#stripper!sam

[teslagraves]

I Was Born to Love You

Dean was in trouble, in a sense. See, he had seen his brother in the showers. And that was fine, except that Sam had been singing and dancing to Queen. In a decidedly not little-brother-innocent way.

And the trouble all came from the fact that he couldn’t possibly ask Sam about it, because then he’d have to admit he’d been spying on his brother’s showers. Like the pervert he was. And Sam knew he was a perv. But Sam might feel that watching him in the shower was entirely too much. So Dean just let it be.

Except that something seemed to have gotten into Sam. He was much more provocative, and he started wandering between the showers and his room in just a bathrobe. Dean was losing his mind.

It wasn’t the last time Dean ever saw Sam putting on a show in showers either.

Dean’s baby brother obsession was reaching new heights. It was bad enough he could no longer see Sam without a blush. And Sam, the bastard, didn’t even seem to notice! Dean felt like he had a crush, and Dean didn’t do crushes! Dean was cool. Dean was suave, mature, smooth with everyone…. And Dean was totally flustered by his baby brother. Dammit.

After about a week of this torture, Sam beckoned him. “I got something to show you, Dean.” Dean followed, because of course he did, because it was Sam and what else could Dean do?

Sam brought Dean into his bedroom, then went over to the dresser. He pulled out a box that Dean hadn’t seen for years. It hasn’t shown up since Stanford almost. Dean got nervous. “It’s okay, Sammy, you don’t gotta—“

Sam cut him off with a bitchface. “As if I’d be showing you anything if I hadn’t already thought about it. I thought you’d enjoy finding out how I made money at Stanford.”

Dean tilted his head, confused. “I dunno, I just kinda assumed you made green juice in college, or something.”

Sam’s mouth grew noticeably thinner. “Ha ha,” he said flatly, “but no. I was—“ he opened the box and poured a bunch of photos on his bed “—a stripper.”

Dean choked. “S-sorry did you say…. Stripper?”

Sam nodded cheerfully, picking up a photo showing him in a gorgeous flamboyant pink, sheer robe, complete with dyed feathers. Dean choked again.

“My baby brother…. A stripper. A-are you…. Gay? Was your relationship with Jessica a… what do you call it?”

Sam laughed. “Lavender relationship? Nope. I’m pansexual. Interested in everybody.” He caught Dean’s eye meaningfully. “Everybody.”

Dean flushed.

Sam grinned. “Why don’t you look at those photos? Long as you want, and if you help me install a pole, I’ll even give you a private show.” He winked, and practically sailed out of the room. Dean was left speechless.

[midnightsilver]

My artwork for the awesome story ‘Strip It Down’ by Drasna ( @talltalesandbedtimestories ) written for the @wincestbigbang 2024. The story features Sam stripping in a fireman’s costume, and lap dancing Dean in a pink cowboy hat!! What more do I need to say?! 🙌🏼😄🎉 (but if you still need more info 😁 you can find it here.)

[wincestismyguiltypleasure]

Sam needing that college money so he starts stripping/camming but he goes by John Dean out of spite >:3

Definitely not | No thanks | Meh, maybe | Sure | Yes please | GIVE IT TO ME NOW

T H I S RIGHT THE FUCK HERE. THIS IS GOOD SHIT, NONNIE.

I n e e d bratty but cute as a button twink Sam using that alias like the spiteful little slut he. 🔥

"What's your name, sweetheart?" It's always the grungy lookin' biker types that stuff his g-string full of wrinkled ones and grab at his glitter dusted thighs when the bouncer isn't looking.

"It's John," Sam replies with a toothy grin. "But you can call me whatever you want, baby."

OhmyGod. And can you imagine the look on Dean's face when he accidentally finds out that stripping isn't the only side hustle his baby brother's got going? Of course, he's PISSED about the name that Sam's using but at the moment, his curiosity is getting the better of him. And as soon as Dean sees his little brother on camera, all soft and pretty-boy shy, talking to his "fans", he knows that he can't slam his laptop shut, no matter how much he wants to.

Dean's never paid to get off before. No cash for ass. That's the rule. But after watching just a few minutes of Sammy deep throating his favorite bright pink dildo like he was made for it, Dean is fucking sweating. God damn, this was worth way more than the hundred bucks he'd just dropped. Seriously, Dean would have gladly maxed out every credit card he'd ever applied for just to see those glossy cotton candy pink lips stretched wide around a cock. Fake or otherwise.

"Shit, seriously kid?" he groans as he reaches for the zipper of his jeans with a shaky hand. The amount of noise that Sam's making is obscene. They're sloppy, wet, almost borderline disgusting sounds, and Dean already has them filed under things that shouldn't make my dick hard but here we are in his frazzled mind.

"Jesus, Sam." Dean nearly dies when he watches his brother's throat flex greedily around the well-endowed silicon toy.

Sam's pretty eyes are glassy now and there's stringy wet drool dripping off his chin onto his flushed bare chest. He's a disaster. All disheveled and wanton, and he looks like something straight out of Dean's wettest dream. Every filthy detail making the older boy wonder why the Hell he even had that stupid rule in the first place.

[kansaskissedlips]

Having to go undercover and Sam gets the 'unfortunate' role of a stripper and Dean's sitting in the crowd, ready to see Sam so he can make fun of him later. He's surprised with how hot his brother's body is clad in barely anything. You can't tell me that Dean isn't a little bit curious on how Sam moves like he's done this before. Or that Sam spots him and gives him a lap dance. Or that they're both silent on the way back to the motel until Dean says, "So do I get a family discount next time?" ~∆

O M G.

[formidablepassion]

Stripper Sam Time!

Happy Sunday! I wanted to let you know I had fun writing stuff this week and I hope you’ve enjoyed everything as well. :)

This has very little actual Wincest and I apologize. I just got stuck on stripper Sam. As one does.

~

So Sam had scholarship money for Stanford, but he was still probably eating Ramen every day. And at first he’s okay with that. But after the first year or so he decides to find a job to help pay for actual food. But all the good jobs have already been taken so he starts asking around. Eventually one of his friends hooks him up with a job as a “dancer.”

His first day Jess and some of his other friends come by for ‘moral support,’ aka to stare shamelessly as he strips. (Because honestly who wouldn’t?) A bunch of photos are taken and afterwards Jess gives him some of the ones she took. Sam ends up keeping them, mostly because they’re something Jess gave to him.

But that’s not how Dean finds the photos. Dean finds them when he’s going through Sam’s old social media accounts (for reasons) and sees someone tagging Sam in some very interesting photos.

He prints out the photo where Sam’s wearing the least and shows it to Sam. At first Sam’s embarrassed but that quickly fades when Dean asks him to pretend to be a stripper for him.

(Sam totally does and Dean is really fucking grateful to whoever got Sam that job. He even considered sending them a fruit basket or something.)

I love the idea of Sam stripping for Dean. That makes me so happy. Thank you for this and for all the others over the week. It has been an absolute delight to receive them. 

[pastorpresent]

"Dean... I'm really not sure about this." Sam's timid voice rung out, and normally Dean would try to be a little sympathetic, but his mind was going wild and he was half hard already and if Sam didn't get out the bathroom in the next two minutes he was breaking the door down, security deposit be damned.

Sam could not let it slip that he had stripped in his Stanford days, and that he still had some of his attire, and leave Dean hanging.

"You promised, Sammy. Just pretend I'm one of the guys in the club." He responded and he could hear Sam scoff.

"Pretend you're a gross 40 year old married guy who I'm not remotely attracted to?"

"If it helps, I couldn't care less!" Dean hit back, squirming in his chair.

There was a brief silence, and then music.

Back in Black from ACDC, and Dean smirked at the song choice. Sammy knew him damn well.

The bathroom door opened, and Sam stepped out. He was wearing black lace panties, and a black leather corset, leaving a strip of tan skin visible where the garments didn't quite meet. He had black heals on, and a black studded collar.

Dean had partly expected one of those corny male stripper outfits, fake fireman or a policeman kinda thing, and he had been excited about it anyway.

But this?

This was a thousand times better than anything he had ever imagined, and he had to take a breath and squeeze the head of his dick to make sure he didn't come right then and there.

Sam strutted out with a confidence Dean didn't even know he had, hair mused and lips shining and slightly red as he smirked.

He swayed his hips in time with the music, dipping down occasionally as he danced. He seemed lost in the act, turning and shaking his ass, bending over slightly to give Dean a better view.

Dean swallowed, eyeing Sam's body in a way that was absolutely 100% objectifying him, but it seemed to spur Sam on tonight rather than earning him a lecture.

"Ready for a real show baby?" Sam hummed, voice dripping with sex as he came closer, placing a hand on his thigh.

His choked out yes was a little embarrassing, but Dean was just surprised he managed to get anything remotely legible out at all.

Sam turned, and began grinding down on Dean's lap, head tilted back to rest on his shoulder. His hums of the song were combined with small moans, and Dean was biting his lip so hard he was surprised his didn't draw blood.

He moved his hands to grab for Sam's waist, only for Sam to grip his wrists in an iron tight hold.

"No touching the goods, I'm afraid." He murmured, and Dean actually let out a whimper.

"Sam" he complained, but then Sam was turning in his lap, now fully sitting atop of him. He could feel the soft material of the underwear brushing over the denim of his jeans that he really needed off, like asap.

"Just the rules baby, what's your name handsome?" Sam breathed, his breath deliciously hot as their faces were positioned just inches away, and Dean could definitely smell cherry lipgloss now they were this close.

He wanted to kiss Sam so badly, taste the cherry, feel those beautiful lips pressing desperately against his own, but he knew Sam wouldn't let him. Not yet, and as frustrating as it was, Dean was willing to admit it was hot as fuck.

"Dean. What's a pretty thing like you doing working here?" He asked, glad that his brain had seemingly caught up to reality enough for him to form actual words rather than just whines of Sam's name.

Sam lifted slightly, still moving to the music as he draped his arms over Dean's shoulders, shimmied his lower half before grinding back down with that rhythmic sway of his hips still going.

Dean groaned, forcing his hands to stay at his sides.

"Just trying to pay for school. And may I ask why such a stunning guy had to go to a strip club to find a boy willing to grind on him?" Sam murmured, a mischievous glint in his eye that was making Dean god damn insane.

"Haven't found any other boy pretty enough for the job." He teased back, and Sam grinned, let out a small laugh and finally leaned down to kiss Dean as the song came to a close.

Dean kissed back desperately, finally letting his hand roam over Sam's body.

He yanked him closer, and Sam let out a little yelp in surprise.

"We are definitely doing that again." He said, nipping at his lower lip hungrily, and Sam smirked.

"We'll see."

"That we will." Dean winked, swallowing up Sam's next laugh with another kiss.

[wincestismyguiltypleasure]

*runs by, tossing a glitter-covered, pink-panty-wearing, blushing, newly-18yro Sammy your way* He's all shy about going up onstage for amateur night at the strip club until he looks out & sees Dean, front and center, with a handful of cash.

WIFEY! Glittery, barely legal, panty clad Sam Winchester is what Dean and my dreams are made of! ❤

He is timid at first, biting his bottom lip as he starts to slowly move those cute little hips, peering over at Dean through a curtain of messy bangs. His big brother is leaning back in his seat, sly smirk turning up the corner of his pouty lips. The older man holding up a twenty, wiggling his eyebrows like a dork. And of course, Sam's lovesick feet lead him right over to him.

"Hey sweetheart," Dean purrs, watching intently as Sam sinks down to his knees. Taut, glitter sprinkled body swaying seductively to the music.

"Hi, De." Sam is innocence personified, angel face bathed in the warm glow of neon lights. "Like what ya see?"

"Mmmhmm." Dean licks his lip hungrily, moving closer to slip a crinkled bill into Sam's skin tight panties. Curious fingers softly trailing across his baby brother's firm stomach, making him shiver. He can feel Sam's muscles flex under his playful touch, goosebumps spreading across that flawless sun kissed skin.

Sam has always been so responsive and it makes Dean ache for more. He wants his hands all over that perfect body, to make his little brother come undone.

"Whoa there, cowboy," Sam giggles, swatting at Dean's hand. "No touching, house rules."

Sam smiles wide when he hears Dean let out a string of curses. The younger man crawling forward on his hands and knees, hips twisting and grinding to the blaring bump bump bump of the bass.

"I don't like being told I can't touch what's mine," Dean growls, reaching up to grab a fist full of Sam's hair. And even with the music pounding in his ears, Dean can still hear Sam, breathless and desperate, moaning his name. The younger man now visibly hard, bright pink lace stretched tight over his swollen cock. The sight is enough to make Dean's mouth water.

"Then why don't we get out of here?" Sam is such a slut sometimes. It drives Dean absolutely wild to see how needy his little brother is for him.

And Dean knows that if he asked, Sam would probably bend over for him right then and there. Give all the greedy eyes focused on his little brother a real show.

"Soon, baby boy," Dean chuckles, daring to press a gentle kiss against Sam's throat as security starts to head his way. "Right now you still owe me a dance."

[kansaskissedlips]

What's your thoughts on sam being a stripper in college to help pay for food and books and such, and one night after a long hunt, dean goes to a strip club, and sees the cute twink brother of his, and realizes sam isn't innocent, and he's willing to learn how dirty he is now ;)

Y E S.