#samdeanjess

“Jess,” Sam gasps when her slender fingers dance up the inside of his thigh.

She grins and presses a kiss to the curve of his shoulder. “Yes?”

“Don’t tease.”

“It’s not teasing if we plan to follow through,” Dean smirks and his brother huffs.

“Please.”

“Oh, I like that.” Jess teases at the top of the stocking, her touch sending shivers through his body. “What do you want, sweetheart?”

--

This hadn’t been the plan. They were supposed to go out. There’s a Halloween party down the street at Brady’s place, and they were going to hit up another party at a bar later in the night. All those plans went out the window, though, the minute Dean and Jess laid eyes on Sam in his costume.

They’d picked it out for him, of course. A little plaid skirt, white button-up, and grey sweater, à la Brittney Spears “...Baby One More Time” - Jess’s idea, surprisingly. A pair of black stockings and heels complete the look. Sam had stammered and blushed so pretty but caved easily when Jess turned those big blue eyes on him.

“Just try it on,” she said. “For us?”

Sam huffed, grumbled under his breath, and took the clothes into the bathroom to change. When he emerged about ten minutes later, fully dressed from the tied up shirt to the heels, Dean’s pretty sure his brain broke with how quickly the blood rushed to his dick.

“Oh, shit.”

Sam’s cheeks are burning, adorable spots of color high on his cheeks as Dean takes in the sight of him. His baby brother has grown up a lot in the last few years, shedding almost every bit of lingering baby fat in return for lean muscles that look absolutely sinful wrapped up in the soft fabrics of the outfit. He’s pouting a little, though, and Dean can’t unsee the snarky teenager in that expression. Some things never change, including the slight whine in Sam’s voice when he says, “There's no way I'm walking to Brady’s or going anywhere near a bar in these heels.”

Jess exits the closet at that moment, dressed in a sexy witch costume that Dean had rolled his eyes at in store but is definitely changing his mind about now, and lets out a low whistle when her eyes land on Sam. “Oh, baby,” she says in that tone Dean is quickly learning guarantees all sorts of good things. “That shouldn't be a problem. I don't think you're going any further than our bed.”

--

That’s where Sam is now, sprawled on his back in the center of their mattress. His heels and sweater are gone, his skirt draped between his legs to maintain what little modesty Sam has left. His shirt is wide open, baring his chest to Jess’s questing hands, and his stockings have been left on at Dean’s insistence. They’re just simple, black stockings but Dean’s already thinking of all the possible outfits they might be able to get Sam to wear in the future. Maybe white next time, with lace.

“C’mon, Sam,” Jess purrs. “Tell us what you want.”

Sam squirms, caught between Dean’s hand on his ankles and Jess’s on his thigh and chest. “I want Dean to fuck me.”

Dean can’t suppress a groan at that. “Happily.”

Jess smirks up at Dean, something mischievous in her eyes. “Wanna show Dean the surprise I planned for him?”

Sam’s breath hitches and Dean’s eyes jump between their faces, confused until Sam’s hands creep down to the hem of his skirt.

“Go on,” Jess encourages. “Show him.”

At first Dean’s not sure what he’s seeing, as Sam nervously lifts his skirt, but then things click into place and he has to drop a hand down to press the heel of it against his dick through his jeans. The panties are black, like Sam’s stockings, with little ruffles along the edges and a tiny matching bow at the top, right above Sam’s hard cock.

“Sam,” Dean moans, sliding his hand down to touch the ruffles at the top of his brother’s thigh. “Fuck, you’re gonna be the death of me.”

Jess grins, her hand mirroring Dean’s on the other side. “You like?”

“Fucking gorgeous.” Dean presses a kiss to the inside of Sam’s ankle. “God, Sam, you should see yourself. Never seen anything like you before.”

Sam’s still blushing but he doesn’t seem as nervous as before. “Yeah?”

“Oh, yeah.” Allowing Sam’s leg to slide from his shoulder to the crook of his arm, Dean leans forward to capture his brother’s lips in a kiss. “Gonna give you what you want.”

“‘Bout time.”

Jess laughs and Dean rolls his eyes, reaching over to grab the lube from the bedside table. Not even nerves can kill that little brother sass, apparently.

“Definitely leaving these on,” Dean says as he pulls the panties to the side and presses two lube-slicked fingers against his brother’s hole. “I wanna see you ruin them.”

Jess sits up and reaches down to take over holding the panties out of the way. “I second that.”

Sam just groans, head thrown back against the pillow as Dean begins working him open. His abs flex as he rolls his hips down against his brother’s hand. They haven’t been at it long but Sam already looks debauched. His lips are kiss-swollen and shiny in the lamplight, parted to let out breathy little sounds, each of which goes right to Dean’s cock.

“Should put that mouth to good use,” Dean suggests, two fingers knuckle-deep in his brother’s hole. He meets Jess’s gaze and she grins.

“I like the way you think, Winchester.”

She lifts her own skirt to reveal red panties in a similar style to Sam’s. These are quickly shimmied down her long legs - how did Dean land two partners with absolutely fantastic legs? He’s not sure but he’ll never complain - and tossed aside. Sam is already reaching for her, his hands huge against her thighs as he guides her to straddle his face. Jess tosses her curls over her shoulder with a sigh as she settles into place exactly where he wants her. Dean takes in that sight with a groan, admiring the curves of her body when her back arches with pleasure and her head tips back. He’s going to have to get her to wear that costume again for sure.

“You gonna fuck your brother any time tonight?” Jess asks, one hand flailing a little before Sam catches it with his own and holds her steady.

Dean curls his fingers just to hear Sam’s muffled sounds of pleasure, which are echoed by Jess. He grins. “Get to it.”

It’s Dean’s turn to strip now. His costume isn’t anything special, especially since he left his cowboy hat and boots in the living room, but he did put his belt on already and he regrets that when he has to take the extra time to get that off before he can shed his jeans.

“De-ean,” Sam whines from beneath Jess and Dean looks up from kicking his jeans off to see his brother spread his legs even wider. His panties are still twisted to the side, ruffles caught between his ass cheeks where Dean can see the shine of lube waiting for him.

“Fuck.” Dean scrambles up the bed to kneel between Sam’s legs again. “I gotcha.”

“He’s getting impatient,” Jess says with a breathy laugh, her hips rolling as Sam gets to work again. “Oh, fuck, right there.”

Dean quickly slicks his cock and lines up. Sam’s tight, even after all Dean’s work opening him up, and his fingers flex against Jess’s thigh when the head of Dean’s cock pops inside.

“Fucking perfect,” Dean praises. He pets Sam’s inner thighs, soothing his trembling muscles as Dean works his way deeper. “Feel so good.”

Jess cries out then and falls forward. Dean instinctively throws his arms up to catch her and she clings to him, fingernails digging into his bicep as her body spasms through an orgasm. Sam holds her in place until she’s whining and pulling away. They ease her to lay down above Sam’s head, curled on her side to catch her breath as she watches them through hooded eyes.

Free of Jess’s weight, Sam reaches up to grab at Dean’s shoulders and yank him down into a kiss. He tastes like her but the low growl of “Fuck me” he lets out against Dean’s lips is all Sam.

Dean’s never been able to say no to Sam and he’s not about to start now. He drives in the rest of the way in one smooth push, echoing Sam’s sound of pleasure with one of his own.

“C’mon,” Sam hisses in his ear. “Give it to me, big brother.”

Dean does just that. He would normally start slow, give Sam time to get used to the intrusion, but not tonight. Not with stocking-clad knees tight around his hips and the brush of silky panty ruffles against the side of his dick. Sam’s arms are looped around Dean’s neck, holding him close so he can pant words of encouragement in the elder Winchester’s ear. Dean’s arms creep their way under Sam’s lower back and hold on like Sam will vanish if he loosens up. Sam’s narrow waist fits perfectly into Dean’s embrace. Moments like these, it feels as if they were made to fit together. Maybe they were.

Pleasure coils at the base of Dean’s spine and he drives in deeper, like doing so will somehow connect them together even more. Like he can crawl inside Sam’s skin if he just tries hard enough. He can’t, he knows he can’t, but what he can do is change the angle of his hips just so and punch a wail of pleasure from his brother’s throat.

“Yeah,” Dean grunts, hips working. “Yeah, let it go. Wanna feel it.”

Sam buries his face in Dean’s neck with a cry and his whole body clenches, releases, clenches again as he falls over that edge. Dean doesn’t slow down, even when Sam goes limp in his arms. The sounds Sam’s making shift to something a little whiny, probably oversensitive, but he doesn’t tell Dean to stop and so Dean doesn’t, not until he’s reached his own peak and spilled deep in his brother’s body.

Silence falls over the room, broken only by their breathing as they calm down. When Dean lifts his head, he finds that Jess has rolled onto her back and her hand is working between her thighs.

“Let me,” he offers, reaching out, and she moves her hand to let him replace it with his own. She’s absolutely soaked, wetter than the front of Sam’s panties where the brothers are pressed together, and it doesn’t take much to have her cumming on his fingers. “We put on a good show, huh?”

“Always do,” she replies with a grin and a lazy stretch. “I should probably let Brady know we’re probably not gonna make it to his party.”

Dean takes a glance at Sam’s fucked-out expression and laughs. “Yeah. I’d say the chances of us showing up are pretty low.”

Jess rolls onto her side again and presses a kiss to Sam’s temple. “Still hate Halloween?”

Sam huffs out a laugh, still a bit breathless. “I dunno. If we keep celebrating like this, I might come around to it.”

--

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