Posted originally on the Archive_of_Our_Own at https://archiveofourown.org/
works/6016192.
  Rating:
      Explicit
  Archive Warning:
      Underage
  Category:
      M/M
  Fandom:
      Supernatural
  Relationship:
      Dean_Winchester/Sam_Winchester
  Character:
      Sam_Winchester, Dean_Winchester
  Additional Tags:
      Weecest, Underage_Sex, Feminization, Loss_of_Virginity, Pink_Panties,
      Butt_Plugs, Barebacking, Public_Sex, Dirty_Talk
  Collections:
      Hell
  Stats:
      Published: 2016-02-15 Words: 3398
****** with a cherry on top ******
by dollylux
Summary
     Sam gives Dean a Valentine's gift that keeps on giving.
Notes
     written for adamsdreamthief for wincest love week. thank you to
     leslie for the idea when my brain was so very empty for anything.
     (baby sammy in panties is a surefire way to get me writing ;))
     sam is 13; dean is 17.
     also: sammy's_sweet_little_buttplug. <3
See the end of the work for more notes
The sex store next to the motel had a big sign on the door that said “18 AND
OLDER ONLY,” but little Sammy Winchester has a wholesome smile when he wants to
and at thirteen, he knows how to look innocent in the ways that make adults
think of coloring books and velcro shoes instead of knock-kneed flirtations and
boy cherries kept safe inside of clearance-rack jeans and secondhand underwear.
He’s saving those looks for somebody special.
Leslie who works at the Frisky Business lets him inside on a particularly cold
day when he’s shivering in front of the motel, waiting for Dad and Dean to get
back from wherever the fuck they are. He sits in the back at the store next to
a new order of sex swings and does his homework on a box of pocket pussies.
When it’s busy or she’s on the phone with her best friend, Sam sneaks out into
the shop and looks around.
The cameras in the shop don’t work, and he knows it.
It’s too easy to steal, to shove some things into his bag and form a plan.
Pink fuzzy handcuffs, cherry-flavored lube, a silky, heart-covered g-string,
and a glass buttplug with a heart-shaped handle, all tucked into his backpack
next to his pencil box and his essay about the Louisiana Purchase.
Tomorrow’s Valentine’s Day, and he’s looking to get the virgin fucked right out
of him.
 
There’s a bar connected to the truckstop on the other side of Frisky Business
that Dean likes to go to with his fake ID and his beautiful face, and he’d even
spritzed on some knockoff cologne to draw in the prettiest lot lizards to him,
looking to get his dick wet.
Sam spends about two hours in the bathroom after Dad leaves on some tip that
takes him to a neighboring county, shaving his legs, his pits, his balls, and
his asshole, all places that only have the tiniest bit of hair anyway, all
smoothed away with two pink Bic razors and a bottle of rose-scented
conditioner. He cleans himself out in the shower, fucking into his hole with
the half-empty bottle of conditioner until he’s almost sloppy with it, loose
enough to take the plug with no problem, his bright pink insides sloshing with
cherry lube.
He smooths some shiny red lipgloss on his little boy mouth and looks at himself
in the mirror when he’s all done, making his eyes heavy-lidded and hungry like
he’s seen the girls do before Dean takes them out behind motels across America.
“Fuck me, big brother,” he whispers to his reflection, his asshole clenching
hard around the now-warm glass plug seated deep inside of him, Dean’s filthy
Van Halen t-shirt hanging off his shoulder like he’s already a backseat slut,
knocked-up and dripping for dick.
He’s working on it.
 
The inside of the bar is dark and hazy with smoke, the music low and rowdy as
he makes his way through the faceless lowlifes in search of one in particular.
He finds him talking to a girl with bleach-blonde curls and a pink skirt that
Sam considers killing her for, her mouth the exact same shade of Cherry Coke as
his.
He is wholly out of place here, feels eyes on him, knows it’s only a matter of
time before he’s spotted and dragged out, so he makes his move as gracelessly
as the virgin he is.
“Hey,” he says, soft and petulant. He reaches up to get a handful of Dean’s
soft leather jacket, pulling on it and making sure he looks as sweet as his
cherried insides will taste when Dean turns to look at him.
He watches Dean take in the sight of him: his naked shoulder, his hair long and
girlish over his ears and his forehead, his pouted mouth, and his big brother-
sized t-shirt.
“Sammy.” It comes out as a confused almost-question that wants to be stern, but
Sam watches the heat spread across Dean’s cheeks, sees how dark and rounded-out
his eyes get, and he has to keep his smile in.
“Dean, take me home,” he says, sinking his teeth into his bottom lip and
tugging on Dean with his leather jacket grip.
Dean looks up and around and back at Barbie before focusing completely on Sam,
turning toward him with his whole body, crowding up around him like he’s trying
to hide him.
“Sammy, you need to get out of here. This ain’t the kind of place you need to
be hangin’ out in.” He doesn’t move though, doesn’t stand up, just reaches out
to snag Sam around the waist and pull him into the sprawl of his thighs where
he’s sitting on the bar stool. Sam goes like a sure-bet, keeping his body all
pliant and sweet in Dean’s hands. He blinks up at his brother, long-lashed and
lazy, like he’s already getting fucked.
“Why not?” he asks, cocking his head to one side, giving Dean one of his real
innocent looks. “What would happen to me?”
“There’s some real bastards in here,” Dean says quietly, hands spanning Sam’s
back, his fingers meeting at the pretty arch of it above his tailbone. “They’d
take one look at you and--”
“And what?” Sam sighs, looking down at Dean’s mouth before glancing back up
into his eyes. “Want to fuck me?”
“Jesus Christ, Sam,” Dean sighs, sitting back on the stool and rubbing hard at
his tired face. “Don’t fuckin’ say shit like that.”
“Why are you here, Dean?” He’s frowning now and it’s real, eyebrows drawn
together, allowing himself the luxury of not hiding his jealousy tonight. Dean
looks guilty for a split second, face smoothing out with a caught expression
before he schools it again, stern, father.
(Daddy.)
“You wouldn’t understand,” Dean replies, hands going to Sam’s shoulders now,
one burning hot on the bare one. “C’mon, let’s--”
“You want to fuck somebody,” Sam clarifies for him, saying it quiet and just
for Dean but clear. “And I want to get fucked. I think we can figure out what
to do now, right?”
The loud bar settles into a silence surrounding just them, all the noise
getting blurred out by the shock in Dean’s pretty green eyes, by the hunger
that crowds it out, impossible to hide.
Dean stands up then, towering over Sam’s small body, staring so intensely into
his eyes that he glows around the edges. Sam stays where he is, looking
submissive as a paid whore and quaking in his brother’s gaze.
“You’d better not be fucking with me,” Dean says, voice pitched so low it’s
almost a growl.
“Take me out back,” Sam tells him, nostrils flaring as he breathes hard, his
face burning hot, “fuck me like I’m wearin’ a pink skirt.”
They stare each other down like they’re about to fight, and the silence they
live in that blocks out the rest of the world gets shattered by the loud rumble
of “Big Gun” by AC/DC blasting in from the speakers behind the bar.
Dean gets a firm grip on Sam’s thin arm, squeezing bruise-hard as he drags him
through the bar, keeping Sam tucked almost completely against his body, hiding
him from any eyes that may want to look on the way to the back door behind the
bar.
He can feel the violence trembling in Dean, and he knows it’ll come out in one
way or another, either on the body of a man who looks at Sam wrong or on Sam’s
own body, pressed up against dirty brick.
Dean throws him against the wall when they get outside, the door not even
closed all the way before Dean descends on him, gathering Sam up like he’s
still small enough to hold and kissing his mouth so hard Sam can’t do anything
but part his lips, close his eyes, and fucking take it.
“Little slut,” Dean says before he bites into Sam’s bottom lip hard enough to
draw blood. His hands are frantic but big enough to span whole sections of
Sam’s body as he grips and squeezes at him. Sam whimpers in the affirmative and
Dean moans right after, so sweet and low like it’s being dragged up from his
chest. “Wanna get fucked out back on Valentine’s Day like an easy girl, don’t
you? That what you want, Sammy?”
He doesn’t wait for an answer, doesn’t give Sam’s mouth a goodbye kiss before
he’s gone, nipping at Sam’s neck, sucking kisses all over the small, pale
expanse of it as he gets a hand on Sam’s shirt and pulls hard, stretching out
the neck of it and exposing Sam’s pale nipple to the cold February air.
He sobs when Dean sinks his teeth in, chewing like he’s going to bite it right
off. Sam wraps his arms around Dean’s neck and clings to him, keeping him there
like Dean’s his newborn baby and he’s feeding.
“Don’t have a rubber, sweetheart,” Dean tells him, so beautifully in character
that Sam arches, head falling back to stare up at the rusty gutter above them.
“Think maybe I’ll just fuck you in the ass so you don’t get knocked up again.”
It’s that one word, the again that has Sam’s insides squeezing up hard around
the plug, his stretched-out rim fluttering around unyielding glass as he opens
his ruined mouth and whines up at the clouded out night sky.
“Fuck my ass,” Sam whispers as Dean slurps at his tit, “put your dick in me and
lemme make you come.”
“Think you can make me come, little brother?” Dean says, his eyes glinting in
the dark between them, his breath hot where he pants against Sam’s mouth.
“Think you can take care of my dick better than she could’ve?”
Sam’s eyes narrow, and his nails turn to claws where he’s holding onto Dean’s
neck. He digs them in hard, breaking skin under each one, his smeary-slick top
lip curling into a sneer.
“I’m the only one who can,” Sam grits out, his raw nipple throbbing in the cold
air. “Look and see, Dean. Get my pants off a-and look.”
Dean searches his eyes, both of them aware of the blood pooling under Sam’s
fingernails, and the soft kiss that Dean drops on Sam’s tensed mouth feels like
a blade straight through Sam’s heart.
Sam’s spun around and shoved up against the wall again, but he takes a couple
of steps back and arches hard, face pressed to brick, his ass up like a high
school prom queen, big t-shirt sliding up to expose the bubblegum pink band of
the g-string clutched around his middle school waist just above his too-loose
jeans.
Dean pulls his jeans right down, lets them pool at Sam’s feet, and the sound he
makes is like he got punched in the gut.
Sam knows how cute his ass looks, how supple and illegal and tight he looks,
knows just how adorable the little glass heart of his plug is where it pokes
out from between his cheeks, nudging the thong to one side.
“Jesus fucking Christ, Sammy,” Dean all but sobs, dropping to his knees right
there and coming in at Sam’s ass teeth-first.
Sam gasps, gritting his teeth hard as Dean chews on his ass one cheek at a
time, sucking out strawberry kisses and rubbing his face all over him, Sam’s
ass soft and jiggling around Dean’s scruffy face.
“Dean,” he whispers, one hand back to pet lazily at Dean’s hair while he
worships, “Dean, we gotta hurry. Somebody’ll come out. Somebody’ll see.”
“Lemme see this pretty pussy,” Dean breathes, like he’s in a fucking trance or
something. One of his hands gets a hold on the glass heart, and the plug moves
inside of Sam, presses in deeper. He whines, young thighs spreading as he
widens his stance, generic Converse skidding on the gravel.
He shakes all over when Dean starts to work the plug out of him, going slow,
too slow, and Sam’s thighs are trembling when he gets to the last inch, his
forehead pressed hard to the brick, tears burning in his eyes.
“Dean,” he says, hitching and broken. Finally the plug’s out, gone somewhere
and Dean’s big hands are on his ass again, spreading it out and showing Sam’s
cherry gape to the world.
“Wet little cunt,” Dean sighs, moving in so that Sam can feel his nose bump
against his tailbone. His hole flutters, lube dripping out like girl juice down
his hairless taint. “Lookit this sweet little fuckhole. All ready to be fucked
up, aren’t you, baby?”
Sam flushes at the mouth Dean’s got on him, praying somewhere in the back of
his naive mind that he never talks like that to the girls he fucks. He nods,
makes sure to do it big and emphatic because he can’t talk right now, doesn’t
have a thing to say that his swollen asshole isn’t saying for him.
Dean’s tongue dips into him like he’s the last bite of an ice cream cone, and
the slurpy sound of Dean licking him out is almost enough to make Sam come
right now, untouched, hot little pink prick standing up so sweet under his t-
shirt.
He feels Dean let go of the thong of his panties, feels it snap back between
his asscheeks, and his tummy gives a hot swoop at how slutty it feels.
Dean stands up then, his mouth wet with lube as he kisses at the back of Sam’s
neck when he’s on his feet again.
“Gonna fuck you,” Dean says, so soft, so fucking dirty against Sam’s ear that
he can barely breathe. He closes his eyes to the sound of Dean’s belt buckle,
to the tell-tale slide of his zipper and there it is, that big, thick cock
pressing between his cheeks, Dean’s thumb holding the g-string back again.
Dean’s body is crowding him completely, pressed so close Sam doesn’t know how
he’s not already inside. He can feel Dean’s fingers where they’re gripped up
tight around his cockhead, smearing and spanking at Sam’s runny, puffed-out
little hole as he kisses along the side of Sam’s neck, behind his ear.
“Here I come,” Dean whispers.
It’s white-hot and piercing, coming in like a fist. Sam sobs when Dean fits the
head in, feels his asshole snap up tight like a rubberband around the
impossible thickness of it. Dean’s dick feels like it’s molten, searing hot
inside of him and coated with Sam’s cherry.
“Oh, goddamn, Sammy,” Dean groans, mouthing at Sam’s earlobe, nose burrowed in
his damp curls. “Oh god, you’re gonna fuckin’ kill me.”
Dean drives in harder, tearing at Sam’s insides as he forces his way inch by
inch, not stopping even as Sam cries out and tenses up hard around him, not
stopping until he’s seated all the way in and throbbing in some secret place
Sam didn’t even know he possessed.
“G-Gonna come,” he manages, his ass shuddering against Dean’s sharp hipbones as
they both work to keep Dean burrowed in, the head of his cock bumping against
the back of Sam’s navel. He comes like it’s ripped from his body, choking up
hard around Dean’s dick and gushing out against the brick, completely
untouched.
“So pretty,” Dean praises, sweet and between kisses as he nuzzles along his
cheekbone, his temple. “So fuckin’ pretty, little brother.”
Sam writhes under Dean’s hands, shaking when Dean plays with his spent dick,
when he rubs in the come splotching his belly, when he cups Sam’s chest like he
actually enjoys Sam’s little boy titties. He works back on his cock all the
while, rolling his hips like veteran slut until finally Dean gets down to
business, gets one hand on Sam’s naked shoulder and the other on one of his
tiny hips, punching forward with a thrust that makes both of them cry out.
Sam draws his bottom lip into his mouth, eyes squeezed shut hard as Dean digs
his heels in, bends his knees to get in just right, and starts to fuck his baby
brother.
“Oh, fuck,” Dean mumbles, fingers bruising as he holds on fiercely tight to
Sam’s hip, driving him into the side of the building with each packing thrust.
“Oh fuck yeah, Sammy, Jesus.”
“F-Fuckin’ me in my panties,” Sam manages between hitching little breaths,
pushing out around his brother’s dick just to make the sounds that much wetter,
that much dirtier, his rim clutching up and pulling out around Dean’s dick,
“doin’ me where anybody could see--”
“Couldn’t wait to get you home,” Dean rumbles, mouth bumping along Sam’s cheek,
their lips so close but the angle’s all wrong, “Needed it right now. God,
that’s some good pussy. Sammy, this is some good fuckin’ pussy takin’ care of
my dick.”
“Oh, god,” Sam whispers, knuckles dragging over the wall as his hands curl into
fists and he scrabbles to stay standing, Dean’s words tearing all through him,
making his balls pulse hard, the need to come again so intense that tears are
streaking his face. “Keep t-talkin’, Dean.”
“This little body,” Dean says against his tear-stained cheek, one of his hands
now gripping roughly at Sam’s tiny stomach. “Can feel my dick punchin’ you out,
makin’ you bulge all swollen with my cock. Can you feel it, Sammy? Hmm? Can you
feel it, baby boy?”
Sam scrapes up the side of his face on the brick as he nods frantically,
breathing so hard he feels dizzy just from that as he tightens up around Dean’s
dick again. He can feel his prostate pulsing under Dean’s deep pushes, his
whole body trembling as fire starts to build in him, starting there and working
its way up his spine.
“Gonna come again,” Sam says barely loud enough to be heard, the words slurred
and hazy, drunk on cock as he is. He’s all but lifeless in Dean’s grip, all
slopped-up and loose around his dick, leaking pinked cherry juice all over the
ground, over his dropped jeans as Dean turns him inside out.
He shakes apart violently this time, his eyes rolling up so only the whites are
showing as he comes in a messy, unending stream on the wall. Dean pushes him
completely up against the brick, smashing him there with his own body, his
thrusts getting frantic, driving, cruel.
“Hold still and fuckin’ take it,” Dean growls like a threat, battering at Sam’s
fucked-out guts and driving into him violently as he starts to come. Sam grits
his teeth and tightens up as much as he can just to feel Dean shudder with it,
the salt and cream burning at his torn insides as Dean loads him up. He’s
moaning against Sam’s ear, sounding just like a whore himself, his body pushing
lewd and dirty against Sam’s, dick churning away inside of him like Sam was
made just for this, like his body isn’t too tiny for this still, like he’s
meant to take a man’s cock and stick around while he makes sure he’s nice and
bred afterwards.
“Dirty little bitch,” Dean finally sighs, and Sam grins when he can feel Dean’s
smile on his face, when those lips close into a tired kiss on his burning
cheek. “Fuckin’ love you, Sammy.”
He pulls out so fast it flays Sam open, almost makes him collapse where he
stands. His knees shake but he stays standing, trembling against the wall and
crying out when Dean pushes the plug back into his ass, shoving it in with no
regard for how much it hurts.
Sam wants to fucking marry him right here behind the Booze and Lose.
“Keep it in,” Dean says against the back of Sam’s head, the sound muffled in
his sweaty hair. “Wait ‘til we get back to the hotel so you can sit on my face
and feed it to me.”
“Mm,” Sam agrees, smiling slow and stupid while Dean gives his ass a quick,
rough slap and helps Sam back into his pants. He’s turned after a minute and
Dean’s there, kissing at his mouth, licking into him and all Sam can do is wrap
his arms around his neck and let him.
“Happy Valentine’s Day, Sammy,” Dean grins, tongue flicking at Sam’s top lip.
“You’re goddamn right,” Sam replies, remembering the handcuffs still tucked
into his bag back in the room.
End Notes
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