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: public sex, fem rec oral, orgasms, drunk wedding, teasing, flirting, mentions of threesomes, mentions of f/f, sex, p in v, cum in mouth, cum swallowing

Part WC: 3006

Waking Up in Vegas Masterlist

“Deal… if you can give as good as you get,” Jay challenges, smirking at him. Her lips are still glistening with a hint of spit, and Dean’s cock is still hard and throbbing, desperate for relief. But he pays it no mind as he grabs her and spins her around, dropping to his own knees on the cold, hard ground. He lifts one of her legs to balance it over his shoulder, pushing her skirt up to her waist to reveal her lace panties; from what he can remember of her bra – he’d been a little overwhelmed the entire time she was on the stage – the colour of her panties matches it. He reaches up, hooking his fingers into them and pushing the crotch to one side, feeling that the material is wet. 

His eyes flicker up to her face, and he watches her bite down on her bottom lip, the corners of her lips curling into a smirk. She pushes her fingers through the front of his hair. 

“Do a good job, sweetie, or I won’t marry you and this’ll become a one time deal.” 

The thought of him never getting this with her again only makes him more desperate to please her. He licks his lips and then pushes forward, his tongue starting to swirl around her bundle of nerves, tasting her sweet juices. He sucks it softly between his lips, earning a soft moan from her, so he flicks his tongue over the bud, sucking a little harder. 

“Fuck,” she squeals, tugging on his hair, starting to grind her hips a little. 

Dean lets go of the bud, lapping his tongue down a little lower, tasting the juices much more vividly from source. He moans, lapping more, trying to taste more, and reaches up with one hand to spread her lips apart, giving him easier access to her cunt. He buries his face harder against her sex, desperate to make her moan and writhe – desperate to make her feel as good as she made him feel. He wants to be the best head she’s ever gotten too. As he drags his top teeth over her clit, and curls his tongue up to meet them, Jay cries out, arching her back into his touch, her leg starting to shake on his shoulder. Dean grows more and more confident, wrapping his other arm around her standing leg, carefully hooking it over his shoulder so that he’s now supporting her, keeping her elevated against the wall.

He wraps his hands around the tops of her thighs, his fingertips reaching to once more spread her open for him, and continues to dine on her, noting that she’s the best thing he’s tasted all night; and he’s pretty sure the whiskey they had at the strip club was high shelf. Jay’s thighs clamp down either side of his head, muffling the sounds she’s making, so they’re more of a distant echo, and all Dean can really hear is his own rapid heartbeat and staggered breathing. He rises to his feet, taking Jay with him, raising her higher in the air. It’s going to be pretty obvious to any passers by now exactly what they’re doing, but Dean almost wants to cause a scene. He wants everyone to see how good he’s making her feel. 

“Fuck fuck fuck,” she chants, her thighs shaking even more intensely around him. He can taste her orgasm as it trickles out of her, and then she relaxes, and noise returns to normal around him. 

Dean places one last soft kiss to her swollen bud and then pulls back, slowly and carefully unhooking her legs from his shoulders, wrapping them around his waist instead, bringing her face more level with his own. He continues to hold her against the wall, and then kisses her softly.

“How did I do?” he asks, prompting her to turn her head and look down the alley. 

“I can see a chapel from here,” she smirks, dropping herself down to her feet. She takes his hand and looks him right in the eye. “Let’s go.” 

There’s a bar just outside the room they’re about to get married in, so Dean and Jay take a few celebratory shots as they wait for the couple before them to finish. Dean knows he probably shouldn’t be drinking any more, but with Jay’s orgasm still thick on his tongue, and his own cock still desperate for some relief, he’s sobered up a little now, so an extra couple measures of whiskey won’t kill him. 

“Dean and Jay?” The priest – or whatever he is – stands in the doorway as a couple leave the room. 

The guy is carrying the girl, their mouths seemingly fused together, and Dean watches them leave, chuckling. He finishes his drink and Jay grabs his hand dragging him into the room. There’s a few chairs set up, with an altar at the end, and the priest guy stands in the middle, gesturing for them to take their places. 

“Do you have witnesses?” he asks. 

“Oh fuck, no,” Jay answers, biting her bottom lip. 

“It’s fine,” the priest insists, reaching over and tugging on the rope of a bell as it rings. After only a few seconds, two members of staff enter the room, dropping themselves into chairs in the audience. “What are your full names?” 

“Dean Winchester,” Dean offers, and Jay cocks an eyebrow. “What?” 

She shrugs her shoulders, giggling. “Juniper Miller,” she replies. 

“Juniper?” Dean scoffs, unable to stop himself laughing. 

Jay glares at him, but there’s a small smirk on her lips. “Don’t ever call me that or I will divorce you.” 

“Alright, Dean, repeat after me,” the priest sighs. “I, Dean Winchester.” 

“I , Dean Winchester.”

“Take you, Juniper Miller–”

“Take you, Juniper Miller.”

“To have and to hold, in sickness and in health, for richer or poorer, to love and cherish–” Dean repeats the words, albeit a little slurred because that’s a lot of words to remember and repeat when you’re as drunk as he is. “From this day forward until death do us part.” 

“From this day forward until death do us part.” He smiles broadly at her as she bites her bottom lip.

“With this ring, I, thee wed.”

“Oh fuck, we don’t have rings,” Dean reminds her. He looks down at his hands, seeing the silver ring on his right hand. He pulls it off, and then grabs her hand, sliding it down her finger. It’s a little loose, but it’s better than nothing. She smiles, looking down at it. 

“Juniper, it’s your turn.” 

Jay is giggling and clearly trying not to laugh too hard as she gets through her vows to Dean, wiggling around on the spot like an excitable puppy, and when it comes to exchanging rings, she thinks for a second, biting her bottom lip in thought. Finally, she reaches up for her ear, several hoops adorning it along the outside, and she reaches for one, undoing it. She brings it to Dean’s hand, and it just about fits his finger. It doesn’t feel all that comfortable, but it’ll do for now. 

“Alright, by the power invested in me by the state of Nevada, I now pronounce you husband and wife. You may kiss the bride.” 

Dean reaches for her, pulling her close and smothering her lips with his as they share a passionate kiss, that only breaks when the priest clears his throat. 

“Sign this,” he explains, holding out a clipboard and a pen. Dean signs his name and so does Jay, and then the priest hands over a copy of the certificate. “Alright, congrats, both. Thanks for coming.” 

“Gotta take this off, sorry sweetheart,” Dean complains as his makeshift wedding ring digs into his skin. He manages to pull it off and Jay laughs, taking it off of him to put it back in her ear. 

“I’ve got a ring back at my motel room that might fit you,” she tells him, grabbing her drink and taking a sip. Dean watches her twist the ring he gave her around her finger as she glances around the bar they’ve now found themselves in. “It’s a little big,” she complains when she catches him looking. She reaches up, undoing her necklace and then puts the ring onto it, doing it back up. “That’s better.” Dean smiles, his eyes watching the ring nestle between her breasts. “Stop staring at my tits,” she scolds playfully. 

“You’re my wife, I can stare at what I want,” Dean retorts teasingly. 

Jay giggles, leaning closer. “Guess I am,” she nods, her eyes dropping to his mouth. “How should we celebrate?” 

“Well, I think I should probably get that ring from your motel room. Y’know, in case any other girls try to hit on me, need to show I’m a married man now.” 

“I don’t know, seeing you with another girl could be hot. As long as you share her with me, of course.” 

“Oh really?” Dean asks, the very idea making his trousers a little tighter. It’s not taken much for his cock to stir to life since the blowjob she gave him a couple of hours ago. 

“You sound surprised. I think I enjoyed that strip club more than you,” she reminds him. 

“Yeah, you did seem to be really into that lapdance,” Dean agrees, just the memory doing nothing for the situation arising in his pants. 

“Did you see that redhead? She was fucking hot,” Jay scoffs. “I’ve got a thing for redheads,” she confesses. “What have you got a thing for?” she asks, her mouth still tantalisingly close to his. 

“Brunettes mainly,” he admits. 

“Guess I’ll have to stop dying my hair,” she chuckles, “not that you’ve got any choice now you’re married to me.” 

“Guess not,” Dean agrees, feeling her hand brush up his thigh, stopping just before she can touch it. They’re sitting right there at the bar, where anyone can see them, but Dean’s not sure he even cares right now. “So, should we go and get that ring?”

Jay’s motel room isn’t anything fancy, but he figures she’s been saving her money for alcohol and strippers, so she probably doesn’t really care where she crashes. Dean wonders if she even had any intention of using it at all. 

She moves past him, into the bathroom where some of her things are splayed out over the sink counter, and she comes back with a simple band in her hand, not too dissimilar to the one Dean gave her. 

“I usually wear this on my thumb, so it should fit,” she explains as she grabs his hand and pushes it down his finger, and Dean’s pleasantly surprised to find it fits okay. “There, now you’re my husband.” 

Dean smirks, rubbing his middle and pinkie finger either side to feel the band sitting there. It feels weird to him, because he’s not used to wearing a ring on that finger, and he never did see himself as a guy that would wear a wedding ring – he didn’t ever really see himself as a guy that would get married at all, but now he has a wife. A wife who can 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. Not to forget a wife that is very good at giving head. 

“So, we should consummate the marriage,” Jay tells him, smirking. 

“I mean… yeah, we should…” Dean agrees, trying to remain cool even though he’s getting pretty worked up just thinking about it. 

“Wanna make sure I didn’t make a mistake,” she teases, reaching up to push his open plaid shirt off of his shoulders. 

“Got you off pretty hard in that alley, didn’t I?” he asks smugly. 

“Just because you’re good with your mouth, doesn’t mean that you’re good at the rest of it,” she counters, gripping the hem of his t-shirt and ripping it over his head.  

“Could say the same for you, sweetheart,” Dean sasses back. 

Jay scoffs, feigning insult at his implication and shoves him backwards, sending him crashing down onto the bed. Dean gets up, leaning back on his elbows, excited for what she might do next. Her eyes are dark and hooded as she looks down at him, pulling her tank top over her head and throwing it to the floor, unbuttoning her skirt and pushing it down her legs. She leaves herself in her underwear, climbing onto the bed and over Dean, flipping her hair back over her shoulder, so it all falls on one side. 

“Don’t pretend I’ve not been making your cock hard all night,” she purrs, tracing her fingers up his thigh, keeping her lips so close to his he can feel her breath on them. “You saw the way I worked that pole. Bet you wished it was you I was grinding on, huh?” 

Dean swallows thickly, his cock now fully hard behind his jeans, and Jay flashes him a wink before sliding down his body, opening his jeans and pulling his cock free. She sucks him down as well as she had in the alley, and Dean throws his head back, moaning up to the ceiling. But her mouth doesn’t stay on him for long. She once more stands at the foot of the bed, reaching back to unclasp her bra, letting her breasts fall, her nipples starting to harden in the slight chill of the air. Dean watches speechless, his cock spit sodden and throbbing on his stomach. She hooks her fingers into her panties and pushes them down her legs, stepping out of them and kicking them away. Next, she reaches for Dean’s trousers. 

Once more she climbs onto the bed, straddling Dean’s waist. She traps his cock against his stomach, her wet, hot sex pressing down on him, making him moan and buck his hips up. He’s almost ashamed at how desperate he is, but when Jay moans and rolls her hips down over his cock, slicking his length with her juices, Dean can’t find it in himself to care how he looks; he just wants more. His eyes trail up Jay’s perfect body to her face, as she bites her bottom lip softly and raises her hips, reaching between them to line him up with her centre. Slowly she lowers herself down, her mouth falling slack the deeper she takes him, and Dean’s hands reach up to grip her thighs, his blunt fingernails digging into her skin. 

Jay braces herself, holding onto his shoulders as she slowly lifts and drops herself up and down on his cock, whimpering and moaning softly, her one hand moving to the nape of Dean’s neck as her fingers play with the short hairs there. Dean sits there, watching her fuck herself on his cock, feeling how good every bump and ridge feels inside her, and his hand slowly climbs up her side, and then gropes her chest, rolling his thumb over her nipple. 

“You’re so thick,” she pants, a small smile gracing her lips at the declaration. “Fuck.” 

Dean feels smug, a surge of confidence rolling through him as he quickly flips them over, sending Jay crashing down onto her back, her hair fanned out around her head. He braces himself over her, lifting her legs and pinning them back, and then starts to thrust, captivated by the way her breasts bounce each time he slams his hips against her. She reaches up to hold them, pinching her own nipples, and then starts rolling her hips as best as she can to aid him. Dean lets go of her legs, leaning down over her and wrapping his arms either side of her head. He keeps thrusting, his elbows stopping her from shunting up the bed which only sends him deeper, and he captures her lips in a lazy kiss, feeling her moan into it. 

“You gonna cum f’me again, baby?” Dean prompts, rolling his hips. “Wanna feel it around my cock this time.” 

Jay’s eyes roll back, a breathless laugh leaving her lips as she lets go of her breasts and starts to claw her fingernails down his chest. Dean takes the pain, his cock beginning to throb inside her. 

“Fuck, Dean, keep throbbing like that and I will,” she gasps, smirking. 

So Dean does exactly that, holding off so he can get the sweet reward of feeling her cunt clamp around him, like she’s trying to milk him. Jay sits up slightly, kissing him again, rocking down into his cock. 

“Cum for me, Dean,” she begs, out of breath. “Want you to cum in my mouth, wanna taste it.” 

Dean quickly rolls off of her, his back crashing down onto the bed, and Jay is quick to crawl down his body and take him back in her mouth. She moans around him, sucking off the cream that she’d coated his cock with thanks to her orgasm, and then she laps at the underside of his head, smirking up at him through her lashes. With her spare hand she reaches up to cradle his balls, softly rolling them in her palm. Dean fists the sheets, bucking his hips up a little into her touch. 

“Cum for me,” she encourages again, keeping her mouth open, her tongue teasing his sweet spot. 

Her other hand starts to tug and twist his length, getting him right there to the edge as his balls tighten in her grasp and he watches as he paints her tongue with white ropes of cum. She swallows it down, placing a gentle kiss to his tip, and then sits back on her heels, wiping her mouth dry on the back of her hand. 

“Well fuck, sweetheart, I’m so fucking glad I married you,” Dean chuckles. 

“Let’s see if you’re still saying that tomorrow,” she teases, moving to lay down next to him, laying half on him, half off. Dean kisses her forehead, and finds sleep taking him quicker than he’d anticipated. 

2 responses to “Waking Up in Vegas – Part Two”

  1. pinksparklywitch

    I love the sweetness of this so far and all the teasing and flirting but I know it won’t last long. I think her hearing him say Winchester might have sparked something though. Like a memory or a “I used to know someone with that name” kinda thing

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