Pairing: Mostly Dean x reader, though there is some stuff involving Sam and Leah (OFC)
Word count: 1068
Warnings: Some F/F action, but generally it’s just pure smut.
Summary: This is a part of the CYOSTODA-thing hosted by the awesome @littlegreenplasticsoldier, so if you don’t know what it is about, i suggest you go check out the Choose Your Own Supernatural Truth Or Dare Adventure Mastermess, ‘cause this has been awesome.
If you want to follow the direct path to my little piece, you can use the links below:
Part 1: Setup by @littlegreenplasticsoldier
Part 2: Dean Picks Dare by @eyes-of-a-disney-princess
Part 3: Leah Picks Truth by @revwinchester
Part 4: Sam Picks Dare by @kittenofdoomage
P5 Y/N picks truth by @babypieandwhiskey
Enjoy!
You waited a couple of seconds, eyes gliding over the body of the stunned Dean Winchester as you waited for his answer, the hands massaging your breasts and making you fight to control the sounds trying to escape your lips not stopping for a mere moment.
His mouth was hanging wide open, gaze lingering on the show the three of you were putting on. He was in another world, that much was clear to you.
You nearly whimpered as one of Sam's hands was replaced with the mouth of a certain hot lady sitting in front of you, a wanton moan escaping instead as the combined pleasure of soft, small lips on your breast and big chapped ones on your neck found its way to your core, the dampness of your panties increasing.
The sound seemed to bring him out of his trance, and he let his tongue swipe slowly, teasingly, over his full bottom lip, making you quiver with desire. Looking right into your eyes, he winked at you, before answering the question, that you, by the look on your face, had long forgotten you had even asked.
"Truth."
Oh how you wished he would have picked dare.
You could have dared him to do so many things, and all the clothes he was wearing… damn it. So many possibilities, lost.
The hands and the lips suddenly disappeared from your flushed skin, three pairs of eyes now staring at your nearly naked form, though only two were visible from where you were sitting. They were waiting in anticipation to hear what you would come up with to further speed things up, and with the desperation creeping up on you at the sudden loss of contact, you wanted to hurry up and come up with a good question.
And there it was.
"Would you rather watch or join the party?"
Even though you already had a feeling of what the answer would be, you gasped as he crawled across the floor, old floorboards creaking beneath him as the weight shifted.
And then he was right beside you, warm breath tickling you on your neck, a thread of whispered words filling your ear and making you putty in his hands.
"While the view is great, I would never pass up the chance of getting to feel you around me."
He took both your hands in his, gently helping you untangle yourself from Leah and the younger brother, before scooping you up in his arms and placing you on the biggest of the two beds. You were in for a hell of a ride.
You thought the Winchester brothers looked hot with clothes on, so when they stripped down, you nearly combusted. They were like Greek gods. No, scratch that, they were more handsome than that. You craved their touch, craved the feeling of fingertips running softly down your sides, down your thighs, over your ankles, and up again. Running up the insides of your thighs, teasing you by narrowly missing your core but giving you a bit of what you wanted, what you needed, by rolling your nipples between thumb and index finger. Wet kisses trailed up your stomach. Then down again.
The rest of your clothes came off, pulled from your needy body by his warm hands, and you closed your eyes and let the feeling of his breath ghosting over your newly uncovered skin wash over you. And then the feeling was gone.
You lifted your head from the pillow and opened your eyes. Sam and Leah fell down onto the other bed. And right in front of you was your Adonis leaning over you, watching, appreciating, emerald green gaze sliding over your naked form, his tongue darting out to once again wet his lips, his eyes suddenly meeting yours. Bending over, he puts his hands on the bed, then his knees. Crawling towards you. Mouth now by your ear, he whispers: "So what is your favorite position?"
You turned your head, the green orbs staring directly into your soul. "I'll show you," you whispered back, naked bodies sliding against each other as you made him lay down on his back. Straddling his hips, you leaned down, your chests touching as you let the next words slide over your lips. "I love the feeling of power this gives me."
Scooting down a bit, you pressed kisses on his neck, then collarbone, then chest. Hand gripping onto his throbbing length, lifting your body up, hovering over him, before sliding down on his member. He's stretching you in that perfect way, filling you up completely.
He wanted this as much as you did, you felt that when his fingertips dug into the soft flesh on your hips, undoubtedly leaving bruises. He held you, adjusted the angle, and hit that sweet spot that makes you arch your back, throw your head back, nearly screaming with the surge of pure pleasure rushing through you. You locked eyes with Leah over Sam's shoulder as they sit there, with bodies pressed against each other, Lotus-ing away.
You wanted to do that later. Maybe with Sam, maybe with Dean. Maybe with both.
You wanted to taste Leah's juices on your tongue, and the salty sweat from her skin as you kiss your way down her body.
And when you had had a break somewhere between 2 and 3 am, having taken a shower with the beautiful girl, you would make her sit back and watch as you pleasured both of the Winchesters.
The night was still young, and you had more than enough time to do what you wanted.
Soft, hard, somewhere in between.
Around 5 am you fell asleep with Dean pressed against your back, and Leah against your front, Gigantor laying on the other side of Leah, trying not to roll off the bed, which clearly wasn't meant for 4 people.
A whole year had passed since that night and you still had no idea how you were even able to fit on that crappy motel bed, but at least you still met up with Leah once in awhile, though not always bringing the boys with you. That was your little secret. But when you did bring them, which was actually more often than not, you were sure to have a great night.
Not as good as that first night though. That one, you'll never forget.
Tags:
@wheresthekillswitch
@jensen-jarpad
@27bmm
@notnaturalanahi
@deathtonormalcy56
@just-another-busy-fangirl
@mysteriouslyme81
@mousehybrid
@atc74
@leatherwhiskeycoffeeplaid
@supernatural-jackles
@dontcallmebabe-ok
@impala-dreamer
@katymacsupernatural
@keepcalmandcarryondean - It won’t let me tag you :’(
@onetwothreefuckmeplease - Won’t let me tag you either :’(
A/N: Okay, so if you’re following along, you should know that this is the part where all the sex happens. This is the conclusion for this particular thread of the story. So much love to our captain @littlegreenplasticsoldier for making this happen and for her patience while I had stuff going on. Also, love for @kayteonline and @saenalife for beta’ing and keeping me going when I hit the smut wall. What a crew to be a part of. Hope you enjoy!!
Get caught up:
Part 1 by @littlegreenplasticsoldier
Part 2 by @gemini75eeyore
Part 3 by @deandoesthingstome
Part 4 by @rizlowwritessortof
Part 5 by @saenalife (saena i can’t tag you!)
From part 5:
Although you would have loved to keep going, you didn’t think the game was quite done yet. There was no doubt in your mind that you had won this round, so you pulled away with a lingering kiss to the tip of his thumb and looked up at Dean with a tantalizing smile.
“So… truth or dare?”
His eyes focus on your lips for another few seconds, slick and shiny and hanging open a little. When he finally looks you in the eyes, he still wears a glazed-over expression.
“Dean?” you gently prompt, unsure that he’d actually heard you the first time. You start to reach for him, ready to shake him if need be, but with a clench on his jaw he seems to snap himself out of it. Staring you down intensely, he answers without a flinch.
“Truth.”
Your eyes remain locked with his, both of you unwilling to break the moment. He's finally giving you the look, it's more hungry and needy than you expected, but still exciting. Though he’s still kneeling above you, you've got the upper hand, holding his stare with a fierce look of your own; one you'd never tossed his way before, never really had the opportunity, but there's no reason to back down now.
You close your mouth to swallow, still tasting him on your tongue, before asking, “Have you ever thought of doing anything like that to me before?” You dart your eyes between his, anxious for the honest truth.
He pauses, breathing deeply through his nose as he clenches his jaw, eyes narrowed slightly as he tries to pull back control.
“Fucking yes.” Leah answers, her voice cracking the tension.
Your brows shoot up and you pinch your lips together to try to hold in the laughter threatening to splutter through them, only succeeding slightly. The stare down is over, Dean’s dragging his palm over his face and looking over at Sam, shooting him a look you haven't been able to decipher in all your time with them.
“Good to know, Leah, but I think that was Dean's turn,” you smile wide at her, giving her a mischievous up-down glance. She purses her lips, miming locking them and tossing the key.
Dean's taking the opportunity to settle back into his spot, shifting his hips as he straightens one leg, bending the other at the knee to prop his forearm on it, watching the exchange between you and Leah with interest.
“Dean?”
“Yeah?”
“Well?”
“You wanna know if I've thought of putting my fingers in your mouth?” he tilts his head, “Or are you wondering if I've thought of having anything else in your mouth?”
Shit. Oh, he's good. You look to Leah, looking just as thrown as you, then to Sam who's looking at you smugly. He's got you in it now.
“Both.” You shrug, still trying to hold on to the confidence from a moment ago.
“Yes,” he grunts before sipping down some whiskey.
You bob your head as you wait for him to go on. “Wait, that’s it? Just ‘yes’?”
“You didn’t ask for specifics.” He opens his hands at you in a ‘what can ya do’ gesture.
“Okay, well -”
“Nope, you got your truth. Leah’s turn.”
You turn to both Leah and Sam for help, but she just looks at you apologetically, and Sam ticks his head to the side in silent agreement with his brother.
Dean flashes a wink at you, watches you scowl in return before facing Leah with a grin. “Leah, truth or dare?”
She scans the room, eyeing up each of you and simmering in the tension. So far a few things have happened, but nothing that can’t be brushed off with whiskey and a shrug.
“Truth,” she answers, narrowing her eyes at Dean.
His cheek scrunches up in a crooked smile. His eyes flicker to you, then back to Leah. “Alright, Miss Leah, have you ever been with another woman?”
Her mouth drops open into a nervous grin, and a flush of red runs down her neck. She looks you over as you lean in to hear her answer.
“Sort of.” Your face lifts in amusement and curiosity. She pulls on her lip as she watches your response, her eyes trailing over your face, to your neck, to your chest. “There was a girl a few years ago, we both admitted we were curious, so eventually we got brave and started making out, but we both got too shy to go very far, so it didn’t go much farther than kissing and grabbing each others tits.” She shrugged, “It’s not something I’d be opposed to trying again, though...Just sayin’.”
“Just sayin’,” you nod and toss another wink her way as you look at her hands, noticing how delicate and feminine they seem; quickly the image of her hand on your breast fills your imagination.
“Why, Dean? You got a thing for girl on girl action?” She teases him, breaking you out of your thoughts to check out his reaction.
“Well...I mean…” He mumbles, tilting his head to find the right answer that doesn’t make him sound like a pervert. “I just enjoy beautiful women and sometimes they come in pairs.”
“Ah huh,” she grins then shifts her eyes to Sam. He’s sitting, patiently waiting and watching her fingers as they trail over the rim of her glass, “What about you, Sam?”
“What about me, Leah?”
“What do you think about watching girls together?”
He lowers his head, giving her a playful glare, “You haven’t asked if I want truth or dare?”
She rolls her eyes, pouting, “Okay, so truth or dare, Sam?”
“Truth.”
She practically bounces on the spot, happy that Sam is playing along, “So, Sam,” she tugs her lip between her teeth, taking a quick breath as she looks at you then back to Sam, “What do you think about watching two women together?”
He hums softly, watching her in amusement as she watches him, waiting. “Yeah,” he answers, his voice gravelly and deep, “Yeah, I like to watch.”
There’s a slight pause as you wait to see if he plans to clarify, but he leaves it. Your heart rate increases and you are nearly panting from all the information that’s been gathered with this go-round. Leah looks to be in the same state, her chest huffing out with each breath as she shifts in her spot. “It’s your turn, Y/n,” she reminds you. You nod and turn your attention back to Sam. He’s already staring at you, again with that smolder, which you’re not feeling very confident about resisting this time.
“Hey Sam,” you whisper, like you’re seeing him for the first time that evening.
His lips part in a flirty grin, flashing just a bit of his teeth, “Hey.” He pulls it back, making his expression a bit more serious. “So, truth or dare?”
You look down to the floor, lips pursed in an o-shape as you try to relax your breathing, trying to decide if you’re ready to snap the tension in the room just yet, or push it off with another truth.
“Time out,” you look up to see Leah with her hands in a “t” shape. Sam and Dean share a look, obviously questioning the validity of a time out during truth or dare, but she ignores them, reaching a hand out to you as she stands. “Hang on guys.”
You take her hand and the two of you make your way to the motel room door. She opens it, waiting for you to step outside before following you, both of you huddling from the temperature change.
“Sorry,” she starts, “I just...wanted to make sure you were okay with this.”
“Oh,” you answer, your confusion evident.
“Look, you live and work with those guys, so whatever happens, you still have to see them every day. I get to walk away from this either tonight...or tomorrow,” she shrugs, “I just don’t want to make things awkward with all of you. I mean, Jesus Christ, if you want to keep going with this, I am so game, but if you want to slow down or whatever, we can tone this down.”
“Ohhhh,” you nod.
“You just seemed a little tense and I didn’t want you to feel like, pressured or anything.”
Goodness, she just keeps getting better. “Thanks. Yeah, yeah. I uh, I appreciate that, but I’m good.” You nod, feeling more confident knowing Leah has your back, “I mean, masturbation and wet dreams can only take you so far, right?”
“Right.” She agrees, making you both giggle. “Okay, well, let’s get back in there.” Leah reaches out, pulling you in for a quick, tight hug.
You push the door back open, drawing the faces of Sam and Dean away from their own conversation and toward you with questioning glances.
“Everything okay?” Dean lifts his eyebrows.
“Yup,” you return to your seat. “Things are great. Now where were we?”
Leah settles back in her spot as well, nodding at you in encouragement. You catch Sam and Dean sharing another look, making you wonder what you missed while outside.
“Well,” Sam starts, drawing your attention with his husky voice, “We’re waiting for you to choose truth or dare.”
“Dare.”
He leans back a little bit more, resting his arm on the bed. “Did you like having your mouth on Dean last time, Y/n?”
“That sounds like a tru-uth,” Leah teases in a sing-song way, but he ignores her, watching for your response.
“Yes,” you answer breathlessly, pushing yourself toward Sam anxiously.
“Good,” he leans forward, “Then I dare you to lick Dean-” You suck in a breath, your eyes widening in anticipation. Sam adds, “Just from the waist up...for now.”
You turn to Dean, finding him watching you, his hands in fists and his thumbs rubbing against his other fingers. You’re already nearly on your hands and knees from the way you were leaning into Sam, so you pivot to fully face Dean, crawling the few paces his way. As soon as you start to move in his direction, his hands reach to pull off his overshirt. It’s hurried and ungraceful as he scrambles to get his shirts off, but encouraging.
You’re between his spread legs, your arms on either side of his hips, just lingering; your eyes roam over his shoulders, his chest, his stomach. Taking it all in without having to excuse it for any reason other than wanting to look.
“Sammy,” you drawl as you look at him from the corner of your eye, “You wanna see my mouth on your brother again?” You slide your tongue across your teeth. He nods at you with a ‘get on with it’ kind of tilt of his head. You catch the look on Leah’s face as you return your eyes to Dean, she’s got her lip between her teeth, watching the two of you intently. You lean in, feeling the warmth radiate from Dean’s skin and turn your mouth toward him, barely brushing him with your lips, just tickling him with your soft breaths over his cheek and jaw.
You lean in closer, reaching the hinge of his jaw and his ear, sticking out the tip of your tongue to just skim at the shell, and feeling him suck in a breath beneath you. You quickly dip lower, your open mouth covering the skin over the muscles of his neck, pulled tight as he draws back to give you room. Your tongue just licks at the skin, savoring the same taste you got from his thumb, but also remnants of the motel soap. You pull back as you lower your head to his collarbone, wetting your tongue before you push it between your lips and lick a long stripe from the muscle of his shoulder to the base of his jaw. He tenses beneath you, pulling up straighter with your movement like he’s trying to draw it out even further.
Smiling, you bring your mouth lower to his chest, bringing a hand up to rest over his anti-possession tattoo for balance, you kiss at the opposite side, smacking your lips and licking at the freckled skin, moving over him in no particular pattern - just dragging, kissing, licking at every bit you see.
Leah and Sam both shift, and you glance away from Dean to see what they’re doing. In your peripherals, you can see that Leah’s mouth is hanging open, her tongue licking around at the air, mimicking your movements, her fingers fidget at the hem of her shirt. Sam is leaning back, his eyes watching you, dragging slowly along the arch of your back, staring like he’s got all the time in the world. You let out a low hum of satisfaction, then push your hips up, arching your back to bend further down.
Dean’s muscles twitch under you, his pecs flexing and relaxing as you hover. You close your mouth, wetting your tongue before circling around his nipple in a slow swirl. His chest jerks in a shuddering breath which you mimic before diving in; your mouth covers the pink skin, sucking slightly as your tongue flicks over the little pointed tip and he grunts out a ‘yeah’ above you.
You spread your knees to dip lower, tracing the lines of his ribs, his muscles, then switching to the other side to do the same, sometimes flattening your tongue in a wide stripe, other times just tickling him with the tip; alternating hot breaths and cooling blows of air in your wake. His chest rises and falls, and his body squirms beneath you. You reach the waist of his jeans, his skin bunching a little and you can’t help yourself as you gently scrape your teeth against him, tugging just slightly at the flesh and making him hiss.
“I said lick, Y/n,” Sam scolds.
You pull away from the top of Dean’s jeans, giving Sam a playfully repentant look from under your eyelashes, “Sorry, Sam.”
“S’okay. I think it’s Leah’s turn now, anyway,” he answers, his eyes squinting at you knowingly.
Dean whines from deep in his chest and Leah breathes out a sigh. You plant a soft peck to the spot you’d nibbled and pull away, trailing your fingers down Dean’s leg as you slide back to your seat, licking your lips with an ‘mmm’ of satisfaction.
Dean head is rolled back on his shoulders facing the ceiling. He blows a breath out between pursed lips, his chest arched up as he sucks in more air. “Right. Alright,” he clears his throat, rolling his head to look at Leah, “Truth or dare, darlin?”
“Dare,” she responds, staring at his torso, darting her eyes over the broad stretch of his skin.
Dean shoots upright, pushing off his hands to sit straight, a smile crinkling his face and eyes shining with excitement. “Leah,” he pauses until she looks him in the eyes, “I dare you to put your hand down Y/n’s pants for the next round.”
Her eyes widen as she looks at you, her mouth popped open in surprise and her forehead scrunched with her silent question. You respond with a quick up-down nod. She bites her lip, then slides the whiskey out of her way, shuffling on her knees until she’s in front of you.
“You sure?” She barely whispers.
“Mm-hmm.”
“Okay.” She runs her hands up your arms, over your shoulders until she cradles your neck in her hands. “First though,” she whispers, pulling you toward her as she tilts her head, her eyes fluttering shut. You mirror her, and follow her lead feeling her lips slot against yours in a gentle pucker. She’s soft and small, and it feels a little strange to kiss someone without stubble or rough lips, but it feels good. You tentatively lift a hand to cup her cheek, instinctively parting your lips to dart out your tongue, meeting hers as she does the same, making you gasp into each other’s mouths and then dive into each other, mouths parted and tongues tangling.
“Shiiiiit,” a hoarse voice whispers behind Leah, making your eyes pop open as you pull away.
“Oops,” she giggles against your cheek.
“Yeah,” you smile. “Okay, so, how should we…”
“How about like this?” She again shuffles on her knees, making her way around you until she’s at your back, her legs spread wide for you to rest between them. You pull your feet out from under you, bending your knees and spreading your thighs open as you lean into her, letting her take your weight against her as she rests against the bed.
Your head just rests on her shoulder; the two of you shift until you’re both comfortable and she can reach between your thighs, her arms beneath yours and resting on your torso.
“Ready?” she asks with her mouth on your ear.
You look at the brothers, their cheeks flushed, jaws clenched, eyes focused on Leah’s hands as they rest over your jeans. Her fingers are just settled in the creases where your thighs meet your core, your legs in a ‘V’ with one Winchester seated at an angle at each knee.
“Yeah,” you swallow and she moves her hands to the waist of your pants, sliding the button through the loop and pulling at the zipper. The way she’s settled behind you makes it look like they could be your own hands, working their way beneath your clothes, but the touch is different, every little movement taking you by surprise. Her left hand grips over your hipbone, her right hand slides down, straight to your center, all four fingers slipping between your panties and your folds. Your breath hitches at the unfamiliar touch.
Sam and Dean both choke down appreciative groans at the sight, watching the fabric shift as Leah’s hand slides back and forth over you, her fingers just grazing along the wetness she finds.
“This good?” she asks, her voice high and breathy.
“Yeah. Good,” you answer, swallowing down a gasp.
She nuzzles her cheek against yours, staring at Sam from beneath her lashes. “Sam?” He blinks flicking his eyes from between your legs to meet her eyes. “Truth or dare?”
“Ask Dean.” You and Leah both pull up a bit. He catches the movement, lifting a hand to stop you, “I’m going to give my turn to Dean.” Your forehead wrinkles as disappointment flashes across your features, but again, Sam reads you, offering you a comforting smile. “Just, trust me? Dean, go ahead.”
“O-okay,” Leah’s voice shakes, unsure of the turn of events, but you feel her chin shift on your shoulder as she looks at Dean. “Dean? Truth or dare?”
His shoulders rise and falls with heavy breaths, and you watch the skin and muscles and the lines of his ribs move with each one. His tongue darts out to lick his lips, but his eyes don’t move from watching Leah’s strokes as he answers, “Dare.”
You feel her cheek smush up against yours as she smiles. “Dean, I dare you to kiss Y/nnnn,” she draws out your name as she swipes her fingers over your clit, making you twitch, “everywhere below the waist - except where my hand is.”
Just the thought of Dean’s mouth on you sends a rush of arousal to your core, and you feel Leah’s fingers dipping just inside of you to swirl her fingers in it. Dean watches you roll your hips with it and pushes himself up to his knees, sliding along the carpet until he’s between your feet. His hands settle on your knees, palms hot through the fabric, before trailing down your thighs to the belt loops, hooking his fingers through them.
“These gotta come off, okay?” he asks with a lopsided grin.
You nod and lift your hips, making Leah’s fingers slide deep between your pussy lips. Dean starts to tug at your pants, doing his best to shimmy them over your hips until he can smoothly pull them down your legs, lifting each leg in the air as he pulls them over your feet and crumpling them into a pile at your side. He returns your feet to the floor, soles flat, but legs spread wide.
You tremble, a strange mixture of nerves and temperature making you shiver although you don’t really feel cold with Leah at your back and Dean in front of you and the whiskey warming your blood. He’s staring directly at your core, watching Leah’s hand as she dips her fingers in and out of you, a damp stain on your panties showing your arousal. His hands are spread out over your knees again, the tips of his fingers digging into your thighs, putting pressure on them for balance as he ducks his head, placing a kiss to the inside center of your left thigh.
The smooth skin of his shoulders slips against your legs as he lowers himself between them, and you hear his knees knock against the floor as me moves them back allowing himself room to bend lower, kissing all along your thigh. His mouth feels hot, and soft, contrasted with the shadow of stubble growing in that pull against your skin with a slight burn. His breaths heat your skin as he maps it with his lips.
You inhale a shaky breath, at the same time hearing someone else’s sharp intake of air. You snap your eyes to Sam. His eyes are darting from Leah, to her hand, to your rapidly rising and falling chest, to Dean’s head working its way over your thighs, then finally to your face. His eyes are dark and wide with lust. You stare him down now, watching him as your body reacts to what the other two are doing to you, your hands roaming to grasp at whatever you can.
Dean’s mouth keeps getting lower and lower, licking and mouthing at the sensitive skin of your inner thighs, all hot and wet. Leah’s fingers stroke your skin at a steady pace, her middle and ring fingers sliding through the wetness from your entrance to your clit, her pointer and pinky sliding over the outside of your lips.
With your focus on Sam, you can only feel, and it’s amazing. Leah works you over so easily, it’s different than the usual hard massaging that you’d get on your clit from a guy. She swipes and spreads your wetness around, moving her fingers over your swollen flesh, then putting pressure around you, right against your bones - a slow build from a practiced hand. Dean, for his part, is grunting and almost snarling as he tastes you, flicking his tongue against your skin as he sucks kisses everywhere his mouth can reach, enjoying the flavor of you as much as you did him. Your fingers of your left hand become entwined with the fingers Leah is still pressing over your hip, your other hand rakes through Dean's hair, tempting you to grab hold and push him where you want him.
And Sam - Sam is watching your face - he’s watching your lips part, your teeth bared as you pant. He watches the pink color your cheeks, and the way your eyes widen when one of them hits a really sensitive spot. He watches as your skin goes dewey and shiny from the effort of sitting between those two as they tease and taste you, pushing you until you pull your lip between your teeth, making the pink skin go white from pressure. You lift your hips, trying to get just a little more...
“Y/n.” Sam says, pulling back your focus.
“Uh huh,” you manage to groan.
“Truth or dare?”
Your face pulls an almost painful expression as you try to think about anything other than Dean's face being inches away from your core, or the way Leah’s fingers are now steadily circling your clit. You can't figure out how to make your mouth form words so you grunt out the easier option. “Dare.”
“Show me how pretty you look as you come.”
“Yuh...yes, Sam,” you nod, holding back the whine you want to release at his tone. You swiftly make use of your hands to grab at the hem of your underwear, lifting your hips to pull them off. Dean, without a word, takes over once they're past your ass, dragging them, followed by his mouth, down your legs.
Leah is grinding her hips into the floor behind you, pressing kisses against your shoulder, your neck, tonguing at your ear, whispering about how good you feel. Dean makes a noise, like a broken “oh” drawing your attention back to him, catching his eyes focused in the sight before him, your pussy on display. Leah's fingers glisten with your arousal as she strokes you, her fingertips halting their circling, and now spreading you as best she can to give the boys a glimpse of your most intimate area.
For this moment, it’s easy to ignore the rough, stained carpet beneath you, and how one of the glasses has been knocked over leaving a new dark, wet spot, and how you still have your shirt on because you have better things to focus on. Like the way Dean is staring at you like you’re a Thanksgiving feast, and how Leah has started to rub her free hand up your torso to squeeze at your breast, and how Sam is clenching his jaw and rolling his shoulders like a lion ready to pounce.
“More,” you beg.
Dean obliges, sinking his head between your thighs, planting a kiss to each side as you feel Leah slide her fingers into you, pumping in and out. Suddenly, it’s all heat as Dean’s mouth meets Leah’s hand, and she slides her digits out of you with a moan feeling it, too. You take your eyes away from Sam to catch the sight of Dean poised at your entrance, licking your juices from Leah’s fingers, his tongue performing the same way Sam’s did earlier, only this time she’s coated them with your arousal instead of whiskey. He pushes the pointed tip between her fingers, spreading them apart until he can reach you, the first touch of his tongue causing you to jerk up your hips in surprise. Even at the angle you’re at, you can see the corners of his lips pull into a smile before he dives back in.
“Mo-oore,” you gasp as Dean barely pushes his tongue inside of you between Leah’s still parted fingers as they allow Dean to lick between them at your sensitive folds. She rolls her hips even harder behind you, whining at her own lack of friction as she strokes at you.
“Make her come.” Sam’s voice is soft, but close. He’s moved over, sitting beside you and Leah and talking softly in her ear. You feel her turn her head before you watch as she captures his mouth in a hungry kiss that he returns with equal vigor. You watch them, feeling her shift as Sam leans further into the kiss.
Dean reacts slowly, but after a moment he hums a quick ‘uh huh’ before pushing his mouth against you, licking as far into you as he can. He shakes his head back and forth, devouring you like a starved man as he ruts his hips against the carpet, licking you up and down and humming with each pass.
Leah starts to use the tips of her fingers, circling and flicking your sensitive, swollen clit. Your hips rock and stutter with the motions, chasing the sensations, feeling the peak of your orgasm swiftly approaching. Your eyes flutter closed as you focus on the delicious tension swirling low between your hips.
“Come on, beautiful. You gotta show me,” Sam pleads, deep and strained.
“Sam,” you respond, feeling the air from his words on your cheek. You turn your head toward them, and blindly reach a hand up to grasp at him, just catching the collar of his shirt and pulling him away from Leah to yourself. His mouth meets yours and he immediately takes control of the kiss. You respond with pliant lips, letting him ravage your mouth with his, and it’s just what you needed.
A few more strokes and you’re there, gasping for air as though you’re drowning; hips jerking up as your pussy flutters and convulses from your orgasm, your back curling as it rolls through you, sending an electric rush of relief over your skin.
You cry out repeatedly, nothing but meaningless jumbles of words. Behind you, Leah gasps and whines, desperate for her own release as Dean hums and grunts between your legs, nearly slurping at the flood of wetness you release. Sam whispers praise and curses as he pulls away watching you as you let out your cries of relief.
“Fuckfuckfuck,” you whine when you can finally form words again. “Jesussss fuckingchrist.” Your chest heaves as you regain focus, opening your eyes and staring at the water-stained ceiling. “Oh God.”
“Yeah,” Dean mumbles, still nestled between your legs, placing soft kisses between breaths. You look down to see his hair, messy and damp from sweat, his back rising as he catches his breath.
“C’mere,” you make grabby hands at Dean, making him flash a lazy grin and push up to his hands and knees. He crawls up so that he’s just over you, and you rest your hands on his face and stare at him through your blissed-out daze. “Thank you,” you whisper, pulling his lips to yours. You can taste yourself there, sweet and tangy on Dean’s swollen, soft lips and it’s satisfying in ways you’d only ever imagined. It’s not a long kiss, you’re both still too out of air to keep it up, but you slide your lips to kiss over his cheek, planting your lips onto him firmly with each shift until you reach his ear.
“You should really show Leah how good you are at that,” you whisper. He responds with a stuttering groan and you push on his shoulders to give yourself space. You twist around to face Leah, cupping her cheek to quickly give her a kiss and a thank you as well. She nods and breathes out shakily. You start to try to untangle yourself when two huge hands reach out to grab you beneath your arms.
Sam pulls you out of the tangled mess of limbs and against his chest, your legs straddle over his as he stretches them out again. You can feel the hard line of his cock through his jeans, but you’re still a boneless mess, so you rest against him lazily, letting him hold you and plant kisses all over your face.
“That,” kiss “was,” kiss “incredible,” kiss.
“Yeah,” you agree, nuzzling against him, basking in the heat radiating from him. You can hear movement to your side - clothes rustling, hushed words and giggles, then the squeak of mattress springs, but you can’t bring yourself to pull away from Sam’s chest, savoring the loud thumping of his heart under your ear. It’s not until you hear the high-pitched pornographic moan that escapes Leah that you finally look over.
Dean’s head is between her thighs and she’s laid out over his torso, her mouth hovering over his cock. His knees are bent and you can see the flex of his muscles as he tries to keep himself from thrusting up to her, waiting for her to lower her mouth onto him. His cock is swollen, bobbing with his pulse just beneath her lips, but her eyes are screwed shut, her mouth still hanging open from her moan, and you know exactly what he must be doing to her.
It reignites the need within you and you start to subconsciously rock your hips in time with the way Leah is riding Dean’s face.
“Leah,” Sam snaps her out of her daze, her eyes hazy with desperation. “Suck him off.”
Her eyes roll back in her head as Dean moans against her, but then she’s licking her lips, getting them good and wet as she reaches a hand out to grasp at the base of his cock. Dean’s hips jerk a little at the touch, and you watch as she slides her hand up to just under the head. She places a soft kiss there, her lips spread in a grin, and you hear Dean gasp at the touch. After getting the reaction she wanted, she then lowers her mouth over him. You imagine she’s taking the moment to swirl her tongue over him until her lips meet her hand, and she slides down further, taking more of him into her mouth. At least, you think, that’s what you’d do.
At that moment, Sam ruts up against you, the roughness of his jeans giving a bit of friction to your sensitive core and making you suck in air. Your attention snaps back to him, his eyes watching you with obvious lust and amusement. With his fingers stretched wide, his hands trail over your back, roaming until they reach around to your front, and slipping down to the hem of your shirt so that he can slide them underneath along your skin.
“You should get naked, too,” you remind him, pinching at the fabric of his shirt.
He huffs out a short laugh, but pushes you off his lap, standing to shed off his clothes. You pull your shirt off as well, the sounds from Dean and Leah amplify a fresh wave of need, making your muscles buzz with excitement.
Sam reveals more and more skin, and you're grateful for the opportunity to gaze at him, admiring the long, lean muscles of his form. He snags a condom from his wallet and sets it on the bed before lowering his jeans. You watch as he reveals that v of muscle next to his hips and follow the lines straight to his cock, finally free from the confining fabric of his jeans finding it's more than you could have hoped for. Your mouth waters - actually waters - at the sight, and your hips squirm, anxious to feel him between them.
He continues to undress until he wears nothing but a cocky, lustful grin. You give him a fully appreciative once over as he sits at the edge of the bed before meeting his eyes. He nods his head to beckon you to over to him, flourishing it with a seductive wink.
“Sam,” you giggle in an almost embarrassing girlish pitch, “Are you still winking at me?”
“You still winking back?” He asks, running his hands up your thighs as you place them on either side of his.
“Oh yeah,” you nod enthusiastically, reaching for the condom to open the package and roll it over him. You stroke him a few times, watching the muscles flex in his neck and abdomen as he restrains himself from pushing himself against you. “What about Dean?” you question.
With a quick glance to the other bed, you notice that Dean and Leah have shifted - he's kept her on all fours, but is lined up behind her, dragging his dick in and out of her. He catches your look and tosses a flirty wink your way before sucking his lip between his teeth and slamming hard against Leah's hips.
Sam grows impatient beneath you, hooking a finger under your chin to bring your focus back to him. “See? He likes winking at you, too. You okay?”
“Yes, very much yes,” you assure him, shifting so that you can line him up at your core, quivering again with anticipation and need. You slide up and down over him, slickening him with your come while his hands rest above your hip bones, fingertips clawing at you, anxious to feel you around him. You watch him with hooded eyes, mouth dropped open lazily - waiting, waiting for your moment to pounce. He rolls his head back as he draws in a breath, his chest tight, and that’s when you slide him inside of you.
You sink down, letting your knees push away from his sides as you go lower and lower, inch by inch until he’s filled you completely. He chokes on air for a moment and you feel the throb of his cock.
“Sa-aamm,” you keen as you grind against him, finally satisfying the urge to be filled. He hisses beneath you, then slightly pulls you up before jerking you back down against him, punching the air right from your lungs.
You catch on quickly, taking over the movement since you’ve got the leverage over him, bouncing up and down, taking him in deeply over and over again. Neither of you can focus, too caught up in the feel of him being driven into you - up, down, up, down. Your hands claw at each other, but your eyes are shut tight, heads thrown back as you both heave breaths and moans into the air.
The pace is fast and hard, and it feels amazing every time your bodies meet, sending tiny jolts of pleasure right through you. Another orgasm starts to tingle and you can feel it as it builds and builds, making you chase it until you can’t anymore. Your knees are sore from the way you’re perched on the bed, and your thigh muscles burn, but you’re so close that you’re ready to cry from the effort.
“Sam, Samsamsamsam, I’m so close.”
He sucks in air through his teeth, “What do you need, baby?”
Your face is contorted in frustration as you beg, “Fuck me, please Sam, just fuck me.”
He squeezes you tight as he mouths at your shoulder, his teeth bared and just resting against you while he shudders beneath you, nearly overcome with pleasure himself, muttering a quiet, strangled “fuck” into your skin. Then he shifts, and you slip a leg off of him and roll over onto the bed, barely lying down before he’s on you placing another demanding kiss on your lips. It’s the kind of sloppy, open-mouthed, I-have-lost-control-of-myself kiss and it feels perfect. With a suck to your bottom lip, Sam pulls up until he’s seated on his heels with his hips slotted between your widely spread legs. He drags a hand down to your thigh to pull it over his hip bone while the other teases his tip over your clit then your entrance, pausing just there.
“Beg me again,” he demands, and it’s the last thing that you can handle at this point, especially with Leah and Dean both wailing from their orgasms on the bed over.
“Fuck me, Sam, pleaase!”
He slams into you, digging his fingers into your flesh as he uses your thigh for leverage. The sound you make would normally be alarming, but given the way your body responds and the way your walls clench around him, Sam pulls back to do it again. Over and over, your body gives in and just takes what he gives you. Your back arches and your nerves tingle with the endorphins and pleasure racing through them as Sam keeps fucking into you, catching the spot within you with each drag of his cock and sending your body spiraling into another orgasm.
As your chest heaves and you feel the pulsing clench and release of your pussy around him, Sam leans into you, thrusting fast and shallow and chasing his own orgasm. Another few seconds of pushing and he’s there, his mouth caught open and eyes pinched shut while his hips stutter and jerk, his cock jumping inside of you while he pulses out his come. He finishes, breathless, and settles over you, both of you slick from sweat.
“You good?” he huffs into your hair.
You turn your head to look at the other bed, finding Dean and Leah in a similar state. Dean must catch your movement because then he turns toward you, flashing you a comforting grin and a little nod.
“Yeah,” you nod back before turning and placing a kiss to Sam’s shoulder, “Yeah, all good.”
Characters: Dean, Leah, Sam and Reader (Leah x Reader, Sam x Reader, Leah x Dean)
Location: Motel room, Crappsville, USA.
Word Count: 5127 (not even a little bit sorry)
Summary: The three of you celebrate the 1 year anniversary of you joining the Winchesters, and not dying, with fun and games.
Warnings: cursing, smut - kissing (f/f; m/f), light bondage, lots of teasing, using panties as gags, oral sex (f/f; m/f; male and female receiving), spanking, public nudity, some not so safe practices (under negotiated play; leaving a tied person alone), tickling, dirty talk, dom/sub undertones (ok, maybe a little more than UNDERtones…), penetrative sex
A/N: This is one of the many conclusions you can reach in reading the Choose Your Own Supernatural Truth or Dare Adventure! This was my third time writing for it with the 2 smuttier parts posted here and one more tame part getting posted at @revwinchester. I hope you’ve enjoyed your journey and that the ride has been… satisfying ;) This is a “truth” chapter but prepare yourself for plenty of smut below the cut.
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Part 1: The Set Up by @littlegreenplasticsoldier
Part 2: Dean Picks Dare by @eyes-of-a-disney-princess
Part 3: Leah Picks Dare by @impalasutra
Part 4: Sam picks Truth by @deansdirtylittlesecretsblog
CYOSTODA Part 5 - Y/N Picks Truth
“Truth or dare, Y/N?” Sam murmured.
You were so lost in Sam that you weren’t even sure that you answered him. But apparently you had, though his next question didn’t really help you decide if you’d chosen truth or dare.
His breath danced hotly across your ear as he leaned in and whispered, “Do you want me to show you what I did?” Sam pulled his face back to look at you and his pupils were blown wide with lust. You were pretty sure that your eyes were doing the same thing but Sam was still a step ahead of you because he could at least form words.
When you tried to reply, your tongue decided not to function. Your breath came in gasps as you looked up at the younger Winchester with wide eyes and nodded.
“What did you ask her?” Dean demanded.
His voice pulled you from your daze and you shifted slightly, Leah’s hand fell from your leg but Sam’s arms circled your waist and pulled you onto his lap, his erection pressing against your center through his and your pants.
“You don’t wanna know,” Sam told his brother.
Dean scoffed but, looking at the two of you, took Sam’s words at their face value. “Then it doesn’t count, ask her another question.”
Sam looked at his brother and then turned to you with a gleam in his eye. “Tell us, Y/N, what’s the kinkiest thing you’ve ever done?” Sam was turning your words back on you and you felt your cheeks flush even brighter as a new wave of arousal coursed through your body at the thought of some of your past exploits.
You cleared your throat, managing to find your voice - and your sass - in the process. “You mean kinkier than trading underwear and then making out with a woman who I’d just met in a motel bathroom?” you asked innocently, your eyes still locked on Sam’s face.
You hadn’t thought it was possible but Sam’s pupils dilated even further at your admission. He cleared his throat and blinked a few times before responding. “I mean, if you’ve got a kinkier story than that, you’d have to tell us. Rules are rules,” Sam said, his voice thick.
You thought about the question for a minute and came up with two possible stories to tell the group. “Hmmm,” you hummed, trying to build the tension in the room even higher. You rocked on Sam’s lap a little, pressing your chest up against his as you leaned forward and you heard a distinct hitch in his breath. “I’ve got two that I can think of… which one should I tell?”
“You could tell us both,” Leah suggested. You looked over your shoulder towards her and caught the sultry gleam that shone in her eye. She was most definitely enjoying herself.
You watched as Dean moved across the floor and slid in behind her. His legs spread wide enough for Leah to fit between them and his arm snaked around her waist as she leaned back against his chest. You smiled at the pair; the certainly made a cute couple. Looking at them, you had an idea.
“Well, one is easy enough to tell but the other… it’s a more involved story,” you baited the hook. “It might be easier to show, you know?” You could tell that you had both the Winchesters and Leah eating out of the palm of your hand.
“Show… show is good,” Dean told you, the lust bleeding into his voice as well, and Leah nodded her head.
“OK, show and tell, I can do that,” you replied. “Let’s start with tell, though.” You gulped a little knowing what you were about to reveal. It wasn’t overly kinky, per se, certainly not more so than Sam’s story had been, but you weren’t positive how Dean would react to it.
“About three months ago we wrapped up that inc…” Your eyes caught Leah’s and you quickly shifted the words you used to describe the case, “When we wrapped that case in Pittsburgh.” You had been hunting a incubus; it had been a rough case and you knew Sam and Dean remembered it well. Leah, however, had no idea bout the crap the three of you saw on a daily basis and, even in your inebriated state, you had no intention of destroying her innocence. At least, not that particular area of innocence.
“Finished a case? What, are you guys like cops or something?” Leah asked and you heard Dean chuckle.
You decided to press forward with your story, trusting Dean to field Leah’s question if your tale didn’t distract her enough. “Tensions were high after that one and we were all pretty on edge,” it was an understatement, especially in your case. Having thought you were hunting a succubus, you had been the one doing the tracking and leg work and you ended up falling under its spell. It had appeared in Sam’s form, a secret you planned to take with you to the grave.
“So, we all hopped into the car afterwards and I was still buzzing. I couldn’t really sit still in the back seat. You were driving, Dean, and Sam, you were occupied with whatever podcast you were listening to so I put my jacket over my lap and went to sleep.”
“I remember that,” Sam interrupted. “You rarely sleep in the car but you passed out really quickly on that ride.”
You turned to look at Sam, the flush already creeping into your cheeks. “Yeah, I, uh, I wasn’t asleep,” you admitted quietly. “I kind of, you know, took the edge off. It felt so, I don’t know, naughty. I had to keep quiet if I didn’t want you two to figure out what was going on back there.”
“Wait… you were… in the back of my… while we were…” Dean stuttered and you giggled at his reaction, glad that he seemed more disappointed that he had missed the show than angry that you had masturbated in his car.
Dean was still gaping when Sam spoke up. “So, that was tell… I think you mentioned something about a show?”
“I did, didn’t I,” you replied, sliding off of Sam’s lap and gracefully getting to your feet, or as gracefully as possible considering how much alcohol you had drunk. You extended a hand to Leah and helped her up, too. “Will you help me with this little demonstration?” you asked her.
Leah nodded and a sultry smile graced her lips.
“Sam, Dean, will you guys grab me your ties? I need them for this,” you shared. The boys nodded, obviously thinking they knew where this was going since you had asked Leah for help but really not having any idea. While the Winchesters dug through their bags for you, you explained to Leah what you were about to share with the group. She giggled and agreed to be a part of it, all of it, and when Sam and Dean handed you their ties, she looked at the strips of fabric and commented on how excited she was.
“This is going to be fun,” she said, licking her lips and looking you up and down before turning to Dean and looking at him like she wanted to devour him.
“You guys grab a seat on the beds; get comfortable” you instructed and Sam and Dean complied, the older Winchester even pulling off his shirt as you put one of the ties on each of the beds. “So, I was dating this guy, Josh, and he wanted to have a threesome. I wasn’t sure if I was really into the idea,” you told everyone and Dean scoffed. “Josh was really pushy and I hated it. I think I knew deep down that the relationship wasn’t going to go anywhere but I was still trying to save it or change him or whatever, so, eventually, I agreed.”
You straddled Sam’s lap and watched as Leah did the same to Dean while you continued talking. “I told him that we could give it a try if he would let me set the rules. He was hesitant at first but, in the end he said ‘yes.’” You pressed a kiss to Sam’s lips and pushed him back onto the bed. “So, I told him to lay down on his back with his arms above his head and when he did, I started kissing him.” You did what you said, kissing Sam deeply and trusting that Leah was doing the same with Dean. You ran your hands up Sam’s arms and clasped your hands with his, intertwining your fingers. After a few moments, you released one of Sam’s hands and reached for the tie you had tossed next to him on the bed. You brought it up and wound it around his wrists before securing it to the headboard. You knew it wasn’t your best knot work and you just hoped that Sam and Dean would play along with you and Leah.
You pulled away from Sam and sat back, watching as he gave an experimental tug at his bonds. He knew he could get out of it but he wasn’t trying and for that, you were grateful. “I surprised Josh and tied his hands above his head, just as a reminder that this was all on my terms. And then the girl and I had a little fun.”
You stood up and Leah did the same, approaching you with a sexy smile on her face. You stood between the beds, between Sam and Dean, and began to kiss again. Leah’s hands moved quickly to the button of your jeans and you shimmied out of your pants once she had opened them up. Both of you were practically naked, kissing and touching one another’s bodies while the two men watched. You finally broke the kiss but kept your hands on Leah’s hips, your fingers dancing along the waistband of her - or, really, your - panties.
“Despite the fact that he had been told in no uncertain terms that he would not be in charge, Josh kept trying to tell us what to do,” you said, your voice heavy with lust, “so I took off her panties,” you slid Leah’s underwear down her legs and she repeated the action on you, both of you stepping out of the garments and picking up the pair the other had been wearing, “and I used them as a reminder for him to stay quiet.” You knew the panties you were wearing were already wet and you could tell the pair in your hands had quite the damp spot, too. You smiled down at Sam as you approached his bound form. He was still dressed and you were now completely naked but you still felt like you had all the power. His eyes were locked on you and when his lips parted for his tongue to poke through, you pushed a finger into his mouth and pulled his jaws apart. You stuffed the panties Leah had been wearing into Sam’s mouth, causing the man to groan.
Having watched you, Leah turned to Dean. “Open your mouth for me?” she asked him sweetly. Dean complied without questioning and soon had a pair of panties in his mouth, too.
“Once Josh couldn’t speak anymore, she and I really had some fun with him,” you explained, “and with each other. We kissed and touched some more and she slid down to her knees.”
Leah did what you were narrating while Sam and Dean watched on. She was eye level with your pussy and she licked her lips in anticipation. Leah pulled at your ankles, silently asking you to spread your legs, so you did. Her tongue swept through your folds and started working little circles around your clit.
“It was the first time a girl went down on me,” you whispered, “and, oh God, Leah is so much better.” You moaned your pleasure into the room and out of the corner of your eye, you saw Sam pulling at the tie that was holding his wrists in place. “Josh wanted to join in so badly but,” you paused and practically squeaked as Leah added her fingers to the mix, “...but he just had to lay there and watch.”
Your hands found Leah’s hair and your pants and moans filled the room for another minute or so. You could feel the coil tightening deep within you but before you could come undone, you stepped away from Leah, an involuntary groan leaving your lips. “The girl that night didn’t make me come, she couldn’t figure out how,” you explained. “Leah definitely wasn’t having that issue,” you assured the boys. You helped Leah to her feet and kissed her, groaning at the taste of yourself in her mouth as your hands roamed her body.
You broke apart and turned to where sam was lying, his arms still above his head. Leah moved toward the bed where Dean was bound. “Are you guys cool with this?” you asked, not wanting to push anyone too far. “I mean, with your brother in the room on the next bed?”
Sam and Dean tuned to each other and caught one another’s eye. Sam was smirking and Dean raised his eyebrows at his brother. They were having one of those silent conversations. Even after a year of traveling and hunting with them, you still hadn’t been able to decipher any of the language. Without any warning, Sam sprang up from the bed and threw you over his shoulder. He pulled your panties out of his mouth and dropped them on the floor as he began to speak.
“Actually, I think you and I are gonna head to Leah’s room,” Sam announced, smacking his huge palm down onto your bare ass.
You yelped and squirmed, making Sam laugh at your predicament. He spanked you again, this time drawing a moan from you as he collected the tie he had apparently escaped from and then carried you into the bathroom. Sam fished Leah’s room key from her jeans pocket and made his way to the door.
As the reality of your situation hit you you began to struggle again Sam was about to carry you outside, over his shoulder, completely nude, to another motel room. You kicked your legs and squirmed around. “Put me down!” you squealed as Sam reached for the door handle. “Sammy, don’t you… mmmmmmh…”
Sam distracted you with two more sharp smacks to the meat of your ass and he opened the door, stepping out into the cool night air. The last thing you saw before the door closed behind you was Leah preparing to suck off Dean, who was still tied to the bed.
“You might want to keep it down out here, Y/N,” Sam instructed you, “unless you want to draw extra attention to your situation.” Sam sauntered to Leah’s room, your ass on display for anyone who might happen to step out of their room. He kept spanking and teasing you on the short walk, trying to elicit more sounds from your body but you kept your lips clamped shut so that only the softest of moans could be heard. You had never been more humiliated - or more turned on - in your life.
It wasn’t a long trek to Leah’s room, she was right next door, but it felt like ages before Sam unlocked the door and stepped inside. Once you were in the room and the door was closed, Sam tossed you onto Leah’s king bed and crawled on after you, the fabric of his clothes scraping against your over sensitive skin. He attacked your mouth and dominated the kiss with his teeth and tongue. Sam’s hands found yours and he lifted your arms above your head and secured them to the headboard using the tie you had used to bind him earlier.
Sam pulled back and looked down on your naked form. “It’s my turn, now,” he told you as he got off the bed and went to dht door. “I’ll be right back, don’t go anywhere,” Sam instructed cheekily and, with a wink, he was out the door.
You took the opportunity to test your bonds and realized you were well and truly stuck. Sam was better at knots to begin with and your fingers were clumsy from the alcohol in your system. There was nothing to do but wait stretched out and naked on the bed. From outside, you heard what sounded like a car door or trunk slamming shut and then Sam was back, carrying a small bag.
Sam put the bag down next to the bed and pulled off his shirt. He kneeled down and took something out of the bag, tossing it under the bed. He reached for one of your legs with a wicked glint in his eye and looped a piece of rope around your ankle. Sam went around to the other side and fished around under the bed for the rope - it must be what he had thrown before, you surmised - and repeated his actions on your other ankle, forcing you to spread your legs and leaving you completely exposed and vulnerable. You loved it. You had never shared this particular fantasy with anyone but, somehow, Sam was ticking off all of the boxes.
Sam rose from the floor and placed the bag on the bed next to your hip. He could access it easily but it was well out of your reach; Sam obviously wasn’t done with it and you wanted to know more than anything what else was in there, what he had in store for you.
Sam cleared his throat and you tore your eyes away from the bag to look at the younger Winchester. He had settled between your wide spread legs and he was smirking up at you. “Patience, love,” Sam chuckled, “you’ll find out what’s in there soon enough.”
You whined and pulled at the ropes binding your ankles as Sam’s warm breath fanned over your sex while he spoke. “You know patience isn’t one of my strong suites, Sam,” you reminded him and he laughed again.
“Which is exactly why I plan on helping you learn.” Sam reached into the bag and pulled out a feather. “We had this in the trunk with our summoning spell ingredients,” he explained, “but I think I’ve got a better use for it.” Sam held the feather between his pointer finger and thumb and ran it along one of your thighs, up over your stomach, and down your other thigh. He moved down to the end of the bed and dragged the feather over the sole of one of your feet and then the other, alternating between your feet as he tickled your feet, paying special attention to your soles and toes.
You moaned at the sensation and your toes curled but there was nothing you could do to escape. “Sam,” you gasped as he continued tickling and the hunter looked up at you innocently but he didn’t relent. You giggled as he dragged the feather up your right leg and teased your inner thigh before running the tip along your slit. It didn’t touch anything but the outermost skin and still you moaned and squirmed. “Need more, Sam,” you whimpered.
You thought Sam had acquiesced when he brought his mouth to your core but he simply placed a chaste kiss on your lower lips, or as chaste as a kiss can be down there, anyway. “Patience,” he reminded you before pulling back and dragging the feather up and along your stomach and ribs. Before long, you were shaking with your giggles and squirming in a fruitless attempt to get away from the feather and Sam’s relentless tickling. When he moved the feather to your armpit, you shrieked at the sensation. After what felt like an eternity of torture, Sam moved his attention to your other armpit and you lost control of your vocal chords again.
“Sam!” you squealed as your giggles escalated to full blown laughter. But, all at once, the laughter was replaced with a gasping moan as Sam gently ran the tip of the feather across your right nipple. The sensation shot straight to your core and you would have pressed your thighs together in search of relief if you could.
Sam switched the feather’s attention to your other breast, once again concentrating on your impossibly hard nipple. He lowered his head and used his tongue to continue lavishing attention on your right breast, driving you wild. You bucked your hips as best as you could, connecting with the denim of sam’s jeans as you moaned and threw your head from side to side.
“Aw, does someone want me to give her cunt some attention?” Sam asked, moving so that your meager thrusts were only met by open air.
You whined at the loss of contact and nodded, unsure you’d be able to speak.
“Use your words, Y/N. Do you want me to pay attention to your cunt?” Sam asked before diving right back in to sucking on one nipple and even gently gripping it in his teeth while teasing the other with that damned feather.
Shit. You’d never even imagined Sam would talk like this before but damn if it wasn’t the hottest thing you could ever recall hearing. “Please, Sam,” you managed. “Will you please give my… my cunt some attention?”
Sam smiled and pulled away from your breasts. He shifted down the bed and gave your sex a long look until you were shifting and blushing under his scrutiny. “I told you, love, patience,” Sam smirked.
After an eon (that was probably only another 30 seconds), you felt the feather brush along your sex again. This time, though, Sam dragged it lightly across your clit. You gasped and your back arched at the barely there stimulation; after all the teasing you were dripping wet and so, so sensitive.
Sam pulled the feather across your clit again and the dirtiest sound you had ever heard fell from your mouth. He pulled the feather back to tease at your folds again, still staring intently at your core. “So beautiful, so responsive,” he rasped, his voice impossibly deep and husky with lust, “such a pretty pussy.”
You groaned at his words. “Sam… Sammy, please…” You weren’t sure what you were asking for but you needed something, anything from this gorgeous man.
Sam pulled his gaze away from your sex and his eyes locked with yours. His pupils were so wide, you could barely see the beautiful hazel that usually ringed them. “I’m just doing what you asked, Y/N. I’m giving your beautiful cunt my undivided attention but, apparently, that’s not enough for you” Sam smirked as you whimpered at his words and he turned his attention back to your center. “Ooh, I know, what about this?”
You felt the feather drag a little lower. Your toes curled and your hands grappled with the tie as you let out a sinful moan. Sam was using the feather to circle your asshole and the sensations were nearly overwhelming. “Fuuuuuuuuuck… sssssssshit,” you hissed.
Before long, though, the feather was back on your clit, this time moving in tiny circles, relentlessly dancing across and around your most sensitive spot, never pulling away. You quickly found yourself on the edge of an orgasm but the feather alone wasn’t enough to push you over.
Your hips were rocking and you were practically crying with arousal and frustration. “I… please, Sam, please… I need… Sam... I just… please…” You were begging, the pleas falling from your lips as he continued to tease. “Please… Sam, more…” you finally managed.
As if it were the magic word, Sam dove face first into your folds, lapping up your juices. His tongue ran over your clit once, twice, three times, and you finally exploded. Screaming so loud you knew Dean and Leah would be able to hear it in the next room.
Sam worked you through your orgasm and when you came down, the feather was back on your clit and, quickly, you were over stimulated and struggling to get away but to no avail. Sam kept teasing, spurred on by your wordless moans, until you were dripping wet again and back on the verge of coming. “You want to know the kinkiest thing I’ve ever done?” Sam asked.
He didn’t wait for you to answer, likely knowing you were well beyond words at this point. “I let a beautiful woman tie me to a bed and, while her panties were stuffed in my mouth, I watched her get eaten out by another girl,” Sam breathed. “I was so jealous of Leah.”
You groaned at Sam’s admission and his continued ministrations on your clit.
“So jealous I had to escape and kidnap the woman so I could have her all to myself. I took her to a motel room, tied her to the bed, and got my revenge using only a simple feather,” Sam continued to recap your evening. “I teased her until she was asking for more using the dirtiest words I had ever heard her say and, even then, she only got the feather on her clit and her tight little asshole until she was begging. But she begged so nicely that I gave in and made her cum on my tongue and, God, was it good.”
You were already so needy again, ready to beg some more if that’s what it took, but you were hanging onto Sam’s every word. “Do you want to know what I did next?” he asked.
You nodded and forced your voice to work. “Yes.”
“I fucked her senseless.”
Sam pulled the feather away and stood, finally removing his jeans. He reached into the bag again and pulled out a pair of scissors and a condom. Sam cut the rope that was binding your ankles and then tore open the condom packet and rolled the latex over his erection.
He lined himself up with your entrance and looked to you, a question in his eyes. After all this, he was still asking your permission and you loved him for it. You nodded and Sam’s face shifted back to a sexy smirk. He drove into you in one swift motion, impaling you on his cock.
You gasped and moaned Sam’s name at the sudden feeling of being so full.
Sam gave you a moment to adjust as he reached up and undid the knots that held your arms above your head. Immediately your hands flew to his body, the nails of one digging crescent moons into his shoulder, while the other tangled in Sam’s hair and pulled him in for a kiss. For the second time that night, you tasted yourself on someone else’s tongue.
You sucked on Sam’s tongue and wrapped your legs around him, digging your heels into his ass and encouraging him to move. You were already so wound up from his teasing that you knew it wouldn’t take much to push you over the edge again.
As Sam got the hint and began thrusting his hips, your lips left his and began to explore his neck and jaw. You found an especially sensitive spot in Sam’s pulse point and gave it some extra attention. You sucked and nipped at Sam’s neck and soon his hips were stuttering. One of his hands moved to your center and his mouth claimed yours again. He gently bit down on your lower lip and flicked your clit all at once, causing you to tip over the edge for the second time. Somehow, Sam managed to hold off his own release until yours was complete and when he emptied himself buried deep inside of you, it triggered your third orgasm of the evening.
After he caught his breath, Sam rolled out of the bed and retrieved a washcloth from the bathroom, disposing of the condom on his way. He gently cleaned you up before taking care of himself and crawling back into the bed. Sam reached into the bag one more time and pulled out a bottle of water. He opened it and helped you to sit, supporting your boneless body as he encouraged you to drink, occasionally stealing sips for himself.
When the water was gone, you snuggled into Sam’s side and you both fell asleep.
The next morning, you woke before Sam. The early morning sun was streaming in through the threadbare curtains and the halo of light made Sam’s sleeping form look so innocent. Your head hurt and your mouth was dry but, surprisingly, that was the extent of your hangover. You had drunk way too much to be this lucky but you weren’t going to look a gift horse in the mouth.
Careful not to wake Sam, you snuck out of the bed and quietly collected his clothes. You pulled on his shirt and jeans, adjusting his belt so the pants would kind of fit and rolling up the legs so you wouldn’t trip. You grabbed his underwear from the floor, too, and, as you were about to go back to your own room, you picked up Leah’s bag for good measure.
Luckily, Sam’s room key was in his pocket and you let yourself into your room. Dean and Leah were still sleeping. Leah was draped over Dean, whose arms were still stretched and bound above his head. He was going to be stiff today but you’d put up with his moaning since, if you ever needed ammo against the older Winchester, you could hold this over his head, now.
You quietly dug through your bag for some of your own clothes. The soft sounds woke on of the rooms occupants, though. Leah sat up and yawned, stretching as she took in your form.
“What are you wearing?” she asked, her voice still thick with sleep.
You giggled at your naked friend, glad that there was no awkwardness now that the magic of the night and the alcohol had worn off. “Sam carried me out of here completely naked last night,” you reminded her. “So I figured I’d repay him the favor this morning. I hope you don’t mind that I brought your bag in here with me; didn’t want to give him the option to try some of your clothes.”
Leah just laughed at that, making a joke about not having to take the walk of shame in yesterday’s outfit. “So, you took all of his clothes?” she asked, her voice was hopeful and you realized she still wanted to see Sam naked.
You smiled your most innocent smile. “I left him his tie.”
That’s the end of the ride folks! I hope you enjoyed it all! Head back to the Master List and take another path if you fancy reading some other awesome authors and a completely different sexy story! Many thanks are owed to @littlegreenplasticsoldier for hosting, wrangling all of the writers, and making this such a fun experience!
Summary: The three of you celebrate the 1 year anniversary of you joining the Winchesters, and not dying, with fun and games.
Warnings: language, drinking, sexual innuendos, mentions of sex with another person, flirting at a whole new level
Link to the Choose Your Own Supernatural Truth or Dare Adventure MasterMess moderated by the amazing @littlegreenplasticsoldier
Part 1: The Set Up by @littlegreenplasticsoldier
Part 2: Dean Picks Dare by @eyes-of-a-disney-princess
Part 3: Leah Picks Dare by @impalasutra
Sam passed you the bottle, making a point of keeping his eyes on your face. Dean, on the other hand, was not quite the gentleman his brother was pretending to be and you felt his eyes roaming over your body as you poured yourself another glass of whisky. “Alright, it’s not like you’ve never seen a naked woman before,” you grumbled as you started to feel the last round of alcohol hit your system. “Let’s keep this game moving.”
Leah took that as her cue and turned her gaze on Sam, a wicked glint in her eye. “Truth or dare, Sammy?”
You watched Sam carefully, not realizing you were holding your breath until you felt the burn in your chest. You took a breath, blinking rapidly. Sam was starting to look a little blurry.
“Wait!” Dean interjected. “I thought we were gonna hear what happened in the bathroom?” He stared earnestly at first you, than Leah, silently pleading with both of you to tell him what had happened behind that closed bathroom door.
“Later,” Leah smirked, dropping a wink over her shoulder at him. “Maybe when it’s your turn again.”
Dean sat back, looking like a deflated party balloon, a definite pout on his face. You couldn’t help but giggle. You took another drink from your full glass of whiskey, the room tipping on its axis just a little. You kind of liked it.
Leah turned her attention back to Sam. “Come on, Sam, truth or dare?”
You thought he might say dare, somehow keep the game going in the direction it seemed to logically be headed. You wouldn’t mind that at all, especially if it meant you might get to continue that kiss with Leah that had been interrupted. You were interested to see where that might go. You sat forward, forgetting your nakedness and the fact that Dean couldn’t take his eyes off of you, anxious to hear Sam’s choice.
“Truth,” he smirked.
“Fuck me,” Dean grumbled, sitting back, his shoulders slumping in disappointment.
Leah smiled at him, planted her hands on the floor, and slid closer to the center of the circle until she was sitting right beside you, her knee leaning against yours, her hand resting on your calf. You wished you didn’t still have on your jeans, because you would really love to feel her soft skin against yours again.
“What’s the kinkiest thing you’ve ever done?” she whispered. “In detail.”
One side of Sam’s mouth tipped up in a smirk reminiscent of his brother’s. He lifted his glass to his mouth and took a slow drink. He shot a glance at his brother, rested his arm on his raised knee, the glass dangling from his long fingers, his eyes drifting slowly over you.
“Sex in a public place,” he smirked.
“No way,” you shook your head. “Dean, maybe, but not you.”
“Hey,” Dean protested.
Sam rolled his eyes. “You think my brother is the only one that does stuff like that? Oh, you have so much to learn, Y/N. So much. You see, we were in this club and one of the dancers -”
“So you were in a strip club?” Leah interrupted.
“Yeah,” Sam answered, eyes narrowed. “Okay, we were in a strip club and one of the dancers came over to our table. She was flirting, a lot, hand on my shoulder, running through my hair, making it pretty obvious what she was after. Dean made himself scarce and the next thing I know, she’s in the booth beside me, her lips on my neck, her hand down the front of my pants.”
“Whoa, whoa, whoa, Sammy, TMI,” you groaned. “T. M. I.”
Before you could blink, Sam was right next to you, sliding one leg behind your back, the other bent at the knee, tucked up against you, as close to you as he could possibly get, his face just inches from yours. “Oh, but Y/N, it was so good.”
He was so close to you and his voice was so low that it was like the two of you were the only people in the room. You licked your lips, nodding at him to continue, the movement making your head spin a little. He put his hand, his huge hand, on your waist, leaning impossibly closer, the whiskey scent of his breath blowing across your face. For a second you thought he was going to kiss you, but his lips just grazed the edge of your jaw as he moved to press his lips to your ear.
His fingers drew circles on your bare back as he spoke, soft, easy, like he touched you intimately all the time. His voice was raspy, thick with the alcohol he’d drank, barely a whisper. “She crawled in my lap, Y/N, right there in the back of the club, people all around us. She pulled my hand between her legs and begged me to touch her.”
You closed your eyes and swallowed, heat pulsing through you. “Sam -” you murmured.
But he didn’t stop, his hand sliding up your back and into your hair, his fingers twisting in the strands. “She was so wet and oh, Christ, was she tight. Then she wrapped her legs around me, put her hands in my hair, and she pulled it, just like this -”
Sam’s fingers tightened noticeably in your hair and he tugged, just hard enough to draw a groan from you. His hair was tickling your cheek, warm breath against your cheek, close enough to kiss. You turned your head, just a little, but it was enough for your lips to brush against his in an almost kiss.
Sam pulled harder on your hair, tipping your head back enough that you could look into his hazel green eyes, the black of his pupils blown wide. There was a flush of pink to his cheeks and his lips were wet with saliva. You wanted to kiss him.
You’d forgotten Leah was sitting right beside you, forgotten about her hand on your leg, forgotten about everything, your entire focus narrowed in on Sam. You jumped when she squeezed your leg and cleared her throat.
“That doesn’t count, Sam,” Leah frowned and shook her head. “I wanted detail.”
“It counts, Leah,” you whispered, unable to look away from Sam’s mesmerizing gaze. “Trust me, it counts.”
Summary: The three of you celebrate the 1 year anniversary of you joining the Winchesters, and not dying, with fun and games.
Warnings: drinking, unprotected sex, mentions of little green Dean (a vibrator), smut
A/N: Yay, it is here! Part 5 (and possibly the last part) of this thread in the truth or dare adventure. Also a big thanks to @littlegreenplasticsoldier for organizing this fanfiction festival of sorts and handling it like a boss!! This wouldn’t be possible without you!
Choose Your Own Supernatural Truth or Dare Adventure: Masterlist!!
Part 1 by @littlegreenplasticsoldier
Part 2 by @gemini75eeyore
Part 3 by @deansdirtylittlesecretsblog
Part 4 by @notnaturalanahi
“Wait!” Leah stops him. “Before you go in there to fix your um… problem, Truth or Dare?”
Dean frowned, musing over his options. Truth or dare was the last thing on his mind right now. “Wasn’t it Y/N’s turn?” he asked as he not so discreetly covered his crotch area. His pants were getting very tight and oh how he needed that sweet relief.
All eyes were on you, waiting for your response. “I’m still recovering from my confession so Leah can have my turn,” you grinned at your new found friend. She winked at you and turned back to the older Winchester, her eyebrows quirked up, curious of his choice.
Dean quickly decided it wasn’t going to be truth. Leah would ask him to repeat your words with a 99.99% chance and he wasn’t planning on sharing that kind of information. So he blurted out a quick ‘dare’. The glint in Leah’s eyes worried him more than his imaginary truth did, making him regret his pick already.
“I dare you to do 7 minutes of heaven with the lovely Y/N over here. Do all the naughty things she whispered in your ear, you know,” she winked. Dean stuttered, his gaze shifting back and forth between you and Leah. Your eyes widened as well as the dare left her lips. You’d kill for seven minutes with the Winchester hunk, but saying so and doing it was an entirely different thing. Leah kicked your boot and nodded her head in Dean’s direction, prompting you to take the opportunity while the offer lasted. He hasn’t said no yet, you thought before taking a deep breath and deciding why the hell not.
The overconfident ladies man starting to go shy cliché was unfolding itself in front of you, Dean being a murmuring mess, tripping over his words and shifting from one foot to another. If you wanted that Winchester cock tonight, you clearly had to take the lead.
Without a second thought you stood up and grabbed his hand in yours, pulling him with you. He looked a little bewildered at your sudden leadership, not used this side of you, but followed nonetheless. You walked to your adjacent room under Sam and Leah’s enthusiastic whistling and howling.
As soon as the door of room 14 closed behind you Dean regained his confident composure. “So, do I get the pleasure of meeting little green Dean?” he murmured in your ear, his lips ghosting over your neck, his firm chest pressed against your back. A shiver ran over your spine while your fingers fumbled with the key card. It was getting hard to focus on unlocking the door and not on the hard cock nudged between you.
The light on the door handle turned green and the older Winchester pushed the door open before pulling you into the room with him. The thud of the lock falling shut was followed by Dean’s lips crashing into yours. You poured your feelings into the kiss, some of the sexual tension that had been building up all night finally leaving your body.
“6 minutes!” Leah shouted through the thin walls.
“Better hurry then,” you chuckled as you tugged at the hem of his shirt. In between kisses you stripped yourselves of your clothes until you were standing in front of each other in only your underwear, Sam calling out the 4 minute mark.
Dean picked you up and placed you in the middle of the bed before crawling on top of you. You pulled him in for a deep kiss as your hand traced the hard lines of his chest, inching towards the bulge in his black boxers, precum damping the material. Your fingers wrapped around his cock through the fabric and you pumped your hand a couple of times.
“Hmmm, fuck, Y/N,” he groaned into the kiss. The cocky smile on your lips quickly disappeared when his fingers brushed over your clothed pussy. You gasped as he pushed your panties to the side and dipped a finger into your heat. A soft moan left your lips when he added another one.
“That’s more like it! 1 minute,” Leah cheered.
Suddenly Sam’s voice boomed through the wall. “I dare Y/N to spend another 7 minutes in heaven with Dean.”
“8 minutes,” your new friend called out all giddy, clearly excited that your little adventure would continue a little longer. Your mind barely registered their conversation, completely focussed on the hand between your legs. Dean’s thumb flicked over your clit and circled around the bundle of nerves, slowly driving you insane. Your moans turned wanton, your hands clawing at his back to pull him closer, your hips pushing down onto his fingers.
You were getting tired of his teasing. He kept pushing you towards that edge, the knot in your stomach ready to release and just then he’d slow down his pace, holding you right at that tipping point. With one swift move you were on top of the older Winchester. His hands roamed your sides and cupped your breasts through the fabric of your bra. You quickly discarded the clothing item, Dean’s fingers instantly toying with your hardening nipples. As you whimpered at the touch, you threw your head back and scratched his chest with your nails. Every little caress was enough to turn you into a moaning mess, your body oversensitive with years of build-up anticipation.
The hunter rolled his hips against yours. “Why don’t you show me how little Dean pleases you?” You bit your lip at his words and locked your gaze with his. “And then I can show you that the real thing is way better,” he growled in your ear. His arms snaked around your waist as he pulled you closer to him, placing openmouthed kisses over your chest and breasts.
“I’ll be the one deciding that,” you whimpered. “And I’d prefer your cock over that piece of plastic any day.” With your words you tugged down his underwear and quickly got rid of your panties as well. Dean laid himself on top of you, his cock nudging at the apex of your thighs. Your hand pumped his length and positioned him at your opening, guiding him into your heat.
You both moaned at the feeling of Dean filling you up to the hilt. He cursed under his breath, your name leaving his lips as soft pants. At your sign he built up a slow pace, your hips bucking against his with every thrust. Your bodies moved in sync with one another and your moans filled the room.
“Definitely better than little Dean,” you gasped, capturing his lips with yours, kissing away the self-satisfied look on his face.
Dean thrusted into you again, stilling as he bottomed out. Your load moan was drowned out by a high pitched scream of a very familiar name. “SA-AMMM,” you heard Leah cry out. You chuckled. Of course they couldn’t keep their hands to themselves. Your laugh soon turned into a moan as Dean pistoned his hips against yours a couple of times while his fingers toyed with your clit.
“Fuck, Dean,” you breathed heavily, not bothering to comment on his smirk. When another scream came from the room next door, Dean pulled back out. Right when he was about to drive himself back into your throbbing centre, you stopped him. He frowned at first, but then looked at you worriedly. Yes, you loved the guy’s cock, but there was just one thing that needed to be clarified. “Is this turning into some kind of Winchester brotherly competition of who can make the girl scream louder?”
Dean scoffed and answered with an unconvincing ‘no’. You raised an eyebrow at which he sighed. “Maybe,” he mumbled. “And I’m losing so scream louder.” You laughed at his comment before you pulled him down by his neck and pecked his lips.
“You know, we can all be loud together,” you whispered, licking your lips. “If you can’t win, join ‘em.” The hunter grinned down at you. He attacked your lips for a hungry kiss before he pulled back and banged his fist on the wall above the headboard.
“What?” an annoyed Sam grumbled back.
“I dare the both of you to come join us,” Dean replied back. For a couple of seconds it was dead silent until the sound of bare feet thudding on the carpet reached your room. This was going to be a fun night.
THE END!
OR NOT
If someone feels like writing a foursome with a shitload of dirty dares in a final part 6 then go for it *winks seductively and hopefully* I don’t feel qualified to write a mini-orgy so whoever (of the CYOSTODA writers) wants to continue this, be my guest! If not, it ends here I’m afraid.
(Open spot for a possible link to a possible part 6... maybe)
Following on from Part 1 by @littlegreenplasticsoldier, where you get into a game of Truth or Dare with Dean, Sam, and their motel neighbour, Leah. You’ve just asked Dean Truth or Dare.
CYOSTODA Mastermess here
Dean’s staring at you, those gorgeous green eyes flitting over your face, and you can see the wheels turning, can practically smell the smoke. He locks eyes with yours as he runs his tongue over his bottom lip and you fight your urge to follow it’s path so hard you can feel your eyeballs shake with the effort. Dean smirks at you, like he knows full well what he’s doing to you, which let’s face it, he probably does.
“Dare.” he finally says, low and sure.
Shit. Shit fuck dammit. It’s too early in the night to just come out and straight up dare him to fuck your brains out. Plus, you know, desperate much? Yeah, no. Better think of something else, something more subtle.
“Alright, Winchester. I dare you to remove three articles of clothing from the person of your choice.” You give him your best flirty smile, trying like hell to hide your hope, “You can even pick Sammy if you’re scared.”
Sam laughs next to you, “Don’t even think about it.”
You glance over to Leah again, curious to see her reaction. She’s smiling, eyes hopping back and forth from Dean to you. She catches you watching her and throws you another wink, this one full of support. She straightens her spine and stares at Dean, confidence oozing from every pore, one eyebrow elegantly arched. Wow, you wish you could be so sure of yourself. You lift your glass, needing more liquid courage because no matter who he picks, you’re sure as hell gonna need it. Before the glass can reach your lips, you stop in thought. No one ever picks the person who actually wants to be picked. So why is she being so…? You flick your eyes over to her, confusion all over your face. She doesn’t look at you, eyes staying steady on Dean, the only sign she gives that she’s aware of you watching her is a slight smile tugging at the corner of her mouth. Son of a bitch, she’s good. You just hope he falls for it.
“Y/N.” Dean says just as you toss back your drink. You choke on the liquor, coughing as it burns your throat. Oh God, he fell for it.
He’s still smirking at you, the bastard. He motions at you, thumb jerking up. “Stand up, sweetheart.”
Abort! Your brain’s yelling at you. No, no, see where this takes you. Your vagina reassures you. Alcohol, more alcohol. Your nerves whisper to you. You take your nerves advice, moving to your hands and knees to crawl over and grab the bottle, chugging whiskey straight from the bottle. You catch Sam in your peripheral, his eyes on your lips wrapped around the mouth of the bottle. Jesus, you may end up regretting this idea.
You set the bottle back down off to your side, the glass thunking against the threadbare carpet. You pull your bottom lip into your mouth, worrying the remaining whiskey off the skin. Ok, you can do this. You push yourself up, wobbling a bit when the blood rushes from your head. Dean rises to his knees, as fucking smooth as ever, and shuffles over so he’s in front of you. This is a view you could get used to; Dean on his knees, staring up at you with wide eyes, fanned out eyelashes so long and thick you almost want to punch him, plush pink lips slightly parted.
You get a little lost in your thoughts, alright fantasies, until Dean’s hands on your hips yank you back to the here and now. He glides his hands down your thighs, thumbs reaching towards the inseam of your jeans and you have to put your hands on his shoulders to steady yourself. You were wrong, you can’t do this. Dean gives you a small reprieve as he runs his hands down to just under the knee, sitting back on his heels and tapping one hand on the back of your calf so you raise your foot. He guides you to place it on his thigh then runs his hands up under your pant leg. You find yourself thanking God that you had to wear your Fed suit yesterday and therefore had to shave your legs in order to maintain a truly professional look, this would be so much more embarrassing if you hadn’t gotten rid of the forest you’d been growing.
When his warm, calloused fingers make contact, you practically jump out of your skin. He chuckles lowly as he curls his fingers under the cuff of your sock and slowly eases it down and over your heel, lifting your foot off his thigh as he slides it the rest of the way off your foot. You don’t take your eyes off Dean as he twirls your sock in the air before throwing it somewhere behind you but you vaguely hear Sam and Leah laughing.
“Saucy.” Sam teases.
Dean just smiles as he straightens back up, hands falling on your hips again. He lets his fingertips play against the skin above the waistband of your pants as he moves to your belt buckle. Oh God. He watches your face as he works the buckle open, his eyes darkening as your breath picks up. He grabs the buckle and pulls, the leather making an incredibly arousing sound as he pulls it through the loops. He drops the belt to the floor with a thud and quickly stands up.
Your breath picks up even more when he gives the hem of your shirt a gentle tug and raises a brow at you. Oh God. Oh God, oh God, oh God. Dean’s looking at you so reassuringly, so...is that tenderness you see in his eyes? Or is that just the whiskey? Either way, you nod your head.
Dean grabs the hem of your t-shirt and the tails of your plaid shirt in both hands but doesn’t get any further than your belly button before Sam interjects. “That’s two pieces…”
“Shut it.” Dean points at him, stopping him before he even finishes his sentence.
Dean gets both hands on your shirts and starts pulling them up, the backs of his knuckles dragging against your sides. You shiver as goosebumps break out across your skin. He gets the shirt to your armpits and you lift your arms up over your head. You hear three different gasps fill the room as Dean pulls the shirt up over face and uncovers your breasts. Turns out leaving your sexiest, but least comfortable bra, as your last option until laundry day worked out for you this time. High five for procrastination! You shake your hair back when your head’s finally freed, looking up at Dean to see his eyes are locked on your breasts, following the lacy line over the swell of each one, tongue playing behind his teeth. His eyes meet yours as he drops your shirts to the floor, one hand coming up to brush his thumb over your cheekbone, he drops his gaze to your lips and leans in…
“Dean.” Sam says sternly. “There’s rules, dude.”
Dean rolls his eyes and backs away, grumbling. “You and your fucking rules. Ok, Leah, guess you’re up. Truth or dare?”
Leah picks truth, written by @revwinchester
Leah picks dare, to be written by @revwinchester (yeah, she’s doing both, deal with it)
Our fearless leader, @littlegreenplasticsoldier started us off with Part 1 here
@gemini75eeyore followed with part 2 here
@deandoesthingstome came next with part 3 here
@klaineaholic part 4 is here
Characters: Sam, Dean, Leah, Y/N
Setting: Another no-tell motel, Crappsville, USA
Dean doesn’t respond at first so you say his name, louder this time. “Dean!”
“Huh?” He mumbles, looking dazed.
You look over at him, and you realize Dean Winchester is looking at you like he’s seeing you for the very first time.
You know how he feels. You have crossed some invisible line with the boys tonight, and there is no going back.
“Truth or Dare, Dean.” You whisper, still feeling his hand on your ass, and you bite back the moan that threatens to spill out.
You look over at Sam and he smirks at you, his knowing eyes hot and teasing. “Yeah Dean. Truth or Dare?”
Dean stalls, indecisive. Truth has always served him well, but the dares have been pretty hot so far. Dare. He’d choose dare. But Y/N was sneaky.
The horrific vision of him running around the room naked clucking like a chicken suddenly popped into his head. “Truth, I choose truth.” He blurts out before he can change his mind.
“Truth, huh?” Y/N says, and Dean knows by her tone he’s in trouble.
You turn and wink at Leah. Then pausing a moment to think, you lean forward, lick your lips and say to Dean, “so what’s your favorite thing when it comes to oral sex?”
Leah snorts at Sam’s audible intake of breath and the look on Dean’s face. “Oh this is gonna be good.” She says gleefully.
He doesn’t say anything for a long moment as he looks at his drink. When he finally looks up, his eyes are fairly smoldering with lust.
“I like a woman who knows how to use her tongue. So many women think it’s the up and down that get us off, but it’s not. But a woman with a talented tongue? There is nothing like it. Give me a girl who can lick me like I am her favorite lollypop, and I will die a happy man.” Dean finished.
You toss back the rest of your drink in one swallow. “I’ve never had any complaints, Winchester.” You spy something next to Dean and an idea pops into your head. “Want a demonstration?”
Dean’s mouth drops as you stand up and walk towards him. You can hear a pin drop in the room. Sam’s breathing has gotten heavy. You can see the bulge in Dean’s pants from here. Every eye is on you. You bend down in front of Dean, your eyes locked with his…
And grab the empty beer bottle on the floor next to him and walk back to your spot. “You didn’t really think I was going to blow you right here in front of everyone did you? I mean come on!”
Sitting cross-legged on the floor, you held the bottle in your hand. You licked a broad stripe up the side of the bottle, then twirled your tongue around the head of the bottle while locking eyes with Sam. He swallows hard and starts to sweat. The more you worked the bottle the more he began to squirm.
Then you turned your attention to Dean. Moving your hand up and down the shaft of the bottle, you hollow out your cheeks and took the whole neck of the bottle into your mouth before swirling your tongue around it and releasing it with an audible pop!
Dean groans and balls his hands into fists. “Fuck!” He mutters.
You nonchalantly place the bottle back on the floor and wink at Leah. “Like I said, Dean. No complaints.”
The room was silent except for Sam and Dean’s ragged breathing. You needed a minute to catch your breath. “I’m gonna go get a soda. Leah, you wanna come?”
“Sure.” Leah said, jumping up.
“Be right back guys.” You said as you and Leah walked down to the soda machine at the end of the hall.
“OK Y/N, what’s the deal? Which one is yours?” Leah asked.
“Neither.”
“Well I want Sam. Can you keep Dean busy? I’ll have Sam back in one piece more or less in the morning.” Suddenly Leah didn’t look so innocent.
“I can try.” You told her.
The two of you walked back to the room and you sat on the bed. Sam and Dean must have had a conversation of their own. Within 5 minutes Sam and Leah had gone to her room to “hang out” and Dean and you were alone in his room.
The minute Sam and Leah were out the door, Dean was across the room and on the bed next to you. “You have been driving me goddamn crazy all night, Y/N.” He growled.
“I dare you to do something about it, Dean.” You whispered, and then he was on top of you and he was kissing you like a man possessed.
“I want you, Y/N…. I have for a long time and that’s the truth.” He murmured against your ear.
Characters: Dean, Leah, Sam and Reader
Location: Motel room, Crappsville, USA.
Word Count: 2200ish (wordy4lyfe! It goes quick)
Summary: Sam hits you with an easy truth, but Leah wants to know more, and Y/N ends up daring Dean
Warnings: None really, sexual innuendos, and being in Dean’s lap ;)
See @littlegreenplasticsoldier‘s Master Mess
The road so far..
@littlegreenplasticsoldier Part 1
@gemini75eeyore Part 2
@deandoesthingstome Part 3
@rizlowwritessortof Part 4
You’re blushing, and you’re all getting giggly, and this suddenly seems like the best idea anyone’s ever had. “So, whose turn is it? Is it my turn?”
Sam gets that evil, seductive smirk on his face again as he nods. “Oh, yeah, Y/N. It’s your turn. So, what’s it gonna be? Truth or dare?”
With the whiskey making a nice, warm run through your body, combined with the revelation you’ve been a possible source of a few Winchester wet dreams, you hold tightly to the extra courage it’s given you and mirror his evil, seductive smirk back at him as you mull it over. “Well, as tempted as I am to want your dare, after those barefaced admissions, I’m gonna bet you…” pausing briefly, you glance at Dean making sure you’ve got his full attention before looking back to Sam, “…are curious to know, do I give the two finger salute to you? Or do I think of Dean over there when I need to check my oil?” Looking over to Dean again, his eyebrows lift in interest, lips pulling into a smirk when you throw him a playful little wink for your play on words. “Or maybe, I’m finger dippin’ to the two of you at the same time? So hit me with it, truth. What do ya wanna to know?” You internally high five yourself for the choice of words and slide the smirk back into place.
Without missing a beat, or even so much as a blink he asks, “Y/N, have you ever gotten off on thoughts of me, or Dean?” He’s not letting up on that god awful sexy little smirk of his, and his eyes are practically piercing your soul now; or is it your nether region? He really is loosening up now with that bold question.
Your liquid courage has a perfect answer for him too. “A girl has needs. Of course I get my rocks off as often as I please, but a lady has to have a few secrets, Sam.” Holding his stare you smile sweetly and slowly raise your glass to your lips. Dean grunts out a laugh, his tongue swiping out to wet his lips as he leans back against the cupboards, bringing one knee up to rest an arm on it as the other leg lays relaxed against the grimy carpet.
Sam’s mouth turns down in approval, nodding as he takes that in. The gears are still moving inside of that head of his though, and he’s about to say something more when Leah chimes in, “Well Y/N, I have a truth for you, sticking to this topic of self satisfaction and half naked bodies.” Her smile is wide as she shifts her legs around to cross them. “I want to know, what do you find to be the sexiest aspect of each brother?”
“This outta be good,” Dean smiles.
Your cheeks grow warm at having been put on the spot again. Sure, the brothers had to of assumed you’ve excavated your cave on more than one occasion with your recent lack of action, but damn, now you have to get specific about which parts you literally thought about? You were breathing a little sigh of relief with Sam’s easy truth, but it seems she’s asking what Sam may have been looking for originally.
“Are we talking physical aspects? Or characteristics?” you clarify, hoping you didn’t have to divulge the physical parts you’ve noticed the most day in and day out.
Sam gives her a conspiratorial wink and looks at you with an expectant smile, as Dean’s got his eyebrow pulled up to attention, his face giving zero clue to his thoughts, and Leah’s slyly smirking as she answers, “I know they’ve both been complete gentlemen so far tonight, and since you see them regularly, how about both.”
You let out a slow breath through your nose and decide to go for it. Brave Y/N, be brave. Someone’s gotta bend this tension filled room a little further, right?
“Well…” you begin, looking between each brother, lingering on Dean across the way, taking in the perfect spread of his long legs, eyes gleaming as he sits there patiently.
You set your glass on the carpet and rise to your knees, catching Sam’s eyes. “Sam here, he’s very much a gentleman, and one who’s always willing to put your needs ahead of his own.” You slowly make your way closer to him as you speak, looking over your shoulder at Leah until you’re behind him, and set your hands on his shoulders. “The sexiest thing about Sam, if you ask me… is his mind. He’s smart. Too smart sometimes for his own good. I mean the things he can do with a computer…” You raise one hand, fanning yourself dramatically, Sam’s head dropping forward as his shoulders shake with laughter. “You want logic and fact, he’s your go-to guy. He’s definitely the more logical one of the two.” You give her a playful wink feeling his hand rest over yours and give it a tiny squeeze, catching Dean eye-rolling so hard you can almost feel it.
Threading your fingers with his you pull his hand up. “Then you have these.” You unwind your fingers and he leaves his hand up in the same position as he follows your lead. “Just look at the size of that hand, huge right? Those long, dexterous fingers. I mean they just give a girl all kinds of wandering thoughts watching them at work… or even at rest; paging along a book, through papers, his hair, anything.”
You ruffle his hair some with a smile, before turning your attention to the other brother. “And then you have Dean over here.” He’s a little further away from Sam so you drop your hands to the floor, pulling your bottom lip between your teeth and slowly crawl towards him. And by slow, it’s slow. He’s just far enough away you can drag it out a little bit.
He shifts to sit up straighter at the attention, eyes locking with yours as you move. “Fearless, selfless Dean,” you sigh. Sam’s leaning back some, unable to keep his eyes from dragging over your form in this position; your back arched just so, and you can feel Leah doing the same, her own lip between her teeth as she hangs on each word. “Don’t be fooled by his macho man act, because while he’s 200% man in there, underneath it all lies a huge, bleeding heart of gold. The love he has for his family, blood or not; the amount that he cares about those he’s allowed in, he’d do anything and everything for them… and that, is the sexiest thing about Dean.” You’re between his spread legs when you stop, both of them now raised at the knee to make room for you. Rising up you sit back on your heels. He looks away shaking his head with a disbelieving half smile, but you know you’ve struck something inside; you can feel it pulsing off of him.
Shifting closer to him, you move until your knees rest against the bottom of his thighs. “Then you have that mouth of his.”
His eyes slide back to yours, head tilting along with his mood. He swipes his tongue out to wet his lips, pulling your attention to them, and that damn eyebrow is arching again indicating you’ve got his full attention.
You have to clear your throat to reign in your wayward thoughts the small action provoked so you could speak again. “Those plush lips, full of sass and bad jokes. And as funny as he thinks he is, you will never prepare yourself for his charm. Boy, can he lay it on thick too. He’s smoother than fresh butter when he’s in the zone.”
He scoffs rolling his eyes, and you bust into a fit of giggles. “Aw, you thought I was going to talk about how soft and supple they are, didn’t you?”
“Actually, yeah. I kinda did. Gotta say I’m a little disappointed there, Y/N.”
It’s your turn to roll your eyes. What is with these three calling you out right now? “Ok, fine,” you sigh with fake exasperation.
When you had started this truth, you had a plan of mentioning it, for dramatics, but decided to keep that bit of information to yourself, locked away for those nights you were alone in your own bed. The alcohol, however, had loosened you up a lot further than you originally thought now that you’d made it this far. That, combined with the light headed feeling you got from Dean’s blatant staring at your mouth at the moment, you decide to jump in feet first.
“To say I’ve never looked for extended periods of time, being with them as long as I have, would be a lie,” you start.
“Stared would be more accurate,” Leah interjects, nodding at you suggestively when you look at her over your shoulder.
“True, but I can’t be obvious here. I do se-”
“Sure you can,” Dean cuts in, practically giving you whiplash with how fast your head turns. “I wouldn’t mind.”
You quirk your eyebrow up, pursing your lips as you scan his over his face. “I know you don’t. Just one look at them, pouting naturally, subtly inviting the viewer closer. How could one not want to see just how soft they really are? To run their tongue along the soft, supple flesh, nibble and suck at that full bottom lip, feel them work across their skin.”
His eyes have gone a shade darker as you talked about him, the two of you now staring at the others mouth he responds, “The feelings mutual sweetheart.”
You both bring your eyes up to meet the others at the same time.
“Well Dean, then I dare you to find out if its true. Kiss me.”
He takes an audible deep breath in, slowly leaning the upper half of his body forward, and places his hands on your thighs.
“Whoa, guys, that’s not the rules of the game,” Sam speaks up.
Not breaking eye contact your hand flies up, arm outstretched behind as you to hold a finger up, one of Dean’s hands doing the same, signalling him to give you a minute. He’s moving just a little slower than you thought he would given the vibe he was putting off, and with the nerves bubbling in your stomach to confirm if he actually felt the same, you reach up and place your hands on his shoulders, pulling his mouth to yours.
You both simultaneously sigh when your lips lock, his hands coming up to take your face between his wide palms and press his lips harder against his. You push into it with him, feeling the confirmation he wanted this too as you tilt your head to the other side, sliding your lips along his for a different angle. He follows your lead, and with the warmth of arousal spreading across your body at the contact, you lick along his bottom lip, asking for entrance.
Sliding your tongue tentatively in, he happily meets you in the middle, and the smooth slide of the muscles against one another has you both moaning in appreciation, like you’re devouring the most delicious meal you’ve ever tasted.
It’s getting steamier the deeper the kiss gets. Your hands have run their way into his hair, as his have trailed down your back, settling into the curve of your lower back, pulling you closer as he moves straighter to press you against him. You climb over his raised thighs, accepting the invitation for connection and he lowers his legs in response once you’re over, wrapping his arms tighter around you.
The contact is heady. The kiss is heady. God he’s amazing at this. He was not lying either about how good that mouth of his is. Your breathless and wanting more as you settle down in his lap, melting into his warmth, a grin forming against his lips when you feel how much he’s enjoying this beneath his zipper as he presses his hips tentatively against yours.
You’re beginning to wish the other two weren’t present so you could rip his clothes off, and feel all of his smooth skin against yours. The ache between your legs is quickly going from a dull roar to a full fledged fire, and if this keeps going, your cares might completely fly out the window and they’ll really get a show. But you don’t want it to stop.
Sam clears his throat, and you barely register the sound, too lost in the feeling of Dean’s mouth against yours. He hasn’t noticed either, even when Sam clears his throat again, Leah giving him a shrug as she smirks, amused watching the two of you go at it like horny teenagers.
“You guys want us to leave? Or do you want to continue playing the game?”
It isn’t until Sam speaks that you finally pull away from each other, the two of you breathing like you’d just run a mile. Smiling you shrug at Dean who rolls his eyes at his brothers comment. Someone sounds a teeny bit jealous…
Dean leans closer, dropping his voice so only you could hear. “You have no idea how long I’ve wanted to do that.”
“Yeah, I do. Because I have also…”
You slowly slide off his lap to the ground, and place your hands on the floor behind you as you carefully move away, crawling backwards towards your original spot. “I believe it’s your turn, right Dean?” You put on your best sexy little smile, one you’ve used a time or two to get information you needed. “Truth… or dare?”
Dean picks truth (he tries ;) ) by @kreborn17 HERE
Dean picks dare (well, tries to ;) ) by @deansdirtylittlesecretsblog HERE
