Let it never be said that Sam Winchester couldn’t get up to a little scheming now and again.
The plot was about three weeks brewing before it came to fruition. Step number one was waiting until he and Dean visited a big city. It would have been quicker to do the ordering online, but they just moved too damn much for that. Besides, Sam couldn’t risk Dean seeing the package and spoiling the surprise. So he held his breath through all the dead end, middle-of-nowhere towns and waited until they ran a job in a real, full-blown city.
A city with sex shops.
Sam shifted uncomfortably as he stood alone in the lingerie section, surrounded by coathangers bearing enough lace and leather to make his face red. Thank god he was the only one in here, he didn’t think he could have handled other people watching him do this. The man at the counter was idly flipping through a magazine, not even glancing at Sam, or at the specific article of clothing that Sam was standing in front of and considering buying.
He didn’t know what he was expecting. More fabric, he supposed. The little pink-and-black plaid skirt was barely more than a cloth belt. The satiny black top (matching pink-and-black plaid trim, very nice) looked like it would barely cover the breasts of the wearer, leaving the whole stomach bare. Little more than a glorified jog bra with plaid. And that matching pink tie... Sam was a little confused by it for a moment until he imagined someone yanking on it like a leash.
Sam must have stood there for a solid five minutes, just staring at that one outfit. It was exactly what he needed, but now that he was looking at it, he was petrified.
The sound of the clerk clearing his throat almost gave Sam a heart attack. “Need help finding anything?” the man asked, leaning over the counter.
Now or never. Sam swallowed and picked up the coathanger with the schoolgirl outfit like it was a bomb, carrying it gingerly to the counter. It took him a few minutes to mumble the words, “...Do... do you have this in extra large?”
Sam didn’t know what sort of slut-shaming he was expecting from a man who worked in a sex shop, but all he got was, “Sure, lemme fish one out of the back.”
The man started to walk away and Sam had to grit his teeth before asking. “D-do you have it without the breast cups?”
Sam blew out a long breath, looking over the outfit in his hands. “Cities,” he murmured, impressed.
The clerk came back a few minutes later, holding another coathanger, this one with a substantially larger outfit hanging off it. It still looked like barely enough fabric to Sam’s eyes. “Goes well with tights,” the clerk suggested, handing a stunned Sam the outfit and taking the small one out of his hands. “You wanna try it on before buying it?”
Sam just nodded dumbly. The clerk seemed to sense his helplessness and pointed to the back of the shop. “Changing room’s back there, honey.”
Clutching his outfit like his life depended on it, Sam muttered a “thank you” and raced to the back of the shop, face steaming.
Sam locked the door of the changing stall and then checked about a million times to make sure it was really locked before stripping out of his clothes. His heart was pounding, and he felt so damn dirty about what he was going to do that he wasn’t sure if he could go through with it. He picked up the skirt and just stared at it for a moment. Fuck. Slutty schoolgirl skirt, and he was about to put it on. Sam heaved a deep breath and stepped into the thing one leg at a time, pulling it up his toned thighs and adjusting it around his waist. He was impressed that it actually fit, and furthermore, fit comfortably. Sam glanced at himself in the mirror and his face went as pink as the skirt.
The little pleats of plaid fabric shifted over his skin every time he moved. He didn’t know it was possible to feel this naughty, but the sight of his own body wearing that was borderline surreal. Like his brain couldn’t quite piece together what he was seeing. Sam turned around slowly, and was relieved to see the skirt at least covered his butt. Not much room for error, though. The slightest wrong shift or gust of wind would definitely provide an impressive view. As soon as the thought occurred to him, Sam knew he had to see it. Swallowing, he reached back and grabbed the hem of the skirt, lifting it just a hair at a time, until the round curves of his ass showed.
“Oh fucking hell, Dean’s gonna love this,” Sam breathed. He dropped the hem of the skirt and braced himself on the wall across from the mirror, bending over and pushing his hips out, admiring the view in the mirror. God, the skirt didn’t stand a chance when he was bending over. It rode up his ass and showed off everything. Sam leaned over a little further and spread his legs, groaning at the sight.
“Yeah, I’d fuck that,” he murmured. He straightened up and adjusted the skirt, freezing when he glanced down. “U-uh...”
Apparently, Sam’s cock was totally on board with the “fucking that” idea, because it was standing straight up and pulling the skirt with it. Sam shot an unwise look at the mirror and his face darkened even more as he saw what he looked like right now. That naughty little skirt was being held up by his cock like a brazen flag of arousal. Sam swallowed and turned his body to face the mirror, breath hitching. The rosy head of his cock was clearly visible, precome beading at the slit. The way it lifted his skirt exposed his balls, and when Sam’s cock twitched in response to the view, the skirt slipped off the head and bunched around the base, leaving the entire shaft exposed.
“J-Jesus fuck...” Sam breathed.
It was a few seconds before Sam successfully tore his eyes away. He quickly grabbed the top and pulled it on over his head. He just needed to make sure it fit, because he already knew he was buying it.
It took a few minutes of flipping through the sex shop’s selection of especially weird porn mags to make Sam’s hard-on go away. When he felt he was presentable, he grabbed a pair of black, one-size-fits-all stockings and the first pair of size-large panties he laid eyes on and walked up to the register. The clerk calmly rang him up and asked if he wanted cash or credit, and Sam was on the road again before he knew it.
He had to hurry home. He’d managed to run this errand in secret by telling Dean that he wanted to spend some time in the local natural history museum. Thankfully Dean had reacted in a typically Dean way by saying, “You do that, poindexter, I’m gonna go have a thing that we real people call fun.”
But he couldn’t know for sure that Dean wouldn’t come looking for him. Sam licked his lips and sped home.
Operation Schoolgirl had been hatched about a two and a half weeks ago. It was just after a case, and he and Dean had been celebrating by sitting on the hood of the Impala and working their way through two sixpacks while the stars came out and the sky stained inky dark.
“Best sex stories, come on.”
Sam snorted. “You mean before you, right?”
Dean made a face. “Well, it would just be cheating if we counted me.”
“Arrogant asshole.” Sam snickered and stared into his beer for a moment before beginning. “Stanford. Before Jess. This, uh... this girl in my chem class.”
“Ooo, chemistry in chemistry class.” Dean leaned closer. “Romance by the bunsen burners?”
“Uh... nothing so vanilla.” Sam smirked when Dean’s eyebrows rose. “We were finishing up a lab late one evening and... we finally got the damn thing wrapped up and we cleaned up everything and she kinda... She fucked me on a lab table.”
Dean made a choked grunting noise and cleared his throat before pressing, “Details.”
“She was really pretty. I thought so, anyway. But like... the kind where it looked like she didn’t know she was. Or maybe just didn’t care. Just... big green eyes and olive skin and dark hair she always kept tied back...” Sam snorted, grinning. “She was snarky.” He shot a look at Dean. “Guess I’ve got a type, huh?”
“Yeah, yeah, get to the part where she fucked you on the lab table.”
“First of all...” Sam paused to take a swig of his beer, holding up a hand for emphasis before continuing. “Lab tables? Cold.”
“Do go on.”
“And, uh... glass vials are pretty cold too.” Sam snickered when Dean lurched back, surprise and arousal painted on his face. “Yeah, uh, she ripped my clothes off and threw me on the lab table and... you know, come to think of it, she’s the only person to ever rim me as well as you do.”
“Fuck, Sam,” Dean rasped.
“And, uh, there were these glass vials all over the place, and they were kinda... optimal size and shape, you know?” Sam laughed quietly. “She crawled up on the table and started riding me, really fiercely too, just going to town on my dick... she kept talking about how she wished she could finger me at the same time, it was hot as fuck. Took a lot of willpower not to come in the first sixty seconds. And, well... I was thinking about what it would feel like to have something in my ass while she was doing that, and I’m pretty sure she was thinking about it too, and we both kinda caught sight of the vials at the same time...”
Dean made a low purring noise and leaned close, nosing past Sam’s hair. “Hm, maybe we should break into a highschool this summer,” he murmured, sliding a hand over Sam’s leg. “We can try to recreate this scene...”
Sam laughed and pushed Dean away. “Your turn first, pervert.”
“Oh, I’m the pervert?”
“Yeah, you are. Now tell me a sex story.”
Dean snorted. “Fine.” He licked his lips and took a few sips of beer, gazing up at the stars. A cool wind ruffled Sam’s hair when Dean finally spoke up. “Wendy Hollister.”
Sam’s eyebrows pursed. “Don’t recognize the name.”
“Oh, you wouldn’t. She went to a private, all-girls highschool.”
Sam snorted. “Uh, and what exactly were you doing in an all-girls school? Besides perving out.”
“Running a case with Dad,” Dean snickered, taking a sip of his beer. “I was, uh... twenty three, I think.”
Sam pulled back. “Christ, Dean, how old was she?”
“Who, Wendy? Eighteen.” Dean’s eyebrows jumped. “Legal and willing, I assure you.”
“...That’s still kinda dirty, Dean.”
“Yeah, that’s what made it so good.” Dean smirked and took another sip of beer. “Oh, and her barely-legalness wasn’t even the best part. They wore uniforms there.”
Sam snorted. “Uniforms.”
“Oh yeah. Red and white. Neat, tight button-up tops and cute little skirts that swished when they walked...” Dean was staring off into the distance, clearly lost in a pleasant memory. “I told her to keep it on while I bent her over a table and fucked her.”
Sam’s face immediately heated and the blood rushed to his cock. “...Yeah?”
“Oh yeah. Didn’t even take her panties off, just pushed the skirt up and pulled her panties aside and slid right in.” Dean chewed his lip, eyes closing for a moment. “God, she was tight... and man, the noises she made. She loved it.”
“Hope you were clear that you weren’t sticking around,” Sam managed, trying to keep the groan out of his voice.
“Course I was. You know me, campsite rule. Leave ’em better than you found ’em.”
“And... did you?”
“Oh yeah.” Dean shot Sam a grin that had his heart skipping. “I left her better than I found her several times that week, in fact. Couldn’t keep herself away from me, kept bending over and flashing that cute little butt whenever she thought I was looking. Nearly drove me crazy.” He stared off into the distance and took another sip of beer, shaking his head. “God, I miss that schoolgirl outfit...”
Sam finally grabbed Dean’s chin and pulled his brother into a hungry kiss. “Okay,” he panted when they broke apart, running a hand between Dean’s legs. “Story time’s over.”
Sam shot a nervous glance at the passenger’s seat where the paper bag containing his outfit sat innocently. He licked his lips and turned his eyes back on the road. He couldn’t wait to surprise Dean.
Sam managed to get the outfit hidden before Dean came home. All he wanted to do was put it on and show it off to Dean right away, but they were in the middle of a case and didn’t have time. He wanted to do this properly, when they could really enjoy it. So when Dean got back, slightly tipsy and bitching about people cheating at pool, Sam just smiled and pulled him into a hungry kiss. He had to wait to use the outfit, but he didn’t have to wait to have Dean.
Three days passed before the job finished and Sam finally got the chance he was looking for. There were no new jobs on the horizon, so he’d talked Dean into staying in town a little while longer. Dean had agreed, but only, as he put it, for the kickass burger joint next door.
The morning after the job was over, Sam deliberately brushed off Dean’s sleepy morning advances. He wanted his brother a little pent up for this. Dean had been put out when Sam pleaded “headache” and pushed his brother’s hand off his dick, but he didn’t kick up a fuss.
They spent the day checking out the local scene. It was hard to really be tourists when you were also trying to hack up monsters into slimy little monster bits, so it was refreshing to just kick back and enjoy the location. Sam probably would have enjoyed it a little more if he’d been able to focus on it all, but the only thing he could think about was that schoolgirl outfit sitting at the bottom of his duffel bag. Finally, dinner time rolled around, and Sam again pleaded headache and said he was going to head home. He suggested that Dean pick up some food from that burger place he liked so much and bring it back to the motel room. Sam almost felt bad about the lie when Dean gave him a sympathetic kiss and murmured, “Hope you feel better,” before leaving.
As soon as the motel door clicked shut behind him, Sam ripped open his duffel bag and pulled out the schoolgirl outfit, and all his lingering guilt evaporated.
He probably had about twenty minutes to get ready. Sam chewed his lip and grabbed the clothes, locking himself in the bathroom just in case Dean came back early. He stripped his clothes off and tugged the skirt on, trying not to look in the mirror as he tugged the top on too. But when he started pulling on one of the stockings, he couldn’t resist a glance.
The satiny black top stretched across his chest, leaving his rippled stomach bare. His powerful shoulders were bare too, and he could see every muscle in them flex as he tugged on the stocking. Just in case there wasn’t enough skin showing, the low V-cut neck took care of that, revealing the dusting of hair between his pecs, framed by two triangles of pink, plaid trim.
Sam swallowed and turned his red face away, pulling on the other black stocking. He tugged the elastic up until it hugged his thigh, a boarder of flowery lace just shy of his soft cock. He shot himself another guilty glance in the mirror. Fuck, his legs looked good in those, every toned curve emphasized. He reached for the panties and realized he actually had no idea what they looked like, he’d grabbed them so quickly. He swallowed as he held them up. White and lacy. Weirdly virginal compared to the rest of the outfit, but... he had a feeling Dean would like that. Sam stepped into the panties and pulled them up, shifting his hips to get them on. He had to reach under the skirt to adjust his balls and half-hard cock. Hopefully the panties would keep his dick in check so he didn’t have another raise-the-flag situation. Then again, Dean would probably like that too.
Sam let out a huff and looked himself over. Good, but one piece missing. He picked up the tie and frowned for a moment at the band of elastic that was meant to go around his neck. This wasn’t even a glorified leash, it was just a leash. With a sigh, he pulled it on and tugged at it until it sat comfortably around his neck, the pink tie falling across his chest and tickling his bare stomach. The picture he made was pretty mouth-watering. Sam shifted his hips experimentally, watching the skirt swish against his lace-wrapped thighs. He turned around and lifted the skirt up, swallowing at the sight of those white, lacy panties hugging the curves of his ass.
“Dean’s gonna fucking lose it,” Sam murmured.
Sam left the bathroom and quickly put away his other clothes before finding his cell phone and dialing Dean. It rang a few times before Dean picked up.
“Christ, Sam, it’s only been fifteen minutes. What?”
“Just wondering how dinner’s coming,” Sam asked.
An irritated sigh. “On my way home with it now. God, you couldn’t have waited five more minutes?”
Sam smiled, but kept his voice neutral. “Just wondering when you’d be back.” He hung up and put the phone away. Five minutes, that meant he had time to get started on his final, secret weapon.
Sam reached into his jacket pocket and pulled out a pink lollipop. He smiled when he pulled the wrapper off it.
“Oh, he’s gonna fucking lose it,” he murmured to himself, slipping the hard ball of candy into his mouth and sucking.
Sam stood by the motel window, sucking idly on his lollipop, peeking through the curtains as he waited for Dean to come home. He’d thought about this, and it seemed best to answer the door rather than striking a sexy pose and holding it for five straight minutes. And he certainly wanted to make sure it was Dean before he opened the door like this.
Sam’s heart actually jumped when he saw the Impala pull up in the lot. For one horrible moment he felt absolutely ridiculous and was afraid Dean would just laugh when he came in.
Then he remembered the look on Dean’s face when he talked about Wendy Hollister.
“God I miss that schoolgirl outfit...”
Sam swallowed when Dean climbed out of the Impala, takeout bags in hand. Well, at least he’d have pink cheeks to go with the outfit, Sam thought. A real, blushing schoolgirl. Sam braced himself as Dean approached the door, then walked over and opened it when he estimated Dean was fishing around for his key card.
Sure enough, Dean was rooting around in his pockets when Sam opened the door. He glanced up at Sam and his jaw dropped.
Sam sucked on the lollipop for a moment before pulling it out of his mouth, one hip cocked out as he looked Dean over. “You gonna come in?”
It took Dean a moment to pick his jaw up off the floor and re-learn how the human tongue had evolved to create words. “J-Jesus Christ, Sammy,” he rasped at last, rubbing a hand over his mouth. “Where did you—fuck—”
Sam cleared his throat, smiling nervously and glancing around. “Yeah, uh, could you be flabbergasted inside the motel? Someone’s gonna walk by.”
Dean hurried inside the room and Sam shut the door. Dean still looked completely stunned when Sam turned around.
“If that headache of yours hasn’t cleared up,” Dean groaned, rubbing a hand over his mouth as he looked Sam over, “I might literally explode.”
Sam bit his lip in a way that he knew would look shy and rocked his hips a little, looking at his feet and murmuring guiltily, “...I may have been lying about the headache.”
He couldn’t see Dean’s face, but he could practically hear his smile. Sam’s breath caught when an authoritative hand grabbed his chin.
“Sounds like you’ve been a bad girl,” Dean growled, grinning hungrily.
Sam really wasn’t prepared for the bolt of pleasure those words sent to his cock. He swallowed hard, erection straining against the lacy panties, heart pounding in his chest.
As if he could hear the thump thump thump of Sam’s racing heartbeat, Dean trailed his knuckles down Sam’s chest, over the firm peak of his nipple. “And dressing like such a slut,” he rumbled in that low sex voice that always made Sam’s head spin. “Mmm. Definitely a bad girl.”
Sam bit his lip and whined when Dean tweaked his nipple.
“Hm, what do you think, Sammy? Have you been a bad girl?”
Sam panted as Dean continued to tease at his nipple, still flashing a predatory grin that made Sam’s cock throb.
“Y-yes, sir, I have.”
Dean finally let go of Sam’s nipple, twining the pink tie slowly around his fingers and giving it a possessive tug. Sam’s knees turned to jelly. He had been afraid of feeling ridiculous, but he wasn’t expecting to feel like this.
“You know what happens to bad girls, don’t you?”
Sam swallowed hard, throat bobbing against the snug fit of the elastic around his neck. “Th-they get punished, sir,” he managed, struggling to keep his voice steady.
“Damn right they do.” Dean’s eyes ran down Sam slowly, and Sam shivered. “Lift your skirt for me,” he breathed. “Show me what a naughty girl you are.”
Sam’s cock jumped again. He obediently grabbed the hem of his skirt and lifted it, breath catching in his throat. Dean groaned out loud when he saw Sam’s hard cock bulging against the white lace of the panties.
“Holy fuck that looks slutty,” he panted.
Sam whimpered when Dean’s hand pushed between his legs, feeling him up. “I-I’m not a slut,” he murmured, “I’m a good girl.”
“Oh, are you?” Dean purred, nuzzling Sam’s neck. Sam could feel Dean’s lips and tongue and teeth on his skin, tasting the sweat from the day. Dean teased the nerves into life like he was breathing on coals. Sam wanted to say something, wanted to continue the roleplay, but all he could manage was a shuddering exhale when Dean sucked on his fluttering pulse. He slid a hand under Dean’s jacket and ran it over his brother’s chest, feeling the muscles through the shirt, his other hand squeezing the thin rod of his lollipop like he was trying to compress it into a diamond. Sam shivered when Dean’s hands reached up under his skirt, grabbing at his ass and squeezing.
“Cute ass,” Dean growled against Sam’s neck, and Sam shivered again because the silent words I’m gonna fuck it hung palpably in the air.
Sam limply let Dean guide him to the bed, let his brother push him down onto the mattress and climb on top of him. He panted when Dean settled between his legs, cupping his face and pulling him into a kiss. Dean groaned suddenly and pulled back, panting, “Fuck, Sam, taste like candy.”
Sam lifted the lollipop and slipped it back into his mouth, staring innocently up at Dean while he sucked it. Dean chewed his lip, just watching Sam’s mouth work. Sam let the pink candy slip saliva-slick out of his mouth, trailing it over his lips as he did, and licked it slowly. Dean groaned again and leaned in, sliding his tongue over the hard ball of sugar while Sam licked the other side, working around it until the lollipop slipped away and it was just Dean’s lips against Sam’s, sugar-sticky and ravenous.
“Want me to make love to you?” Dean drawled into Sam’s mouth, gripping Sam’s hip with one hand and grinding his denim-bound hard on up under Sam’s skirt. Sam shuddered and bucked his hips up, spreading his legs as wide as he could.
“Y-yeah, please,” he panted, running his hands down Dean’s back.
Dean slipped a hand between Sam’s legs and felt his ass through the panties, rubbing the lace against his hole. “Want a nice, slow, sweet fucking?”
Sam almost melted, shivering when Dean sucked on his throat. “Y-yes, god—”
“Tender and gentle, my cock sliding in and out of you nice and easy while I call you sweet names,” Dean purred. “That what you’re hoping for?”
Dean bit Sam’s neck suddenly, hard and sharp, and Sam gasped. “That’s what good girls get,” Dean growled. “But you’re not a good girl, are you?”
Sam swallowed hard. He was shaking a little when Dean pulled back and gave him a hard look. The love was still there, but it was hiding beneath the surface.
“...N-no, sir,” Sam stuttered. “I-I’m a bad girl.”
Dean’s lip curled in something between a sneer and a grin, and he crawled off the bed suddenly, grabbing Sam’s hair and dragging him to his feet.
“Bad girls don’t get slow fucks and sweet names,” Dean mocked, dragging a yelping Sam to the bathroom. “Bad girls need to be put in place.”
Sam let Dean pull him through the bathroom door and brace him over the counter, facing the mirror.
“Take a look,” Dean panted in Sam’s ear, holding Sam’s hair firmly and forcing him to look in the mirror. “Does that look like a good girl to you?”
Sam shivered. He’d looked naughty enough just wearing the outfit, but now... his face was flushed and his lips kiss-swollen, his eyes hazy with desire, his arms shaking slightly where he was bracing himself on the counter. His skirt wasn’t quite pitching a tent, but there was a definite bulge where Sam’s cock was defying the constraint of his panties.
“...No, sir,” Sam replied submissively.
“Damn right.” Dean held Sam’s hair firmly and forced him to bend over the counter. “You’re a naughty slut. Got that?”
Sam nodded, panting against the cold porcelain of the counter. He could feel Dean’s hand slide under his skirt, pushing it up, exposing his ass. “Y-yes, sir.”
Dean bit his lip and gave Sam’s ass a teasing smack. “So sweet and pretty in that lace.” Another smack, harder. “You really wanted me to see this, didn’t you?” Smack. Smack. Smack. “Been dying to have someone push up that little skirt and fondle you.” A smack hard enough to make Sam gasp. “Slutty, slutty girl.” Three more, even harder, and Sam moaned into the counter. “Mmmm, that lace’ll look even nicer once I get your cute little butt nice and pink...”
Sam panted as Dean spanked a sore sting into his ass. “I-I’m sorry, s-sir,” he gasped out between spanks. “P-please, I’ll be a good girl—”
“Only one thing to do with a slut,” Dean growled, finally laying off the blows and leaving Sam’s round cheeks a blushing pink. Sam heard the sound of the lube bottle being snapped open, and he shivered.
“A nice thick cock in your ass. That’s what you want, isn’t it?”
Sam spread his legs, shivering with anticipation. “Yes, sir!”
Sam bit his lip and reached back, grabbing the frilly hem of the panties. He dragged them down slowly, letting them slip just over the curve of his ass so the lace still hugged his balls, but his hole was exposed to Dean’s view.
“...Fuck that’s hot...”
Sam rocked his hips eagerly when three slick fingers slipped over his hole, lubing it up. Dean pushed one in slowly and Sam moaned.
“Greedy slut,” Dean teased, grinning as he pumped the finger in and out. Sam shuddered, panting against the counter, his breath leaving a steamy cloud of moisture on the cold surface. He could see Dean’s face in the mirror, see his brother biting his lip as he pushed another finger into Sam’s body.
“Gonna get you all nice and loose for my cock.”
Sam pushed his hips back, driving Dean’s fingers deeper. Dean pumped them a few more times before letting them slip out, leaving Sam slick and ready. Sam’s heart jumped when he heard the scratch of a zipper being dragged down.
“Mmmh, ready to prove you’re a good girl?”
Sam whimpered when Dean’s cock pressed against his hole. He gasped when Dean grabbed his hair suddenly, roughly, holding him still and pushing into his ass.
“You’d better be,” Dean smirked.
Sam shouted and clenched around Dean’s thick length as it slipped into him. His cock throbbed, straining fiercely against the panties. Dean let out a low purr, holding still and letting Sam get used to the stretch. Sam squeezed around Dean’s cock, whimpering, panting at his own reflection. He felt Dean’s hand grope his ass, squeeze one cheek, and he imagined his brother staring at his stretched-out hole.
“Mmh... fuck, Sam, got no idea how hot you are...” He gave a teasing little tug on Sam’s hair, snickering. “Shoulda put this up in pigtails for me, sweetheart. You make such a cute schoolgirl.”
Sam chewed his lip, cheeks reddening. Dean finally let go of his hair and slid both hands over Sam’s ass, holding it as he started fucking slowly in and out. Sam was in heaven, eyes lidded and hazy, panting as his brother’s cock pumped in and out of him nice and slow. He slipped a hand down between his legs, groaning in relief as he worked his cock free of the panties and it sprang up.
“Yeah, there you go,” Dean panted, thrusting just a little harder. “Know you love getting your ass filled up. Touch yourself for me, baby.” He ran a hand up Sam’s tense back. “Makes you so nice and tight...”
Sam squeezed a hand down his aching cock and bit his lip in response to the shivering wave of pleasure it sent through him. God just that one stroke was borderline overwhelming. Dean shoved into him, harder then before, and Sam’s knees almost gave out. He fell into panting a mixture of “Dean,” “please,” and “sir” as he was stretched out on his brother’s cock. He could hear Dean groaning, feel a slight, beautiful burn as Dean really picked up speed.
“F-fuck, such a tight little ass—” Dean’s hand suddenly slapped into Sam’s ass and he yelped. “Does my bad girl like getting fucked?”
Sam whined against the counter, spreading his legs even further and letting Dean slip in deeper. He could feel his brother’s balls bumping against his through the lace. He was seeing stars, he wasn’t going to last much longer. “Y-yes, sir!”
“Stroke that cock nice and fast, baby, wanna see you come like the slut you are.”
Sam grabbed at the counter with his free hand, breathing hard and jerking his dick as Dean plowed him. His cock jumped in his hand.
Dean was whispering low and filthy, alternating between grabbing Sam’s ass and grabbing the short little skirt, holding Sam still as he went as hard as he pleased. “You should see yourself right now, slut, should see how you look bent over a counter, letting me fuck your nice tight ass. You’re gonna let me do this whenever I want, aren’t you? Gonna offer this nice ass up every time I so much as ask, bend over and lift up your skirt and show me everything—”
Sam groaned frantically and his cock pulsed in his hand, leaving a sticky mess on the wood wall of the counter. He gasped and squirmed on Dean’s dick as the pleasure shot through him, shivering, squeezing his brother. Dean grunted and squeezed Sam’s ass hard, spreading it nice and wide and pumping into it.
“F-fuck, that’s it, so fucking hot—”
“A-am I a good girl now, sir?” Sam stuttered, looking over his shoulder at Dean, body rocking with each thrust. Dean made a choked noise in response and groaned.
“F-fuck yes, been such a good little slut for me—”
“Do good girls get come, sir?” Sam wiggled his hips back against Dean, satisfied when his brother groaned desperately. “I’m your good girl, please come in me—”
Dean’s shouts sounded almost alarmed, like he wasn’t expecting his orgasm to hit as hard as it did. He doubled over above Sam, shaking as he gushed inside Sam’s body. “Fuck, fuck, fuck, Sam, fuck...”
Sam caught his breath slowly, feeling Dean squeeze his ass and let out a long, shuddering breath. “Holy fuck, Sammy...”
Sam craned his head around, smiling. “Did you like your surprise?”
Dean laughed and gave Sam’s ass a gentle pat, still buried in it. “God, Sammy, you sure know me well.” He pulled out slowly, groaning when his cock slipped free. “Fuck... should see my come in your ass...”
Sam grunted as he pushed himself upright, exhaling heavily. “God... that was more fun than I was expecting...”
Dean grinned. “Oh, really?” He turned Sam around, holding his brother close and rubbing their noses together. “Soooo... you’d do it again?”
“Well, I’ve bought the outfit, haven’t I? Might as well.”
“Good. ’Cause I really, really—”
Sam smiled, chuckling. “I could tell.”
“—really liked it.”
“Yeah, I know. You let your favorite burgers get cold.”
Dean’s eyes snapped open and the smile evaporated from his face. “Burgers!” he shouted in alarm, running to the main room. Sam laughed and followed him out, stepping out of the panties and stripping off the stockings as he did. Dean was staring mournfully into the takeout bag.
“There’s a microwave,” Sam reminded him, sitting down on the bed.
“It’s not the same,” Dean lamented.
“Well, was it worth it?”
Dean looked up at Sam, sitting on the bed in a pink miniskirt and a slutty schoolgirl top, and smiled reluctantly. “...Okay, fine. It was totally fucking worth it.”
Sam grinned and pulled the skirt down. “That’s what I thought. Let’s have dinner.”