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: teasing, flirting, heavy drinking, stripping, lap dance, minor f/f, public blowjob

Part WC: 3085

Waking Up in Vegas Masterlist

“Dude, answer your phone, where the fuck did you go?” Dean grunts, flagging down a waitress. He holds his phone to his shoulder, ordering another beer, and he can’t stop himself from staring at her ass as she walks away, swaying her hips. Dean suddenly remembers what he’s meant to be doing and snaps out of his reverie, bringing the phone back to his ear. “Just call me back when you get this.” 

Dean drops his cell to the table in front of him and smiles at the waitress as she puts a bottle down, flashing him a wink before slipping away. He takes a long swig, licking his lips, and then he hears cheers coming from further back in the bar and turns his head to see what the fuss is about. 

“Aw man, I thought I was gonna win.” Dean’s eyes land on the girl whose voice just about carries across the bar towards him, and he finds himself captivated. She flicks her dirty blonde curls over her shoulder, huffing heavily as she starts to remove her leather jacket, only a tank top tucked into her skirt underneath. “Alright, rules are rules, this round is on me, I guess,” she announces. 

As she heads towards the bar, getting closer to Dean, he notices a small smirk on her full lips, and there’s a glint in her green eyes as she glances at him. Dean finds himself getting up, abandoning his almost full beer, silently following her like some lost puppy towards the bar. He slots in alongside her, still staring at her like some creep, but when she turns her head in his direction he looks away. He glances back catching her eye and she smiles at him, before bringing her attention to the waitress to be served. 

“Seven beers and a shot of something strong please,” she orders. She catches Dean’s eye again and giggles. “They’re not all for me,” she explains, smirking. 

Dean struggles to find his voice for a second, but then he clears his throat, telling himself to grow some fucking balls, and speaks up. “I’d have been pretty impressed if they had been.” 

She starts laughing, nodding her head, “it’s too early to be that drunk, yet.” 

“You’re hanging out with the wrong guys if you’re paying for their drinks,” Dean tells her confidently. “Surely your boyfriend should be paying?”

She glances back over her shoulder at the gang still huddled around the pool table, some of them keeping their eye on her, and then she looks back at him and bites her bottom lip. 

“A bet’s a bet, I lost at pool,” she tells him, leaning on the bar, squeezing her boobs between her elbows to accentuate her cleavage. Dean pretends she’s doing it on purpose to tease him. 

“Well, if you need help learning, I’m a pretty decent shot.” 

She’s served her drinks, and she instantly grabs the shot she’d ordered. “I’m sure you are, pretty boy.” She knocks the drink to the back of her throat and licks her lips. “But I’m a big girl, I’m sure I’ll be fine.” 

She doesn’t say anything else as she grabs the tray of beers and heads back over to the pool table, and Dean finds himself mindlessly returning to his table, taking a different seat, so that he can watch her play. He grabs his beer and takes a slug, keeping his eyes on her as she passes around the beers to each of the guys and then drinks some of her own, and he just about hears her asking if they wanna make things interesting and play for cash instead, this time. 

Dean continues to watch her, missing shots, sighing and whining each time, but always refusing any of the guys’ help, and as he watches her hand over fifty bucks he sighs himself, shifting in his place and resisting the urge to go over there and win her money back for her. She demands to play again – double or nothing – and the guys try to turn her down, until she starts insisting. 

“D’you even have another fifty, sweetheart?” the tall bald one asks condescendingly. 

“I’ve got another thirty?” she offers. 

“How are you gonna make up the difference?” 

“I can think of something, Mike,” one of the other guys calls out. 

The girl glances over at him, looking back at her challenger and biting her bottom lip anxiously. “I need to at least try and get it back,” she pouts. 

Eventually, they agree, and Mike racks up. Dean’s practically shuffling in his seat, telling himself that it isn’t his business, that it’s not his place to go over there and help this girl out. She’d seemed pretty insistent on handling herself. He watches nervously, taking another swig of beer, and she lets her opponent break. Dean can tell from the first go that he’s going easy on her, and relaxes just a little. 

The girl rounds the table, biting her bottom lip and twisting the cue in her hands, and then she drops her face towards the table, her eyes scanning the balls. Dean can tell what ball she’s aiming for from here, and he winces slightly. Even he might not have risked that shot, it’s not an easy one to make. But she seems calm and collected as she lines up her cue, and strikes the white, guiding it exactly where it needs to go for the perfect shot. 

“YAY!” she exclaims excitedly when she pockets two balls. “I got some in, did you see?” 

Dean sits up a little straighter in his chair, hardly believing it for himself, and then she takes her second go. Another risky shot that pays off. And by her forth shot, Dean realizes this definitely isn’t her first rodeo, and these definitely aren’t flukes. She’s practically clearing the table. Unfortunately, the guys she’s hustled seem to have made the same realization, and all of them are looking a little irritated by the fact they’ve been duped by a girl. Dean can’t help but smirk though. If he thought the girl was hot before, she’s going to be his wet dream for weeks now. 

When she finally wins, she reaches across for the money, but baldy stops her, placing his hand on top of hers. 

“You cheated,” he accuses. 

“I didn’t cheat, I played the game,” she argues, standing her ground, not seeming phased by the anger in his tone. 

“You little bitch,” Mike grunts, and Dean finds himself on his feet in seconds, charging over to the pool table to protect her. 

“You okay, sweetheart? Sorry I’m late,” Dean tells her, instantly wrapping his arm around her, kissing her cheek. She frowns at him for a second but then goes along with it. 

“Hey baby, let me just collect my earnings,” she tells him, her tone blunt as she glares at baldy. 

“Winnings?” Dean asks, frowning, “baby, you never win pool, you feeling okay? All those lessons finally sunk in, huh?” 

“Must’ve done,” she agrees. 

“I’m not fuckin’ buying it. Your little slut here hustled me out of a hundred bucks,” Mike insists. 

“She won it, fair and square,” Dean tells him stubbornly. He glances to see baldy’s hand still over hers and thinks on his feet. “Get ready,” he tells her, before throwing a punch in his face. The guy instantly reaches up to protect himself, and Dean watches her seize the opportunity to snatch the money. He instantly grabs her hand. “RUN!” 

Together they dart out of the bar, the guy running after them both yelling, and Dean pulls her down a side alley out of sight. Once he can tell the immediate danger is gone, he reluctantly drops her hand, clearing his throat. 

“Sorry,” he mumbles.

“I told you I was a big girl,” she reminds him, glaring playfully at him. Dean laughs, nodding his head. “But thank you,” she adds, softer. 

“You’re welcome, sweetheart, didn’t wanna see something bad happen to you,” he confesses with a blush. She bites her bottom lip, looking down at her feet. “Who are you here with?” 

“No one, for now,” she tells him, wrapping her arms around herself. 

“You’re in Vegas alone?” Dean asks, skeptical, raising an eyebrow. 

“So are you, apparently,” she retorts teasingly. 

“Lost my friends a while back,” Dean explains. “Are you cold?” he adds, when he notices her rubbing her arms. 

“Just a little, left my jacket inside.” 

Dean instantly shrugs off his own leather jacket, handing it over. She stares at it for a moment.

“It’s not gonna bite you,” he laughs. 

She smirks as she takes it, shrugging it on. She looks fucking hot. “It’s not that,” she tells him, making sure it’s sitting on her shoulders properly. “It urm… it looks familiar.” She shrugs, like she’s brushing it off. “I’m fucking starvin’ wanna grab some burgers?” 

“You ate the entire meal?” Dean asks, looking down to see her plate empty. 

“Told you I was starving,” she scoffs, reaching across to steal a fry from his plate. 

Dean glances up from his plate to her face and she winks at him, wrapping her tongue around the fry before pulling it into her mouth. Jesus fucking christ, she even makes eating fries look hot. The fact she ate the entire thing definitely makes her more attractive. She grabs her beer and takes a long swig, and Dean relents to not finishing his meal, sitting back. 

“Not many people can out eat me, especially not a girl.” 

“I’m not just any girl,” she smiles smugly, leaning back herself. Dean now knows that her name is Jay, and he can’t help but repeat it in his mind a few times. It’s unusual for a girl, but he likes it. “Could probably drink you under the table too,” she challenges, bringing him back to the diner they’re sitting in.

“Yeah, right,” Dean scoffs. “I’ve been getting drunk on my Dad’s beer since I was fourteen.” 

“Alright, let’s keep this night interesting,” she says, biting her bottom lip. She sits forward again, pushing her boobs together like she’d done at the bar, and Dean resists the urge to let his eyes noticeably drop to them, so he settles for respectfully looking out the corner of his eye instead. “You match me drink for drink the rest of the night. Whoever taps out first owes the other a lap dance.” 

“A lap dance?” Dean questions, just the image of Jay dancing on him, rubbing herself on his body, is making his heart start to race. And he’s fairly confident he could out drink her, so he doesn’t have to worry so much about having to give her one, because that would really end badly for both of them. “Alright, deal, sweetheart.” 

“Great, then let’s get outta here, I know a place down the road, went there last night.” 

As Jay stops outside a club, Dean looks up at the name. Your Eyes Only. 

“Is this a strip club?” he asks, recognising that style of pink neon sign anywhere. 

“Where else did you think we’d be getting a lap dance?” Jay scoffs, “c’mon, it’s good in here, why do you think I’m low on cash?” she smirks, reaching for his hand and dragging him inside. 

When Dean steps in he’s instantly greeted with women dancing on poles, more of them passing him in lingerie, trays of drinks balanced on their hands. Dean’s not a stranger to a strip club, but this one is a little more on the classy side, compared to the seedy dive bar vibe he’s used to. The girls are prettier, more expensive jewelry and lingerie, the music a little crisper, and the whole place doesn’t smell like beer and ashtrays, which is definitely a bonus. He follows Jay to the bar and lets her order the drinks. Two glasses of what Dean presumes is whiskey are placed in front of them, followed by two shots of tequila. 

“Keep up, sweetheart,” she warns, holding up her shot glass to toast with his. 

They take the shots and Dean watches as she sucks on the lime, throwing it down onto the counter and grabbing her whiskey. Dean follows suit, and she takes his hand and drags him towards one of the stages, sitting them down right next to it. He knows he should be watching the attractive blonde that’s swaying her hips and grinding up and down a pole in her underwear, but he can’t help himself from watching Jay instead, her green eyes sparkling as she watches the show, cheering and wolf whistling. Dean didn’t think he’d ever see a woman enjoy a strip club this much. 

The blonde finishes her dance and leaves the stage, and now she’s not got something else to watch, Jay catches Dean looking. She smirks, leaning in close to him so she’ll be heard above the music. 

“Your eyes were meant to be on the topless blonde,” she reminds him. 

“I’d rather see you up there,” he confesses, the drinks loosening his tongue a little. 

Jay bites her full bottom lip, her green eyes glancing around the club, and then she knocks back her whiskey and quickly scrambles up to the stage. Dean laughs as she heads towards the pole, and there are cheers around the room when she’s noticed by other people. Suddenly a spotlight shines onto her and she looks at Dean, shrugging and giggling, and then starts to sway her hips to the music. She wraps her hands around the pole and spins around it, shrugging her – Dean’s – jacket down her arms and tossing it down to him. He catches it, laughing, secretly wondering just how far she’s going to take this. She sways her hips again, slowly pushing the pole between her legs, and then rolls her body up. 

The laughter Dean had been infected with dies, as he realizes more and more that this is turning him on, especially when Jay removes her tank top, and throws it towards him, revealing her pink lace bra. She leaves the pole and gets on her hands and knees, crawling the strip of stage, and she even stops to let men tuck notes into her cleavage or the hem of her skirt. Dean only feels a tiny pang of jealousy, but it’s quickly gone when she sets her eyes on him and crawls over to him. 

“Enjoying yourself now?” she asks, bringing her face close to his. 

“Could say that,” Dean agrees, swallowing slightly. 

She reaches for his whiskey on the table, bringing it to his lips. “Catch up, sweetheart.” 

Dean tries his best to hold the moan in as he feels the blonde grind down into his crotch again, her hands gripping his shoulders, and he quickly turns his head to see Jay enjoying herself too, the redhead dancing on her practically putting her tit in Jay’s mouth. Jay looks over at him and giggles. 

“Having fun there, Dean?” she asks. Dean’s pretty drunk now, because apparently Jay hadn’t been lying when she said that she could outdrink him, and he hears her laugh. “Thanks ladies, I think that’s enough.” 

“Bye, sugar, come back to see me soon,” the blonde winks. Dean thinks he remembers her saying her name was something like Candy, but he can’t say he was paying much attention, because he had also just learned that Jay would be getting a lapdance too. 

Jay shrugs Dean’s jacket back on and takes his hand, leading him out of the club and back onto the street. The fresh air only makes Dean feel even more drunk, and he blindly follows Jay, letting her take him wherever she wants, which happens to be down a dark side street, apparently. 

“What do you wanna do next?” he asks. 

“I don’t know, what else is there to do in Vegas?” she asks, biting her bottom lip. 

“It’s Vegas, probably a lot,” Dean chuckles. 

“Vegas, the city of sin,” she smirks, stepping closer to him. “We’ve gambled, we’ve drank, we’ve caused a scene in a strip club…” She stops directly in front of him. “Guess there’s one more sin we could commit.” 

Dean is taken by surprise when he feels her shove her back against the wall, and then her lips are on his, and she’s kissing him passionately. He instantly closes his eyes, reaching up to cup the side of her face and snake his tongue into her mouth. He moans softly against her mouth. He’d been imagining kissing her all night, and it only feels better than anything he could’ve dreamed up. Her hands stroke down his chest, and she begins playing with his belt buckle. Dean should be concerned about the constant stream of people passing the entrance to the alleyway a little further up, but he’s too drunk and too desperate to let her continue. 

Jay pulls his belt apart, unbuttoning his jeans as she pushes her hand inside, palming over his rapidly growing cock. Dean moans louder, feeling her capture his bottom lip, and then her lips are gone, and so is her face. He looks down his body to find her on her knees, lifting his shirt and kissing just above his waistline, before pulling his cock free and instantly sucking him down. The back of Dean’s head hits the wall behind him with a thud, and it should hurt if the alcohol hadn’t numbed him. At least it hasn’t numbed his cock, because he can feel every lick and suck as Jay pays full attention to every inch of his length, swirling her tongue around, taking him deeper. Dean throbs between her plump lips, gasping for air, his head spinning. 

“Jesus fucking Christ,” he grunts, twisting his fingers through her hair, noticing it’s darker at the roots; a natural brunette. “This is… fuck… the best head… you’re something else, baby,” he moans, unable to keep his thoughts straight. He’s not sure he’s ever felt this good in his entire life. Who the fuck is this girl? She can play pool, she can out eat him, out drink him, she likes strip clubs and lap dances, and she can fucking suck cock like a pro. “I think I wanna fuckin’ marry you,” he gasps, not really realising he’s said it outloud. 

She pulls back, wiping her lips dry on the back of her hand and rising back to her feet. 

“Deal… if you can give as good as you get.” 

5 responses to “Waking Up in Vegas – Part One”

  1. pinksparklywitch avatar

    The matching eyes, the familiar jacket, the same personality traits 👀 This is going to be so good 😏

  2. @Siospins2 avatar
    @Siospins2

    I love this – she sounds very familiar somehow! Maybe he’ll finally see what the rest of us see in him. This is so damn good!

    1. Bee || neganslucilletblr avatar

      Hmm I wonder how 😏😂 thanks for reading!

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