Posted originally on the Archive_of_Our_Own at https://archiveofourown.org/
works/5887102.
  Rating:
      Explicit
  Archive Warning:
      Underage
  Category:
      M/M
  Fandom:
      Supernatural
  Relationship:
      Dean_Winchester/Sam_Winchester
  Character:
      Sam_Winchester, Dean_Winchester
  Additional Tags:
      Sam_is_13, Crossdressing, Sam_In_Panties
  Stats:
      Published: 2016-02-02 Words: 2857
****** A Perfect Pair of Size Sevens ******
by SammysGirl666
Summary
     Sam finds a gorgeous, well-loved pair of stilettos and Dean walks in
     on him trying them on.
Notes
See the end of the work for notes
Sam finds these beat up, size-seven pair of ruby red stilettos in a box at a
yard sale on his walk home from school one day. They steal his breath. They’re
beautiful, perfect, in his size, a treasure in disguise. Everything he’s been
looking for, worn yes, but perfect. Steals them, can’t help himself, and would
feel guilty for it, except the guy manning the tables gives some teenage girls
a lecherous grin and wolf whistles at them. Then, he feels more justified as he
slips the heels into his bag. Practically trips over his feet as he runs out of
there, backpack slipping around on his scrawny shoulders, a little too big on
his still rather slight frame.
Excitement twists his belly and his face flushes, reddening with the thoughts
running through his mind. When the motel is finally in sight, it’s all he can
do not to run the rest of the way there. Downright lewd imaginings assault his
mind and more hot anticipation wells up in his 13 year old, hormone-wild body.
He grips the straps of his backpack tightly in his hands as he speed walks
through the parking lot of the motel, fumbling with the keycard before getting
it in and bolting inside. Latches the door behind him, as the excitement takes
over him, skin buzzing pleasantly with it, a little shaky as he moves across
the room.
The hot flush has spread down to his neck, and his palms turn clammy as he
tosses his backpack down onto the bed and hurries to his duffle, falling to his
knees and unzipping it enthusiastically. He rips it open and shoves his arm
deep inside, reaching for the deepest corner of it. Comes up with a ball of
black lace that he clenches between his fist before racing into the bathroom.
He closes and locks the door behind him, even though there’s no one else there.
Breathes in and out deeply, closing his eyes and biting his lip, keeping his
hands on the door before slowly backing away. Takes time in his undressing,
always liked this part, barring his skin slowly. He’s still soft and round with
his youth, he notices as he strips off his shirt. He looks at himself once he’s
shirtless. A baby face and pouty, cherry-red lips, big hazel eyes and chestnut
hair that curls over his forehead messily.
Thinned out some, a flat stomach with a little bit of a pudge and narrow hips.
His legs are slightly hairy, but it’s still soft and fine, easy to shave if he
wanted to. Tonight, he wants too. He strips off his shorts, leaving him in his
boxers, and he pulls the razor he bought out of one of the drawers in the sink.
Tries to make quick work of it, using the water from the showerhead and soap
from his duffel; takes enough time so that he doesn’t leave any rough patches.
When he’s done, he cleans up and strips off his boxers. He examines himself in
the bathroom mirror, looking at his flaccid cock, still not fully grown,
sprouting out of a thatch of sparse brown curls. Pretty, he thinks smugly, and
then picks up the ball of black lace from the counter, untwisting the fabric
and pulling the pieces apart.
The first piece he pulls on is pair of black lacy panties, the only ones he
could find in his size. He pulls them on slowly, letting them graze against the
newly soft skin of his legs, enjoying the sensation. Sexy and snug, the panties
sit beautifully on his hips, gripping them just right and holding his cock
perfectly. He turns around and smirks at the way the panties curve around his
ass cheeks.
He picks up the next piece, a garter belt with hooks that attach to sheer black
stockings. He pulls on the garter belt and then puts the stockings on, one by
one. Loving the way they feel against his smooth legs; hooks them to the garter
belt to complete the look. He looks at himself in the mirror again and twirls.
Now he just needs the final touch.
Unable to help himself, he checks the room before he exits the bathroom,
bolting out quickly grabbing his backpack and sprinting back inside. No one
will be home for at least an hour but he’s vibrating with nerves. Flushed hot
and excited all over. In the bathroom, he pulls out the beautiful stilettos,
picking them up reverently. They’re nearly perfect, scuffed a little on the
toes and there are places on the back of the heel where the red coating is
coming up to reveal the beige material underneath.
But these are small blemishes and Sam is enamored with them, shoving his feet
into them eagerly. A little small on his wide feet but nothing he can’t
tolerate. He does up the straps and stands up carefully. Wobbles to the kitchen
sink and then slowly backs up until he has a full view of himself. The heels
are the perfect addition, tying the outfit together, the ruby red contrasting
flawlessly with the sheer black. His little butt, more pronounced by the way
his they push his legs up. And his legs, looking miles long in sheer black
material.
He walks, experimentally, getting used to the height change. The pointed heels
easily take his meek 5’2” to a staggering 5’7”. It’s hard to be graceful in the
sexy shoes and he doesn’t quite master it but gets to a point where he can walk
without stumbling around and takes that as a victory. Then, the anticipation
that’s been buzzing in him piques. He feels hot all over, the flush of
excitement taking him completely. Now all that’s left is to wait for Dean.
He leaves the bathroom, eyes darting around, feeling exposed but thrilled. Sits
on the bed but can’t handle the stillness; stands again and paces slowly back
and forth around the room. Nerves bubble up and the vibrating feeling under his
skin intensifies. He runs his hands obsessively over the lacey material of the
garter belt as he walks and then he hears the door click. Surprise and
adrenaline zing up his spine and his heart rate spikes. Doesn’t have time to
strike an alluring pose, is stuck looking like a deer caught in the headlights
as Dean walks through the door. He’s early but, at this point, Sam doesn’t
mind.
The older boy stops in the doorway, face going blank and mouth dropping open as
his hungry green eyes eat up every inch of Sam, top to bottom, lingering
heavily on the panties and the stockings, sticking on the stilettos until he
seems to remember himself and drags his eyes back to Sam’s face.
“Sammy,” he croaks, then clears his throat, closing the door behind him. He
continues to ogle Sam as he swaggers forward. “God Sammy.”
Sam is practically shaking, red all over, can’t help but quake under the
intense lust of his big brother’s gaze, and feels himself caving to it. Dean
gets close enough and immediately puts his hands on Sam’s hips, running his
fingers over the garter belt and panties. Digging his thumb between the
material and the skin and snapping the elastic. Sam gasps and Dean growls,
dragging Sam forward so that their bodies are flush together. With the hells
on, Sam’s just tall enough that Dean doesn’t need to lean down to kiss him.
“How long you been hidin’ this from me, sweetheart?” Dean asks, voice dangerous
and low.
“Had to finish getting the outfit ready,” Sam excuses breathlessly, throwing
his head back as Dean starts to nose at the skin there, leaving a trail of
small, wet open-mouthed kisses. “Got the heels today.”
Dean hums, doesn’t seem too worried about how Sam got his hands on the heels,
just hastily tears off his jacket and t-shirt as he pulls and shoves Sam to the
bed. Sam is more than willing, trying not to stumble on his way to the bed,
shuffling along in the heels, letting Dean get a good view of his ass before he
turns around and sits on the bad, scoots backward as Dean crawls over him.
“Got me so hard so fast, Sammy,” Dean says, almost sounding impressed. “Look so
fucking pretty.”
He runs his hand over Sam’s hip where that pale skin is abruptly cut off by the
devastating black lace, the soft curve of his brother’s tummy disappearing
under the garter belt. Dean runs his hands gently over the soft roundness of
his baby brother, going slow and following his hands with his eyes. He looks to
Sam’s face, those big hazel eyes staring at him like starving man in the
desert. Candy red lips, pulled into a pout, messy hair pushed back from his
forehead. Dean groans, leans forward to devour that sweet tongue. Sam whines,
responds eagerly and grips onto his big brother as the older boy slides down
his body, licking and nipping as he goes.
Sam lets his legs drop open and Dean grabs, them holds them there, runs his
large hands down Sam’s skinny leg, running over the straps of the stilettos
until he gets to the heel where he squeezes and runs his hand back up. Gets to
the top of the stocking where he dips his finger in and elicits and needy gasp
from his baby brother.
He grins, continues his exploration, lifting Sam’s hips so he can get too
handfuls of his butt, squeezing, letting his fingers get in the crack. Sam
gasps again. Then Dean pulls away, abruptly, hastily stepping out of his jeans
and boxers, flinging them aside.
“Fuck Sam,” Dean chokes, “wanna take my time with you but you look so good.
Wanna fuck you, little brother, want to feel those panties rub against my cock
as I fuck you in them.”
Sam groans in agreement, too ready for his brother to follow through. Dean is
sliding down his body again though, this time his intent quite different this
time. He stops to play with Sam’s nipples, to nip and bite at the little buds
until Sam is whimpering. Goes further, tongue trailing down Sam’s torso until
he gets to the narrow hips. Dips his tongue into the hollow where the skin
caves in and the rest is covered by black lace.
No hesitation in the way he mouths along the black lace that covers Sam’s cock,
lets his warm saliva soak through the material and sucks up the precome seeping
through the fabric. He seems to consider taking the panties off but doesn’t and
continues his trip downward until he’s nosing at the part of the panties that
cover up Sam’s fluttering, needy hole. He pulls it aside, yanks harder when
there’s resistance. There’s a tearing sound but neither boy pays it any mind as
Dean breathes over Sam’s entrance.
Sam shivers, the feel of his brother’s breathe tickling the soft brown curls
that cover his anus. Dean leans forward, opens his mouth and swirls his tongue
around the rim. Sam sighs and melts back into the bed, widening his legs even
further. Dean eagerly devours Sam’s ass, licking inside, getting it sloppy and
wet with his saliva, making Sam scream.
“Taste so good, little brother,” Dean says; makes obscene slurping noises as he
goes back to it.
Each jab of his tongue has Sam bucking his hips up, needing friction on his
aching cock. Dean shows no mercy, though, continues to pummel Sam’s hole with
his tongue, seeming to want to get as deep as possible, like he’s trying to
taste the back of Sam’s throat from the opposite end. Sam can’t help but push
back into the feeling, the wet slide of his brother’s talented mouth is nearly
too much. Sam can feel his cock leaking more and more, getting the panties
sticky and wet as he helplessly writhes in pleasure.
“Could probably make you come like this, huh, Sammy? Think you could come on
just my tongue working your pretty ass open? Like to see that, like to see you
spill all over yourself with just my tongue in you.”
Dean seems to be trying to kill Sam with this alone, his mouth working wonders
as Sam’s hips move of their own accord. His mind has already short-circuited,
already fucked into a pleasure haze, unable to string two thoughts together as
Dean holds his hips down and continues his quest to end Sam’s life with
pleasure. Perhaps it’s the sound of Sam’s desperate, choked off moans, or maybe
Dean is just as hard up for it as Sam is. Whatever it is, he finally brings a
hand up to finger Sam alongside his tongue.
Sam watches as, with his free hand, Dean reaches for his discarded jeans, never
ceasing in his oral activities with Sam’s ass. He digs in the pocket and comes
with a bottle of lube. He pops the cap open and then takes his finger out to
coat three of them in lube.
Again, the first one slides in easily and Sam keens, already needing more.
Deans works the digit in and out, taking his mouth away and using his finger to
drive Sam wild. The second one is more sensational and Sam bucks his hips until
Dean’s got two fingers deep inside him, working to open him up.
Dean picks up the pace, curls his fingers and strikes Sam’s prostate. The boy’s
hips come up off the bed and the fabric of the panties tears more. Dean is able
to work a third finger in and seems to enjoy watching Sam ride his hand because
he doesn’t hurry. Let’s Sam drag his hips back and forth until he’s sweating
and panting.
At this point, the garter belt has come unhooked from the panties. The
stockings are around Sam’s knees and the stilettos are aimed high in the air as
Dean pushes Sam’s legs up and lines up his cock with his wet, open entrance.
“Jesus Sammy, so fucking perfect,” Dean grunts, rubbing his cock along Sam’s
wet crack, “so fucking hot.”
He enters Sam slowly, ignoring the way the younger boy moves his hips
frantically in an attempt to get more of him faster. Dean takes his time, works
himself inch by inch, dragging his hands over the black panties over and over,
teasing Sam’s cock with his wandering fingers.
When Dean bottoms out, Sam chokes on a pleasured gasp, gripping fruitlessly at
the sheets. Dean hikes Sam’s legs up so that the point of his heels dig into
the flesh of Dean’s shoulders. The older boy hadn’t been kidding and something
in Sam’s belly lights on fire. His hips surge up and Dean slams them down
before he begins fucking him into the mattress.
No time for gentle and slow, just a quick brutal fucking as Sam’s beat up heels
dig into tender flesh and Dean fucks into the sweet tight warmth of his little
brother. Sam tries to meet his brother thrust for thrust but he can’t, his cock
is straining against the panties which have loosened some due to the tearing.
He can see the precome beading up on the fabric, can feel the pressure at the
base of his spine.
It’s too soon, Dean’s just really started fucking him but Sam’s been hard up
for it since he first saw the heels in the box and he can’t hold it in, can’t
possible hold the pleasure back as it goes fire-crackling along his skin,
burning him up from the inside as Dean fucks him harder and harder, nailing his
prostate and making starts erupt behind his lids.
It’s useless to try and stop what he’s feeling as it builds as Dean fucks the
very life out of him. He gasps, chokes, screams, begs for his big brother, digs
his heels in until he’s sure he’s left deep purple bruises on Dean’s shoulders.
And then he sobs in pleasure as his orgasm takes him, come seeping through the
panties, in what can only be described as globs, drop after drop sliding down
the fabric until Sam is wrung dry.
His legs go lax and drop open. Dean holds them and drives into Sam with
punishing force. Sam lays there, relaxed and holding Dean’s shoulders, still.
Then his brother’s body seizes up as he spills inside Sam, gasping and
grunting, whispering Sam’s name.
When it’s all over, and they’re lying in the afterglow, Sam looks down at
himself. The front of his panties, covered in come, the garter belt askew, and
stockings around his calves. Completely debauched. Dean stares at him for a
long time as they get their breaths back.
“And what did I do to deserve a surprise like this?” Dean asks, pulling Sam
closer to him. Sam grins.
“Just wanted to give you a present, big brother.” Dean chuckles, calls him a
brat and tells him to sleep. They’ll nap now and clean up later. Sam smiles too
and tucks his head under Dean’s chin, mind already firing away on what to
surprise Dean with next. 
End Notes
     More writing at veganweecest.tumblr.com
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