh escapes you, but you still start sliding the tie up around his neck and under his collar.
“That’s because I’ve apparently made a career out of babysitting a grown man. Move your hand,” you say, batting his digits away from doing the tie himself. You know how he likes it, done in a Pratt knot rather than an old-school Windsor.
He snorts. “I’ll tell you what, it’s your fault, okay? Before you waltzed your way in here—”
“Before you hired me?” you interject.
He smirks. “Fine, before I hired you, with barely a scrap of professional experience besides a little college internship and an eight-month stint in an office—at one of our competitors, I might add—”
He grunts when your hand “slips,” making the knot tight enough to choke him. Amused, but still giving you a censuring look, he slips a finger between the fabric and his neck, loosening it a little as he clears his throat.
“I was entirely capable of running my life without you. I made make-or-break decisions for this company every damn day,” he says. But slowly, his smile slips. The way the green of his eyes roam over your face, your familiar hands, your softly parted lips while you pretend to be concentrated on what you’re doing.
“Now, I don’t know,” Dean says. He swallows, his throat sticking. “I’m in a meeting, and I can’t get comfortable until I know you’re sitting right there to my left. You don’t even need to be taking notes or anything. All you need to do is sit there, and I’m good.”
You pause, finally meeting his eyes.
“I close on a deal, and I’m not satisfied,” he says. “Not ‘til I tell you about it. Because I know you’ve been busting your ass just as much to help make it happen in the first place.”
Your hands begin to release his tie, but he gently grips your arms, keeping you in place.
“Dean…”
“I would say it’s a crying shame that bastard knocked you up before you really got your shot over there at Ashland, but that would mean I wouldn’t have the benefits of your many talents,” he says.
You try to ignore the thing that’s creeping into his tone. The thing that makes your cheeks prickle, and warmth bloom between your legs. You sigh and smile up at him, half exasperated.
“That might just make you the most selfish man in the world,” you say.
He smirks, his thumbs beginning to brush back and forth against your arms. Even in this little number you got on, a plain white blouse tucked neatly in a long pencil skirt, he can’t help his imagination. He’s fantasized about helping you for a change, with that pointless collection of fabric and buttons on this very floor, and his mouth anywhere you want him.
Anywhere you let him taste you.
“Yeah, I wonder if Emma thinks so, seeing as I’m the one who got her mom a raise so she could go to that fancy private school,” he says, with an arch of his brow. “Looking forward to that little play they’re putting on. What was it again?”
“Matilda,” you supply.
Dean frowns. “What? Isn’t that the one where the asshole principal locks little kids in a closet and stuffs ‘em full of cake like she’s making pâté? Little heavy for Kindergarteners, huh?”
You laugh, showing off that smile he gets out of you more often than not.
“She’s kind of nervous about that, actually. But she did ask if you were coming,” you say. Your eyes lower, just like your hands smoothing down his collar, then lying flat against his chest. “God knows if her father’s going to show up.”
Dean releases his hold on you, just so he can take your chin between his fingers and raise your eyes to meet his.
“I’ll be there,” he says. Finality and promise—something a man’s never given you.
Dean knows enough to know what he’s doing, what he’s saying. His free hand molds to the curve of your waist, tightening with the edge of possessiveness.
“Dean,” you breathe a warning in his name. His lips hover near yours, one decision shy of getting his way. “We…we can’t do this again.”
“See, I get that, but I’ve been having a hard time remembering why,” he says. All the while, his fingers are toying with the zipper on the side of your skirt. He guides it down, and down, and his practiced hand slips behind the waistband, behind white lace underneath, skimming bare flesh and heat against the palm of his hand, until his fingers find the wet slit of your pussy. A shaky breath falls from your lips.
“You damn well know why.”
And yet, your hand slips across his cheek, caressing there briefly as your eyes lock with his. Then your fingers sink into his hair, and you’re pulling him into you, tangling your lips and tongue with his in a way that makes you both moan.
The hand that’s not buried between your legs has a stronghold on your hip. He guides you back against his desk, but you’re the one lowering your skirt further so he has more room to torture your clit. Rough finger pads strum you mercilessly, drawing slick arousal from your entrance.
“Oh, fuck. Dean,” you gasp against his mouth. Your fingers curl tighter in his hair. Your hips buck to the rhythm of his hand, begging for more. His lips claim wherever they burn their path, from your jawline to sucking hard against your neck. You’re not even quite on the edge of his desk, half leaning, half clinging to him for survival as his fingers plunder you deeper.
Until he withdraws his hand entirely. You’re heaving for breath, uncomprehending, but you don’t even really have time to ask him just what the hell he’s doing by stopping. Because he’s already sinking to his knees.
He grabs your thighs and pulls you in, burying his face right between your glistening folds. A gasp and a whimper choke out of you at the pleasurable invasion of his tongue. Your hand flies to his hair as you try to steady yourself on the desk.
“Dean! Jesus,” you whisper-shout. Suddenly you remember, worried, that you two haven’t bothered to lock the door this time. He’s supposed to address the entire staff body in exactly ten minutes, and he’s not even fully dressed yet. Now, neither are you.
The man doesn’t seem to give a fuck about anything sensible like that, other than devouring your pussy. Your panties are a torn scrap of fabric around your ankles, along with your skirt that you spent thirty minutes ironing this morning. But you can’t bring yourself to give much of a fuck either, not when his tongue licks up to your clit, and his lips suck around the swollen bud like it’s butterscotch candy.
His fingers join in, slipping into your hot, throbbing core. By then, it doesn’t take more than a few strokes against your sensitive walls to have you coming hard around his fingers. Black and white brittle stars burst behind your eyelids, your mouth falling open in a harsh cry.
You can’t even breathe, because he’s still fucking you with his long, talented fingers. It’s too much. It’s like pushing you off the edge of the volcano while you’re still falling, still erupting. Still want his cock too.
Your fingers tighten in his hair to stop him.
“Dean, Dean, Dean, please…”
Mercifully, he stops. His fingers slip out of you, though his tongue laps at you one more time, just to feel you squirm and shudder against him. But as he pants for breath, he presses a kiss against the inside of your thigh, reverent, an unspoken declaration.
You soften as you look down on him. Your eyes show your conflict and your fondness as you cup his face with both hands, caressing his wet, stubbly cheeks with your thumbs.
“God, baby, you’re a mess,” you laugh, grabbing a tissue off his desk to wipe at his glistening mouth, nose, and chin. He smirks in satisfaction beneath your hand.
“There you go, still takin’ care of me,” he teases, rubbing your thighs.
This is a far cry from the cocky asshole you met a year ago.
Dean Winchester, CEO of HunterCorp, who hadn’t thought he needed an assistant when you came in for your interview. He hadn’t even looked at your resume beforehand and didn’t think he was going to remember your name by the end.
Now, that man is on his knees, willingly covered in your arousal. It’s obscene, but it’s also pulling at your heartstrings.
You guide him back up to your lips, where you can stake your claim on him. You don’t know yet if it’s going to stick, but he’s finally worn you down.
You’re willing to try.
AN: Some of my Patreon members suggested I write a Part 2 to this. What did you think of “part 1”?
And are you thirsty for more CEO!Dean? 😉
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I've come to love me some CEO!Dean, and yours is absolutely no exception.
I've only seen a little bit of it, but this entire thing was giving Suits vibes. Especially this part:
You hold up the burgundy tie for his inspection. Dean’s lips twitch at a grin. It’s like you’re in his goddamn head.
“See? You already know what I want before I gotta ask,” he says. A small sigh escapes you, but you still start sliding the tie up around his neck and under his collar.
It ties in really well to the part of the summary "Behind every powerful man is a resourceful woman." And I am always a sucker for a whipped-ass man (aka, Dean in every form lol)
I also thought his reaction to the reader's daughter's school play was adorable and very spot on to his character.
“She’s kind of nervous about that, actually. But she did ask if you were coming,” you say. Your eyes lower, just like your hands smoothing down his collar, then lying flat against his chest. “God knows if her father’s going to show up.”
Dean releases his hold on you, just so he can take your chin between his fingers and raise your eyes to meet his.
“I’ll be there,” he says. Finality and promise—something a man’s never given you.
Like, this part just melts my heart, especially as someone with a bonus dad who showed up for me. I have a hard time with characters/reader inserts with kids, but yours are always very thought out and well executed; they are not just thrown on the end and deemed a "happily ever after" nor are they a driving plot point/device.
Tags/Warnings: One instance of mentioned physical violence (not between Dean and the reader), the reader has a homophobic dad, allusions to alcoholism, flangst with a happy ending, coming out scene, language
Summary: After a disastrous meeting with your dad, you end up back at Bobby's and have a heart to heart with Dean
Word Count: 2.9k
Author's Note: This is for the @fanficwritersofthespnfandom June Monthly Prompts using the "Found Family" prompt
This also counts for the Getting Disowned square for @j3bingo
Thank you very much to @gappyswife for beta-reading this for me!
Dividers: Line Divider 1 by @olenvasynyt Line Divider 2 by @omi-resources SPN Divider by @talesmaniac89
Tag List: @copperboom82 @zepskies
Family Doesn’t End in Blood
Dean’s head shoots up at the sound of the screen door slamming shut violently. Sam’s at the library working on some history project for school, and Bobby is down in the garage tinkering with his latest project, which only leaves one person who’d come into the house guns blazing like that.
Peering around the corner of the kitchen, he just catches a flash of your jacket before you’re gone again, feet stomping up the stairs. He can’t help but wince as your door slams just as hard as the screen door, and all he can think is that you’re lucky that Bobby’s not around.
He can’t remember how many times the old man has raised his voice at the three of you for slamming doors, both in the house and the car.
“Pretty soon I’mma start taking doors off’a hinges,” Bobby had threatened maybe a few months ago, after Sam shut the door to their shared room a little too hard when Dad dropped them off for what seemed like the 10th time in the last 6 months.
Sammy still didn’t understand why Dad would leave them behind, going radio silent for weeks and then showing up to rip them away from school and the friends he’d made.
Dean learned quickly to not get attached to the schools, the other kids. The sting and awkwardness of being the new kid had worn off a long time ago, and now that he was almost finished with high school, his peers were less interested in who was new and more interested in what colleges they were going to.
Sam still tried, as green a freshman as they came, but as smart as a whip. Where he got that, Dean didn’t know.
Nor did he know where the persistence for friendship came from. Dean resigned to the fact that friends didn’t exist outside the kids of other hunters– which is where you had come into their lives.
Your dad was friends with Bobby, from what he understood, and your old man would leave you for months at a time to the point Dean had thought you were Bobby’s daughter at first.
He knew the old man and Mrs. Singer never had kids, but at the time he thought maybe it was just another lie Dad had told him for the sake of his age.
“You’re too young for some things, Dean,” Dad would say to questions that he didn’t want to answer. Dean knew it was bullshit, but he knew better than to say anything in opposition.
You were always there when Dad would drop him and Sam off. At first you were shy, but the more time they spent with you, Dean learned just how much of a spitfire you were, and slowly he’d let himself get used to the idea of you being a constant in his life whenever they were shacked up at Bobby’s.
Just a year younger than him, you never acted like it, and he could count on one hand how many times he’d seen you cry. Even when you’d wiped out on the bike you found lying around the junkyard when you were nine, and you knocked out your front tooth. Not a tear was shed, just the goofy, crooked smile he’d come to associate with you.
You weren’t smiling now, though, if the heaviness of your footfalls and the force with which you closed yourself off from the rest of the house— from the rest of the world.
You sling your backpack off your shoulder, the bag hitting the corner of your room with a loud thud. Not a thought is spared to if Bobby was home and if he’d be up here after you with the way you shut his doors.
You couldn’t be bothered to care, not as you claw at your jean jacket, chucking it in the same direction as your bag.
The tightness that has been growing in your chest ever since you fled the meeting with your Dad is growing unbearable. There’s barely enough room for you to breathe, let alone think straight beyond the aching in your fists to put them through a wall.
Instead, your fisted hands rub at your eyes as that dreadful pain in your throat made itself known. The sting of tears are soon to follow, you know, and the flames of rage inside of you are stoked by that thought.
There was absolutely no reason to cry. The asshole had never been a father to you.
He made an appearance a few times a year, just enough to ruffle your hair and pretend that he cared before he was gone again. Hunting was his life and it would always come before you. He’d made that clear for as long as you could remember.
Your mom had been a one night stand he’d picked up in some roadhouse, and she’d only cared enough to get a bead on your Dad and drop you off with a box of diapers and a ‘good riddance’ to the both of you.
Or so you’d been told. You didn’t really care, too old by the time he gave you most of the truth to fall for the allure of a mystery woman out there who might want you back.
There should be no tears shed for either of them, but especially not the man you had the shit luck of sharing DNA with, but they came anyway.
Hot and tinged with ire, you wipe them away angrily.
The ache for arms around you creeps up slowly, but when it finally hits, it comes with enough force to kick your knees out from beneath you. You sink onto the bed, burying your face in your palms while trying to breathe through the tension holding your body hostage.
Your dad may not have been there for you, but the man who was no doubt down in the shop, covered in grease and cursing over some hopeless engine, had never let you down. Neither had either of the boys who called this place a temporary home just as you did.
The boy’s door was open when you came blazing past, and you hadn’t seen Sam in there. Vaguely, you remembered him blabbing on about some kind of boring project his World History teacher had assigned earlier that week—one that would require looking at some historic documents on display in the library archives.
Dean though, you’d seen sitting at the kitchen table, spoon laden with his typical afternoon meal of cereal halfway to his mouth when you’d stormed in.
Being only a year his junior, you’d clicked easier with the older Winchester boy. You shared a few classes, but you really didn’t rub elbows in public. Sam tried to assimilate, but Dean didn’t care to, much to the dismay of the girls you’d overhear in the bathroom.
You’d created a life, or what good of one you’d curated for yourself. There were a handful of girls you’d sit with at lunch or laugh with in the halls during passing periods on the way from one class to the next.
As soon as classes were finished for the day, though, Dean would be at your locker and Sam not far behind. You’d walk to the parking lot, the three of you with your elbows linked. When you’d get to the car, Sam would always call shotgun, but that was a contest he never won.
But even with your “normie” friends, as Dean called them, you felt alien.
You knew the things in the movies they’d jokingly screech at and jump into their boyfriends arms at were real, and even though your dad kept you at a mile-long arms length from the life, you were too entrenched of it to unpeek behind the curtain.
Not to mention, you were at the mercy of the pit in your stomach that the moment you got too comfortable here, your dad would whisk you away and send the life you’d built out of blood, sweat, and tears crumbling into the Earth in a cloud of dust.
Well, guess I don’t have to worry about that anymore, you think to yourself bitterly as another wave of angry tears crashes over you.
“Fuck,” you whisper under your breath, suddenly too aware of the copious amount of self pity you’re wallowing in.
There’s other stuff too. Stuff Sam, having the most emotional intelligence out of the three of you combined, would probably know the names of.
Disappointment is there, sure, and unhoned anger. It’s the kind that is so big, so strong, that it doesn’t care who its target is: yourself or your dad.
You hear the door quietly creak open. The hinges are never oiled, and you never cared to fix it. The knife under your pillow, Bobby down the hall, and nearly 17 years of hunting conditioning let you sleep soundly.
The only creature that dared enter your room uninvited is Dean.
“Go away,” you say, hating the way your words lack the conviction with which you want to say them.
He doesn’t, of course.
“Bobby would’a beat your ass if he saw the way you came in,” he says with the slightest hint of amusement.
Your hands drop from your face and your head shoots up to give him an incredulous look. “If you came in here just to lecture me, you can go. I don’t need it right now, De.”
Dean raises his hands in a placating gesture from where he’s standing across from you. “Just saying.”
“Yeah, well you can just fuck off. Can’t a girl get some fucking peace around here?”
You groan, flopping onto your back on the bed. Surprisingly, it wears the edge to your massive block of emotions down just the tiniest bit.
The yellow-orange glow of the setting sun fills your room, illuminating the sloppily painted stars and constellations smattered across your ceiling.
Bobby had helped you paint them probably around the same time he realized you were on a fast track to becoming a permanent fixture in his household—a fact you had realized while laying in bed unable to sleep one night a few years ago. A set of sheets and duvet in your favorite color with a matching throw blanket had followed, replacing the threadbare grey ones that had been on there previously.
You’d been too proud to say it then, but it was the first time you felt as though you had a real home. Every time you’d tried to voice it since then had ended with you choking on your words and quickly changing the subject when the old man tried to call you out on your shifty or quiet behavior.
A small scream exits you when you are nearly bounced a foot off the bed as Dean flops down beside you. The fact the mattress is a Queen size is the only thing that keeps you from tumbling off the side.
“God, you are so annoying!” You reach over and backhand his chest, which only dissolves him into a fit of laughter.
It’s a sound that has become as familiar to you as your own voice, and it’s contagious in its own right. You try but fail to keep a straight face, and end up breaking into a reluctant grin.
“Yeah, but you love me anyway,” Dean says once his laughter dies down.
“Whatever helps you sleep at night, De,”
He hums a noncommittal sound that you know means he doesn’t believe you.
Those three words haunt you in ways you’re not sure you’ll ever be able to fully process. Said in jest? Sure, many times. But they clog up your vocal cords, clinging to them and refusing to budge when the sense of fondness stifles your chest, needing to be heard.
You see it in the way Bobby and Sam and Dean look at you, that they know you love them. None of them are particularly good at it either, but it makes you angry you can’t say it back.
A stretch of silence follows, you’re not sure how long, but the pair of you lay there staring up at the ceiling. Your eyes trace the constellations, all of them copied out of an astronomy book that is no doubt lost in the mess of the house by now.
But, if someone asked you to pick them out in an actual night sky, the only thing you’d be able to pick out is Polaris, the North Star.
That’s the only one that truly matters to me, anyway, you think.
“Wanna talk about it?” Dean asks, breaking the comfortable silence.
The tightness that had eased through easy laughter coiled back around your ribcage. Your fingers curled into the mess of your sheets, gripping them tightly.
“I met my dad for coffee,” you started, keeping your eyes fixated on the ceiling. “And he asks me all the usual bullshit. You know how it is. ‘Bobby doing good? How’s school? Getting good grades?’ The small talk that makes him feel like he’s not a total piece of shit.”
You can feel Dean nod beside your head and you are half tempted to leave your story there.
Dean knows the meetings with your dad never go well. More than once he’s come to pick you up when the bastard bailed on you completely or skipped out on lunch or snacks leaving you to cover the bill including the excessive amount of alcohol he likes to order no matter the time of day.
Dean might press a bit, given your outburst, but he wouldn’t question it hard. You loved and hated that about him; most of the time it worked in your favor, but sometimes you wished he would ask deeper questions or push the issue when you knew he could tell there was more.
Shame burns hot, and your voice shakes when you continue. “Then he asks ‘Any boyfriends yet?’”
It’s like trying to swallow concrete when you pause, and there’s nothing you can do to stop a singular tear slipping out of the corner of your eye. It slides down the side of your face to soak into the bed.
You flinch when you feel Dean’s hand brush against yours. Wordlessly, you release your grip on the blanket and let him thread his fingers in between yours. The callouses on his palms scrape the matching ones on your own. He gives it a gentle squeeze as if saying: go on, I’m listening.
Scoffing and full of terror, you finish. “And I’m dumb enough to say ‘No, dad. I don’t like boys.’ ‘Cause he’s my dad. He shouldn’t care, right?”
The words bleed out now, and you’re horrified as you can’t stop them.
“And right there, in the middle of the cafe, he stands and slaps me across the face. Saying that if that’s true, then I’m no daughter of his and to lose his number. And then he was gone.”
There’s a wobble to your voice as you finish, and all you can do is lay there, petrified and waiting for Dean to do or say something—anything.
The few times John Winchester showed his face when you happened to be around was enough for you to form a solid opinion on the man and you’d be polite by saying it wasn’t a good one.
Within that verdict, you don’t think his reaction would have been much different than your dads. You know Dean well enough to know that while he all but idolizes the man most of the time, he is his own person.
You just don’t know how removed he was from his father on this matter, and the longer silence stretched between you, taut like a string threatening to snap under the smallest shift, you feel yourself start to shake.
Another tear slips out, then another as the stomach-dropping fear that you’d just lost another part of the family you’d made for yourself becomes more and more real.
“Well,” Dean says finally, squeezing your hand again. “Chicks are pretty cool.”
The sense of relief that floods you is like nothing you’ve ever experienced, and considering the circumstances, you hope to never feel it again.
You can’t help the half-sniffle laugh that comes from you. “You’re so fucking annoying.”
“You love me,” Dean replies, and you don’t need to look at him to know he’s smiling at you. You’re too fixated on the North star painted above you, knowing his smile is just as bright.
“I do,” you say softly, and slowly your smile fades “Do you think Bobby will care?”
Finally turning your head to look at him, you find Dean already looking at you. The unconditional love you see staring back at you is enough for more tears to well at your eyes.
“No, Sweetheart. He’s not gonna care,” he says softly. “You’re our family. Nothin’s ever gonna change that. Definitely not you liking chicks instead of dudes.”
“You think?”
“I know.”
It takes less than a second for him to pull his hand from yours, wrapping his arm around your shoulders and tugs you closer to him. You shudder a sigh, wrapping your arms around him in kind.
“Thanks, De.”
“Yeah, ‘course,” he says, rubbing his hand up and down your upper arm.
The familiar warmth glows in your chest, and for the first time, your brain doesn’t stop the words from coming out this time.
“I love you, Dean.”
His hand falters for a split second, the only sign of surprise he makes before resuming.
“I love you too, Sweetheart.”
Please like, reblog, and/or comment if you enjoyed. Feedback is appreciated and encouraged!
supportive Dean squeezing her hand had me melt, as did her saying "I do" back to his "You love me." Aaaaaaaa!
Screw reader's dad! He doesn't know what's up at all. Dean's right, chicks are cool. Next thing you know, he'll play wingman for her and help her score a date with a girl.
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Kinktober is a kinky October prompt challenge that’s been running in one form or another since 2016. There are three prompts for each day in October, and the challenge is to use one (or more!) of the prompts to create something for that day. If you don’t want to use any of the three daily prompts, you can swap them out for the bonus prompts at the bottom of the prompt list.
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Tags/Warnings: One instance of mentioned physical violence (not between Dean and the reader), the reader has a homophobic dad, allusions to alcoholism, flangst with a happy ending, coming out scene, language
Summary: After a disastrous meeting with your dad, you end up back at Bobby's and have a heart to heart with Dean
Word Count: 2.9k
Author's Note: This is for the @fanficwritersofthespnfandom June Monthly Prompts using the "Found Family" prompt
This also counts for the Getting Disowned square for @j3bingo
Thank you very much to @gappyswife for beta-reading this for me!
Dividers: Line Divider 1 by @olenvasynyt Line Divider 2 by @omi-resources SPN Divider by @talesmaniac89
Tag List: @copperboom82 @zepskies
Dean’s head shoots up at the sound of the screen door slamming shut violently. Sam’s at the library working on some history project for school, and Bobby is down in the garage tinkering with his latest project, which only leaves one person who’d come into the house guns blazing like that.
Peering around the corner of the kitchen, he just catches a flash of your jacket before you’re gone again, feet stomping up the stairs. He can’t help but wince as your door slams just as hard as the screen door, and all he can think is that you’re lucky that Bobby’s not around.
He can’t remember how many times the old man has raised his voice at the three of you for slamming doors, both in the house and the car.
“Pretty soon I’mma start taking doors off’a hinges,” Bobby had threatened maybe a few months ago, after Sam shut the door to their shared room a little too hard when Dad dropped them off for what seemed like the 10th time in the last 6 months.
Sammy still didn’t understand why Dad would leave them behind, going radio silent for weeks and then showing up to rip them away from school and the friends he’d made.
Dean learned quickly to not get attached to the schools, the other kids. The sting and awkwardness of being the new kid had worn off a long time ago, and now that he was almost finished with high school, his peers were less interested in who was new and more interested in what colleges they were going to.
Sam still tried, as green a freshman as they came, but as smart as a whip. Where he got that, Dean didn’t know.
Nor did he know where the persistence for friendship came from. Dean resigned to the fact that friends didn’t exist outside the kids of other hunters– which is where you had come into their lives.
Your dad was friends with Bobby, from what he understood, and your old man would leave you for months at a time to the point Dean had thought you were Bobby’s daughter at first.
He knew the old man and Mrs. Singer never had kids, but at the time he thought maybe it was just another lie Dad had told him for the sake of his age.
“You’re too young for some things, Dean,” Dad would say to questions that he didn’t want to answer. Dean knew it was bullshit, but he knew better than to say anything in opposition.
You were always there when Dad would drop him and Sam off. At first you were shy, but the more time they spent with you, Dean learned just how much of a spitfire you were, and slowly he’d let himself get used to the idea of you being a constant in his life whenever they were shacked up at Bobby’s.
Just a year younger than him, you never acted like it, and he could count on one hand how many times he’d seen you cry. Even when you’d wiped out on the bike you found lying around the junkyard when you were nine, and you knocked out your front tooth. Not a tear was shed, just the goofy, crooked smile he’d come to associate with you.
You weren’t smiling now, though, if the heaviness of your footfalls and the force with which you closed yourself off from the rest of the house— from the rest of the world.
You sling your backpack off your shoulder, the bag hitting the corner of your room with a loud thud. Not a thought is spared to if Bobby was home and if he’d be up here after you with the way you shut his doors.
You couldn’t be bothered to care, not as you claw at your jean jacket, chucking it in the same direction as your bag.
The tightness that has been growing in your chest ever since you fled the meeting with your Dad is growing unbearable. There’s barely enough room for you to breathe, let alone think straight beyond the aching in your fists to put them through a wall.
Instead, your fisted hands rub at your eyes as that dreadful pain in your throat made itself known. The sting of tears are soon to follow, you know, and the flames of rage inside of you are stoked by that thought.
There was absolutely no reason to cry. The asshole had never been a father to you.
He made an appearance a few times a year, just enough to ruffle your hair and pretend that he cared before he was gone again. Hunting was his life and it would always come before you. He’d made that clear for as long as you could remember.
Your mom had been a one night stand he’d picked up in some roadhouse, and she’d only cared enough to get a bead on your Dad and drop you off with a box of diapers and a ‘good riddance’ to the both of you.
Or so you’d been told. You didn’t really care, too old by the time he gave you most of the truth to fall for the allure of a mystery woman out there who might want you back.
There should be no tears shed for either of them, but especially not the man you had the shit luck of sharing DNA with, but they came anyway.
Hot and tinged with ire, you wipe them away angrily.
The ache for arms around you creeps up slowly, but when it finally hits, it comes with enough force to kick your knees out from beneath you. You sink onto the bed, burying your face in your palms while trying to breathe through the tension holding your body hostage.
Your dad may not have been there for you, but the man who was no doubt down in the shop, covered in grease and cursing over some hopeless engine, had never let you down. Neither had either of the boys who called this place a temporary home just as you did.
The boy’s door was open when you came blazing past, and you hadn’t seen Sam in there. Vaguely, you remembered him blabbing on about some kind of boring project his World History teacher had assigned earlier that week—one that would require looking at some historic documents on display in the library archives.
Dean though, you’d seen sitting at the kitchen table, spoon laden with his typical afternoon meal of cereal halfway to his mouth when you’d stormed in.
Being only a year his junior, you’d clicked easier with the older Winchester boy. You shared a few classes, but you really didn’t rub elbows in public. Sam tried to assimilate, but Dean didn’t care to, much to the dismay of the girls you’d overhear in the bathroom.
You’d created a life, or what good of one you’d curated for yourself. There were a handful of girls you’d sit with at lunch or laugh with in the halls during passing periods on the way from one class to the next.
As soon as classes were finished for the day, though, Dean would be at your locker and Sam not far behind. You’d walk to the parking lot, the three of you with your elbows linked. When you’d get to the car, Sam would always call shotgun, but that was a contest he never won.
But even with your “normie” friends, as Dean called them, you felt alien.
You knew the things in the movies they’d jokingly screech at and jump into their boyfriends arms at were real, and even though your dad kept you at a mile-long arms length from the life, you were too entrenched of it to unpeek behind the curtain.
Not to mention, you were at the mercy of the pit in your stomach that the moment you got too comfortable here, your dad would whisk you away and send the life you’d built out of blood, sweat, and tears crumbling into the Earth in a cloud of dust.
Well, guess I don’t have to worry about that anymore, you think to yourself bitterly as another wave of angry tears crashes over you.
“Fuck,” you whisper under your breath, suddenly too aware of the copious amount of self pity you’re wallowing in.
There’s other stuff too. Stuff Sam, having the most emotional intelligence out of the three of you combined, would probably know the names of.
Disappointment is there, sure, and unhoned anger. It’s the kind that is so big, so strong, that it doesn’t care who its target is: yourself or your dad.
You hear the door quietly creak open. The hinges are never oiled, and you never cared to fix it. The knife under your pillow, Bobby down the hall, and nearly 17 years of hunting conditioning let you sleep soundly.
The only creature that dared enter your room uninvited is Dean.
“Go away,” you say, hating the way your words lack the conviction with which you want to say them.
He doesn’t, of course.
“Bobby would’a beat your ass if he saw the way you came in,” he says with the slightest hint of amusement.
Your hands drop from your face and your head shoots up to give him an incredulous look. “If you came in here just to lecture me, you can go. I don’t need it right now, De.”
Dean raises his hands in a placating gesture from where he’s standing across from you. “Just saying.”
“Yeah, well you can just fuck off. Can’t a girl get some fucking peace around here?”
You groan, flopping onto your back on the bed. Surprisingly, it wears the edge to your massive block of emotions down just the tiniest bit.
The yellow-orange glow of the setting sun fills your room, illuminating the sloppily painted stars and constellations smattered across your ceiling.
Bobby had helped you paint them probably around the same time he realized you were on a fast track to becoming a permanent fixture in his household—a fact you had realized while laying in bed unable to sleep one night a few years ago. A set of sheets and duvet in your favorite color with a matching throw blanket had followed, replacing the threadbare grey ones that had been on there previously.
You’d been too proud to say it then, but it was the first time you felt as though you had a real home. Every time you’d tried to voice it since then had ended with you choking on your words and quickly changing the subject when the old man tried to call you out on your shifty or quiet behavior.
A small scream exits you when you are nearly bounced a foot off the bed as Dean flops down beside you. The fact the mattress is a Queen size is the only thing that keeps you from tumbling off the side.
“God, you are so annoying!” You reach over and backhand his chest, which only dissolves him into a fit of laughter.
It’s a sound that has become as familiar to you as your own voice, and it’s contagious in its own right. You try but fail to keep a straight face, and end up breaking into a reluctant grin.
“Yeah, but you love me anyway,” Dean says once his laughter dies down.
“Whatever helps you sleep at night, De,”
He hums a noncommittal sound that you know means he doesn’t believe you.
Those three words haunt you in ways you’re not sure you’ll ever be able to fully process. Said in jest? Sure, many times. But they clog up your vocal cords, clinging to them and refusing to budge when the sense of fondness stifles your chest, needing to be heard.
You see it in the way Bobby and Sam and Dean look at you, that they know you love them. None of them are particularly good at it either, but it makes you angry you can’t say it back.
A stretch of silence follows, you’re not sure how long, but the pair of you lay there staring up at the ceiling. Your eyes trace the constellations, all of them copied out of an astronomy book that is no doubt lost in the mess of the house by now.
But, if someone asked you to pick them out in an actual night sky, the only thing you’d be able to pick out is Polaris, the North Star.
That’s the only one that truly matters to me, anyway, you think.
“Wanna talk about it?” Dean asks, breaking the comfortable silence.
The tightness that had eased through easy laughter coiled back around your ribcage. Your fingers curled into the mess of your sheets, gripping them tightly.
“I met my dad for coffee,” you started, keeping your eyes fixated on the ceiling. “And he asks me all the usual bullshit. You know how it is. ‘Bobby doing good? How’s school? Getting good grades?’ The small talk that makes him feel like he’s not a total piece of shit.”
You can feel Dean nod beside your head and you are half tempted to leave your story there.
Dean knows the meetings with your dad never go well. More than once he’s come to pick you up when the bastard bailed on you completely or skipped out on lunch or snacks leaving you to cover the bill including the excessive amount of alcohol he likes to order no matter the time of day.
Dean might press a bit, given your outburst, but he wouldn’t question it hard. You loved and hated that about him; most of the time it worked in your favor, but sometimes you wished he would ask deeper questions or push the issue when you knew he could tell there was more.
Shame burns hot, and your voice shakes when you continue. “Then he asks ‘Any boyfriends yet?’”
It’s like trying to swallow concrete when you pause, and there’s nothing you can do to stop a singular tear slipping out of the corner of your eye. It slides down the side of your face to soak into the bed.
You flinch when you feel Dean’s hand brush against yours. Wordlessly, you release your grip on the blanket and let him thread his fingers in between yours. The callouses on his palms scrape the matching ones on your own. He gives it a gentle squeeze as if saying: go on, I’m listening.
Scoffing and full of terror, you finish. “And I’m dumb enough to say ‘No, dad. I don’t like boys.’ ‘Cause he’s my dad. He shouldn’t care, right?”
The words bleed out now, and you’re horrified as you can’t stop them.
“And right there, in the middle of the cafe, he stands and slaps me across the face. Saying that if that’s true, then I’m no daughter of his and to lose his number. And then he was gone.”
There’s a wobble to your voice as you finish, and all you can do is lay there, petrified and waiting for Dean to do or say something—anything.
The few times John Winchester showed his face when you happened to be around was enough for you to form a solid opinion on the man and you’d be polite by saying it wasn’t a good one.
Within that verdict, you don’t think his reaction would have been much different than your dads. You know Dean well enough to know that while he all but idolizes the man most of the time, he is his own person.
You just don’t know how removed he was from his father on this matter, and the longer silence stretched between you, taut like a string threatening to snap under the smallest shift, you feel yourself start to shake.
Another tear slips out, then another as the stomach-dropping fear that you’d just lost another part of the family you’d made for yourself becomes more and more real.
“Well,” Dean says finally, squeezing your hand again. “Chicks are pretty cool.”
The sense of relief that floods you is like nothing you’ve ever experienced, and considering the circumstances, you hope to never feel it again.
You can’t help the half-sniffle laugh that comes from you. “You’re so fucking annoying.”
“You love me,” Dean replies, and you don’t need to look at him to know he’s smiling at you. You’re too fixated on the North star painted above you, knowing his smile is just as bright.
“I do,” you say softly, and slowly your smile fades “Do you think Bobby will care?”
Finally turning your head to look at him, you find Dean already looking at you. The unconditional love you see staring back at you is enough for more tears to well at your eyes.
“No, Sweetheart. He’s not gonna care,” he says softly. “You’re our family. Nothin’s ever gonna change that. Definitely not you liking chicks instead of dudes.”
“You think?”
“I know.”
It takes less than a second for him to pull his hand from yours, wrapping his arm around your shoulders and tugs you closer to him. You shudder a sigh, wrapping your arms around him in kind.
“Thanks, De.”
“Yeah, ‘course,” he says, rubbing his hand up and down your upper arm.
The familiar warmth glows in your chest, and for the first time, your brain doesn’t stop the words from coming out this time.
“I love you, Dean.”
His hand falters for a split second, the only sign of surprise he makes before resuming.
“I love you too, Sweetheart.”
Please like, reblog, and/or comment if you enjoyed. Feedback is appreciated and encouraged!
Summary: When Dean comes back from Hell, you quickly realize that his subconscious remembers more than his waking mouth admits.
AN: Requested by Ashley Klann on Patreon! I’ve written a “back from Hell” piece before with an Omegaverse twist, called Make it Right. But here’s a more canon-rooted drabble. 💜
Request: After Dean comes back from hell, he has nightmares and a breakdown. The reader is there to comfort him and just holds him, and he ends up letting all pent-up feelings out.
Posted on Patreon: May 15, 2026
Word Count: 1.3K
Tags & Warnings: Set around mid-season 4 (when Sam was traipsing around with Ruby). Established relationship, angst, feels, hurt/comfort to the max
Dean might’ve been able to shrug off ghost sickness. He might’ve been able to look you and Sam in the eyes, with his third beer in hand, and claim he didn’t remember anything about his four months in Hell.
But what he just couldn’t do was make you believe it. Not a month ago, not last week, not tonight.
He climbed into the dingy motel bed, slow and groaning. You could see the exhaustion in the darkness under his eyes, and in the dull green of his irises. You saw the evidence of his lack of sleep pulling at his limbs, because he hadn’t truly rested since he got “topside.”
Since he showed up at your apartment with Bobby in tow, scaring the shit out of you with his half-cocked smile before he proved he wasn’t a shapeshifter or a demon.
The way Dean held you then had been so strong and fragile at the same time; you felt the shake in his arms, the tension embedded in his frame, even while he was burying his face in your hair. You’d blinked hot tears that clung to your lashes, cupped his face between your hands and kissed him just as hard and desperate.
He was alive, so you were alive. That was what that day felt like for you: coming back to life.
But this was a different kind of living.
When you slid into bed beside him, he didn’t reach for you. He didn’t welcome you against his side or wrap his arm around you. He didn’t even pretend to meet your eyes, let alone kiss you goodnight. He just mumbled the empty word, like he already knew it wouldn’t be one.
Sam was still out by himself. He was doing that more often lately, ducking out and taking the car or walking into town by himself. His excuses were always valid on the surface, like getting breakfast at the diner early, or doing some research at a café, or getting an early morning run in before you or Dean rolled out of bed. Still, you had half a mind to call bullshit.
Dean had stopped trying, even though he’d noticed too, sometimes with lips pursing, jaw clenching.
Tonight, he didn’t seem to care about his brother’s nighttime habits or your soft frown as he turned onto his side, away from you.
“You okay?” you asked, despite knowing what it would get you.
“‘M fine,” he said. “Just tired.”
You nodded, even though he couldn’t see it. You wished he wouldn’t bury it all so deep. You wished he would let you help him. But Dean had always carried layers behind that stupid devil-may-care attitude, behind that cocky grin on just the right side of charming, and the old leather that draped his shoulders like a second skin of bravado.
You’d noticed that his father’s jacket was still folded up somewhere in the trunk of the Impala. Dean hadn’t been wearing it since he got back.
You couldn’t help but think that mattered, even as you laid a hand on his shoulder and pressed a soft kiss near his neck.
“’Kay, goodnight,” you said.
You felt slightly raised flesh under the thin fabric of his shirt, and you realized then that you were accidentally touching the handprint burned into his skin—the mark of Castiel, the angel who rescued him.
You quickly let your hand slip away, feeling the tension in Dean’s body.
Your heart clenched, and you had to blink the sting out of your eyes when you turned onto your side and tried to get comfortable.
The first jolt stirred the mattress, then tugged at your subconscious.
The second one, and his painful groan, made your lashes flutter. Your eyes slid open as you fought through the dregs of sleep, but his fingers clawing against your arm finally yanked you out of it.
You sucked in a confused, pained hiss, looking over at Dean. You realized that he hadn’t meant to hurt you. He had a desperate grip twisting in the sheets, his brows tightly knitted, jaw clenching so hard you could almost hear his teeth grinding. But the sounds that were escaping his barely parted lips were too heartbreaking, like a wounded animal unwilling to let their whimpers escape, afraid for something worse to follow.
“Dean,” you rasped, reaching for his shoulder cautiously. You were wary of him trying to knock your hand away, or worse, but he just flinched harder.
It did manage to wake him up though.
His eyes flew open with a sharp intake of breath, following by more labored ones as he struggled to take you in, to realize where he was.
He rolled onto his back and stared up at the ceiling. He dragged a hand over his face, rubbing his eyes.
“Dean?” you prompted gently. You were slow in the way you slid closer, smoothing a comforting hand up his arm.
He looked over at you, tired of lying, but still unwilling to answer you.
But in that moment, you knew the truth. You knew what he was hiding, deep and dark behind his eyes when they met yours.
He couldn’t hold it for long though. His own self-loathing won out. Even just having you beside him with love and concern in your eyes was too much for him to handle.
He sat up in bed and swung his legs over the edge, but that was where he hesitated. He either lacked the strength to get up and leave you, or he was just that shaken. His eyes closed and an uneasy sigh fell from his lips, making his shoulders sag.
You crawled over to his side of the bed and bent a knee underneath you as you sat just behind him, just barely keeping yourself from touching him. You didn’t want to smother him, but you wouldn’t leave him alone either.
“You do remember everything, don’t you,” you said. The heartbreak was in your throat, but you thought it might help him to say it out loud.
Dean shook his head slowly, but this time, it wasn’t a denial. His tongue was heavy in his mouth, but he still forced himself to speak, his voice thick and rasping.
“Not just…what happened to me,” he said, his voice coarse with fatigue and pain. “What I did.”
Your brows furrowed in confusion. You didn’t understand, but he couldn’t bring himself to explain it to you—why he hadn’t been able to let you in. Why he couldn’t allow himself to touch you with his hands. Every time he looked at them, they were drenched in blood.
And when he tried to look at you, the words died in his throat. It felt selfish to try.
His lips trembled. His shoulders heaved. He covered his face as his eyes burned, and the first sob shuddered through him.
You didn’t understand, but it didn’t matter. Not tonight. Once the first tear drew down your cheek, you couldn’t let yourself do anything else but hold him from behind. Your lips pressed to his shoulder, and you held onto him as tightly as you dared.
He held you back, his hand clasping over your arm to keep you there. It gave you the encouragement you needed to slide closer, your hand cupping his cheek and stroking your thumb across his chin. His glassy eyes met yours.
“I love you,” you reminded him. “That doesn’t change.”
Again, Dean shook his head. “You don’t know. You don’t know what I…”
“Right now, I don’t need to know,” you said.
Just then, he was desperate to believe you.
He bowed into your kiss, desperate for your warmth too.
One touch couldn’t make him forget. It wouldn’t heal him either.
All you could do was stay.
AN: My heart gets ripped out every time I watch that ep where he tells Sam about his experience in Hell. 🥲💔 But let me know what you thought of this hurt/comfort snack!
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Poor Dean...I have a love-hate relationship with this era. Love it because we get to see Dean show emotion and kind of break out of that anger-fueled soldier who feels nothing and get to peel back some of those layers, of which he has too many to count; I really admire how you are able to capture that in this, especially here:
The way Dean held you then had been so strong and fragile at the same time; you felt the shake in his arms, the tension embedded in his frame, even while he was burying his face in your hair.
I also hate, but love it, because I relate to Dean in the way he has such a hard time opening up and talking about his feelings and his trauma. I can feel his exhaustion through the way you wrote this, both the physical and the emotional.
This part though, really broke my heart:
“I love you,” you reminded him. “That doesn’t change.”
Again, Dean shook his head. “You don’t know. You don’t know what I…”
Because, again, I can relate to not feeling worthy of love. Not to mention how well you portray Dean's self-deprecation and the emotional toll Hell had on him, especially in this point in canon where it is super fresh. I wish they'd made his trauma and the trauma of losing people on hunts more prevalent as the seasons wore on.
But that's what we have amazing and talented writers like you, Alex, for!
(Title banner and chapter headers made by me. Images found on Google.)
My submission for the @storytellers-contest-tjac
Pairing: Beau Arlen/Original Female Character
Word Count: 50,599 (over 8 chapters)
Rating: Explicit -MDNI-
Summary: Beau Arlen had never been the type to ask for help, but when new evidence surfaces, causing the acting Sheriff to reopen a twenty-year-old cold case, he really doesn't have much of a choice.
What he got was a 5'6' brown-haired, brown-eyed ticking time bomb that could throw her wicked right hook at any given moment. Jordan was full of surprises, the biggest was how professional she could be under pressure, for now at least...
Additional Tags: Not Canon Compliant, Enemies to Friends to Lovers, Angst and Fluff and Smut, Angst and Hurt/Comfort, Explicit Sexual Content. Sexual Tension, Heartbreak, Past Infidelity, Loss of a Love One, Abduction, Minor abduction, Non-Graphic Violence, Shooting Guns, Slow Burn, Domestic Fluff, Fluff and Angst, Angst and Feels, Idiots in Love, Emotional Baggage, Emotional Hurt/Comfort, Post-Divorce, Finding Love Again, Angst with a Happy Ending, Serial Killer On The Loose, Protective Beau Arlen.
Special thanks to @copperboom82. Thanks for always being there and letting me yap your ears off about this story for the past 6 months. I couldn't have done it without you.
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