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@princessdeanwinchester222
sorry if I'm just saying things that have already been said but dean winchester is SO bottom coded like he looks at every single man like he wants to be fucked by them... Cas, Benny, the dr sexy guy, Gabriel, uhhh everyone else... like please did we watch the same show or was Dean like bending over for every single dude
dean winchester consumes my mind LAWDDD I beg for anything with that man, surviving off of scraps looking for more top male reader x dean 🤕
- 🛸
No Longer a Mentor
Sub!Bottom Dean Winchester x Top!Male Reader
☆ Word Count: 1,512 ☆
After spending his young adult years with you, his mentor, more than his father, Dean found himself falling for you. He eventually made a move and forever changed the dynamic of your relationship
🕯️: well luckily for u, i just finished this draft :3
CW: Age Gap, First Time Bottoming, Blowjob, Fingering, Frottage (Sort Of), Creampie
Dean’s known you for a couple years, you're a friend of his dad’s and a fellow hunter. You became his mentor in place of his father, who often hunted on his own and left Dean in your care. You liked to stay in your state since the area was basically a supernatural magnet while his father preferred to travel the country so he chose you to finally allow Dean to stay in one place for more than a week. If you were anybody else, Dean would've been annoyed that his dad didn't take him along despite his age and experience. Instead of going to college, Dean spent those years learning to hunt with his father and mostly you. Thanks to all the time you spend with each other, his allegiance to you is almost stronger than his allegiance to his father. He hangs on your every word and treats you like a god. It's thanks to you that he finally accepted his bisexuality. But he doesn't want to tell you that.
He first started feeling differently towards you when you started to become more physical with him. You often hold onto his shoulder with your strong hand or pull him out of the way by his waist and it drives him crazy. He so desperately wants to feel your hands on other parts of his body and vice versa. Your voice makes him weak in the knees and you sound especially attractive when you've found your prey. You're much older than him but he can't get rid of his feelings for you. He tries his best to be content with just having a crush.
After you two had dinner, you decided to drink with him. The two of you laughed and talked over a few cans of beer and deepened your relationship further.
“You ever been in a relationship, [Name]?” Dean asks, slightly tipsy.
“A few. I mostly slept around in my college years and experimented a bit with other hunters but in the end I decided to marry my job instead.”
“Why?”
“I wanted to marry someone I could tell everything to so I tried dating within my circle but none of the hunters seemed to click with me in the ways that really matter.”
“That makes sense…then you probably haven't…” He trails off.
“I probably haven't what?”
“Had sex…lately……”
You laugh. “No, I haven't. Honestly, I think getting laid would really help me. It's been a rough couple weeks.”
“I…” Dean gulps. “I could help with that….if you don't mind…….being with a guy..”
You look at him in surprise. “You're drunk.”
“I’ve only had two cans and a half…You know I don't get drunk that fast.”
You look at him differently, no longer with the eyes of a mentor. “You’ll bottom?”
Dean nods.
You smile in amusement. “I might be a little rough, can you handle that?”
He nods again, more enthusiastically this time.
“Come here.” You motion for him to come over to your side of the table. He stands in front of you. “Kneel.” You order. Dean immediately kneels, his cock steadily growing in size. You unbuckle your belt and pull down your underwear. Dean stares at your cock in awe, body heating up as he watches you jerk it to its true size.
“Fuck. You’re big.” He breathes out.
“Too big?”
“I can handle it.” He says, licking his lips.
“Attaboy.” You run your hands through his hair. Dean blushes. “Ever done this before?”
“Never..” His eyes are trained on your length.
“Is this your first time with a man?”
“Yeah…”
Your gaze changes. Dean shivers in arousal. “How long have you wanted this?”
“A long time…I’ve been…fingering myself, in case we….” He looks away.
You grin, turned on by the thought of that. “You'll have to show me that some day.”
Dean’s face gets redder.
“Now, let me see how you suck cock.”
He's so hard right now. He opens his mouth and slowly swallows your length. He makes a dragged out moan in pleasure as he feels your thickness enter him. Pre cum leaks out of his cock as he imagines how it’ll feel in his ass. He bobs his head up and down enthusiastically, mimicking his past girlfriends by simultaneously swirling his tongue around your shaft.
“Fuck–” You moan. “That's it– good boy.”
Words can't express how happy Dean gets when you praise him.
“You're better at this than I expected, baby.” You smile at his cuteness. He can't hide how pleased he is. “You like sucking dick, don't you? I never thought you’d be a cock slut, Dean.”
He moans. He’ll happily be your cock slut. He pulls away and licks your length in a very sexy way, gaining more confidence thanks to his elevated horniess. “I love your cock, sir.”
“Of course, you’re my cock slut.” You press your hand against his cheek. “Stand up and take your clothes off, I wanna use your other hole.”
Dean’s cock throbs even more. He stands up and quickly removes his clothes, shivering under your hungry and lustful gaze. You pat your lap and he quickly sits on top of you, your shafts pressed against each other.
You grope his ass. “I don’t have any lube..” You trail off, mesmerized by his soft butt.
“I already fingered myself earlier.” He smiles.
“Good boy.” You praise him. “Then spit’ll be enough. Say ‘ah’.” You bring two fingers into Dean’s mouth. He sucks on your fingers in the sluttiest way he can before you take them out and gently push one of your saliva covered fingers inside his soft hole. You give him a moment before adding the second, then you start to finger him.
Dean lets out the prettiest moan you’ve ever heard. “[Name]~” He arches his back and subconsciously thrusts his hips, his cock rubbing against yours. “Your- yours feel so- fuck~” He groans. “So much better!”
You moan as well thanks to the sudden friction. You bring him into a sloppy kiss, the temperature between the two of you steadily rising. Dean pulls away first, more desperate for air, and presses his forehead against your shoulder. “Don't stop– mm- gonna come~” He whimpers. Your fingers find his prostate, an immediate gasp of pleasure leaving Dean’s lips. He throws his head back. “There! Yes!” He moans, grinding against your cock even faster. The combination of his moans, his expression, and his cock against yours all contribute to bringing you to closer your orgasm.
Dean comes first, cum splattering over the two of you. Yours comes second thanks to the amazing look on Dean’s face.
“You're so fucking sexy, Dean, you know that?” You take your fingers out and knead his ass.
“I know.” He gives you a kiss. “I want you inside me.”
You lift Dean up and slowly lower him down on your cock. You both let out noises of pleasure as you penetrate him. He bites down on his lip, thoroughly enjoying the feeling of his ass stretching to accommodate your girth. Once you bottom out, you give him time to get used to it. “Your cunt feels fucking amazing.” You groan. It's hard to hold yourself back but thankfully for you, Dean has no intention of waiting any longer. He places his hands on your shoulders and starts riding you. He quickly loses his momentum as the pleasure begins to overwhelm him. You help him out by grabbing his waist and doing the work for him, allowing Dean to fully enjoy himself.
He knew anal sex would feel good, especially because it's anal sex with you, but he never really had an idea of how good it’d feel until now. Now he's completely blissed out and only able to moan like a slut. It's especially thanks to your quick and rough speed that he's unable to think properly. You couldn't get yourself to go slower even if you tried. His ass just feels way too good.
“Your ass is perfect, Dean–” You groan. “So fucking good-” You hold him and stand up then gently place him on the table after clearing it of the empty cans. You rut into him like a monster, so horny that you feel like you could fuck him all night. You can never get enough of him.
Dean arches his back and shakes as ropes of cum spurt out of his dick. You know you should stop, or at least slow down, but you can't. “‘M sorry baby, fuck–” You moan, hanging your head low as you find your orgasm approaching. “‘M gonna come inside, okay? Gonna fill up your tight fucking cunt with my seed–”
Dean’s conscious enough to understand you. “Ye- yes!” He grins. He's been wanting to know what it feels like to get creampied. “Co- come inside!”
Encouraged by his words, you spill your cum into his warm and welcoming hole. Your thrusts come to a stop and the two of you start to catch your breaths.
“That…was so fucking good.” Dean says, leaning back.
A Stray Mutt
Sub!Bottom!FTM Dean x Dom!Top!Hunter!Male Reader
☆ Word Count: 3,706 ☆
Dean goes through some rough training sessions to become the perfect dog for you
AFAB Language Used | [Kinktober Request]
This one was so fun to write
CW: Non-Con AND CNC, Masochist!Dean, Abuse, Age Gap, Daddy Kink, Drugging, Blood and Injury, Oral Sex, Virginity Loss, Cum Swallowing, Rough + Painful Sex, Choking, Masturbation, Creampie, Spanking
“If you keep fucking up like this, I’ll kick you out.” You push Dean up against the wall, choking him with a firm grip. “I’m losing patience with you.”
You were in the midst of pursuing the dangerous monster that killed one of your friends a few months ago, it escaped the first time and second time because of Dean. During missions, he doesn't listen to anyone but himself, whatever his father taught him before his death, and the things you taught him. Emphasis on the things you taught. He often goes rogue and does whatever he thinks is best instead of listening to you or anyone else. It really only happens when you're working in a group though. When it's just you and him he acts like a loyal dog but with everyone else, he's a mutt.
Funnily enough, you met him on a rainy night and he looked just like a wet puppy that lost its home. He was covered in bruises and blood but you could tell most of that blood wasn't his. He was slouching on a park bench and fumbling with a roll of gauze.
“Werewolf, right?” Your strong voice snapped him out of his focus. His head shot up to look at you. He didn't look confused or put off, he instead had curiosity and hope painted on his face. He could tell by your clothing and equipment that you were a hunter. Not an animal hunter but a real hunter. One with experience and strength. “The moon won't stay too long. Where did you last see it?”
Dean gave you directions and stumbled to his feet to follow you. “You can come with me but don't get involved. I don’t want to carry you home.”
His heart was pounding. Home. He hadn't had a home in months. “I have silver bullets-" He reached into his pocket.
“Don't bother, my gun is already loaded. Keep them for yourself.” You shook your head. “You didn't get bit, did you?”
“No, it didn't scratch me either.”
“Good. John told me to take care of you from now on but I won’t force you to stay with me.” You handed him a letter. “He's dead, isn't he?”
“He is.” Dean gulped as he unfolded the paper. His father knew he wouldn't survive and mailed this to you. He included a somewhat recent picture of Dean so you could tell who he was. That's why he told Dean to stay in this town for a couple months. He gave him more than enough money to pay for his motel room and food. Dean figured that John intended for you to help carry out the revenge the two of them have been trying to enact for all these years. Dean was only 19 when he saw his father die in front of his eyes, he was mature enough to admit that there was no way he would've been able to keep going on his own.
“I know he taught you well so if you want to stay, I’ll take you under my wing.” You suddenly halted your movements. You raised your finger to wordlessly tell Dean to stay quiet. Then within minutes, you were able to further weaken and kill the werewolf. Of course, it was made easier by Dean’s previous efforts and you made sure to let him know that.
From that moment on, you were Dean’s idol. You gave him the comfort and love he needed while he was grieving and you gave him confidence with your strength. He's attached to you like velcro. However, he's still too independent and defiant, which often results in outcomes like this. It doesn't help that when he sees a supernatural creature he gets too angry to think straight. He wants to kill them all and that desire frequently takes precedent over everything else. You eventually lost patience with him and got more rough with your discipline.
“Please– I–” His voice is cracking. Your grip is too strong for him to speak properly.
“Since you keep acting like a wild dog, I’ll treat you like one.” You let go of his throat. “Kneel.”
“I’m sorry, I—”
“Kneel, mutt.”
Dean shakily gets down on his knees. He looks up at you with curiosity and fear as you reach into your bag.
“I never planned to use this on one of my own but I don't have a choice. You won't learn unless it's rough.” You pry open his bottom lip. He swallows the small amount of liquid in the bottle you’re holding even though he doesn't know what it is. He trusts you. “Why is that when we're alone, you're good? How am I supposed to punish you if you act like a damn angel?”
“The…they just make me so angry..” Dean feels himself getting lightheaded.
“You're not the only one. It's not an excuse.” You unbuckle your belt.
“What is this?” Dean asks, his head swaying a bit to the side.
“It's a drug. Don't worry, you’ll stay awake. I just don't want you biting me.”
Dean quickly understands what you mean as you pull down your underwear. “Sir..” He gets interrupted by your thick cock in his mouth. You grab his hair and fuck his throat. He looks at you pathetically with tears welling up in his eyes. Just seeing your quick and rough thrusts is making him dizzy. His mouth hurts from how wide it has to open for you.
“From now on, this is how I’ll be punishing you so you better start behaving yourself if you don't want me to keep fucking your throat.” You groan in pleasure. “Shit, ‘s like your mouth was made to take my cock.”
Dean’s body reacts strangely well to your words. He won't acknowledge it though.
“If you get any worse, I might just use your ass too. Bet it feels even better down there.” You pull on his hair to lift his head. You slowly reel back and stop before pulling out so you can rest your cock on his tongue, like a doctor telling their patient to say ‘ahh’ as they give them a routine checkup. “Make sure to swallow it.” You drag his head back and forth before coming down his throat. You pause to make sure he swallows it then pull out.
Dean coughs as he struggles to breathe normally again. His mouth and throat hurt, along with the other parts of his body from when you used your hands and boots to discipline him earlier. “Sorry…I’m sorry..” His voice is hoarse. He reaches for his neck. He can still feel your hand around it.
You scoff, pulling up your pants. “Then act like it. You're gonna stay here until I catch that freak. Understood?”
“Yes, sir.” Dean tries to stand up but his body is too weak from everything you did to him.
“It’s daddy when we're alone.” You grab him by the collar of his shirt and drop his body onto the couch. “I have to go. It should wear off in an hour or so.”
Dean closes his eyes, listening to your heavy footsteps as you leave the house you're both staying in. You have a lot of connections and money, allowing you to own and rent houses all over the country so you can hunt without worrying about fees and complaints. You're pretty much the hunting equivalent of a mafia boss, which is why Dean likes you so much. You know what you're doing and you have a genuine shot at helping him kill Lucifer. So despite all the abuse, he's not going to leave any time soon.
He lets out a shaky breath as he unzips his jeans and pulls them off for the sake of being comfortable. He tosses them to the ground. He doesn't know how to feel or why he feels what he currently does. Nor does he know why his hand is sliding down his boxers or why its destination is his throbbing hard t-cock but he won't try to figure it out. He just wants the feeling to stop, so he's dealing with it. Physically, that is.
He touches the red marking on his throat. You're so strong. He's sure you could've snapped him in half if you wanted to. Considering how big your dick is, you probably could in a more figurative sense. Dean moans with a little noise of pain following afterward. The drug dulled his pain just enough to make him forget that you almost broke his left wrist while you were dragging him here. He remembers now that he's using it but he doesn't switch to his other hand. He likes that it hurts, that you can make it hurt this much without even straining yourself, that the pain you just inflicted will last days so he’ll have the constant reminder of what you can do to him and a warning that you can do much worse.
Of course, Dean won't acknowledge that.
“Daddy..” He gasps and raises his hips as he orgasms. He feels…he wants to feel gross. He's decided that he feels gross instead of admitting that he wants you to come back and use him however you want. He shakily gets up and stumbles to the bathroom, removing his clothes on the way to leave a paper trail. A viable excuse for why his jeans were thrown in the living room so that you think he was just trying to take a shower as fast as possible and not that he jerked off. It's a preventative measure, in case this shower takes up all his energy. Masturbating definitely made that more likely.
He just hopes he can get back on his feet before his favorite burger joint closes. Maybe he’ll find a pretty girl to flirt with and forget about how much he enjoyed what just happened.
“Get up.” You kick the frame of Dean's bed, shaking him awake.
He can smell the familiar scent of a bacon cheeseburger and he can hear the clanking of glass, one is placed on his bedside table. It's gotta be beer. He shoots up in bed. “Oh my god.” He practically moans at the bag that contains the burger. The bag itself is enough to make his mouth water, as if it hadn't been already.
“Take it.” You shove the bag in his face while reaching into your pocket.
“Thank you!” He's already forgotten what happened earlier.
“I’m gonna be training you tomorrow afternoon so make sure you eat breakfast too.” You place a couple bills on the table at a safe distance from the beer to protect them from its condensation. “I didn't think I had to until today.” You shake your head.
“You're not– mmffh-” He can't stop himself from digging in. “Staying?”
“You really are a dog.” You scoff. “I have to meet up with the group to debrief them so they can fix your mistake.”
“Sorry.” He apologizes again. You're sure there isn't a single person who’s heard him say that so frequently and genuinely in a single day.
“Just get your energy back up.” You leave.
“Now sit.” You raise your hand, using the same gesture a dog trainer would use. Dean kneels down in front of you. You’ve been training him for a few hours now with your final lesson being focused on commands. You expect Dean to be able to understand your gestures without speaking, it’ll make things easier while you're hunting when you have to be cautious of sound. Everyone on the team is already able to do that, with different gestures of course, but Dean never bothered to learn from them. He barely even listens when they talk. How’s he supposed to take them seriously when you're obviously better off on your own? Their only use is to make things more convenient for you, nothing more. He’s far more valuable to you than them.
“Good boy.” You unbuckle your belt.
Dean's body tingles with excitement. He swallows back the urge to drool. You might just be Pavlov himself.
“Don't bite or I’ll drug you again.” You grab his hair and shove your dick into his mouth. Dean looks up at you in awe and arousal. The way that you look at him makes his cunt throb with need. This time, he can't stop himself from imagining what it’d be like if you took another step. Maybe you’d use his thighs or just skip right to fucking him. You probably wouldn't even bother to prepare him and you’d barely have to anyway, he's sure he’d be more than wet enough to make your entrance easier. It would still hurt regardless and he’d love it. He wonders how you’d sound, what you’d say. Would you get addicted to him? He's sure he’ll become an even more valuable asset to you if you take that next step. He's a virgin but he has enough confidence to convince himself.
He wonders how many more times he needs to act up to reach that point. He can't lie to himself anymore, he wants it.
You grin at his reddening face. “Are you embarrassed, mutt?” You fuck his mouth more roughly. “As long as you keep doing well, I won't use your mouth in public after today.”
Part of him wants to be good for you and the other part wants to be bad. Maybe he can keep a steady balance between the two. He swallows your cum without even thinking about it.
“I’ll take you out for lunch. You deserve it for being such a good puppy.” You pull out of his mouth. His heart pounds at your words.
For the next couple of weeks, everyone who works under you has noticed a lot of changes in Dean. They've noticed that he's sharpened his skills and he's an even better shot than he was before. They've also noticed the bruises and red marks on his body. Once they found out you’ve been training him, they started to understand why and they never questioned how exactly you were training him. They know you're not a gentle person so it's only natural for Dean to bear the markings of your discipline. They have no idea that whenever he shows up with a dreamy look on his face it means that he just got done swallowing multiple loads of your cum, sometimes after being on the verge of passing out.
Whenever you weren't available, you’d send Dean out on his own to complete jobs in your stead. He always did well on those missions but there was one particularly difficult job that required the participation of everyone who was available. You trusted him to be good but he failed and now he's experiencing the consequences.
Dean looks up at you with tears in his eyes. His hair is messy and his mouth is full of your cock. “You keep fucking up because of your pride. I must not have been doing a good job in training you.” You pull him off of your cock. He's breathing heavily.
“No– I—”
“I didn't give you permission to speak, mutt.” You slap him. “I’ll have to change tactics. Get down and raise your ass.”
“Wait-”
You slap him again. “Now.”
His body is shaking as he changes his position. He presses his chest against the cold wood floor while raising his ass in the air. He gulps when he feels your hands undoing his jeans and pulling them down.
“Despite all your flaws, you do have a pretty nice body.” You spank him. Dean lets out a sudden gasp.
“You're—”
You spank him again. “What did I tell you, mutt? This is what I’m talking about. You never learn.” You pull his underwear down next. He shudders at the sound of you whistling. “I don't know if I’ll let you hunt anymore. Might just keep you—”
“No!” He shouts. “I- I’m sorry!” He turns his head to look at you. “Please! I won't do it again!” You're the only person who gets to see him looking this pathetic.
“If you want to hunt so badly, why can't you follow orders like everybody else? I knew I shouldn't have let you go on that mission with them. You're too fucking conceited to work with anyone.” You give him another sharp spank, making his skin turn a bright red. “I thought you were getting better. I can't believe I actually trusted you.”
Dean whimpers. He didn't want to disappoint you. He didn't fail on purpose but you won't listen to anything he has to say and he's not sure he’d want you to anyway. “I’m sorry.”
“I won't dull your fangs as long as you act like a good pup from now on.” You shift targets and spank his pussy. Dean whimpers. You gently grope his ass. “You understand what that means, right?”
“Ye- yes, daddy..”
You rub your dick along his pussy. “You're my favorite, you know. Even though you're a pain in the ass.”
He knows. You liked him from the start and you used to be pretty nice to him. Stern, but nice. The only reason he hasn't left, at least to your knowledge, is because you're the only person he knows who can help him. You’ve also encountered Lucifer and you've been on the hunt for him too.
Dean bites down on his lip as he feels the tip of your cock teasing its entrance. “Wait!”
“What?” You furrow your eyebrows.
“condom…” He mumbles. He doesn't really want you to wear one but tonight, he’d rather lean towards being a mutt rather than a puppy so you have a reason to be rough with him.
“Don't worry, puppy. I’ll make sure you're neutered next time.” You force your cock inside him. “You're so tight. Anyone ever told you how good you feel?” You groan.
“No- no, daddy.”
“How come? If I were a stranger, I’d pay billions to be inside you.”
Dean's face is completely red. “I was a virgin-” He lets out a pained whine.
“Oh yeah? Is my cock the first one you’ve ever sucked too?”
“Yes..” He still thinks about that day. He barely ever goes a week without jerking off to that memory.
“I’m honored.” You run your hand down his back as you ruthlessly thrust yourself inside him. “You know, I wouldn't be doing this if you just did what you're supposed to. Even though I’d still want to.”
Dean sniffles. That's why he keeps acting out. He knows you only used his behavior as an excuse to fuck him and he loves how forceful you are. He keeps doing whatever necessary to feel your hands on his body without actually asking for it. He needed to know what it would feel like when you finally reached this point, when you finally went all the way. But he didn't mean for this to happen today. He knows how important this job was to you. Part of him is excited and the other half is sorrowful.
“You're lucky I like your body. Otherwise you wouldn't even be here at all.”
He sniffles again as tears well up in his eyes. He hadn't cried in years before he met you. You make him feel weak and he knows that turns you on. You like when he's vulnerable, when he doesn't bare his fangs and attack, so he won't pretend to be tough.
Everyone knows you punish him thanks to the mark around his throat, it always gets more obvious after he fucks up. He never hides it nor do you tell him to. He likes to stare at it in the mirror and while thinking about you, how it almost never fades, and how he can never go a week without you roughly disciplining him. His pussy would throb as he observed it and sometimes he'd touch himself while imitating your hand around his neck. He didn't want to admit it at first but it was too difficult for him to not acknowledge the way he felt, physically and mentally.
Especially now with your cock so far inside him, it's impossible to ignore it. Your thickness and your aggression are sending constant chills down his body. Knowing that you're completely in control, that everything is up to you, makes him so fucking horny. “Daddy~” His voice is scratchy.
“Aw, does it hurt, puppy?” You fake sympathy, slowly pulling out. You see your cock coated in a layer of blood and lick your lips. He lets out a soft mewl. “It's supposed to.” You thrust into him, gripping his hair as you roughly drill into his pussy.
Dean cries out in pain. His moans are whiny and loud.
“If this doesn't get you to submit, I don't know what will.” You groan.
Something in his brain just wants you to break him over and over again. Harder. Rougher. Force him to take your cock until he can't do anything else. He's starting to forget why he's in this situation at all.
“You know what? I think I’ll keep fucking this tight pussy of yours regardless, Dean.” You spank his ass once again. “Does that scare you, puppy? Are you afraid of getting addicted to daddy’s cock inside you?”
He only responds with sexy noises.
“No? You want daddy to keep using your pussy? Say it.” You tug on his hair for emphasis.
“I– I want daddy to kee~ keep using uhn~! my pussy~!” Dean’s eyes twitch as he feels his orgasm approaching. Drool dribbles down his chin as he finds himself unable to keep his mouth closed.
“Attaboy.” You unload into his cunt. Dean’s eyes flutter closed as he comes. “You're the best cum dump I've ever had, Dean.”
He watches your boots as they carry you out of the room, each footstep reminds him of how little you care for him. He's only your cum dump and your punching bag, nothing more. He feels his pussy flexing its walls in desperation for your cock to return to its rightful place. He wants more but he knows he doesn't deserve to be given what he wants.
His vision slowly blurs until he goes unconscious.
IM CRYİNG
Off Limits
$ log - dean winchester's not supposed to crave you like this — to the point his pussy aches at the sight of you. you're bobby's best friend, you're double his age, probably even slain thousands of demons compared to dear ol' dean. so, when the opportunity spreads itself wide in front of him, boy does he hang onto it tight like a fucking vice. $ warn --nsfw --dark(mild) --dubcon(light, at end) --older!amab!reader --dom!top!reader --mean!reader --afab!dean --sub!bot!dean --age-gap(older man/younger man) --wet-dream --masturbation --prep(heavy) --praise --condescending --degradation --humiliation --fingering(vag) --impact-play(spanking) --size-diff-kink --anal(mentioned) --mirror-sex(light) --positions(reverse cowgirl, doggy) --p-in-v --dirty-talk --dumbification --orgasm control(overstim) --clit-play --pussyjob --thigh-grinding --begging --dacryphilia --creampie --rough --somno(hinted) $ wc -w 7.2k $ cd masterlist / dean-winchester # authors-note = the demon of crude, mean sex possessed me while writing this # note = dad's bsf!reader, but like you're bobby's bsf here. heavy unresolved sexual tension. he's fucked to passing out.
You’ve been a fixture in the hunting world for as long as Bobby can remember, a seasoned veteran whose reputation for grit and wisdom precedes you.
When you’re called in to help the Winchesters with a particularly nasty case, your presence brings a heavy, grounded authority to Bobby’s place. Sam’s immediately drawn to your expertise, eager to soak every bit of hunting knowledge you have to offer. But Dean?
Dean’s struggling to even breathe.
He watches you move with a calm confidence and his pussy actually pulses. Every time you walk into a room, the air feels thicker, and he can feel that familiar, humiliating heat pooling between his legs, his pussy getting ridiculously wet from just the sight of you.
During hunts, you offer brief commendations with a hand on his shoulder or a simple good work on that trap that sends jolts of electricity straight down his spine.
You drink heavily and smoke long into the night, but unlike John, you carry your strength with a lazy grace that never turns into anger. Seeing you laugh with Bobby makes him crave the heated stability.
Sometimes, Dean finds himself staring, unable to look away from the way your jeans, staring against the heavy, unmistakable bulge of your cock, a silent promise of the size he knows he needs.
The darkness of the room was suffocating, thick with the scent of old wood and Dean’s own frantic arousal. He lay sprawled on the mattress, his body trembling with a need so sharp it felt like a physical wound. His fingers were slick, sliding deep into his needy pussy with a desperate friction, while his other hand slapped hard against his own jaw, trying to sting himself into silence.
“Fuck — please — ” he mewled a tiny sound, before swallowing it back.
Every time a quiet, broken moan escaped his lips, he froze, heart hammering against his ribs — absolutely terrified that Sam or Bobby would hear the sound of him unravelling late at night.
Then, the fantasy took over, pulling him under like a tide. Suddenly, he wasn’t alone. The scent of leather and stale smoke overwhelmed his scenes, while all he felt was the unyielding weight of you crushing him into the cushions. His legs were shoved wide and his back curved as you hovered over him.
“That’s it, Dean,” your voice rumbled in his ear, low and commanding. “Take it all. You’re so fucking greedy for it, aren’t ya?”
Then, the phantom sensation of your cock hit him thick, hot, and unyielding, driving straight into his messy, overstimulated pussy. He let out a choked sob real-time, his hips jerking upwards to meet the imagined thrusts.
“God, you’re so wet f’me,” you murmured, voice a rough vibration against his skin. “Wrap those legs around me, take it all, Dean — show me how much you want it —”
His fantasy seemed to reach its peak in tempo, followed by a white-hot sensation that sent Dean over the edge.
Back straining off the sheets, he buckled hard as he orgasms — a silent, shaking mess in the dark. He buried his pace into the pillow to muffle the desperate, broken cries of your name, his heart was a frantic patter against his ribs.
“Fuck — you're —,” he gasped with a trembling whisper as he lay there in the cooling dark, trembling and spent from the illusory feeling of your weight. That soothing voice was still echoing in his mind, leaving him more desperate for the real thing than he’d ever been in his entire life.
Minutes later, Dean stumbled towards the bathroom, his legs feeling like jelly and his skin still flushed from the friction. He cleaned himself up with the cool water doing little to dampen the remaining pleasurable sensation of you. He felt wrecked, a shivering version of himself, desperately trying to pull his composure back together before the sun came up.
Thirsty and feeling the post orgasmic ache in his core, he crept down towards the kitchen, hoping to grab a glass of water without making a sound. But as he rounded the corner, the sight of you stopped him dead in his tracks.
You were sitting on the couch, a half finished whiskey in your hand, a stack of lore books spread out on the coffee table in front of you. The low light of the lamp casting long shadows across your face, making you look even more formidable, even more grounded.
“Can’t sleep?”
The question came in that same coarse rumble that had been haunting his dreams only minutes before. Dean felt his knees actually weaken — a traitorous heat instantly blooming at his clit as if he hadn’t just finished coming to the thought of you. He had to physically grip the doorframe to keep from swaying.
“Nah,” he managed, forcing his voice to stay steady, though it came out a fraction higher than usual. He plastered on his best ‘tough guy’ nonchalance, leaning against the wall with a practise ease that felt entirely fake, “Just… thirsty. Brain won’t shut up, ya know?”
He kept his eyes averted, terrified that if he looked at you too long, he’d lose his fucking mind. But, he could feel the heat of your gaze on him, a heavy masculine weight that made his skin prickle. He focused intensely on a random spot on the floor.
“I hear that,” you replied before taking a slow sip of your drink, the movement effortless. “Sometimes the world’s too loud, even when it’s quiet.”
Dean nodded, a very jerky and unconvincing movement. “Yeah, tell me about it.”
He finally risked a singular glance at you, and his heart nearly stopped. You were looking at him, your expression unreadable, but your eyes sharp. It’s as if you could see right through his ‘tough guy’ facade and straight into the trembling mess.
You set the whiskey down, your gaze softening with a genuine, steady warmth that only makes his heart hammer harder. “What’s going on, Dean?” you ask, voice dropping into a comforting register. “You know you can talk to me about anything, sport. Whatever’s on your mind — I’ll help.”
Sport.
The term of casual, masculine endearment hits him like a physical blow, that makes his pussy throb with a sudden, shameful ache.
How the fuck am I supposed to tell you that?
He wants to scream it. He wants to grab the front of your shirt, pull your frame down until your lips are inches from his and tell you that the only thing keeping him sane is the desperate, pulsing need to feel you inside him. He doesn’t want you to just be a listening ear; he wants you to act on your words firmly too.
Ugh, fuck.
He needs your calloused hands pinning his wrists or your thick fingers stretching him wide till he sobs — or better yet, your heavy cock driving into his weeping pussy till his brain’s fucking empty. The ache is getting unbearable by each grovelling minute. It’s a heavy, wet throb that him want to sink to his knees right there on the kitchen linoleum. He needs the pressure, the weight, the stable masculinity.
He needs you to stop being his “mentor” and start being the person who ruins him.
“Just… thinking about the case,” Dean lies, the words feeling like ash in his mouth. He forces a lopsided, cocky grin — the kind he’s used a thousand times to hide the fact that he’s falling apart.
Unfortunately his eyes betray him. Pining green lingers a second too long on the way your throat moves when you swallow or the way your large hands were splayed upon the case studies.
“The case can wait ‘til morning, Dean. You look like you’re wound tighter than a guitar string.” You chuckle while gesturing to the empty spot on the couch beside you, “Sit, drink your water — you’re pacing like a caged animal.”
Dean hesitates, his heart performing a frantic drumroll against his ribs. He should go back to his room, back to the safety of his blankets and his lonely aching silence.
But the pull of your presence is too fucking strong.
With stiff movements, he moves towards the couch, trying to mask the way his thighs rub together with every step. He sinks into the cushion beside you, careful to leave a respectful distance — though every instinct in his body is screaming at him to close the gap.
“Yeah, well, the Winchester brain never really shuts off right?” he says, as he takes some heavy sips of his water.
As he drinks, he can’t help — he really can’t help — but steal a glance at you.
Composed and steady, you’re leaning back with the lamp light catching the rugged lines of your face. You look so damn comfortable, so entirely in control of yourself, while he feels like he’s one second away from shattering.
The silence between you stretches thick with everything he isn’t saying. He sets the glass down, his knuckles white as he grips the cushion’s edge. He’s trying to play it cool, trying to be the legendary hunter, but the heat radiating from your body is making it impossible to focus on anything but the proximity of your thigh to his.
“You’re a terrible liar, Dean,” you say softly, not even looking up from your book, though the corner of your mouth twitches with a knowing smirk.
He stiffens, a flush creeping up his neck. “Yeah? And since when did you become an expert on me?”
“Since you started looking at me like you’re starving — and I haven’t even fed you yet?”
The sheer audacity of the comment leaves him breathless. Dean opens his mouth to snap back a witty retort, but the words die in his throat.
You don’t even look up from the page as you reach out, your large hand landing on his thigh. You don’t move it far, but the stable heat was enough to make his breath hitch. His reaction is instinctive. His legs don’t move nor straddle; they widen, his knees falling open in a silent, desperate invitation that he can’t control.
Then, your hand shifts.
Your fingers slide upward, moving with a terrifying, calm precision. Because he was so frantic to get back to bed, he hadn't even pulled his boxers back up, leaving himself completely exposed to the cool air and your sudden touch.
Your digits find the wet heat of his bare pussy, grazing a stripe of his labia, your blunt fingertips catching on the sensitive flesh. Dean lets out a strangled, high pitched gasp, his entire body jolting as if he’d been struck by lightning. He tries to pull his legs back together — to hide the evidence of his shame — but your hand is a heavy anchor, holding him wide and vulnerable.
You finally shift your gaze from the book, your eyes dark and knowing as they land on his flushed, trembling face. You don't pull your hand away; instead, you press a little deeper, your finger curling slightly into his wetness.
"You're soaking," you murmur, your voice a low, dangerous rumble that vibrates right through him. A smirk tugs at the corner of your mouth. "Naughty boy, been watching some porn late at night?"
"I — it's not — " Dean stammers, his cocky facade completely demolished. He's staring at you, his eyes wide and glazed with terror and lust. He looks like a man caught red-handed, his chest heaving as he tries to find a lie that doesn't sound pathetic.
"It's not — it's not like that," he breathes, though the way his hips instinctively tilt toward your hand tells a completely different story.
You let out a low chuckle, finally closing the book and setting it aside. You don't pull your hand back; instead, you increase the pressure, your thumb beginning to grind slow, heavy circles against his clit, catching on the wetness he's been producing all night.
"Then what is it, Dean?" you demand, your voice dropping an octave, becoming that commanding tone that makes his insides melt. "Because you're dripping all over my hand, and you're shaking like you're waiting for me to do something about it?"
Dean can't even find the breath to argue. His head falls back against the couch cushion, his eyes fluttering shut as he lets out a broken, needy whine. The sensation of your thumb grinding against his clit is too much; it’s the exact friction he’d been trying to mimic with his own fingers in the dark, but your hand is larger, heavier, and infinitely more authoritative.
"Please —" he whimpers, the word slipping out before he can censor it. He doesn't even know what he's asking for. More pressure? More fingers, or the real thing he just knows the ache in his pussy is screaming for relief?
You lean in closer, your shadow swallowing him whole. The scent of your skin, mixed with the faint aroma of alcohol and tobacco, wraps around him like a physical weight.
"Please what, Dean?" you murmur against the shell of his ear, your warm breath hot against his skin. "You want me to stop — or do you want me to show you exactly what you were dreaming about?"
Dean's eyes snap open, glazed and unfocused, as he lets out a shuddering breath. He can't even lie anymore; the truth is written in the way his hips buck weakly against your hand, seeking more of that brutal, grounding pressure.
"Don't stop," he chokes out, his voice a mere thread of sound, stripped of all its usual bravado. "Please — don't stop."
You grin, a slow, predatory curve of your lips, as you slide a second finger deep into his tight, pulsing heat. The sudden fullness makes him cry out, a sharp, needy sound that echoes in the quiet kitchen, but you don't let him recover. You start to move, your fingers working with a rhythmic, punishing pace that drives him straight back toward the breadth of you.
You haul him up effortlessly, dragging his body until he's straddling your massive thigh, his back pressed flush against your chest. Your left hand fists in his hair before sliding down to grip his jaw, tilting his face at a sharp angle. You press your lips to his in a bruising, demanding kiss, then abruptly yank his head to the side, holding him there so he can feel your breath against his ear.
"Look at you," you murmur, your voice a controlled, gravelly purr. "You're fucking soaking, Dean. Every time I move my fingers, you squelch. Tell me truthfully, have you been touching yourself like this all night?”
Dean swallows hard, his throat working against your grip. "No," he gasps out, the lie tasting bitter even as his hips betray him by grinding harder against your palm. "Just, some lousy porn — nothing else."
You don't call him out immediately. Instead, you let the silence stretch, the only sound is the wet, rhythmic slap of your fingers working inside him.
In the corner of the room, Dean's eyes catch your reflection in the dusty mirror. The sight of himself completely exposed, helpless, and being handled like a toy sends a fresh wave of shame and arousal crashing through him. He knows he's lying; he knows you can see every tremor in his body. But he can't stop looking.
His gaze drops down the mirror's reflection, trailing past your broad shoulder to where your hand is buried between his thighs. He watches as your fingers disappear into his slick folds, working with a ruthless efficiency that makes his vision blur.
In the mirror, he sees your thumb hook under the sensitive edge of his flesh, pulling his labia wide to expose the raw, swollen pink of his entrance.
"Look at that," you murmur against his ear, your breath hot enough to scald. "Look how fucking open you are for me. Look at how you're begging for it."
Dean's breath hitches as he stares at the reflection. Seeing it from the outside — seeing how your thick fingers stretch him apart — how his own pussy glistens and pulses around your knuckles makes the reality of his degradation hit him like a freight train.
"Fuck," he chokes out, his forehead dropping against your shoulder as his hips buck involuntarily. "Fuck, please — please!"
"Shhh, easy now, Dean," you coo, your voice dripping with that infuriatingly calm, patronising affection. You sound less like a lover and more like someone soothing a needy puppy — which only makes his blood boil and his pussy clench tighter. "There we go. Just let it happen, don't fight it."
You pick up the pace, your fingers working with a cruel, precise rhythm that targets every nerve ending he has. Dean's hips buck violently against your thigh, his back arching until his spine cracks audibly.
A wrecked, high pitched keen tears from his throat as his orgasm hits sudden and overwhelming. His body shudders uncontrollably as he spills over your fingers, his vision swimming behind closed eyelids.
But you don't slow down. You don't let him collapse into the afterglow. The moment his tremors begin to subside, you immediately resume the punishing stroke.
Dean gasps, his eyes snapping open in genuine shock.
"Wait fuck no, I can't — " His voice breaks as he glances back at you over his shoulder, his expression one of pure bewilderment.
His brain is short circuiting; he knows he's already come multiple times tonight, alone in his bed, exhausted and desperate. His body should be spent, his nerves fried, but the way you're touching him the overwhelming authority of your hand is forcing new waves of arousal through him that shouldn't exist.
"What's wrong, champ?" you murmur, your thumb finding that sensitive spot again with unerring accuracy. You tighten your grip on his jaw, forcing him to meet your amused gaze. "Already spent? After all that lying?"
"I'm — I'm already —" he stammers, his hips jerking involuntarily as your thumb finds that perfect, swollen nerve again. "I can't — I'm already fucking empty, I swear to God — "
"Empty?" you interrupt, your chuckle dangerously as you lean closer, your lips brushing against his ear. "You don't know shit about being empty, Dean. You're just sensitive. Your body is still screaming for more."
You increase the pressure, your fingers sliding deeper, stretching him wider with each thrust. You're working him open, your blunt fingertips slick with his arousal as you relentlessly massage the walls of his pussy.
"If you want the real thing tonight, you need to be ready for it," you murmur, your voice dropping into something darker, more utilitarian. "You need to be loose — you need to be fucking dripping so I can slide right in without tearing you apart. Consider this an investment."
Dean's head lolls back against your shoulder, his breathing coming in shallow, confused pants. "An investment? What the fuck are you — "
His words die in his throat when he shifts slightly, his ass grinding against your thigh.
In that movement, he feels it: the unmistakable, rock hard ridge of your cock pressing through the denim of your jeans, poking insistently against the sensitive cleft of his ass. The heat of it radiates through his clothes, a promise of something far more devastating than your fingers.
The realisation hits him like a physical blow. You weren't just tormenting him for sport, nor were you being cruel. You were prepping him. Every punishing stroke, every forced climax, every stretch of his labia had been calculated to make his body surrender completely to what was coming next.
"Oh," he breathes, the syllable more of a whimper than a confession. His clit throbs painfully, slick with the evidence of his own undoing, while the hard bulge behind him promises a different kind of fullness entirely.
"Oh," he repeats, his eyes blown wide as they fix on your reflection in the mirror, seeing the way your erection strains against your jeans right where his ass meets your thigh. "Oh god," he chokes out, his hips stuttering in a helpless attempt to both escape and press closer.
"I'll pull one or two more orgasms out of you, Dean," you state plainly, your tone as matter of fact as if you were discussing the weather. "Maybe three, if you're as good as I think you are."
"No — fuck you, I can't — " Dean protests, his voice cracking as he tries to twist away from your relentless fingers. But there's nowhere to go.
Your body is a wall behind him, and your hand on his jaw is an iron vise that keeps him exactly where you want him. He can only squirm, his hips bucking uselessly against your thigh in a desperate, futile attempt to regain some semblance of control.
Smack!
The sound of your palm connecting with his jaw is sharp and startling in the quiet room. It isn't enough to hurt him, but it's firm enough to shock the protest right out of his lungs.
You hold his face steady, forcing him to meet your gaze. "Listen to me, Dean. What you see in those stupid fucking porn videos — that's all bullshit. Real sex requires preparation — and I'm the one teaching you how to actually handle it. You need to learn how to take this."
You lean in closer, your lips grazing his earlobe while your fingers work deeper, stretching his slick walls with increasing urgency. "Now, you're going to be a good boy and accept this. Say it, say you'll take whatever I give you."
"I — I won't —" Dean starts to protest, but you tighten your grip on his jaw, applying just enough pressure to remind him who holds the power here.
"Wrong answer," you command, your voice dropping to that stern register that leaves no room for argument. "I want to hear you say it properly, through every one of those pathetic little gasps."
Dean's body betrays him completely. His hips roll forward in a desperate, involuntary search for friction as your fingers stretch him to his limit. A broken, strangled noise escapes his throat as he finally surrenders to the authority in your voice.
"I'll — fuck — I'll take it," he manages to choke out, his words punctuated by sharp, hitched gasps that leave him panting. "I'll take — whatever you give me."
"Good boy," you murmur, the praise dripping with that same patronising satisfaction. You give his jaw one last firm squeeze before releasing him, though you don't pull away.
Instead, you let your hand slide down from his face to rest heavily on his chest, feeling the frantic, rabbit quick hammering of his heart beneath his ribs.
"See?" you whisper, your breath hot against his neck. "That wasn't so hard, was it? Now we know you're listening."
The room falls into a heavy, charged silence, broken only by the ragged sound of Dean's breathing. His body has finally gone boneless against you, his muscles twitching with the aftershocks of the orgasm you forced out of him. He drips freely, sending warm rivulets of cum down your thigh.
You withdraw your fingers slowly, the wet sound of your exit making him whimper. Without hesitation, you take those slick, swollen fingers and press them against his mouth.
He doesn't resist, leaning into the touch, his eyes rolling back as he begins to suckle on your fingers — tasting the salty, unmistakable evidence of himself. He heaves against your chest, his mouth working around your knuckles with a desperate, unconscious hunger, seeking comfort in the very thing that just broke him.
While he is momentarily occupied, lost in that haze of shame and sensory overload, you give him a moment to catch his breath against your shoulder. Your fingers slip free from his mouth, leaving him panting and dazed, but you don't release your hold on his waist. You keep him pinned against you, anchoring him while you shift to the next phase of your plan.
With one hand still possessively wrapped around his middle, you reach down with the other. Your movements are efficient, practiced, and utterly calm as you unbuckle your belt with a metallic click that sounds deafening in the quiet room.
You work the zipper down, and then, with a gradual motion, you free your aching cock from your jeans.
Dean's breath hitches audibly as he feels the sudden change in temperature and weight beneath him. He shifts his hips slightly, and his eyes go wide as he sees the thick size of you lying just beneath his thighs.
The heat coming off your cock is staggering, a physical force that makes his entire lower body tremble. His gaze drops to where your cock presses against his swollen pussy, already wet with the mess of his own orgasms.
"Oh god —" he murmurs, his voice barely a thread of sound, thick with awe and terror. "It's so — it's so big —"
He can feel the sheer girth of you spreading his folds apart even before you make contact. He's terrified of how much he wants it, terrified of how perfectly his body seems to be reaching for you despite the exhaustion still clinging to his limbs.
As you prepare to make your move, your hand dips into your pocket. The crinkle of plastic fills the space between you as you tear open a sachet.
Dean catches the sound, his eyes darting to the packet in your hand. A weak, self deprecating laugh escapes his lips — a pathetic attempt to reclaim some dignity through humor.
"You — you always carry lube around with you?" he manages to wheeze out, trying to sound teasing when his voice is clearly trembling.
"I was going to go out to the bar tonight," you reply, your tone casual, and utterly unbothered by his attempt at levity. "But then I heard your pretty little whines coming down the hallway." You let out a dark chuckle at the way his face instantly floods with a deep, mortified crimson. "Figured I'd come see what all the noise was about instead."
The implication hangs heavy in the air between you.
You begin to lather the sweet scented slick over your cock, the clear gel catching the dim light as you coat yourself from base to tip. Then, with deliberate slowness, you smear the rest over his dripping labia, ensuring every inch of his entrance is glistening and ready.
Even after the work you've put in, you can feel the resistance beneath your touch; despite the lube and his arousal, his body is still coiled tight.
"Your walls are quite thin, Dean," you murmur, watching how his pupils dilate at the implication.
His heart hammers against your chest. The realisation that you've been listening to him every desperate moan, every wet slap of his own hand against his thighs every single night since you arrived here threatens to overwhelm him. But there is no room for shame now.
His entire universe has shrunk down to the point of contact between his pussy and the massive heat between your cock and his pussy. He's too far gone, too consumed by the physical presence of you to even process the humiliation of being caught.
So, he gives a tentative, desperate grind, his hips rolling against your cock in a silent plea for friction.
You glance down at the sight of him in your lap, watching how his hips stutter against you. His desperate self is thinking exactly the right way. You can see it in the way he arches, seeking that contact, begging for the fullness he knows is coming. Good. You'll let him have this — you'll let him work for it, getting a job out of him first, letting him ride that slick heat until he's begging for mercy.
But you aren't planning on being gentle when you finally decide to fuck him mean. You've spent the last hour preparing him, stretching him, and breaking his resistance, all so you can fuck him without hesitation.
"Slow down, Dean. I told you we're still prepping."
You grip his hips with bruising force, your fingers digging into the soft flesh above his pelvic bones to anchor him. However, you don't let him sink down. You simply hold him just at the threshold, forcing him to hover there, suspended between desperate need and the agonising promise of fullness.
"But please — " Dean gasps, his voice breaking as he tries to push downward, his hips stuttering in an involuntary attempt to impale himself on your cock. "I need — I need you inside — fuck, please."
"I said slow," you growl, your voice dropping into that stern tone that brooks no argument. "You're still too tight. If I push you now, you'll tear, and I'm not interested in hearing you scream from pain instead of pleasure."
It's a lie, and his younger, desperate mind knows exactly what you're doing, but he's too far gone to care about the deception. He can feel the truth in the way your cock pulses against his pussy, teasing the very edge of his folds without giving him the release he's starving for.
"I'm not fucking you yet," you murmur, your breath hot against the nape of his neck as you begin to move him. "We're going to work this friction until you're completely slick, until you're begging me to ruin you."
Instead of pushing inside, you begin to guide his hips in a slow, punishing grind. You force him to slide his pussy along the entire length of your cock, but only on the outside.
You make sure his clit catches repeatedly against the sensitive ridge of you, the friction sending sparks of electricity straight to his brain. The wet, squelching sound of your cock sliding between his labia fills the room as fills the space between your bodies.
Every time he grinds down, you make sure he feels the full, unforgiving texture of your cock sliding between, never letting him slip past the entrance
You keep him exactly where you want him: hovering on the precipice of ecstasy, his pussy’s stretched taut and glistening with lube as it rubs relentlessly against you.
"Please, please, please —" Dean whines, his head tossing back against your shoulder as his hips stutter in a desperate rhythm. "It's — it's too much, I can't — "
"You can, and you will," you cut him off, your grip tightening on his hips to control the pace. "Feel that? That's what happens when you don't know how to prepare yourself properly."
You deliberately angle your cock so that each downward roll of his hips forces his clit to scrape directly against the edge beneath your cock's head.
"Please — fuck, please just fuck me already," Dean sobs, his voice breaking into something raw and pathetic. His hips are working in frantic, uncoordinated jerks, trying to force his way down, but your hands are like iron shackles around his pelvic bones.
You move him with effortless, terrifying strength, sliding his pussy up and down your cock as if he weighs nothing at all, controlling every millimetre of friction.
"Shhh, easy, sport. Don't get ahead of yourself," you coo, pressing tender kisses to his sweat slicked temples.
You sound like a guardian angel soothing a frightened soul, but internally, you're scoffing at how goddamn easy this is. His body is responding to every single movement with desperate, unguarded need; his pussy is practically begging for the invasion, slick and pliant under your expert torment.
"I can't — I'm gonna — " he gasps, his entire body trembling as he teeters on the razor's edge of another orgasm, his breath coming in short, broken whimpers. His hips stutter helplessly against you, his pussy already raw from the relentless grinding — each movement sending fresh waves of overstimulation through his already fried nerves.
"I'm gonna fuck, I'm gonna cum —"
"Not yet," you murmur against his ear, your voice dripping with mock concern. You maintain that torturous rhythm for three more agonising seconds, pushing him to the absolute brink where his vision blurs and his muscles lock up, before suddenly stopping.
You pull back just enough to feel the cool air hit his slick skin, then you give his ass a cheerful, affectionate pat. "Okay, now you're ready."
Before he can even process the sudden absence of friction, you manhandle him. With practiced ease, you flip him over on the couch, pressing his chest down into the cushions while forcing his hips high into the air. You plant yourself behind him, your knees bracketing his thighs as you spread his ass wide with both hands.
The sight is perfect — his pussy all flushed a deep shade, glistening with lube and his own releases, stretched open and waiting.
"There we go," you murmur, the tenderness gone from your voice, replaced by something hungry and predatory. "Now we can actually begin."
You don't pound into him straight away. You don't give him the violent release he's begging for. Instead, you press the broad, blunt head of your cock against his entrance and begin to push, inch by agonising inch.
Dean's entire body jerks as he feels the intrusion. "Ah fuck! Oh god, it's — it's too — " His voice cracks as he realises you aren't rushing. You're taking your time, forcing his tight walls to accommodate your girth one excruciating inch at a time.
You reach forward, threading your fingers through his hair and yanking his head back just enough so you can watch his face. His eyes are blown wide, pupils swallowed by irises as they fix on yours, glassy with tears and overwhelmed by the sensation of being split open.
"Look at me, Dean," you command, your voice a low, dangerous purr. "See how well you take it?"
You push again, a slow, inexorable advance that forces his pussy to stretch to its absolute limit. The wet, sucking sound of your cock sliding past his tight entrance echoes in the quiet room.
Each inch feels like an eternity, each millimetre a new lesson in surrender. His walls flutter around you, clenching desperately as they try to accommodate the invading girth, but you don't give an inch of slack.
"Fuck — it's so big — you're stretching me so much " Dean whines, his fingers clawing into the couch cushions.
His breath comes in ragged, terrified gasps as you continue your methodical assault. The resistance is delicious the way his muscles spasm and fight against the intrusion before finally yielding to the overwhelming pressure.
"That's it, Dean. Take it all," you whisper, your voice devoid of any real sympathy as you drive deeper. "Every single inch."
You watch with clinical fascination as his body reacts to the fullness. The sensation of his tight pussy gripping you is intoxicating — a warm vice that threatens to undo even your own composure.
"I'm — I'm full, oh god — you're so deep — " he chokes out, his back arching involuntarily as you finally bottom out against his cervix.
The teasing is over. The performance of the gentle mentor has been discarded like yesterday's trash, replaced by something far more primal.
You shift your weight, planting your knees wider to brace yourself as you settle into a brutal, relentless position. One hand remains buried in his hair — not to soothe him this time — but to hold his head exactly where you want it tilted back. Just enough so you can watch every expression of his degradation.
"That's enough playing around, sport," you growl, your voice dropping the pretense of sweetness. It's cold now, hard as flint, the voice of someone who has stopped asking permission and started taking what belongs to them. "Time to actually fuck you properly."
Without warning, you drive forward. You don't ease in anymore; you thrust into him with powerful, piston-like paces that send his entire body bunching forwards against the couch cushions.
Each thrust is deep and utterly relentless, forcing the air from his lungs in ragged, broken cries. You're not interested in his comfort anymore; you're only interested in his capacity to endure you.
"Look at this pussy," you sneer, your free hand coming down to slap against his thigh as you drive home again. "So fucking messy. So fucking desperate." You lean down, your mouth close to his ear as you continue the brutal rhythm. "Bobby talks about you like you're some kind of legend, Dean. A grand hunter — the best there is. But right now? All I see is a needy little boy who can't even handle being filled up."
Dean can't even form coherent sentences. He just nods dumbly against the cushion, his brain short circuiting from the intensity of the penetration.
He's lost in the sensation of you stretching him apart, shattering under the onslaught. He can only manage weak, incoherent sounds that dissolve into wet whimpers every time you bottom out against him.
"Listen to those moans, Dean," you chuckle darkly, the sound vibrating against his spine as you pick up the pace, your thrusts becoming faster, more punishing. "Goddamn, they're fucking pornographic. If Sam or Bobby heard you right now, they wouldn't be able to tell the difference between you and some R-rated video — you sound exactly like what you are: a fucktoy."
The words hit him harder than the physical impact, but he has no defense.
His body betrays him with every word, his pussy clenching around your cock in desperate, involuntary spasms that only make you want to fuck him harder. You reach around, your palm connecting with the meat of his ass in a sharp, stinging spank that makes him cry out.
"Such a pretty ass, too," you drawl, your voice dripping with cruel amusement as you deliver another smack that leaves a blooming red handprint across his pale skin. "All flushed and shaking for me."
You watch with predatory satisfaction as his body arches involuntarily, his hips stuttering against your cock in a futile attempt to find some kind of rhythm amidst the chaos you're creating.
His tears have begun to spill freely now, dampening the couch cushions as he sobs through each deepening thrust, but you don't stop. If anything, the sight of his breakdown only fuels your hunger.
"God, you're gorgeous when you're breaking like this," you murmur, your grip tightening on his hair to yank his head back further, forcing him to meet your cold, hungry gaze. "So helpless — so fucking perfect."
As you drive yourself into him again, your cock sliding through the slick, messy heat of him, your free hand slides down, fingers tracing the sensitive edge where his pussy meets his ass.
You pause there for a heartbeat, the tip of your cock grinding against his inner walls while your touch lingers dangerously close to his tight, puckered hole.
"You know what I'm thinking about, Dean?" you chuckle darkly, your breath hot against his ear as you watch his hips quiver in terror. "All this mess, all this wetness — it's a shame it's only coming from one hole."
You deliver one last, devastating thrust that makes him cry out in a high, broken note, before leaning down to whisper the promise that makes his entire body freeze.
"Next time, I'm not stopping at your pussy — I'm going to open you up right here, too. I'm going to stretch that pretty little asshole until you can't even remember how to walk straight."
You watch as the threat sinks in, his entire body going rigid beneath you, every muscle locking up in terror at the prospect of what's to come. The way his breath hitches, the way his pussy clenches around you in a desperate, instinctive attempt to protect itself — it's intoxicating.
"That's it, freeze for me," you growl, feeling the delicious tightness of his internal muscles as they spasm around your cock. "Let that fear sink in. Let it make you even wetter."
You don't give him a moment to recover. You resume the mean rhythm, each thrust more punishing than the last, driving him further into the cushions.
You want him to remember this feeling — the feeling of being completely owned, completely exposed — and utterly powerless against the promise of what you'll do to him next.
The final thrusts come with an unrelenting force that leaves Dean completely undone.
His body has reached its absolute limit; his muscles have gone beyond exhaustion into a state of pure, boneless surrender. As you feel your own orgasm building your balls heavy and aching with the need to release you lean down, your voice rough and demanding.
"Should I cum inside you, Dean? Should I fill you up with everything I've got?"
He doesn't even hesitate. His mind is too fried, his body too overwhelmed to consider the consequences. He simply nods dumbly against the cushion — a pathetic, desperate movement that says he doesn't care if he gets pregnant, doesn't care about Bobby, doesn't care about anything except the relief of your cum flooding his abused insides.
"Attaboy," you growl.
With one last, bone-deep lunge, you bottom out against him, cumming in hot, thick pulses that fill him to the brim.
Dean's body convulses beneath you, a final, weak tremor running through his spine as the overwhelming sensation of being filled sends him spiraling past the point of conscious thought. His breathing becomes shallow, erratic gasps before smoothing out into the heavy, unconscious rhythm of someone who has simply given up.
"Fuck, sport," you grumble, a snarky, almost disappointed sound escaping your throat as you feel his strength drain away entirely. He's teetering on the edge of passing out, his limbs going limp as his brain shuts down to escape the sensory overload. "Look at you. Can't even stay awake for the best part."
You feel him slipping away, his forehead pressing limply against the couch cushions. You lean down, your voice dropping into that dark, possessive comfort that promises no escape. "Don't worry, you'll stay right here — I'll continue fucking my fill. After all, this is exactly what you've been craving all these weeks, isn't it?"
You watch with cruel satisfaction as his consciousness finally fractures.
Dean's body goes completely boneless, his face pressed limply into the fabric of the couch, tears still wet on his cheeks. He has passed out, his mind unable to process any more of the exquisite torment you've inflicted.
He lies there in a state of beautiful, broken surrender: face down, ass up, completely exposed to your whims.
Even as he sleeps, you aren't finished.
The rhythmic slap of flesh against flesh fills the room as you continue to claim him, your thrusts methodical and unhurried now that he can no longer fight back or beg for mercy. Poor boy.
Maybe he should’ve thought twice before desperately chasing after the heat of someone double his age, double his intelligence, and double his lust.
Watching his tired form twitch under your touch brings a surge of dark triumph that no supernatural battle could ever match.
You think to yourself how fortunate you were that you agreed to take on Bobby's request for this particular case; it had promised danger, but it delivered something far more intoxicating. The raw power of breaking a legend, the feel of his flooded pussy clenching around you even in his stupor is undoubtedly the most exhilarating sensation you have ever experienced.
It surpasses every hunt, every demon slain, and every supernatural victory you've ever claimed. As you drive yourself home one last time, you realise that this conquest is the only reward that truly matters.
$ tag @twentytomidnight @i-gotta-go-so-much-bigger @hisokamywaifu
$ join taglist
$ cd masterlist / dean-winchester
Bench Press
Bottom!FTM Dean x Top!Male Reader
☆ Word Count: 1,930 ☆
AFAB Language Used | [Kinktober Request]
CW: Daddy Kink, Mirror-ish Sex, Size/Strength Kink, Oral Sex, Cum Swallowing, Manhandling, Creampie, Squirting
Dean leans back against your couch as he digests his very unhealthy meal. You're his best friend and since you're rich, he treats your house like his second home. He isn't worried about crumbs or stains because of your fancy rich boy toys, which are just a vacuum and stain remover…He likes to tease you for no real reason. You're not even here right now and he has his feet up like he's the man of the house.
Dean notes the sound of the door opening and the chime of the fancy pants door sensor but keeps his eyes on the TV. “Man, you have to see this.” He says as your footsteps get closer.
“What?” You lean over the couch to look at the screen. Dean's heart pounds as the movie switches to a darker scene, allowing him to see you in the TV’s reflection. The dog tag he gave you is dangling beside him and your tank top is showing off your firm body and tattoos. If he knew you were going to the gym, he wouldn't have put on a movie with such dark lighting…as if he’d be able to predict that. “It's dark.” You squint, leaning further in. He looks at your chest in his peripheral vision.
“You– you were too slow.” Dean turns his head to grab his beer.
You stand up straight. “And you're too fast at making a mess of my living room.” You give him a playful flick to the forehead and hop over the couch to sit down next to him.
“Take a shower, dip shit.” Dean’s thoughts aren't going to stay pure if this continues.
“I already did. You know I have at least 20 of these.” You pull on your top for emphasis.
He tightly grips the neck of the bottle. “Right, you spend all your money on shirts instead of a home gym.” He takes a generous sip of beer.
“One should separate home and duty.” You say jokingly.
Dean chuckles. “Just go to the military if you're gonna act like that.”
“I’m already a soldier, sergeant.” You flick the dog tag. Dean blushes. He only gave it to you because he thought it'd be a funny gift, not something you’d wear everyday.
“Then get down and gimme twenty.”
“Sir, yes, sir!” You drop down onto the ground and do twenty pushups. His heart pounds harder as he watches you and listens to your subtle grunts.
“Fuck.” He squeezes his thighs together.
You pause and look up at him. His eyes widen as his face becomes piping hot. “That– I meant—” He stutters. His thighs are still pressed together. He's not usually nervous around his crushes but this one is different. For one, you're his long-time best friend and he doesn't want to lose you. He's also heavily intimidated and turned on by you so he can't think straight when he indulges in his thoughts towards you.
“Did that get you hard?” Your voice contains hints of a restrained laugh but Dean can tell you're not making fun of him. Doesn't make him any less embarrassed though. “Should I help you out, sergeant?” You get onto your knees.
Excitement travels down his entire body. Thank God you're not grossed out. He turns the TV off to get rid of the distracting noises of agony and murder. He nods softly and crawls over to you. He leans in to kiss you as his hands explore your body. “You're too muscular.” He squeezes your pecs.
“No, you just don't have enough muscles.” You smile, understanding that he doesn't really mean what he said. “You're so small, I bet I could bench press you.”
Dean looks at you like a desperate, malnourished puppy in front of a thick slab of steak. “Please.”
You pull him into a sloppier kiss. You fall back onto the ground while Dean follows suit. He lifts his leg to kneel on the ground next to yours and presses his ass against your boner. He moans as both of your lips get wet with each other's saliva.
He reluctantly pulls away for air. You grab his waist and raise him high up. You’re carrying him like he's no heavier than a case of beer. “You owe me a dime.” You say jokingly, as if Dean placed his bets on anything other than you being able to do so.
He can feel a nosebleed coming on. “I don't owe you anything, Gatsby.” Dean retorts, referencing the book the two of you had to read in school. Your generous financial situation was enough for Dean to have that become your nickname.
“You won't even sit on my face?” You pout and set him down.
“Fine.” Dean rolls his eyes, pretending to not be extremely turned on. He stands up and removes his clothes. He can't see your boner too well from your baggy pants but he can definitely see how much more horny you are based on your expression. He walks over to your face and sits himself down, facing your lower half. You immediately dig in while Dean twitches uncontrollably as he pushes your pants down. “Of course you're big here too, you—” He arches his back as your firm hand slides down to his t-dick and your tongue finds the right spot. “God–” He gasps. You're too good at this. He doesn't want to go another day without your hands on his body and your tongue inside of him.
His eyelashes flutter erotically as he brings his mouth closer to your dick. He wraps his lips around it and tries to suck you off but gets too overwhelmed by your skills to move at all. He makes up for it by using his tongue as best as he can. “Mmh– mm~!” Dean’s basically functioning like a vibrating cock warmer. His mouth sinks down lower as he squirts. You slightly lift him up so you can properly lick him clean, with no concern for all the hair in your mouth, then you fully lift him and place him down on the carpet. He looks at you as you get up with his mouth slightly parted, he didn't want to leave yet.
You help him stand up. “Are you still as flexible as you used to be?”
Dean blushes. “Why?”
You turn him around and reach in between his legs. “Just…interested in seeing if my imagination is too wild.” You lift him up by his thighs. “What do you think? Can you handle it?” You raise his thighs up just a bit higher.
Dean throws his head back against your shoulder. “You're a fucking pervert..” His body twitches from how turned on he is. “Of course I can handle it, I’ve been–” He purses his lips, stopping himself in his tracks.
“You’ve been what?” You move his body so that his pussy rubs against your cock.
“Just put it in!”
“I wanna know what you’ve been doing first. I'm not the one who has to follow orders here.” You smirk. “I could get off just like this.”
He looks at the pre cum dribbling down your throbbing cock and tosses out his own reluctance. “I trained my flexibility…for you.” You have no idea how many nights he spent jerking off to the idea of you manhandling him. He always does his workouts when he's home alone because of how worked up he gets looking at himself in the mirror and imagining you there with him.
“Yeah? How long?” You lean over to look at him. He turns his head away from you and pouts. “Well, I’ve been thinking about this for years. I've always wanted to know how you’d look if I got to fuck you.” You look at him through the reflection of the TV. He looks adorable and you know he'll look even more so once you're done with him. You slide your hands up to his knees. “Ready?”
“Mhm-” Dean bites down on his lip as you lower him down on it. Tears trickle down his eyes from the stretch but not from pain, not the bad kind. You raise his legs up higher until his knees are pressed against his shoulders. The two of you look at him in the reflection and Dean squirts in response to the clear view of his bulging stomach. “Oh my God.” He groans.
“I don't know if I can hold back now…I can come inside, right?”
Dean laughs softly. “You think I wouldn’t let you?”
You grin and thrust your hips up, immediately starting at a rough pace that Dean can't keep up with and he has no plans to change that. He instead graces your ears with his moans as you finally make up for lost time. Since you don't have a camera, you're embedding the image of Dean's reflection deep into your mind. His hair is messy from the sweat that's dripping down his body, his beautiful, wet lips are parted wide for you, his nipples are rock hard, and you can just make out the reflection of the shiny slick your cock is covered in. He could be a model.
You can even see the way his mind is melting with every other thrust, you're already fucking him dumb and you only just started.
His attempts at words are pathetic and almost incomprehensible but you can understand everything he's saying very well. Harder, more, fuck me, please, oh my God!
Your laugh reverberates like your TV’s fancy speaker set. “You're a greedy slut.” You can feel his walls squeezing you tightly. Your breathing is labored but your voice is still steady and firm, as opposed to his shaky and whiny one. “Am I not fucking you right now? Do you want me to destroy you? ‘Cause I can be a lot rougher than this.”
Dean’s back arches. “Daddy–!” He shouts it like it's your activation code and it works exactly as it should, you fire off on all cylinders and fuck him exactly how he deserves to be. He’d be embarrassed as hell if he weren't already so far gone. “Gonna- gonna come~!”
“You’ll pass out by the end of this.” Your voice is rougher and more strained now, it instantly triggers Dean’s orgasm. The poor TV is covered in his slick. “At this rate, you’ll end up dehydrated too–” You groan. You never imagined he'd be like this. He takes you so well and he squirts every time. He's driving you crazy.
He giggles. “You’ll gimme yer cum, replenish-” He rolls his eyes to the back of his skull.
“Not fuckin’ you hard enough if you can still talk like a pornstar.” Your grip on his legs become tighter as you really fuck him.
“Ah– ye- yes~!” He's fighting his own body’s urge to rest, too motivated by the knowledge that you’ll come inside him soon. He can barely see it now that he's moving so fast but he loves the way you're looking at him, he can tell your eyes are trained on his reflection. He'll have to get you to buy a tripod later, he knows you’ll love having this view immortalized. He certainly will.
You finally come inside of him and your thrusts slowly come to a halt. Even though his vision is blurry, he can see that you're burning a new photo of his reflection deep into your memory once again.
“Take a pic next time.” He passes out with a smile on his face. You could've gone another round but you’ll stop for his sake.
meoooowwww🫣🫣🫣 dom cas anyone? ik that’s my favorite 👀
A Proper Teachin'
$ log - you’re a very disgruntled sheriff, tired of a repeating offender trespassing. so, you decide to give dean winchester a proper reminder of how the heavy the law feels. $ warn --nsfw --dark --dubcon(heavy) --older!amab!reader --dom!top!reader --corrupt-sheriff!reader --mean!reader --sub!bot!dean --bratty!dean --d/s(heavy) --power-dynamics --older-man-younger-man --age-gap --size-diff-kink --bondage(handcuffs) --positions(doggy) --anal --impact-play(spanking) --rough --overstim --finger-sucking --begging --titles(sir) --authority-abuse --orgasm-denial --sex-tape(hinted) --toys(butt plug, implied) --pretty-crier --dirty-talk --praise --degradation(heavy) --no-aftercare $ wc -w 3.3k $ cd masterlist / dean-winchester # note = you're practically breeding him. sex on the impala. cum as lube.
The blue and red strobes of your cruiser cut through the heavy darkness of the outskirts, casting long, rhythmic shadows against the rusted chain link fence.
You watch through the windshield, a tired smirk tugging at your lips, as a figure tumbles over the top, landing in a clumsy heap on the dirt. You don't even wait for him to brush the dust off his jacket before you've swung the door open, the heavy crunch of your boots on the gravel sounding like a death knell.
You catch him by the scruff of his jacket before he can even scramble to his feet, your grip iron tight as you wrench his arms behind his back. The harsh, white glare of your headlights hits his face, and you recognise that insufferable, cocky expression immediately.
It’s Winchester. Again.
The tickets haven't worked, the formal warnings have been ignored, and the reports are just piling up on your desk like a testament to his stubbornness. This brat thinks he can just dance around the law, playing the part of the untouchable rebel, but he’s about to learn that the law has a very physical way of enforcing its boundaries.
Without a word of warning, you shove him forward, forcing him down until his chest hits the warm metal of the Impala's bonnet. He stumbles, a startled "Hey!" escaping him, but you don't give him a second to recover.
You pin him there, the weight of your authority pressing down on him, and you know that tonight, the paperwork is done. Tonight, you're going to give him a lesson he won't be able to write off so easily.
Bent over his hood, sirens colouring the bare treeline, and he wasn’t even a tad scared. In fact he was quite proud - this’ll be another grand story to brag about. He glances over his shoulder at your disgruntled look, shaking his hips with a tease.
"What are you gonna do, old man? Arrest me again? Fuck me?" Dean sneers, leaning back against the Impala with that insufferable, cocky grin.
You don't even give him the satisfaction of a smile. You wrench his wrists behind his back, the metal cuffs biting into his skin with a sharp click. As you roughly undo his trousers, you look him dead in the eye, voice flat and dangerous. "That’s exactly what I’m going to do. The ticket machine is broken; this will have to do."
The smugness vanishes instantly. He freezes, eyes wide as he stares at you, the reality of your intent finally sinking in. "Wait are you serious? You're actually — " He cuts himself off with a sharp gasp as you push his face down against the hot metal of the bonnet.
"Hey! Watch the hair, you old bastard!" he yelps, his voice cracking as he tries to regain some semblance of dignity.
You don't let him. You grab a thick fistful of his hair, yanking his head back so he’s forced to look at the dark sky, before shoving his face back down into the paint. "Shut up, Winchester. You've been a very loud, very annoying trespasser. It's time you learned some goddamn respect," you growl, your voice dripping with authority.
Smack!
The heavy sting of your palms against his bare, pale ass makes him jump, a muffled "Fuck!" escaping him.
"You think you're so tough, don't you?" you sneer, leaning over him, your heat radiating against his trembling skin. "But right now, you're just a brat who needs to be put in his place," you growl, your voice thick with a hunger that makes his breath hitch.
You don't wait for a retort.
You're already hard. You’re so goddamn easy, but can you blame yourself? The sight in front of you was gorgeous: Dean bent over his beloved car, fumbling at his cockiness while his cute ass sticks just easy for the taking.
Your cock’s leaking pre-cum that drips onto the metal of the Impala. You wrap your hand around yourself, a few rough, desperate strokes to ease the ache before you do leak, painting his trembling, pale arse in thick, hot streaks of cum.
So damn easy. Long night, sheriff, just been’a long night, and a long week.
"God, damn —" Dean stammers, his snarky bravado fracturing into a series of breathless, incoherent sounds. He tries to pull his head up, to find that defiant glint in his eyes again. "You think — you think a little jizz and — and a few spanks makes you the boss? You're still just an old —"
"An old what, Winchester?" you cut him off, your voice a low, dangerous rumble. You scoop up a handful of your own warm, sticky cum, prodding your fingers into his tight, twitching hole to coat him thoroughly.
The sensation of him clenching around your digits makes your vision swim.
Dean huffs, trying to sound indignant even as his voice trembles and his hips instinctively tilt back toward your touch. "Just — just get on with it! Stop playing with me!"
"Patience, boy," you growl, the sound vibrating deep in your chest as you angle your tip to his hole. You savour the tiny whimpers as you tease — you know damn well he’s fighting against himself to just beg for it.
Slow and steady was the way you’d decided to push in, but perhaps that was the worser option.
"Mmhm, fuck —" he groans languidly into the metal of the bonnet, his eyes rolling to his skull as he's filled to the brim. "God you're — you're too big! You're gonna break me, you crazy ol’ bastard — gah!”
"Shut your mouth and take it," you growl, your voice a low, predatory rumble. You don't give him a second to adjust to the sheer, stretching girth of you. You begin to move, your hips pushing into his ass with a rhythmic, punishing force that makes the entire Impala shudder.
"Oh god," Dean’s snarky bravado is completely gone now, replaced by desperate, high pitched moans that he tries and fails to swallow. "Is this — is this part of the — the fine? You're fuckin’ killing me —"
"Consider it a lifetime subscription to my personal attention, then," you growl, your voice thick with lust as you drive into him again, harder this time, making his entire frame shudder against the Impala.
You reach down, grabbing his chin to force his head up just enough so he has to feel the vibration of your voice against his skin. "You wanted to play rough, Winchester? You wanted to see what an 'old man' could do? Well, here it is. Every inch of me, claiming every inch of you."
"Fuck — fuck —" Dean gasps, his head lulling back as your girth stretches him to the absolute limit. The snark is almost entirely gone, replaced by a raw, desperate need. "You're — you're a goddamn animal —" he manages to choke out, his voice a wrecked, breathless mess. "Just, don't stop — don't you dare stop."
The sound of your hips hitting his arse is a wet, heavy slap that never stops. You aren't being gentle; you're driving that massive, thick cock of yours into him like you're trying to split him in half.
Every time you lunge, your girth wedges itself so deep into his tight, puckered hole that he lets out a choked sound, his whole body jerking forward against the metal of the Impala.
He looks fucking wrecked, his eyes rolled back in his head and his mouth hanging open, completely mindless because his brain can't even handle how much of you is shoved inside him. He’s just a mess of spit and tears, staring at nothing because you’ve stuffed him so full he can’t think.
Jesus, you think, your teeth gritting as you watch your cock slide in and out of him. The sight is fucking hypnotic, the way his skin stretches and pulls around your thick, heavy head with every brutal lunge. If he had a pussy, you'd have knocked him up real quick, you think, a dark, hungry heat blooming in your gut.
That tight little hole of his is making you delirious; you're just as gone as he is, lost in the sheer rhythm of breaking him.
"Look at you, sport," you growl, leaning down to his shoulder. "Fucked so hard you can't even remember your own goddamn name, can you?" You don't wait for an answer. You just drive that thick, heavy length back into him, bottoming out so hard his entire frame lurches.
He’s babbling, an incoherent mess of "sorry, sir — please — sorry," his voice cracking as he fumbled against the bonnet.
"You like trespassing, don't you, boy?" you sneer, your voice dripping with condescension as you pull back almost all the way, letting the cool air hit his stretched, wet hole before driving back in. "You like thinking you can just wander wherever you want, disobeying every little rule? You think you're too big for the law to handle?"
Every lunge is slow, deliberate, and fucking brutal. You aren't rushing; you're making sure he feels every goddamn inch of your heavy self as it slides in, pressing snug against his insides.
You want him to feel the exact moment your head wedges deep into his gut.
"Look at me when you're getting handled like this," you bark, grabbing his chin to force his tear streaked face toward yours. "Don't you dare look away. You're a delinquent, and it's time you learned some respect for your elders."
He can barely keep his eyes open, his head lolling as he lets out a broken, high pitched mewl. "No, sir — please — so big," he whimpers, the words barely intelligible through the sheer sensation of you filling him.
You cum deep inside him, a hot, thick flood of seed pumping into his core, filling him to the absolute brim. You can feel his insides spasming, clenching around your girth in a desperate, attempt to milk every last drop.
"There," you grunt, your voice thick with satisfaction as you hold yourself deep inside him, letting him feel the heavy, warm weight of your release. "Now you've got a real reason to remember the law, you little brat."
You aren't done with him. You're going to milk every last drop of submission out of that brat.
Even as your seed floods his insides, you don't pull out. You keep your hips moving, a heavy, relentless rhythm that forces him to endure the sensation of your thick, leaking cock sliding through your own warm release inside his tight, aching walls. The wet, slapping sound of your pelvis hitting his ass is constant, a rhythmic reminder of who owns him.
You glance down and see his cock, neglected and twitching, leaking a mess of pre cum all over the hood of the Impala. He lets out a desperate, choked sound, his hips bucking instinctively, trying to find some friction, some relief.
"Look at that," you growl, watching the thick, white cream overflow from his puckered, overstretched hole and drip down his trembling thighs, staining the rim of his own goddamn car. "You're leaking all over your own ride, you little delinquent. Can't even hold a single drop of the law inside you, can you?"
You don't slow down.
If anything, the slickness of the cum makes you even more aggressive. You're fucking him with a wet, slapping intensity, the sound of your cock sliding through the overflow making a disgusting, slurping noise that echoes in the quiet night. Every time you bottom out, you can feel the excess fluid being forced back in, only to squirt back out the second you pull back for the next lunge.
He's a total wreck, his voice nothing but a series of broken, high pitched whimpers and pathetic, wet sobs. "Please, sir, it's too much — so much —" he gasps.
He's completely at your mercy, his body reacting to the sheer, unyielding weight of you even as he begs for a break he isn't going to get.
"Too much?" you chuckle, a low, mean sound that vibrates through his spine. "You haven't seen anything yet, brat. You wanted to play in the wrong territory, now you're gonna take every goddamn bit of what comes with it."
You don't stop. You keep thrusting into him, the sound of your cock sliding through the thick, white mess of his own leaking insides making a disgusting, slurping noise. You reach down, your fingers slick and heavy with the overflow, and you scoop up a handful of your own warm cum from where it's dripping off his thighs.
With a mean smirk, you bring your hand up to his face. He looks up at you, eyes glazed and pathetic, and you shove your fingers, coated in that thick cream, straight past his trembling lips. Dean doesn't even fight it; he just opens up like a hungry, desperate puppy, his tongue swirling around your fingers, suckling at the taste of you with a mindless need.
"That's it, attaboy. Clean it all up," you murmur, watching him desperately try to swallow every drop of your essence. The sight of him, so broken and submissive, makes your blood boil with a fresh wave of lust. You can't help yourself; you want to see just how much of him you can dominate.
You pull your fingers from his mouth, leaving him gasping and dripping, and then you shove them into his throat.
He's so small compared to you, his throat constricting around your thick digits as he chokes, his eyes watering as he struggles to breathe.
You love the way he looks completely overwhelmed, his body reacting to the sheer size of your palm as it wraps around his throat, making him feel like he's being swallowed whole.
"You're just a little thing, aren't you?" you growl, your thumb pressing hard to force a choked, desperate sound from his lungs.
You can feel the frantic pulse in his neck thrumming against your skin, a rhythmic, terrified beat that only makes you want to squeeze harder. He's gagging on your fingers, his eyes rolling back as he tries to reconcile the sensation of being choked with the heavy, rhythmic pounding still happening in his arse.
He's caught between two kinds of ruin, and he's taking every bit of it like the good, obedient little delinquent he is.
"Look at you," you mutter, watching a string of saliva and cum stretch between his lips as he tries to catch his breath. "Completely owned. From your mouth to your ass. You're a fucking mess, Winchester."
You don't let him recover. While your fingers are busy stretching his throat and making him gag, you drive your hips forward in a devastating lunge. The impact is so heavy it makes the whole Impala rock on its suspension.
Heavy-hitter.
You bottom out with a force that feels like it's bruising his very soul, your massive cock burying itself so deep in his leaking, cum filled hole that there's no space left between you.
He lets out a muffled, strangled cry against your hand, a sound of pure, unadulterated ruin, as he's caught between the choking pressure in his throat and the overwhelming fullness in his gut.
"Don't you dare get greedy," you growl, your voice a low, commanding rasp. You reach down, not to stroke him, but to firmly press his hips down harder against the metal. "I'm not touching your cock, sport. You take it like a champ and you cum like one. You don't need a hand when you've got me filling you up like this, do you?"
Dean lets out a broken, high pitched sob, the sound of a man completely undone.
Pretty, shimmering tears track down his cheeks, smearing against the hot paint of the car as he whimpers, "Please, sir, please, just — sir —" He’s practically begging, his body trembling with the unfulfilled ache of his ignored cock and the overwhelming sensation of you continuing to hammer into him.
Smack! Smack!
Two heavy, stinging spanks to his reddened arse cut his pleas short, forcing a startled gasp from his lungs. You lean down, your mouth hovering just inches from his ear, your breath hot and smelling of lust.
"Hush now," you cooed, lowly. "Only need those pretty sounds outta you. Keep the whining for when you're actually in trouble. Right now, you're just being a good, quiet boy for me, aren't you?"
You watch with dark satisfaction as Dean tries to swallow his sobs, his breath coming in ragged, uneven hitches, his body forced into a state of pure, mindless receptivity.
He’s completely at your mercy, a broken, beautiful mess of a man, and as you continue to fuck into him, you know he won't be thinking about trespassing for a long, long time. He'll only be thinking about the weight of your hand, the heat of your cock, and the way you made him beg.
The morning sun bleeds through the dusty windows of the Impala, stinging Dean’s eyes as he groans, his consciousness returning in heavy, painful waves. His first sensation is the ache a deep, throbbing soreness in his hips and a raw, stinging heat in his arse that makes every slight movement feel like a monumental task.
He tries to roll over, but his body feels heavy, uncoordinated, and utterly spent. As he shifts, he realises with a jolt of disorientation that he’s lying face down in the backseat, his hips propped up at an awkward, vulnerable angle, his trousers pooled around his ankles.
The reality of the night before hits him like a physical blow. He remembers the heat of the bonnet, the heavy, rhythmic thrusting of your hips, the way you’d gripped his throat, and the sheer, overwhelming weight of you claiming him.
His eyes wander blindly to the seat pocket beside his face, finding a crumpled citation and a small, plastic tape reel. The label on the tape is written in your sharp, authoritative scrawl:
How the Law Works.
It’s a mockery, a dirty piece of evidence that turns his humiliation into a public record, a grim sex tape disguised as official body cam footage.
Beside it, the citation sits, but it's not just a list of infractions. There's a handwritten note scrawled in the margin, the ink dark and mocking:
Consider the plug a memoir, Winchester. A little something to keep you full of me, and of the law until you learn to behave.
The realisation of the note sends a fresh wave of heat rushing to his face, a mix of shame and a terrifying, involuntary arousal. He reaches back, his fingers trembling as they brush against the cold, hard base of the plug still slotted deep inside him.
He stares at the tape reel, the thought of anyone anyone at all watching the footage of him being broken, of him whimpering "yes, sir" while you fucked him into the metal of his own car, making his head spin.
It wasn't just a punishment; it was a total deconstruction of everything he thought he was. He wasn't the rebel, the hunter just a messy, overstimulated boy who couldn't keep his hands off the wrong things.
He tries to shift his weight to sit up, but the movement causes the heavy plug to shift deep within his bruised walls, sending a jolt of unbidden pleasure and sharp ache straight to his core. He lets out a choked, pathetic sound, his forehead dropping back onto the leather seat.
$ tag @twentytomidnight @i-gotta-go-so-much-bigger
$ join taglist
$ cd masterlist / dean-winchester
everyday i mourn the fact that in the original script for yellowjackets misty was suppsed to have an unhealthy obsession with jackie instead of coach scott
My beautiful wife Jackie Taylor, oh how I love you♡♡
i love babygirl dean winchester…. he is my unicorn kitty bunny puppy omega princess. 😭💗
Raspberry Delight
The css for the buttons is from a skin made by @ao3commentoftheday with the colors changed to make them more pink.
The pink icons were made by @zerafinacss
@zerafinacss also has pink stat icons that look really good with this skin. It would replace the language/words/chapters ect. with some cute pink icons.
If you want this skin, the code is under here!
First, you have to put these codes into the wizard.
After you save that, you just copy and paste this code:
#header .logo {
background-image: url("https://images.squidge.org/images/2024/03/30/AO3_imageset_pink.png");
background-size: 250px 1044px;
padding: 42px 0 0 60px;
width: 0 !important;
height: 0 !important;
background-position: -140px -749.6px;
}
#header ul.primary,
#header h2 {
box-shadow: none;
}
.required-tags .rating-notrated,
.required-tags .rating-general-audience,
.required-tags .rating-explicit,
.required-tags .rating-mature,
.required-tags .rating-teen,
.required-tags .category-femslash,
.required-tags .category-gen,
.required-tags .category-slash,
.required-tags .category-none,
.required-tags .category-het,
.required-tags .category-multi,
.required-tags .category-other,
.required-tags .complete-no,
.required-tags .complete-yes,
.required-tags .warning-yes,
.required-tags .warning-no,
.required-tags .warning-choosenotto,
.required-tags .external-work,
.status .private .text,
.status .public,
.status .hidden,
.status .rec,
.status .count,
.index .skins .icon,
.index .mystery .icon,
.index .tag .icon,
.index .tagset .icon,
.comment .icon .anonymous,
.comment .icon .visitor,
.abbreviated .icon .visitor,
.abbreviated .icon .anonymous,
.skins .primary .icon,
.admin .primary .icon,
.tagset .primary .icon,
.tag .primary .icon,
a.rss span,
p.kudos,
#symbols-key dl img,
#bookmark-symbols-key img,
img[src$="/images/skins/iconsets/default/icon_user.png"],
img[src$="/images/skins/iconsets/default/icon_collection.png"],
img[src$="/images/lockblue.png"] {
background-image: url("https://images.squidge.org/images/2024/03/30/AO3_imageset_pink.png");
background-size: 200px 835px;
}
#symbols-key dl img,
#bookmark-symbols-key img {
width: 0 !important;
height: 0 !important;
padding: 25px 0 0 25px;
}
img[src$="/images/skins/iconsets/default/rating-notrated.png"],
img[src$="/images/skins/iconsets/default/category-none.png"],
img[src$="/images/skins/iconsets/default/warning-no.png"] {
background-position: -150px 0px;
}
img[src$="/images/skins/iconsets/default/rating-general-audience.png"] {
background-position: -50px -25px;
}
img[src$="/images/skins/iconsets/default/rating-teen.png"] {
background-position: 0px -25px;
}
img[src$="/images/skins/iconsets/default/rating-mature.png"] {
background-position: -75px -25px;
}
img[src$="/images/skins/iconsets/default/rating-explicit.png"] {
background-position: -25px -25px;
}
img[src$="/images/skins/iconsets/default/category-femslash.png"] {
background-position: -25px 0px;
}
img[src$="/images/skins/iconsets/default/category-het.png"] {
background-position: -75px 0px;
}
img[src$="/images/skins/iconsets/default/category-gen.png"] {
background-position: -50px 0px;
}
img[src$="/images/skins/iconsets/default/category-multi.png"] {
background-position: -100px 0px;
}
img[src$="/images/skins/iconsets/default/category-other.png"] {
background-position: -125px 0px;
}
img[src$="/images/skins/iconsets/default/warning-choosenotto.png"] {
background-position: -125px -25px;
}
img[src$="/images/skins/iconsets/default/warning-yes.png"] {
background-position: -150px -25px;
}
img[src$="/images/skins/iconsets/default/warning-external-work.png"] {
background-position: -75px -50px;
}
img[src$="/images/skins/iconsets/default/complete-no.png"] {
background-position: -100px -25px;
}
img[src$="/images/skins/iconsets/default/complete-yes.png"] {
background-position: -175px -25px;
}
img[src$="/images/skins/iconsets/default/bookmark-rec.png"] {
background-position: -100px -50px;
}
img[src$="/images/skins/iconsets/default/bookmark-public.png"] {
background-position: -125px -50px;
}
img[src$="/images/skins/iconsets/default/bookmark-private.png"] {
background-position: -175px -50px;
}
img[src$="/images/skins/iconsets/default/bookmark-hidden.png"] {
background-position: -150px -50px;
}
img[src$="/images/skins/iconsets/default/icon_user.png"],
img[src$="/images/skins/iconsets/default/icon_collection.png"],
img[src$="/images/lockblue.png"] {
width: 0 !important;
height: 0 !important;
}
img[src$="/images/skins/iconsets/default/icon_user.png"] {
padding: 100px 0 0 100px;
background-position: 0px -75px;
}
.index:not(.comment) .abbreviated img[src$="/images/skins/iconsets/default/icon_user.png"] {
padding: 75px 0 0 75px;
background-position: 0px -375px;
}
.index:not(.comment) img[src$="/images/skins/iconsets/default/icon_user.png"] {
padding: 55px 0 0 55px;
background-position: 0px -525px;
}
#greeting img[src$="/images/skins/iconsets/default/icon_user.png"] {
padding: 1.786em 0 0 1.786em;
background-position: 0 -19px;
background-size: 201% !important;
}
img[src$="/images/skins/iconsets/default/icon_collection.png"] {
padding: 100px 0 0 100px;
background-position: -100px -175px;
}
.index img[src$="/images/skins/iconsets/default/icon_collection.png"] {
padding: 55px 0 0 55px;
background-position: -55px -525px;
}
img[src$="/images/lockblue.png"] {
padding: 15px 0 0 15px;
background-position: -155px -305px;
}
button,
.actions a,
.actions a:link,
.action,
legend .action:link,
input[type="submit"],
.actions a:visited,
.actions li label,
a.action.modal-closer {
color: #FCF5ED;
background: #A0153E;
border: 1px solid #A0153E;
box-shadow: none;
}
button:hover,
.actions a:hover,
.action:hover,
input[type="submit"]:hover {
color: #00224D;
background: #ff2071 !important;
border: 1px solid #ff2071;
box-shadow: none;
}
.actions li .current,
.current,
#dashboard .current {
color: #FCF5ED;
background: #ff2071;
border: 1px solid #ff2071;
box-shadow: none;
}
dl.meta {
border: 1px solid #a0153e;
}
.wrapper {
box-shadow: 1px 1px 5px #a0153e;
}
.actions input:focus {
border-top: 1px solid #a0153e;
border-left: 1px solid #a0153e;
box-shadow: none;
}
#dashboard .secondary {
background: #ff2071;
box-shadow: inset 2px 2px 5px #a0153e;
}
.alert .userstuff {
background: #ff91ba;
border-color: #ffd6e6;
color: #8a0035;
}
.qtip-content,
.notice:not(.required),
.comment_notice,
.kudos_notice,
ul.notes,
.caution,
.notice a {
color: #fcb6d1;
}
.notice,
.comment_notice,
.kudos_notice,
ul.notes,
.caution,
.error,
.comment_error,
.kudos_error,
.alert.flash {
background: #a0153e;
border: 1px solid #ff91ba;
}
.required,
.error,
.alert.flash {
color: #fcc2d8;
}
button:hover,
.actions a:hover,
.action:hover,
input[type="submit"]:hover {
color: #4f001b;
}
.comment img[src$="/images/skins/iconsets/default/icon_user.png"] {
padding: 55px 0 0 55px !important;
background-position: 0px -525px !important;
}
^ If you only read on desktop, this last bit is unnecessary. It fixes the blank profile pics from being too big on mobile, but in doing so, it does keep the pics small on desktop
EDIT: If you have any problems with the tags on mobile, go to media and select: "max screen and (max-width: 42 em)" and it should fix it!
AND FINALLY, THEY ARE DONE!!!
here are my frutiger aero, frutiger eco, and helvetica aqua aero ao3 skins! you may get the code here ::}
including shortening long tag fields by Xparrot on ao3, warnings/rating/etc icons in text form by ao3commentoftheday, and ao3 default icon replacements by ferager!
and who knows! might do more of the frutiger family in a later date!
and this is for the wonderful people who have requested i tag them once done ::} @decimv3, @lupus-444, @iggyeng
mcbling [ao3 site skin]
hi... i'm showing off😻
i tried creating my own ao3 skin guys i spend my whole day doing this🙀
updated with pc photos
link to og ccs
link to ccs (kinda changed)
the shiny borders and buttons (when you click on them) are gifs
code is based on:
hello kitty! [ao3 site skin]
and i used that one for icons
replace the AO3 Icons [site skin]
hi guys i made a pink ao3 site skin
get it here:
https://docs.google.com/document/d/14ZeGpbET06n1dUmUkG7_M856-KqxjwrwlhLwh0S7OsU/edit?usp=sharing
that's all thank you 🤤
