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You had stormed off a while ago now and slammed your bedroom door. Yet you can still hear Sam and Dean arguing about the reason you’d left in the first place. Even though it wasn’t their decision. There had been something snatching women from a nearby strip club, with all of you still being at the bunker you were by the closest hunters available. So you and Sam had agreed that you would take the case, Dean had been completely on board with the plan, right up until you’d suggested that you were going to be the bait. Since it would mean that you and the monster you were looking for would be alone in a private room.
He was always so damn protective of you, it felt like a lot of the time it was because he didn’t trust you. Sam had been worried about you of course, but he correctly said that it was your decision and he would support whatever your choice turned out to be. Forever the big brother, Dean was not having any of it.
Although the two of you had flirted on occasion, you were sure it was just friendly, you weren’t his type, not at all. Especially when times like this would come around, you felt just like he was treating you like the other sibling he needed to look out for, except that you weren’t, he was only a year older than you and you’d been a hunter almost as long as he had.
You already know that you’re going to do this, with or without their help. Tossing the outfit you’d chosen for tonight on your bed, you hear what you assume is Dean’s door slamming a few minutes later. You were crazy nervous for tonight, this was something you’d never really done before, unless it was in private, for the one or two guys that you had ever stripped for. This was an entirely different ball game all together.
There’s a knock at your bedroom door and you call out for them to come in. The door cracks open revealing the shaggy head of hair that you’d expected.
“Hey Sam, he’s still not on board is he?” you ask, wincing when you hear Dean’s door slam again as if to prove his point.
“He’s on board with the plan, but he isn’t happy about it. Sorry Y/N, I tried” he sighs leaning against your door frame.
“It’s okay Sam, I know you did. Thank you.” you smile gently, trying not to wring your hands in front of him. “You wanna come in for a minute?”
“Yeah, sure.” he smiles back, stepping into your room, you close the door behind him when he sits on the bed. “You know you can talk to me, if there’s something bothering you, right?” he asks sweetly, patting the spot beside him telling you to take a seat which you do.
“Honestly, I’m completely terrified. I’ve done this once or twice before and never in front of more than one person,” you confide in him, the way you always do and Sam nods in understanding.
“Well, I do have to go out and do a few inquiries at the morgue. But maybe speak to Dean, he’s been in a hell of a lot of strip clubs, maybe he can help you out?” Sam suggests as he stands from the bed and adjusts his tie, “Is this straight?”
You can’t help but laugh a little at the adorably confused look on his face, “No, come here,” Once you’re finished straightening the tie you pat his chest gently, “Well, wish me luck with your ass of a brother. Gonna take a shower and I’ll go speak to him,”
“It’s a good idea. Just give it a try and ignore him when he goes negative on the plan,” Sam advises, pulling you into a bear hug that quickly makes you smile. “I’ll be back soon,” he promises, leaving you to your shower.
Pulling off your clothes you wrap your towel around yourself and head out into the hall towards the shower. You squeak in surprise when you walk into Dean, so distracted that you hadn’t been paying attention. Luckily enough you had a tight grip on your towel.
He tries to silently walk around you but you reach out quickly and grab his bicep, “Just do me a favour, please. Come to my room in like half an hour. I really need to talk to you.” before he can say no you sigh, “Please, it’s important. I need your help,”
“Yeah, okay. Fine, I’ll be there, but I’m not happy about it.” Dean grumbles sounding irritated, walking around you as soon as you let go of his arm.
Making sure that you turn the shower on hot, since you’re in major need of something to distract you from the way that Dean had just looked at you. It was about to make your conversation that much harder. You make sure that you shave everything and you’re sure that the water has run out by the time you finally turn the shower off.
Wrapping your towel back around yourself you quickly head into your room, deciding that you probably have time to try on your outfit for tonight before Dean comes to talk, you wanna make sure that it at least looks okay.
You lock the door as soon as you walk inside, nervously glancing down at the outfit on the bed. The tight leather hot pants, and revealing leather crop top aren’t exactly your normal attire and you find yourself swallowing hard. Drying off properly you slip on a small thong, so it would hide beneath the leather hot pants easily, then you pull on the top.
You do your hair and make up, not daring to look at your reflection until you’re completely ready. Slipping into your high heels you slowly walk over to your floor length mirror, gasping at what you see reflected back at you.
Part of you wonders if you’d ever looked this hot before, normally you weren’t one to admit something like that, but right now you were feeling more confident than you had ever before.
You jump in surprise when there’s a sudden knock at the door, quickly grabbing your robe you pull it on, clearly it has taken you longer to get ready than you’d realised.
“One second!” you call out, fastening the belt of your robe.
You can do this, you can talk to Dean about this, right? It’s just Dean. You tell yourself repeatedly, as you slowly walk over to the door. With a deep breath you pull it open, not missing the way that Dean’s eyes drop to the shoes you’d forgotten you were wearing, before quickly snapping back to your face.
“Hey. So, you wanted to talk?”
“Yeah, just uh, come in.” you breathe out nervously, stepping away from the door and letting him by, he takes a seat in the armchair by your bed. But you’re too nervous to sit down, so you just stand in front of him.
Dean clears his throat, looking up at you a little awkwardly as his teeth worry at his lip.
“So? You gonna tell me what the problem is?”
“Yeah, I’ll apologise now in case this gets awkward. But I need your advice for tonight.” you tell him truthfully.
“Okay. What do you wanna know?” he asks trying to keep his voice calm, but you can see that he’s noticed your legs are bare beneath your dressing gown, thanks to the opening in it shifting.
“First of all, ignoring the danger and everything, do you think that I can do this?” you ask watching his face for a reaction.
Dean rubs his hand over his slightly stubbled chin as he sighs, “Yeah I do. Of course you can.”
“Thank you. So, I’ve done this literally twice before and they were both in private. I’m just scared it’s gonna be obvious, I don’t wanna blow my cover before I even get started,” you explain, finally letting him see your nerves.
Dean seems to swallow hard as he thinks this over, never taking his eyes off of your face.
“Do you have to dance on stage before the private room?” he asks, voice a little deeper as he stands from the chair, so he’s taller than you again.
“Yeah, but I’ve got that down. One of the girls showed me yesterday,”
“So, it’s just the more close up stuff that’s got you freaked out?” he questions, walking around you over to your dressing table and grabbing the small chair there he turns it around the right way and takes a seat.
“Yeah.” you answer simply, slightly confused by his behaviour.
“Only one thing you can do sweetheart. Practice.”
“I don’t have time for that Dean!” you exclaim annoyed, throwing your hands in the air. Stopping short when he tugs at the belt of your robe. Causing it to fall open, just like your mouth.
“I can’t do this, not with you,”
“Well it’s either me or wait for Sammy to get back. Of course, you can just wing it, I’m just offering you choices.” Dean says no longer hiding when his eyes drop to your body, this time your outfit is almost on full display.
You know he’s right and honestly if you had to pick anyone then it would be Dean, that’s half of the problem you would have to try and ignore.
“Okay fine. You it is,” you answer, dropping your robe to the floor, feeling a little smug when all Dean can mutter is a quiet curse word or two. You walk towards him slowly, the click of your heels echoing around the room with every step you take.
“Just keep telling me how I’m doing,” you say quietly, as your knees finally bump against his.
Dean slowly reaches out and runs his hands up your thighs, you’re a little taken aback, breath hitching in your throat with the look in his eyes. But then you remember the rules, that this club in particular had, there was no touching at all. You gently smack at his hands and watch him pull back, biting into his bottom lip and rest them beside his legs.
“Well remembered.” he rasps, letting his eyes wander shamelessly across your body once more. But they quickly move back to yours when you straddle his thighs. “Don’t forget, try and get a little dirty talk in.”
His voice is so deep all of a sudden that you’re finding it hard to focus. You wrap your arms around his neck and roll your hips slowly, grinding down into him when your fingers push into the back of his hair and tug his head back. Dean clenches his jaw when your lips brush across it, but never press down.
Your lips slowly move down to his ear, “Dean, get your hands off of my ass before I smack you,”
“Can’t blame a guy for tryin’” he chuckles, dropping his hands back to his sides again.
You pull back to look at him, dragging your hand down his stomach, you grip his t-shirt and drop your body back, keeping your hips rolling down as your hair skims the floor. You flick your body back up and press your chest tightly against his. Dean swallows hard, seeing how close you are and you’re staring into his eyes and it’s like you can’t stop yourself.
Pulling back, you get up onto your slightly shaking legs, Dean sits forward and watches you closely. You turn your back on him and bend over, rolling your hips back against him until you’re sitting in his lap. Carefully you lean forward, remembering something you’d seen in one of the videos that you’d watched, you place your hands on the floor. Gripping his thighs tightly with your knees, your feet press against the chair just above his shoulders as you rock back into him.
“Fuck sweetheart, you sure this is only your third time?” he groans and you can feel the thick line of his cock beneath you.
He wraps an arm around your waist as you pull yourself back up, sliding your legs back down so they’re almost touching the floor. With your hands on the sides of the chair you drop your head back against his shoulder, continuing to roll your hips down against him, watching the way his eyes drop to your tits which are almost pressed against his face.
“So, is this your first time here?” you purr, fingers brushing his cheek as you turn him to face you.
Dean clears his throat and nods, “Yeah first time. Can’t wait to come back,” he smirks, licking his lips when you stand and turn to face him again. Dropping down seductively, your hands slide up his legs and push his knees apart, slowly sliding your hands up his thighs stopping dangerously close to where he’s hard and straining against the material of his jeans.
“I’d love it if you came back, I don’t often get customers as hot as you.”
You slide up his body, pushing your breasts up his chest until they’re pressed against his face. Dean groans and you swear you can feel his tongue against your breasts but you chose to ignore it, maybe it had been an accident.
Dean’s hands fall to your waist when you straddle one of his thighs, you can feel the sweat that’s starting to cover your skin, but his hands aren’t much cooler. Your hands slide beneath the flannel that he’s wearing and push it easily from his broad shoulders. Dean tugs it from his wrists and his big hands settle on the bottom of your back, the tips of his fingers just barely pushing into the waistband of your leather hot pants.
Leaning back slightly you feel Dean’s hands tighten as he supports your weight and keeps you up, your hands move slowly up your stomach, continuing to rock your hips, the trouble is that this is really starting to affect you. You can feel the slick gathering between your thighs, barely contained by the small thong beneath your hot pants.
“Does that feel good?” you ask in a breathy voice, watching the way that Dean’s tongue presses against the back of his teeth. You easily find the poppers on your top, watching Dean chewing on his bottom lip when you pop the first button.
“Best one I’ve ever had,” he grunts as you slide perfectly over his cock, “honestly, I’m just trying not to come in my pants.” His voice rumbles, completely focused on your fingers where they linger on the third and final button of your top.
“I’ll take that as a compliment from you.” you breathe out with a smile, feeling his fingers slip inside your hot pants a little further and his finger dig harshly into your skin. “You wanna see?” you ask nervously, swallowing around the lump in your throat as you continue to rock your hips.
“I’d fuckin’ love to see sweetheart. But you can just pretend you’ve finished, if you want.” he offers sweetly, but it’s like you can feel the sexual tension in his voice dripping from his every word.
You shrug with a slight smile pulling at your lips, “No point in doing half a job, like you said, it’ll help to practice.” Your voice is just barely above a whisper when you finish speaking and finally pop the last button on your top.
You can see the tick in Dean’s jaw when you pull the leather from your arms and drop it to the floor. The routine you had planned was still in your mind so you went with it, trying your best not to get distracted by the intense look in Dean’s darkened green eyes.
Dean’s fingers are so tightly digging into the tops of your ass cheeks that you’re sure it’s going to bruise, but you continue to roll your hips, switching it up every now and then and circling them.
“Can I please be your guinea pig whenever you need help again?” Dean asks through a muffled moan when you press his face between your tits, feeling the scratch of his slight stubble against your sensitive skin.
Your heart is thudding hard in your chest and you can hear it in your ears, not to mention you’re starting to feel the pull of your stomach muscles from how hard you’d been working your body. Gripping his hair you tug his head back again, his lidded eyes find yours when he draws his bottom lip between his teeth.
“Yeah, I think I could live with that,” you smirk cheekily, letting your forehead drop against his. Your nose brushes against his as you pop the buttons on the sides of your hot pants and pull them away.
Dean’s hands move to your hips, “shit sweetheart, got me so damn hard.”
Your nails are digging into his shoulders through the thin black t-shirt he’s wearing, continuing to rock and circle your hips you can feel the hard line of Dean’s thick cock pressing into your slick pussy, through the barely there thong that’s the only remaining clothing you’re wearing.
Dean’s lips press against yours and take you completely by surprise, you can’t help the groan that slips past your lips. You pull back as soon it hits you what was happening and he catches your hand before it connects with his face. His free hand cups the back of your neck and he roughly presses his lips against yours again, this time you melt against him, threading your fingers into the hair at the back of his neck tugging roughly.
Finally pulling away from his lips to breathe, you stand from his lap smirking when he stands with you. Tugging at his belt buckle until it clangs open.
“So, to be clear in the club. This should have stopped before you kissed me right?” you giggle, pushing him back into the chair once he pulls off his t-shirt and pushes down his jeans.
Dean chuckles as he stumbles back and falls into the chair behind him.
“Oh yeah, definitely throw a better punch if it’s anyone else.”
“So, is this why you were pissed about the hunt? Didn’t watch me dancing all over other guys because you wanted to fuck me.” you ask as you straddle his thighs again and his hands slide up your legs, groaning loudly when you drag your teeth across his earlobe.
“It definitely has a lot to do with it.” He answers quietly, “I thought you’d be sick of riding by now.”
“Turns out I kinda like it, even more when it’s you.” You whimper when Dean pushes your panties to the side and drags them through your slick, right before he pushes two of those thick fingers inside you.
You gasp at the feeling, enjoying the stretch and the drag of his fingers as he curls them against your fluttering walls. You stand with your legs still spread either side of his, moaning when his lips wrap around your nipple, tongue swirling around the hardening bud as they continue to move inside of you at a hard pace. You cling to his shoulders, creating crescent shape marks against his freckled skin.
Dean drags his teeth over the hardened bud as he pulls away, looking back into your eyes as his free arm wraps around your waist to hold you up. You roll your hips down into his hand the best that you can, the flick of his thumb against your clit moves in time with every thrust of your hips.
Your thighs start shaking and your mouth drops open, as you start to feel that familiar feeling in the pit of your stomach. Then it ebbs away as Dean pulls out his fingers, a cocky smirk before he sucks them between his lips with a satisfied groan.
You huff out in frustration as he pulls his fingers from his mouth with a lewd popping noise.
“You ever get tired of being such a smartass,” you grumble wrapping your fingers around his thickness.
Dean’s retort is quickly cut off when you press the head of his cock into your soaked entrance, the new feeling has him growling into your neck, fingers gripping your ass tightly as you let him fill you perfectly in one movement.
“When you stop lovin’ it, you just let me know,” he grits out as you start moving, you push one of your hands into his hair and grip tight as you ride him, keeping your eyes locked on his. The fast rise and fall of your hips forcing his cock inside you deep and hitting you in the spot that makes your thighs shake and your back arch. “Fuck you feel good, so wet baby, keep going. Wanna feel you come all over my cock.”
His filthy mouth paired with the feeling of every thrust of his cock has you whimpering his name, pressing your lips against his, needing to feel as much of him as possible. His tongue quickly finds yours, there’s no fight for dominance, the kiss is deep and passionate, all teeth and tongues.
“Dean, please. So c-close,” you gasp, pulling away from his lips and resting your forehead against his.
Dean drops slips a hand between your legs, quickly finding your clit, the tips of his fingers start to rub it in hard fast circles. You cling to him like your life depends on it, continuing to move your hips at the fast and hard pace, until your orgasm hits you at full force and your pussy clenches around his cock like a vice. You squeeze your eyes shut, as Dean helps you move while you helplessly whimper his name.
When you finally start to come down you lift your head and lean back, resting your hands on his knees. Dean groans feeling your walls clamp down around his cock tightly with the new angle.
“Come on baby, I know you’re close. I can feel your cock throbbing,”
Dean groans watching you roll your hips, seeing his cock slipping effortlessly in and out of your slick pussy. “Fuck. You look so damn good riding my cock sweetheart,”
One of Dean’s large rough hands slides up from your thigh, over your hip and presses into your stomach. Sweat glistens on your skin, you can feel your slick against your ass as it runs down his balls. You’re not sure that you’ve ever been this turned on, every nerve ending feels like it’s on fire. “Son of a bitch! Yes Y/N! Fuck.” Dean moans loudly, as his hips stutter slightly beneath you.
You finally stop moving when Dean relaxes back in his chair and you collapse against his chest. “Jesus fucking Christ,” you half laugh, half pant. Pressing a kiss to his shoulder his hands slowly move against the soft skin of your back, tracing patterns against your skin.
“Can’t argue with that,” Dean laughs, turning to face you and brushes the sweaty hair from your forehead. “Are you sure I can’t talk you outta this whole thing?”
“Dean,” you sigh, but your voice holds clear warning.
“Fine. This once I’ll drop it. But don’t expect me to leave you alone with this creep,” Dean grumbles as he gently helps you to your feet and you both hear the main bunker door clang closed.
“Thank you. Now get dressed, this is not something Sammy needs to see,” you laugh followed quickly by Dean. You hurriedly pull on your robe as Dean pulls up his boxers and jeans. You quickly throw him his t-shirt when Sam knocks on your door. “Shit,”
You grab your clothes and hide them under your duvet. Smoothing it out, you turn back to Dean seeing him pull on his flannel, you walk around him and open the door.
“Hey Sam, is everything okay?” you ask trying to keep the nerves out of his voice when you let him in.
“I, uh. Yeah.” He stutters, seeming confused as he looks between you and his brother.
“Change of plans. No more undercover needed,”
“Thank fuck for that,” Dean grins, throwing you a wink, which you have to stop yourself from smiling at, failing miserably.
“Okay. You two are being strange, more than usual. What did I miss?” Sam enquires suspiciously.
You and Dean look at each other and you can’t help but blush.
“Y/N just gave me a lap dance,” Dean shrugs, bursting out laughing when you smack him.
You’re blushing so hard when you finally look back up at Sam, “I needed practice.” you defend, before Sam can actually say anything.
“Trust me, you didn’t.” Dean winks when you turn back to face him.
“I don’t wanna know.” Sam laughs holding up his hands as he turns to leave. He’d seen that look in his brother’s eyes before and he knew where it was leading before it even happened.
“So, you don’t wanna be my guinea pig anymore then?”
“Oh now, come on sweetheart. Let’s not say anything we’re gonna regret here.” you smile at him as you follow after Sam without saying a word. “Y/N! Hey!” Dean shouts, running after your retreating form.