Summary: During a trip to Vegas for a boys’ weekend, Dean finds himself alone, and bumping into Jay, the girl who could probably beat his ass at pool, eat more than him, drink him under the table and is more likely to cheat with another girl than he is. Dean finds himself married to her by morning, but the drunken impulse decision leads to more than either of them could have predicted.
Part Tags: angst, strip club, flirting, teasing, f/f, threesome, oral sex (both), voyeurism, exhibitionism, intentional incest, incestuous dirty talking, orgasms, fluff
Part WC: 3720
A/Ns: Hope you’ve enjoyed this smutty little mini! <3
“Here,” Jay sighs, holding her hand out in front of her.
“How did you find me?” Dean asks, glancing over at her and then looking back out at the view in front of him.
Jay sighs and drops her hand, sliding her ass onto the hood of the impala to stare out at the view with him. “Sammy said you might be here,” she replies.
“He hates being called Sammy,” Dean tells her.
“That’s what John calls him.”
“Yeah, and he hates it.” Dean lets the silence grow for a moment, and then takes a deep breath. “Why did you lie to me?”
“When?” Jay asks, frowning at him.
“When we got married, you said your last name was Mills, but it was Winchester, and you knew that, and you didn’t even say anything when you found out my name was Winchester.”
Jay clears her throat, starting to kick at stones beneath her boots. “I haven’t used the name Winchester since I was eighteen, when I cut John out of my life. Mills is my mother’s last name. I wanted to be like her. And we’re not the only Winchesters in America, Dean. I don’t know, I was drunk and… I didn’t think about it. We hardly made any great decisions that night.”
“But it wasn’t just the name. You recognised his jacket, and the car, didn’t you?” he presses, feeling a little irritated by the very thought.
Jay huffs, clearly annoyed now. “Do you really think I knew who you were and carried on fucking you?” she accuses. “I thought they were all coincidences, Dean. I didn’t know that John had other children, he never talked about you. He was just some guy that showed up now and then and took me to a baseball game or bought me diner food, we weren’t exactly close.” She stops, kicking her feet some more. “And I guess, the more I got to know you, the more I excused all the things that seemed strange. I guess I just liked you too much and I was in denial.”
Dean looks across at her at her confession, seeing her cheeks turn a darker shade of pink.
“You liked me?” he finds himself asking, almost hopefully, even though that’s really fucked up.
“Well, I did keep getting naked with you, so what do you think?”
“Yeah, but you also kept going on about the divorce,” he reminds her.
“Because we barely know each other, and the only thing we were good at was having sex. We got married the day we met, drunk off our faces, all because you liked the way I sucked your dick,” she needlessly reminds him. “If that’s not the start of a doomed marriage, what is?”
“I don’t know, I think we could’ve made it work,” Dean tells her honestly.
“Well, none of that matters now. At least me lying about my legal name made the annulment quick and easy,” she offers with a fake smirk.
“Guess so,” Dean replies, nodding softly.
“We’re brother and sister, and we’ve gotta live with the fact that we’ve done some stuff that no brother and sister should ever really do with one another, and that’s tough–”
“Yeah, especially with the way Sam keeps teasing me about it,” Dean grunts, glaring into thin air at the very reminder.
“I wanna stay in your life, though, Dean,” she confesses, turning to face him completely. She grabs his hand and uncurls his fingers, placing something in his palm and then closing his fist. “I can learn to love you in a different way.”
Dean opens his hand once she lets go, and sees his ring sitting in the centre of his palm. He takes it, twisting it between his fingers for a moment, before taking a deep breath and pushing it down onto the finger it had always lived on before Vegas. It feels weird being back on his hand, and he’s not sure that he likes it.
“It’s getting late, wanna grab a burger and then try and drink me under the table at a strip club, for old time’s sake?” she smirks. Dean laughs in disbelief, wondering if she’s serious, but the way she cocks her eyebrow makes him realise she is. “Your first lap dance is on me, as a divorce present.”
“You’re such a lucky boy,” the red head purrs, grinding her barely covered ass down into his crotch. Dean chokes on a moan, smirking slightly.
“Why’s that?” he asks, trying to remain some semblance of calm and collected.
“Because not only is your girlfriend very good looking, but she’s treating you to a dance.”
“You think she’s good looking?” Dean asks, brushing over the mistake the dancer has made.
“I’m not blind, sweetie,” the red head scoffs, bringing her mouth close to his. “I’m close to offering her a freebie.”
“Well, given the way she was staring at you on that pole earlier on, I’m sure she’d appreciate that.”
The red head smirks, her brown eyes sparkling a little. “Is that right? You wouldn’t mind me stealing your girlfriend’s attention for a while?”
“Are you kidding?” Dean scoffs, finding his hands on her hips. Once he realises what he’s done, he goes to pull away, knowing that they run a no hands on policy here, but she just grabs his hands and guides them to her bare chest. Her breasts fill his palms perfectly, and Dean swallows hard.
“Not often we get a couple as hot as you two in here, and it’s even rarer for me to want to take my work home with me.”
“I’m not paying extra for that,” Jay’s voice speaks up, entering the private room with fresh drinks for the two of them. Dean instantly drops his hands, not wanting to make Jay uncomfortable, but she just smirks, taking a gulp of whiskey. “Don’t stop on my account,” she tells them, taking a seat, crossing one leg over the other as she sets her eyes on them.
The redhead flashes Dean a wink and climbs off of his lap, making her way over to Jay, as Dean tugs his trouser legs down a little, needing some relief, and then reaches across for the drink Jay bought him. He almost spits it back out when the stripper climbs into Jay’s lap and starts giving her the same treatment she’d given Dean.
“He was touching… Can I?” Jay whispers seductively, biting her bottom lip.
“Please do,” the redhead giggles, bringing Jay’s hands to her chest like she’d done Dean’s.
“Jesus Christ,” Dean moans softly behind his glass, watching the two women so close to kissing but resisting. He finishes his whiskey, and desperately needs another, but he’s not leaving this room any time soon.
“I’m getting off soon,” the stripper tells Jay, grinding her hips down.
“Yeah, you will be if I have anything to do with it, sweetheart,” Jay replies far more smoothly than Dean would’ve ever pulled it off. The dancer giggles, climbing off of Jay’s lap.
“Time’s up, I’m afraid, sweetie,” she sighs, reaching for her bra she’d discarded on the floor when stripping for Dean. Dean watches her redress in her lingerie, and Jay finishes her drink, her eyes fixed on their company.
“I haven’t paid you,” Jay reminds her as the redhead turns to leave.
“You can pay me when you meet me outside in fifteen minutes,” she tells her confidently.
“Am I bringing him?” Jay asks, nodding her head towards Dean.
Her brown eyes land on him and she smirks. “Oh, you should definitely bring him, he’s not gonna wanna miss it.”
Dean swallows hard as they’re left alone, and then he finally looks at Jay. “Did you just rope me into a threesome?” he asks.
“Are you actually complaining about that? Did you see her?” Jay scoffs.
“That’s probably not a good idea, we shouldn’t be doing that stuff anymore,” Dean reminds her.
Jay sighs and licks her lips, nodding her head. “No, you’re right,” she agrees. Dean’s disappointed with her acceptance, realising he’d been hoping she’d fight him on it, make him give in. The idea of seeing Jay with that girl is already doing things to him that it shouldn’t. “I’ll just hook up with her, you can go home.”
“That’s not fair,” Dean complains. Jay just smirks, shrugging nonchalantly. “Well, I mean… if we only fuck her and we… keep ourselves to ourselves,” Dean finally offers, shrugging slightly. “Not like we’ve not seen it all before…”
Jay bites her bottom lip, smirking softly. “One last drink before we meet Elle?”
“Her name is Elle?” Dean questions, frowning slightly.
“You didn’t listen to a word she said when she entered this room, did you?”
“I’m a guy, all I saw was tits,” Dean defends, making Jay laugh.
“Well, tits has a name, and it’s Elle, and you should probably learn that before we fuck her.” Jay gives him a cocky smirk and then leaves the room, making Dean wonder what he’s gotten himself into.
Dean’s not sure how much longer he can keep his cock in his pants. It’s painfully hard, pressing against the denim, restricted by his pants. He pours himself another whiskey and lounges back on the dining chair he’s sat himself on, facing the bed, for the perfect view of the show. It was Jay’s clever idea to get a motel room, making them look like some couple on a mini vacation or something.
Elle moans softly as Jay kisses her deeper, pushing her red hair back over her shoulder and then moving her lips down her neck. Elle’s fingers are teasing the buttons of Jay’s pants open, her delicate hand pushing inside, making Jay gasp against the dancer’s neck. Dean can’t hold off any longer at the sounds of their soft gasps, and he unbuckles his belt, opening his trousers and earning Elle’s attention as she watches him out of the corner of her eye. Dean takes in every little detail of the two girls kneeling opposite each other in the centre of the bed, Elle already in her underwear, Jay close behind, her shorts now wide open, her shirt on the floor. This is better than any porno Dean’s ever seen – he’s not sure he can ever watch two girls fuck for a camera the same way again.
His hand wraps around his cock as he pulls it free, making it throb in relief, and then he starts to softly jerk.
“Fuck, you’re a lucky girl, Jay,” Elle giggles, her eyes on Dean’s erection.
Jay glances over at him and smirks, reaching around for the clasp of Elle’s bra and undoing it, revealing her hardened nipples. “He feels as good as he looks,” she breathes against Elle’s breast, before taking the bud into her mouth.
Elle moans softly, biting her bottom lip. “Why don’t you come here, Dean? Let me help you with that,” she offers with a purr. “If that’s okay with you, baby.”
“He’s all yours, I’m focusing on you right now,” Jay tells her, kissing across to her other breast.
Elle smirks, beckoning Dean over with a flick of her fingers, and Dean finds himself on his feet and approaching, before his brain has even registered what’s happening. He stands in front of her, his cock still in his hand, and she leans across, capturing his lips in a kiss. Dean’s head is spinning now, her hand trailing softly down his chest towards his cock, and Dean lets go so she can take over. Dean can’t help himself from reaching forward, pushing Jay’s hair back out of her face, so he can see what she’s doing clearer from this angle, and Jay looks up at him through her lashes, her green eyes sparkling. She smirks, and then sucks Elle’s nipple into her mouth again, biting down on it and then letting it go with a soft pop. Elle’s grip tightens on Dean’s shaft, making him moan, and then Jay climbs off of the bed.
Elle’s attention turns completely to Dean, as she bites her bottom lip and looks up at him through her lashes. She lowers her head slowly, maintaining eye contact the entire time as she gets closer and closer to his cock, then she starts sucking him down, swirling her tongue. She’s not quite as good as Jay, but Dean’s not about to complain, either. Not when she takes him deeper and gags softly, making him throb harder.
When Jay climbs back onto the bed he realises she’s ditched her shorts, now only in her underwear; a matching pink lace set that looks incredible on her. Dean tries to focus back on Elle, because he should not be thinking about how good his sister looks in her underwear, not anymore, not now he knows who she is. He watches her comb her finger through Elle’s hair, holding it at the back of her head and aiding her movements, smirking as she watches.
“That looks so good,” she hums, “making me so wet.”
“It feels good,” Dean admits. Jay’s eyes flicker to Dean as he moans, and she smirks softly before bringing her attention back to their company.
“Lay back for me, sweetie,” she commands softly.
Elle pulls off of Dean’s cock and does as she’s told, laying down on her back on the bed. Jay’s smirk is mischievous as she hooks her fingers into Elle’s panties and pulls them down her legs, leaving the dancer completely naked. Jay’s hands smooth up Elle’s thighs, spreading them open.
“Let’s see if she can still suck your cock as well while I’m eating her out,” Jay suggests with a wicked grin.
Dean scoffs, moving to Elle’s head as she looks up at him and opens her mouth wide, sticking out her tongue invitingly. Dean bends his knees, pushing his cock past her lips, watching the way it bulges in her throat from this position. His eyes wander down her body towards Jay, finding her lips on her thigh, moving higher towards the redhead’s core. Jay licks her lips and locks eyes with Dean as she finally lowers her mouth to Elle’s core. If Dean wasn’t engrossed in Jay’s every movement, he’d still have been able to tell the minute Jay’s tongue touched her, from the way Elle’s throat closed up a little more around him.
Seeing Jay’s tongue and lips move so effortlessly around Elle’s cunt, the dancer’s juices leaving behind a shine on his sister’s full lips, only makes Dean’s cock harder. Jesus, how can she look so hot doing that? Jay notices him looking and pulls back, reaching up with her hand and pushing two fingers into the redhead’s cunt, making her moan around him. She smirks at him, biting her bottom lip, bringing her mouth really close to his.
“Turns out I can eat pussy too,” she teases, and Dean can smell Elle’s arousal on his sister’s lips. He wants so desperately to kiss her, his mind screaming fuck it, I just want her. But then Jay disappears, and once more her mouth is on Elle’s core, moaning as she tastes her.
Dean has to pull back, freeing his cock from Elle’s mouth as it drips with her spit onto her face below him. He’s not sure he’s gonna survive this threesome, not without finishing embarrassingly early. Jay doesn’t stop though, she continues to hold Elle’s thighs and feast on her, smirking when Elle starts moaning and arching her back, telling her that she’s so close. Dean’s still close just watching, his cock abandoned in front of him. Elle comes undone on Jay’s face, and Jay licks her lips, smiling triumphantly.
Elle slides herself out, getting back on to her knees, bringing her mouth close to Jay and kissing her once.
“Fuck for me?” she asks.
“What?” Jay laughs slightly.
“Want to see you two fuck,” Elle tells her, “I bet you’re so tight.” Elle’s hand smoothes down Jay’s body, over her lace panties. She reaches up, pushing her hand behind Jay’s panties, and Dean watches Jay’s mouth fall slack. “Wanna watch him stretch you open.”
“Fuck,” Jay whispers, her eyes landing on Dean.
God help Dean, but he wants that too. He can’t help it. He knows how good she feels, how good he can make her feel, and he’s more turned on than he’s ever been in his life.
“You can make her cum right, Dean?” Elle teases, and he’s only just realised that her attention is on him now.
“Yeah,” Dean swallows, nodding.
“Prove it,” she whispers, kissing his lips briefly before sliding off the bed. She takes the chair Dean had been observing from and grabs his drink, sipping from it herself, and Dean looks back at Jay and smiles nervously.
Dean wants to ask Jay if she’s okay with this, because they really shouldn’t be doing this. They’d agreed to stick to their own corners, but the lines have been blurring all night.
“C’mon, sweetheart, what are you waiting for? Prove it,” Jay tempts, biting her lip.
Dean reaches for her, pulling her close and kissing her passionately, his whole body tingling to feel her lips on his again. He’d thought that it would feel different now that they know the truth, but it doesn’t. It doesn’t feel weird or wrong, it doesn’t feel any less electrifying. It just feels good, like it’s meant to be this way. Dean’s desperate – desperate to feel her, to remind himself what he’s been missing the last couple of weeks that they’ve stopped doing this.
He spins her around, pushing her down onto her hands and knees, pulling her panties down over her ass to expose her wet core to him. Jay moans, glancing back over her shoulder, at him, and Dean barely hesitates to line himself up and thrust inside her, feeling her clench around him in all the right ways. Fuck, he’s missed this, so much.
“Fuck, Dean,” she whimpers, fisting the bedsheets. Dean starts to thrust, deep and hard and fast, his hips snapping loudly against hers, almost drowning out the sounds of her moans.
She starts rocking back on his cock to aid him, sending him deeper, her walls tightening around him. Dean pays no mind to Elle, or the soft moans that leave her lips as he notices her touching herself to the scene out the corner of his eye, and he wraps Jay’s blonde hair around his fist tugging softly, encouraging her to lift off of her hands, her back pressing to his chest. Dean brings his face over her shoulder, furthest away from Elle, pressing his mouth to her ear.
“Feel so good, baby,” he whispers, making her moan, his hand reaching up to grope her chest. “Feel so fucking good around my cock.”
“Fuck, Dean,” she whines, reaching up behind her to grip the back of his neck. “Don’t stop, right there.”
“Gonna cum soon, baby? Cum on your big brother’s cock.” He doesn’t realise what he’s said until it’s out of his mouth, and he’s surprised to feel his cock throb at his own words, Jay’s cunt clenching him like a vice.
“Holy fuck,” she gasps, sounding as surprised as he is at the revelation.
“That’s it baby sis,” he carries on, talking quietly enough that Elle won’t hear him over the sound of their bodies connecting, and Jay’s mewls and moans. “Feel so good, love your brother’s cock inside you, don’t you?”
“Yes,” she squeals out, her nails digging into his neck. “I’m gonna cum, Dean.”
“Cum f’me, baby,” he grunts a lot louder now. He holds himself still, feeling her clenching around him, panting heavily. She drops her hand, her body sagging in his hold, and Dean kisses her shoulder. “Fuck, I love you.”
Jay pulls away, turning around to face him, her eyes glistening but Dean can’t be sure if that’s the aftermath of her orgasm or tears. She offers him a weak smile and then kisses him.
“I love you too,” she whispers.
“Holy fuck,” Elle gasps, clearly oblivious to what’s going on. “That was so fucking hot, please tell me it’s my turn?”
Dean looks up from the ring on his finger at the sound of the motel door closing, and he watches Jay make her way back to the bed, his shirt the only thing covering any of her body. She bites her lip anxiously as she climbs on, sitting at the foot of the bed and creating a little distance.
“Are we gonna talk about this?” she asks, bringing up the elephant in the room straight away.
Dean sighs, “What’s there to talk about?”
“How good it felt when you were saying all that fucked up shit to me,” she replies bluntly.
“What fucked up shit?”
“Don’t make me say it, Dean,” she pleads, her eyes soft and wet.
“Guess I’m fucked up,” Dean shrugs, not sure what else to tell her.
“Then I am too,” she sighs. “I didn’t think it would feel that good now that we know the truth, but it… it felt…”
“Better,” Dean finishes for her, staring back down at his ring.
“Fuck,” she scoffs, shaking her head. “I regret it.”
Dean looks at her, frowning slightly. “The sex?” he checks.
“No, that’s the fucked up part. I don’t regret the sex… I regret the divorce.”
Dean sits up straighter, swallowing hard. He reaches for her chin, lifting it up so she’s looking at him. “It couldn’t be real… it wasn’t real,” he reminds her.
“I know,” she nods, smiling sadly.
Dean bites his bottom lip, reaching down and sliding his ring off of his finger. “But that doesn’t mean that we can’t pretend.” He takes her hand, slipping the ring onto her finger like he did that night in Vegas, and she smiles slightly, looking up at him with even wetter eyes than before.
“No one can know about this,” she tells him, sniffling.
Dean shakes his head, “no. But I quite liked you being my little secret,” he smirks.
She laughs through tears and twists the ring around her finger. “What am I gonna tell John when he sees this?”
Dean shrugs easily. “Tell him it’s a chastity ring, he’ll love that.”
Jay laughs again and leans in to kiss him.
“You do want me, don’t you?” Dean checks, worried he’s done the wrong thing.
Jay smiles, kissing him softly. “I do.”
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