Work Header


Chapter Text

It started out barely noticeable. Dean would go on dates and Sam would sulk and whine. 

"I don't want anyone to get suspicious, Sammy. If I suddenly stopped being the playboy, dad would notice. Not to mention, how do I keep 'em off'a me?"  Dean had chuckled, trying to lighten Sammy's mood one night. 

Sam hated it, but knew Dean was somewhat right. Not to mention Dean can charm them plenty of food, clothes, and sometimes even hotel rooms with his nice face and silver tongue. Not to mention: Dean had a reputation to uphold. 

But the younger Winchester couldn't exactly stop his brother. He could whine and moan and threaten no sex for a month, but Dean would swoop in, all kisses and charm.

Not to mention, a voice peeped in from the darker side of Sam's head, Dean could get sex from anyone he wanted. Any time he wanted. 

Unable to stop his big brother, he decided to start up a reputation of his own. 


The changes were slow. After Dean drove them to school, he'd slip into the bathroom and put on some mascara or lipgloss, something to catch some of the other guys' attention, but nothing scandalous. 

Dean noticed him getting a little closer, a little more touchy with some of the other boys, not only his age, either. In fact, he'd heard his little brother's name in a senior only class. 

"You're just being ridiculous, I'm making friends, isn't that what you wanted? You can't possibly be jealous, considering what you do..." The sneer in Sam's voice was definitely not missed. 

"I suppose I am, Sammy, but you're just so adorable, how could I not get jealous hearing them talkin' about you..." Sam cut him off with a kiss. 

"Don't be such a girl. You have a reputation to uphold," Sam smirked, whispering the last sentence under his breath. 


"And I have one to create..."

Chapter Text

Dean never claimed to be a genius, but he sure as Hell wasn't an idiot. He noticed things pretty quickly.

Like, for example, when his baby brother started wearing eyeliner to school, or started painting his nails. Or when Sammy's name kept appearing in social conversation, similar to the way girls say his, but these were guys, senior guys. 

Dean knew that something was going on, and early on he knew he wasn't going to like the answer. He just didn't know how much.

It was your typical Wednesday as a Winchester, new school, new state. Already flirting with new girls by his new locker, the only things consistent being his name and his little brother. 

He had another new face up against a locker. She was pretty, blonde hair, blue eyes, feminine and soft, but nothing like his Sammy, with smooth, but calloused fingers, ear length brown rats' nest he calls hair, tall and scrawny, almost to the point of concern. But it didn't matter, nope. He wasn't about to think about Sammy with this beautiful girl right in front of him. 

But he did. More specifically, how the boy was just yards away, in clothes that he definitely didn't leave the hotel room in this morning. 

Sam was in an outfit Dean would prefer stayed inside their bedroom. A spaghetti strap tank top, covered only by a 'shirt' that slid down his shoulders, barely any support keeping it up. He was wearing the shortest shorts Dean had ever seen, up above his mid thigh and perfect for showing off his mile long legs, some black garters holding up his white knee socks. Dean's boots completed the look, his ankles disappearing into clunky shoes made to last. Dean had bought him most of those clothes at various thrift shops, and damn, did he not regret it. 

The problem was that other guys seemed to not regret it either. There were the typical looks of disgust from some guys, but a majority seemed to be lust. With Sam's ass practically on display, his makeup making him look softer, prettier. If looks could kill, Dean would be the only man left in the building. Some teachers even seemed to stare.

Dean's glaring was cut off by the girl under his growling. 

"Don't tell me you wanna fuck the new kid too!" She rolled her eyes in disgust. "I'm pretty sure he's a guy you know! I bet by this time next week, the little trap'll have sucked every dick in this school!"

The glare didn't go away, rather it shifted positions. Suddenly, those eyes and that little figure wasn't so compelling. 

"That's my baby brother..." Dean growled. Her expression shifted. 

"Oh, God, I'm sorry, I was just a bit jealous..." the blonde immediately tried to cover her tracks, but Dean was already pissed. 

Pissed at her for calling his baby brother a slut, pissed at Sammy for dressing like that, pissed at every guy in the school for noticing. Pissed at himself for being jealous. 

Sam was mid conversation when Dean grabbed his arm, pulling him away. 

"What the fuck, Sam?"

"What do you mean?" Sam looked up at Dean through his heavily mascaraed eyelashes, giving his 'innocent' babydoll eyes. 

"Don't play that shit with me, Sammy. What's with the outfit?" Dean growled, resisting the urge to kiss Sam right there, make the leers stop and the jealousy in his gut cool. 

"I've dressed like this for a while, De. You just never noticed..." Sam sighed, as though he were bored. "I like looking like this, it makes me feel pretty. Aren't I pretty, Dean?" He fluttered those damn eyelashes again.

"Of course you are, baby boy, but I just-" Dean stopped himself. Who was he to tell him that? Him, who slept around constantly, couldn't talk to a female without a wink, telling Sam not to dress how he wanted because what, he was jealous?

"Nothing, Sammy... you just look really pretty today..." Sam's eyes lit up in that way dean loved and he couldn't control the jealousy in his stomach.

"Well, I suppose we all have reputations we want to keep."

With a glittery wink, Sam was gone, leaving Dean to imagine him walking around dressed like that all day. This was going to be hard.