Sam’s got his cock buried halfway inside, skin and sheets sticky with the amount of lube it’s taken to even get him this far; he’s not just long, he’s thick, stretching that un-tested little hole to its limit.
But Sammy’s taking it like a champ, keeping those soft-skinned, shaking thighs apart, two fingers tangled in soaked pink panties to hold them off to the side like he was told. He’s already creamed them once, Sam’s tongue buried in his ass and Dean’s hand rubbing him through the silky material, sucking at those tiny, rose-pink nipples he loves so much.
“He’s not gonna break, Sam,” Dean says, runs a hand down Sam’s spine until he reaches the waist of Sam’s own panties–a few shades deeper in color than Sammy’s, the front of them tucked behind his balls to free his cock, but the back still stretched tight across his ass. Seeing the two of them in nothing but panties–and cute white stockings on Sammy’s skinny legs, torn and covered in damp fingerprints, now, barely hanging on around his knees–is the best damn gift he’s ever gotten, and it’s not even his birthday. “Ain’t that what you told me every time I tried to be gentle with you?”
He dips his fingers under the panties to find his brother’s hole–still wet and stretched from earlier use, Dean’s favorite–rubbing his own come around the rim of it.
“Remember how bad you wanted it when you were his age? God, Sam, you were hungry for it. Never met anyone that wanted to be railed the way you did–all the time and rough enough you’d be walking funny the next day. Look how little you were, but you’d take that dick and ask for seconds every time.”
Sam gets his feet further apart and nudges his ass back against Dean’s hand, enticing Dean’s fingers into that pre-prepped hole because some things never change.
“Such a good boy for me, little brother.”
Both Sams shiver at that. A reminder that Dean’s always going to be the big brother is bulletproof for Sam; apparently all versions of him.
“So how ‘bout it, Sammy? Y’want Sam here to take it easy, give it to you sweet and slow?”
Sammy shakes his head emphatically, bangs stuck to his forehead with sweat. He looks up at Sam with the needy fuck-me eyes Dean’s fallen victim to so many times.
“I wanna feel it, wanna feel you. I can take it, Sam, I promise,” he says, voice already wrecked. It’s not far-off from what Sam said his first time, breathless and whispering ‘I’m ready, Dean, please’ as he clung to his brother’s shoulders in the dark. “Want it so bad and you’re so big. God, you’re both so big.”
He reaches up with one trembling, slim-fingered hand until Dean takes it in his own. He runs his lips over the bumps of knuckles, presses a reassuring kiss to Sammy’s palm.
“That’s it, just relax and let him in. We’re gonna give you exactly what you need, baby boy, fuck you up and treat you so good.”
Sammy’s panting by the time Sam manages to cram himself balls-deep inside of him, and Dean’s not doing much better when Sam spreads his younger self’s cheeks apart, one huge hand on each, so they can both get a good look at that newly-opened hole clenching compulsively around the base of Sam’s cock.
Sam mimics the clenching around the fingers Dean has inside him, and Dean bites down on his shoulder with a groan.
He brings the hand that’s still holding Sammy’s down between the boy’s legs, presses Sammy’s fingers to the rim of his own hole, where he’s hot and wet and quivering like a well-primed pussy ought to be.
“Feel how tight you are? Look so pretty stretched out for us. Sam’s gonna open you right up on that dick, make you take it so deep you’ll never be this tight again.”
Sammy’s whole body shivers as Sam draws back until just the tip is caught inside his quick-closing hole, presses a finger in on either side of his dick to expose the space he’s carved for himself. It’s so pink and inviting inside, slick and puffy with use and they’re just getting started.
Dean brings two fingers of his free hand to Sam’s mouth and he gets his lips around them like it’s second-nature, working his tongue to wet them. The kid whimpers, fingers white-knuckled around his panties and Sam’s wrist when Sam bends his fingers, pulls him open so Dean can fit one of his fingers in, too, up to the second knuckle and nestled in beside Sam’s cock.
He’s like a furnace inside, just like the hole Dean’s got the fingers of his other hand in. He moves them in unison, slow-fucking them both, and he never thought he’d be this lucky in his life.
Sam grins at him like he knows exactly what Dean’s thinking, leans over for a kiss.
“Gonna fuck me while I pop his cherry?” he breathes against Dean’s mouth.
Dean nips at his his lower lip, drives his fingers deep in both of them to hear the sweet sounds they make.
“Greedy,” he scolds, and there’s absolutely no shame in the way Sam ‘mmm’s in response. “Lemme save it for round two, after you’ve got him broken-in a bit.”
He looks back down at Sammy–red-faced, hazy-eyed little Sammy, whose eager mouth closes tight around the fingers Dean had in his ass when they’re offered, sucks his own taste from them without hesitation.
“Got a once in a lifetime opportunity on our hands, here. Y’always talked a big game about how much you could handle, and now we’ve got a chance to see how much he can really take.”
Sam’s eyes light up with understanding, licking his lips as he stretches that hole impossibly wider with his fingers, until Sammy’s got his eyes clenched closed, whining around Dean’s fingers.
“D’you really think we can…?”
“Only one way to find out.”
Sam groans as he sinks his cock fully back inside, gets a firm grip on Sammy’s thighs, bends him nearly in half and sets to work fucking him properly. It’ll take some doing if they want to get him open enough to fit them both, after all.
“Give it to him the way I gave it to you that first time, sweetheart, ‘til the only words he can remember are ‘please’ and your name,” Dean murmurs against Sam’s ear, biting down on the lobe a bit at the memory. His fingers slip out of Sammy’s dropped-open mouth, damply tracing his lower lip. “God, you’re always so cute when you’re begging for it. You gonna beg for us, too, Sammy?”
Sammy swallows hard and tries to school his dazed, fuck-drunk features into something resembling confidence as he rolls his hips, grinds himself down on Sam’s dick.
“O-only if you make me.”
Sam and Dean share a smirk above him, looking down at Sammy’s teen-tiny body, spread out and held down, vulnerable under them but still clinging to that bit of false bravado.
He’s perfect; they’re going to ruin him.
Sam drives his cock as deep as he can in one go, makes Sammy take more than half his length then pins those bony hips down to the bed and does it again when he gasps and digs his stocking-covered heels into Sam’s back, all Sam’s gentle, stop-start hesitation long gone.
“M’gonna fuck you so full you’ll feel empty without one of us inside you,” Sam growls, leans down to put teeth to Sammy’s jaw. “And when you’re worn-out, sore and sloppy, then you’ll take us both, split so wide you can barely stand it. You’ll moan and cry and love every second of it, and believe me, Sammy, you’re gonna beg for it, first.”
Sure enough, the next word from Sammy’s smart little mouth is ‘please.’