
Posted originally on the Archive_of_Our_Own at https://archiveofourown.org/
works/10720155.
  Rating:
      Explicit
  Archive Warning:
      Underage
  Category:
      M/M
  Fandom:
      Supernatural
  Relationship:
      Dean_Winchester/Sam_Winchester
  Character:
      Dean_Winchester, Sam_Winchester, John_Winchester
  Additional Tags:
      Wincest_-_Freeform, Weecest, One_Shot, Smut, Fluff, First_Time, First
      Kiss, Bad_Parent_John_Winchester, John_Winchester's_A+_Parenting,
      Underage_Sex, Oral_Sex, Blow_Jobs, Face-Fucking, Kissing, Boys_Kissing,
      Dirty_Talk, Happy_Ending, Feminization, Sam_in_Makeup, Sam_In_Panties,
      Panty_Kink, Size_Kink, Coming_Untouched, Love, Love_Confessions
  Stats:
      Published: 2017-04-24 Words: 2414
****** All Dolled Up ******
by ds9trekkie
Summary
     Sam's been alone while Dean and John are away on a long hunt. The
     boys have an unexpected, yet arguably inevitable, reunion that
     changes their relationship forever.
     "Dean takes in the sinful image of Sammy's lips painted thickly with
     dark red lipgloss, his cheeks dusted with almost too much blush and
     those bright hazel eyes lined in perfect black."
Notes
     Read the tags!! This is literally just my excuse to write some
     delicious and kinky Weecest. Enjoy!
Two long weeks on the road has Dean tired and frustrated. John decided to take
his oldest on a hunt that would be too intense for Sammy, so they left him
behind.
Which is way too fucking long for Dean to be away from his baby brother. Sure,
over the years Dean taught Sam how to take care of himself. The boy can cook,
get to school, study, and go to bed on time. That stuff isn't an issue. Sam
doesn't need Dean for those things anymore.
However, that doesn't mean Sammy doesn't need him. Because Dean sure as Hell
needs him. They need the addictive comfort that comes just from their close
proximity. They need the pure, unfiltered love from behind one another's eyes
that provides the other with the strength to carry on.
But Dean needs something else from Sammy too. Something he definitely shouldn't
need or want from his sweet, twelve year old little brother. Dean knows he's
sick, damaged beyond repair for wanting to touch his kid brother. He may be
able to rewire the Imapala's engine, but unfortunately things don't work the
same way for his brain. He can't change who he is and how he feels.
Lingering on these thoughts is toxic, there's no use dwelling on what can never
be. As long as the fantasies stay tucked away inside his fucked up head
everyone will be fine.
They're headed back right now, the Impala speeding towards the latest motel
called home. Towards Sammy. John pulls up in the parking lot and grunts for
Dean to go ahead, he'll catch up later.
Dean feels tragically torn by his father's behavior. He knows what 'catch up
later' means. It means John would rather go drown himself at the local dive bar
than reunite with his younger son. It breaks Dean's heart knowing Sam's not
worth that to John.
On the other hand, Dean is ecstatic to be alone with Sam. They can hug as long
and intimately as they want, no John around to judge them or clear his throat
when he deems their embrace over.
Walking up to the motel door, Dean thinks Sam might be sleeping already,
despite the lights being left on. It's really late and the kid probably got up
at the crack of dawn for school that morning.
If that's the case, Dean plans on immediately stripping down to his boxers and
t-shirt and crawling right into bed next to him. Dean could use the sleep and
it never comes easier than when his Sammy is spooned safely inside his arms.
Opening the door, Dean learns two things. Sam is clearly awake and tonight
might just be the goddamn night Dean loses all self control.
Sam is sprawled out on one of the twin beds, naked apart from...pink lingerie.
His brother is wearing a pair of lace panties with a bra to match. Sam's cock
is out, the panties pushed to the side as he strokes himself, panting and
whimpering the sweetest little noises Dean will never unhear.
It's automatic, as Dean stands there dumbstruck his dick begins to fill. This
is everything Dean's ever wanted and more presented to him on a silver platter.
He wants to spring into action, take Sammy in every way possible, all for his
own. He silently thanks God that John decided to go out, because Dean would not
have been able to hide his arousal from this delicious obscenity.
Catching his eye, Sam gasps and stops wiggling, "De-Dean?"
Sam's voice, although only a whisper, sounds earth shatteringly loud. It
prompts Dean to scramble, forcefully shutting and locking the front door. Dean
closes his eyes and points his face down towards the floor. "Sammy, you got ten
seconds to get up and go to the bathroom..."
Or else I'm gonna fuck you and I'm never gonna stop.
Although technically unsaid, it's obvious what Dean means. Sam's an expert at
reading Dean, so there's absolutely no hiding what's happening.
It's one thing to get turned on by your little brother, but it's another to
actually do something he can never take back. They can still stop this, it's
not too late to pretend it didn't happen. It's all up to Sam now.
Dean opens his eyes and looks back at Sam, who is confidently stationed on the
bed with no sign of running. He holds Dean's stare and picks up where he left
off, pumping his cock ever so slowly.
"Do you want me to stop?" Sam breathes, arching his back as he teasingly puts
on a show.
"Fuck no, don't stop." The words tumble from Dean's lips before he can even
think them. His dick is beginning to strain painfully in his jeans. Dean palms
himself lightly as he approaches Sam, the view becoming more intoxicating by
the second.
Sam's not just wearing feminine undergarments, he's wearing fucking makeup too.
Dean takes in the sinful image of Sammy's lips painted thickly with dark red
lipgloss, his cheeks dusted with almost too much blush and those bright hazel
eyes lined in perfect black.
Dean's breathing is irregular, his mouth agape as his gaze travels lower over
his brother's petite form. Sammy barely just hit puberty, his development so
far from complete. Skin as fair and creamy as a princess, Dean gets stuck on
the bra. He's seen Sam shirtless hundreds of times, but now it seems forbidden
to look at his chest. His pretty little boy tits are wrapped up like a present
begging to be revealed.
Sam keeps mewling and Dean keeps looking, lower and lower, until finally he
lands on his prize. Sammy's cock, still so small and baby soft, the dark velvet
tip leaking rivulets of precome.
Dean bites back a moan as he notices one more addition to the masterpiece Sam's
cooked up, nail polish. Five expertly trimmed nails, coiled tightly around his
tiny cocklet, are decorated in a sparkly purple. Dean dares himself to complete
the vision, observing Sam's hairless legs, knobby knees, and toenails that
parallel his lavender fingers.
Sam looks delicate and fragile like this, the epitome of everything Dean wants
to tear apart.
Dean prowls on top of him, leaving his cock caged inside his pants. He doesn't
trust himself to be free just yet, Sammy's not ready for what Dean's cock wants
to do.
Planted on all fours, Dean traps Sam beneath him. He examines the intricate
detail to which Sam applied his makeup, it's really fucking good. A brownish
pink shimmer coats Sam's eyelids, making the already gorgeous color of his
autumn sprinkled eyes stand out even more. His lashes, naturally long and inky,
are now doubled in their intensity.
How long has Sammy been practicing this? How long has it been a secret? Dean's
glad that Sam didn't cower away to the bathroom, ashamed and scared as he wiped
away something that made him happy, that made him feel good. He's glad Sam was
able to trust Dean to see him this way.
"Look so pretty all dolled up like this, baby girl...so pretty..."
Sam squeezes his eyes shut and moans loudly. Dean smiles wickedly at Sam's
positive reaction to his words, egging him on to spew more filth.
"What flavor's all over these slutty red lips?" Dean wonders, faces so close
together their lips almost touch.
"Cherry," Sam says quietly, eyes reemerging and connecting with Dean's. Sam
pokes out his wet tongue, sweeping it tantalizingly over his top lip, goading
Dean into finding out if he's lying about the taste.
Dean takes the invitation, bringing his large, plump, lips down until they
press firmly onto his little brother's. Dean's mouth is overbearing, consuming
every inch of Sam's thin lips. Sam kisses him back the best he can, moving
languidly with Dean's rhythm.
Sam wasn't lying, as the exquisite cherry flavor smears between them it reminds
Dean ridiculously of pie. There's a panicked yet excited voice screaming in the
back of his head, he's kissing Sammy, it's actually happening.
Parting his lips, Sam abandons his cock and both hands fly clumsily into Dean's
hair. Dean groans when Sam opens up for him, beautiful and needy like a flower.
He never wants to stop kissing Sam, in this moment it feels like enough, this
simple act suffocating Dean's mangled heart.
"Taste so good, Sam," Dean growls, his hunger growing dangerously.
"Dean!" Sam's voice is breathy and high pitched, "More!"
Dean instinctually cups a hand over Sam's left pec, rubbing his thumb over the
smooth fabric of the dainty bra. Feeling how hard Sam's nipple is, he decides
to ask, "Gonna show me your titties, Sammy?"
"Yeah, please," Sam sounds wrecked, on the edge of erupting prematurely.
Dean pulls himself away from the kiss to sit back, straddling Sam's waist
comfortably. "Show me."
His chest heaving up and down, Sam scrunches up one side of the bra to expose
his nipple. Peaked and swollen, it's no bigger than a dime. Dean is barely
aware of what's happening when he takes it into his mouth, suckling on it
roughly and swirling his tongue around the area feverishly.
"Oh! De...yeah, yeah," Sam whines, puffing out his chest and running his
fingers through the short bristles of Dean's hair.
Leaving the nub angry and puffy, Dean switches to the other side, tugging the
material away carelessly. "Like this, Sam? Like the way big brother sucks you?"
"Deeeeean!"
"Want me to suck on something else, sweetheart?" With this offer, Dean's lost
his mind. He's drunk with lust for the one thing in the entire world he should
not be lusting after.
Sam can't form words, instead he just pants and moans louder, more deliriously.
His porcelain hips thrusting up into nothing, Dean truly wants to alleviate
Sam's suffering. But first he wants to play with him just a little bit longer.
Dean grabs Sam's wrist, slurping one of his polished fingers into his mouth.
Sam looks horrorstruck, not expecting this turn of events. He watches in awe as
Dean slides up and down the length of his finger, Dean can tell he's surprised
at how good it feels. Dean grows bolder, holding eye contact as he takes in
another finger and another. Sammy's chubby fingers are cushioned with baby fat,
making the experience that much more taboo.
Dean releases him to say, "What's next? C'mon, Sammy, tell me...tell me what
you want big brother to suck next."
It's dirty talk, but it's also something else. Dean needs permission for this
one, peace of mind that Sammy wants this.
Sam chokes, "You know, Dean..."
"Not good enough," Dean husks. He can't risk it, he actually has to hear Sammy
say it.
Apart from the heavy breathing that clouds the room, there's only silence.
Sam's eyes are glassy, like he might burst into tears from how bad his cock
hurts.
"Dean, please, suck my...c-cock," he says the last word bashfully, afraid that
he screwed up and went too far.
Dean nearly comes from hearing the words alone, his baby brother begging so
pretty for him to suck his cock. Preserved for eternity, life or death, Dean
will never forget this moment.
Flashing a wolffish grin, Dean slithers into position, maneuvering Sam as well.
Sam sits at the very edge of the bed, his bare feet not even touching the
ground. Dean slots himself between the boy's slender open legs, admiring the
cock in front of him.
Sam caresses his face, the gesture so loving that it stops Dean from breathing.
The realization finally hits him, this is so much more than perversion or horny
teenage hormones. They love each other, more than just brothers.
They're in love with each other.
Dean plunges forward, engulfing Sam's throbbing cock all at once. It's not
difficult to fit the whole length inside his mouth, Dean's nose bumping against
Sam's newly born peach fuzz. Sam shouts, his hips twitching erratically from
the pleasure, but Dean steadies him with two calloused hands on either thigh.
Dean allows his eyes to flutter shut, the feeling of nursing on Sammy's little
cock immensely soothing. Listening to the musical sounds Sam produces above
him, Dean loses himself to the increasing tempo in which he bobs his head. His
own neglected cock is aching, but Dean's more interested in Sam.
"Dean! I'm gonna! I'm--" Sam sputters, hands cradling Dean's face as he
attempts to jut spastically.
Dean temporarily pulls of to tell him, "Fuck my face, Sammy...do it, baby, fuck
my face 'til you come down my throat..."
Sam slips swiftly off the bed, his feet leveled firmly on the crusty old
carpet. Dean submerges Sam's dick back into his wet heat and looks up at him,
his mouth slack and pliant.
Sam does what Dean says, starting to move his hips meekly at first. That is,
until Dean starts moaning, then Sam gains the courage to fuck his cock deep and
hard into Dean's willing mouth.
"Oh, oh, oh, fuck, Dean!" Sam screams, going rigid as his cock spurts it's
release directly down Dean's happily abused throat.
Feeling Sam come inside him is the last straw, Dean is creaming his pants,
untouched, as he tastes his brother for the first time.
Eventually, Sam begins to soften and Dean let's him slip out. Sam tucks himself
back into the panties and readjusts his bra. "Did you just...did you come from-
-"
"Yeah," Dean admits quickly.
Sweaty and mind boggled, the boys gawk nervously at each other. Dean refuses to
let this become awkward. Standing up, he hoists Sam onto his lap as he relaxes
against the headboard. Sam hugs him, the younger boy's heart thundering as they
come down from their high. There's so much to be said, so much to discuss and
work through, but right now Dean can only think of one thing to sum it all up.
"I love you."
It covers so much for Dean. I accept you, I want you, I need you, I admire you.
All things he'll get to in time, but for now he'll start with love.
Sam sniffles and pulls back from the hug to see Dean properly. "Dean, I love
you too."
A smile is born onto Dean's face. So refreshing and real, it could never
compare to any of it's predecessors. He wipes away a stray tear that escaped
Sam's eye, taking with him a streak of black liner.
"So beautiful like this, baby girl...all dolled up."
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