Sam didn’t know why he was drawn to the skirt. He didn’t know why he got a little giddy when Dean mockingly called him a girl, when he would call Sam his nagging wife, when he would smack Sam’s ass and call him a bitch. He didn’t like it, he was certain that he didn’t, but it always managed to send a rush through his body when Dean treated him like a girl.
He hid the skirt at the bottom of his bag for three months as he went back and forth on whether he wanted to dump it into another thrift store’s donation bin before he came home to Dean holding it in front of him, smirking like he’d discovered his little brother’s deepest, darkest secret. And in a way, Dean had.
“I can explain,” Sam started, but Dean quickly cut him off.
“When were you going to put this on for me?”
The thick strip of dark red fabric mocked him, and Sam, at first, thought Dean was only setting out to embarrass him. His face flushed to the color of the skirt, and Sam assumed that Dean would be pleased with just that.
He turned out to be dead, dead wrong.
An hour later, Sam’s skirt was out across Dean’s lap, thrifted jersey fabric hiding the intersection of their sweaty bodies. He rolled his hips easily, rocking himself back and forth on Dean’s cock while his fingers dug into the bare skin of Sam’s waist.
“Don’t get the wrong idea,” he grunted, a lopsided grin spreading across his face, “I don’t take just anybody home with me.”
Sam exhaled shakily and lowered himself fully onto Dean, grabbing at his leg for support. “Well, you know how to make a girl feel special.”
He breathed quickly as he adjusted to the fullness that was Dean’s cock in his ass, and he felt himself practically drooling onto Dean’s lap the longer he sat in place, occasionally clenching around the base of his shaft.
Dean reached up Sam’s side, his fingers skimming the tight, cropped shirt that stretched across his chest, before he was holding the back of his little brother’s head. Sam’s half-lidded eyes met his, and it sent a rush of pride through him seeing Dean so into this. He pulled Sam close, practically clapped their foreheads together, and Sam smiled at the feeling of Dean’s nose tip brushing against his own.
“My dad didn’t let a day go by without telling me how to treat the special lady in my life.”
Sam laughed breathlessly as he pulled himself up Dean’s length only to sink down onto it again, slowly and deliberately so that he’d get impatient and manhandle Sam some more. His other hand was still clasped tightly against his side, and Dean knotted his fingers into Sam’s hair, pulling hard when Sam fell flush into his lap.
“You like it, Sammy? You like being a good girl for your big brother?”
Sam gave a small nod and an even smaller “yeah” before he leaned in to kiss Dean.
“C’mon,” Dean chided him once he broke the kiss and locked eyes with Sam again, “tell me how good of a girl you are.”
Sam blushed, looking away to try and calm his fluttering heart. He felt a rush of electricity between his thighs as he smiled to himself.
“I’m a good girl.” He shuddered and dug his nails into Dean’s thigh.
“Say it like you mean it, Sammy.”
Dean reached underneath the skirt and found Sam’s cunt like his fingers were heat-seeking missiles. He only waited a moment, watching Sam blush and laugh dismissively at the idea, before he started circling his fingertips across his little brother’s clit.
Sam gasped and closed his thighs around Dean, squeezing him tight.
“Who’s a good girl?” Dean continued stroking his clit, his eyes glimmering as his smirk grew.
“I am,” Sam moaned, rocking himself against Dean’s fingers, “I’m a good girl!”
“Hell yeah, you are! You’re such a good little sister, Sammy.”
Dean cupped his hand around Sam’s cunt and rubbed at him, spreading his slick across his labia and his clit with each roll of his wrist. Sam whimpered and struggled to fuck himself on Dean’s cock, his hips trembling with each thrust and his thighs threatening to collapse underneath him with every brush of Dean’s calloused skin against his clit.
Sam’s clit started to ache as he closed in on orgasm, and he raked his sweaty hair out of his face.
“I’m gonna lie down, Dean,” Sam panted, “I can’t sit up anymore.”
Dean laughed as he followed Sam down, his cock momentarily popping out before he shoved it right back in. He hiked his skirt up to his waist and held it up as Dean rammed hard into his ass. Sam rocked against the comforter with each hard thrust and moaned with the same fervor, shuddering as Dean started sucking and biting at the junction of his shoulder.
Just as Sam came, Dean pulled out of him and left him feeling horrifically empty. When he opened his eyes, his mouth still gaping and taking in sharp, small breaths, he saw Dean jerking himself off and pointing his cock at his cunt. He had no time to protest, however, as Dean burst and left two ropes of come splashed across his labia. His clit throbbed, and Sam quickly realized how he could distract himself from his empty anal cavity.
Dean still had his mostly-hard cock in his hand when Sam spread his legs, putting himself on display for Dean.
He raised an eyebrow and gave himself a lazy, languid stroke. His cock twitched in his hand, and Sam grinned.
“You wanna know something?”
“What?” Sam asked, reaching his hand between his spread thighs and parting his lips. Every second he went without Dean touching him felt like a cold eternity, but he resisted touching himself, instead insisting on exposing himself until Dean caved and took his rightful spot between Sam’s legs.
Dean inched closer, rolling his thumb across the flushed head of his cock and preparing himself to dive into Sam’s cunt. He slotted into place and put his free hand on the underside of Sam’s thigh, his eyes crawling up and down his body.
“I don’t think I’ve ever seen a prettier girl than you.”
As Dean stretched Sam’s desperate hole open, he made a mental note to himself: keep skirt.