Posted originally on the Archive_of_Our_Own at https://archiveofourown.org/
works/9240422.
  Rating:
      Explicit
  Archive Warning:
      Underage
  Category:
      M/M
  Fandom:
      Supernatural
  Relationship:
      Dean_Winchester/Sam_Winchester
  Additional Tags:
      12_Days_of_Wincestmas, Wincest_-_Freeform, Weecest, Underage_-_Freeform,
      Bottom_Sam, Top_Dean, sex_kitten_sam, Sam_is_a_Tease, Sam_In_Panties, Sam
      in_a_Skirt, Feminization, Dirty_Talk, Rimming, Oral_Sex, Sam_Has_a_Large
      Cock
  Collections:
      12_Days_of_Wincestmas_2016
  Stats:
      Published: 2017-01-08 Words: 3400
****** Sam's Adventure at Victoria's Secret ******
by NaughtyPastryChef
Summary
     He bought the skirt as Dean's Christmas present but at the last
     minute, he decides he needs something more and slips out to the mall.
     Written for damnthosefuckingbrothers for the 12 Days of Wincestmas
     2016/2017
 
Sam stood in front of the mirror in his bedroom with the door barricaded shut
against nosy older brothers and frowned into the mirror. It wasn’t working. He
tugged at the hem of the red and black plaid skirt, but all it did was shift
down low on his hips for a moment and then it lifted right back up. He looked
down and tried to see what he could do but it looked like nothing was going to
work unless he went back to the store; his cock was too big and the tip was
showing beneath the hem of the slutty skirt he’d bought.
He’d really wanted to go commando under the skirt but it just wouldn’t work. It
wouldn’t give him the image that he was going for. He tugged the skirt off and
took a moment to hide it before he stepped back in front of the mirror, naked.
He turned to his left, then to his right, and frowned again. He was too skinny.
He looked like a skinny, dorky kid. He didn’t know how to do what he wanted to
do.
What if Dean laughed at him?
Sam turned away from his reflection and pulled on his too-big, hand-me-down
jeans over his naked hips. He grabs an inside-out, balled up tee shirt that
doesn’t smell noticeably and pulls it on over his scrawny chest before shoving
the dresser away from the door and yanking it open. He can hear the distant
sound of the tv on in the living room and heads that way.
Dean’s slouched on the couch, legs splayed open casually and looking sexier
than anyone ever should. Sam’s head hangs low, bangs in his eyes, as he slips
past the back of the couch and into the kitchen to grab an apple on his way to
the door.
“Where you headed, nerd? Back to the library?” The words ring out in the
silence of the room and Sam steels himself to be as calm as he can. He looks
down to see that his hands are shaking with nerves and he curses himself.
“None of your business, jerk. I’ll be back for dinner.” He shoves his arms into
the sleeves of his too small jacket and heads for the door, praying that’ll be
the end of it. A hand reaches out and grabs his shoulder and he knows it’s
going to be hard to get out the door.
“What’s with the attitude Sammy? It’s Christmas time. Just wanted to spend some
time with my little brother.” Dean’s mock pout is irritatingly hot and that
combined with his proximity has Sam’s skin prickling with heat and cock
twitching. He yanks his shoulder from Dean’s grasp and twists towards the door.
“I just gotta do something. I’ll pick up a pizza on the way back, okay?”
Without another chance to let Dean grab him or say anything, Sam is out the
door, mentally adding up the assorted bulls in his pocket and hoping he has
enough for pizza.
Dean sighed as the door slammed behind Sam; he missed his Sammy. Some of the
days, anyway. Some of the days… well this new teenaged Sam? With the moody hair
and the brooding eyes and the legs for days? Dean hadn’t seen anything so good
for his libido in years, and Dean’s libido was pretty amazing. Add to that
fact, this kid was wearing his old clothes? See through tee shirts and jeans
hanging off the hips that Dean’s mouth watered to get closer to and, well, Dean
found himself running a little hot lately.
He veered off from heading back to the couch, figuring he could indulge a bit
since Sam was getting out of the house for a bit. He slipped his hand up his
shirt until he could rub a fingertip over his nipple, getting it to peak and
tingle as he pushed his bedroom door mostly closed. He kicked off his boots and
socks and shoved off his pants and underwear leaving them pooled on the floor
in his haste to get naked.
His balls tightened when his warm skin met the cool sheets on his bed but it
just added to all the pleasurable feelings.  Finally made himself let go of his
nipple so that he could shove his shirt off and finally he was naked and on his
back, on his bed.
Dean never got the chance to tease himself, but he took a chance and let
himself take the time. He trailed his fingertips all over his torso.  He
rubbed, then pulled, then pinched his nipples until he couldn’t keep his eyes
open from the pleasure.  He dug his heels into the mattress and rocked his hips
upward into the air.
When he finally, finally, allowed himself to sneak his hand downwards and play
with the base of his cock, he was near to bursting. He closed his eyes tight
and grit his teeth as he imagined his lean and beautiful Sammy coming into the
room. Wrapping those pink, pink lips around the swollen and aching head of his
untouched cock and sucking. Sinking his perfect, ripe ass down onto Dean’s cock
and riding him like the pony neither of them ever wanted for Christmas.
His cock was drooling so much that his hand, still down at the base of his cock
and teasing against his drawn up balls, was wet with it. Between the rushing of
blood in his ears and the sound of his wet hand on his own skin and the fantasy
running through his head, he never hear Sam come back into the house.
 
Sam wandered to the run-down mall in their small town and tried to blend with
the rushed and harried Christmas shoppers as much as he could until he was
swept along to the tiny Victoria’s Secret. He stood, indecisive, outside the
store but only for a moment. Sam screwed up his courage and stepped inside only
for his senses to be assaulted with colors and textures and scents.
 
“Hi, can I help you find something?” A frazzled looking employee, a girl not
much older than Dean, came up to Sam with a genuine smile on her face. She
peered at Sam curiously for a moment before she leaned in closer. “If you’re
just here to peep, my manager will kick you out. Are you looking to buy
something?” She asked again, kindly.
 
Sam screwed up his courage again, and told her honestly what he was looking
for, though his eyes remained fixed on the floor. “I have this skirt...it’s for
my boyfriend, I mean I’m wearing it for my boyfriend, and I need something
pretty for underneath it.” He whispered.
 
“Say no more. What’s your name? I’m Kara.” She said as she dragged him away
from the perfume and the teddy’s and towards a wall of pretty, silky panties.
 
“I’m Sam.”
 
“Sam, we don’t get a lot of guys in here as brave as you so not only am I going
to find you the perfect thing but I’m also going to make sure that you can get
two by using my employee discount.” Kara said as she gently but insistently
turned him this way and that, sizing him up. “Hmmm, you got skinny flat hips
but they’re not too wide and, damn, nice ass.”
 
Sam felt his cheeks flame at Kara’s bold words but he felt a smile on his lips
too. His eyes went from her face to the wall of panties and were immediately
drawn to a silky pair of beautiful green panties. They had black edging and
black lace and a matching garter. Sam felt his whole body break out into a
sweat- those were the ones.


“Ohhh, that kind of gift for your boyfriend. Well, sweetie, you’ve got the ass
for it and I’d be willing to bet all of my commissions from today that you’ve
got the legs for it too. Let’s find your sizes.” Kara turned and started
rifling through the matching pile of green satin as Sam stood there and tried
not to feel too awkward as he waited.
 
Twenty minutes later with a tiny pink bag shoved deep into his pocket, he was
on his way to pick up pizza and head home to Dean. He shoved open the door and
didn’t see Dean on the couch in front of the tv, so he threw the pizza on the
counter and dashed towards his room, to stash his prize with his skirt.
 
Dean’s bedroom door was slightly open and he peeked in without thought,
freezing when he saw Dean on his bed, naked and jerking off. Sam held his
breath so that he could watch until Dean was done. His cock, hard off and on
since he’d tried on his skirt earlier, plumped quickly causing him to shift on
his feet.
 
The first time he heard it, he thought he was hallucinating. His name, whined
from the back of Dean’s throat. Sam cursed his heart for beating so loudly in
his ears and shook his head tightly to clear it. He watched Dean’s lips move as
he heard it again. “SAM” was nearly shouted into the air as Dean’s body
clenched up and he came so hard he nearly hit his own mouth with come.
 
Sam dashed across the hall, breath heaving and heart pounding as he slammed the
door loud enough to know that Dean for certain heard it and knew he was home.
He hurriedly hid his new panties, garter and stockings with his skirt and wiped
as much sweat off as he could before running past Dean’s bedroom door and
heading for the kitchen and the now-cold pizza.
 
Dinner was quiet. Sam had eaten half of the pizza before Dean joined him in the
living room, wearing different but cleaner clothes than he’d been wearing
before Sam had left the house and smelling of the generic “manly” body wash
they both shared.  They sat close on the ratty couch and watched the old
Claymation Christmas specials.
 
“I … got you something. For Christmas. Even though, I know, we don’t really… I
mean there’s no tree and, well, pizza but still.” Sam forced the words out
through a dry mouth as he stared at the tiny tv screen and not the curious but
hopeful look on Dean’s face.
 
“Yeah? That’s really nice of you Sammy. I got you something too but I was gonna
wait till morning. BUt if you wanna go now we can do that. I think I can even
fake up some hot cocoa if you want?” Sam’s courage almost vanished when he
heard hot cocoa; Dean still thought of him as a little kid. He shook his head
and stood abruptly.
 
“No cocoa. It’s gonna take me a minute to get your gift from where I put it.
Just…” He motioned with both hands for Dean to stay “ just stay here.” He
tripped over his own feet on his mission to escape the living room before he
lost his nerve and ran to his room. He leaned up against the closed door and
let his breathing come back down. His heart hurt from all the strain today.
 
He stripped off all his clothes as he pulled out his prizes. Kara had told him
the proper order to get everything on properly; panties, garter, stockings and
skirt. He pulled everything on meticulously wanting it to be perfect. He made
sure the straps weren’t twisted on his garter; made sure that the seam of his
stockings were straight up the back of his legs.
 
He’d pulled everything on when he realized that he didn’t have a shirt to
complete the outfit. He could go downstairs just like this, of course, but he
wanted something else. Something that would call to Dean. He slipped across the
hall on stockinged feet and stole into Dean’s room, searching for his faded Led
Zepplin tee shirt. Taking a deep breath and refusing to look in the mirror
again, he headed downstairs.
 
“Damn, Sammy, for a minute I thought you’d left or fallen through the back of
your closet into Narnia or something….” Dean’s words vanished when he finally
got a good look at Sam and his getup.
 
Sam’s long, coltish legs looked like they belonged in a magazine encased in
dark stockings. Dean’s eyes followed them all the way up to the scrap of red
tartan fabric that was masquerading as a skirt around Sam’s slender hips.
Topping off the ensemble was Dean’s dirty Led Zepplin tee shirt.
 
“Oh fuck me Sammy.” Dean sighed, sitting down heavily as all the blood rushed
out of his head. Sam laughed softly before replying, “I was hoping you’d fuck
me, actually. This time anyway.” Sam took a hesitant step towards Dean on the
couch, waiting for a sign.
 
Dean lifted his hands and made a “grabby motion” with his hands to make Sam
come even closer.  Dean’s fingers were shaking by the time his fingertips
touched the silk of Sam’s stockings and slid upwards to palm his skinny hips.
“Look so pretty for me baby. You wanna be my pretty girl? Wanna get treated all
soft and sweet?” Dean asked with his face pressed into the soft give of Sam’s
lean stomach.
 
Sam looked down as Dean pulled his face away and looked up, waiting for an
answer to his question. Sam nodded slowly, his eyes never leaving Dean’s.
Dean’s smile spread across his face, lighting it up with happiness as Sam
nodded down at him.
 
“My sweet girl. M’gonna treat you so soft and nice. Can I ask you one more
question sweetheart?” Dean’s voice was soft and gentle; the opposite of his
possessive and roaming hands. They were up under his tee-shirt, ghosting across
the small amount of exposed skin at the back of Sam’s thighs and across the
front of Sam’s tiny skirt as it bulged out. Sam nodded again, unable to speak
in the face of all of Dean’s sexuality directed right at him.
 
“Is this your first time sweet girl?” Sam’s eyes went wide with fear. He
couldn’t lie to Dean but… he knew Dean’s opinion on virgins; “more trouble than
they’re worth, usually.” He had to tell the truth. He nodded again and the look
of wonder and amazement that passed across Dean’s face was a sigh of relief.
 
“What a perfect gift for me sweetheart. C’mon, soft and pretty girls like you
don’t have their first time on some dirty couch in the living room.” Dean stood
quickly and, faster than Sam could process, swept Sam into his arms to carry
him upstairs. Sam’s head was spinning when Dean lay him down gently on his bed
and he resisted the urge to roll around in Dean’s scent.
 
“Gonna take such good care of you sweetheart. Can I take a peek up under your
skirt? Oh, red and green for Christmas. Christ, baby, you look so fucking
good.” Dean was speaking in low, soothing tones almost constantly as he put his
hands all over Sam.
 
Sam looked down the length of his body to see the bulge and wet spot on his
brand new panties where his cock was stretching the fabric and he whined. His
hips cocked to one side and then the other as he tried to pull Dean’s attention
to where it was really needed. Dean glanced up from his intense study of Sam’s
thighs to see what Sam needed.
 
“Oh, sweetheart, are you hurting? You need it, huh? I’m a gentleman, let me
take care of that for you baby.” Dean unclipped the garters from Sam’s
stockings and tugged the whole thing down Sam’s legs and off. Then he reached
up and gently pulled the elastic of Sam’s satiny, green panties away from his
skin and pulled them gently down, leaving the skirt and the stockings on.
 
“Oh baby. Look at your big cock. So big and fat and delicious looking. And
hard, huh?” Dean crooned as he gripped the base of Sam’s purpled cock and aimed
it towards his mouth.
 
The first touch of Dean’s warm, wet mouth on the head of his cock made Sam’s
eyes cross with pleasure, but he forced himself to keep them open, unwilling to
miss even a second of his first time with Dean. It was an embarrassing amount
of time later that he was gasping out a warning to Dean, who smiled up at him
around his mouthful and kept on sucking until Sam lay back on the bed,
exhausted.
 
“Oh sweet baby, darling girl, what a wonderful Christmas gift for me. Should we
have a little nap and start again when we both wake up?” Dean slid up the bed
to gather Sam into his arms and pull him close to his chest, cocooning Sam in
warmth and familiarity. In love and happiness.
 
In Dean. He drifted to sleep with a smile on his face.
 
Sam woke up with his face pressed into Dean’s pillow and Dean’s face in his
ass. He moaned and curled his fingers around the sides of the pillows, arching
his back to press his ass even closer to Dean’s amazing tongue.
 
“Sweet girl, my sweet girl, I know that you needed your rest but you looked so
delicious, I had to have a taste. And you taste so damn good baby.” Dean took a
deep breath and dove back in, tongue first, spearing into Sam’s sweet, tight,
virgin asshole. He moaned and pulled back again, “you want it sweetheart? You
gotta tell me you want it, I’m not the kind of guy that just takes.”
 
“Dee please. I want you in me big brother.” Sam cried into the pillow, heaving
for breath, his whole body twitching with need. He didn’t know how long he’d
been asleep, but he knew he was ready for this; he’d been ready for it for so
long. He whimpered when the heat of Dean’s body moved away from him but Dean
was back quickly, running soothing hands up and down his twitching legs.
 
“I know you need it baby girl. I got you.” Dean slid his fingers into Sam’s
eager hole easily and felt the throb of arousal run through his whole body when
he realized he was going to be inside there. Sam was so ready for it that he
almost opened his mouth to question the “first time” of it all, but he decided
not to ruin the moment. Sammy wouldn’t lie to him.
 
Sammy was just made for him.
 
He pulled his fingers out and away when Sam’s whining became more arousal and
less pain. He snugged his hips up right behind Sam’s and let his cock ride the
warm, wet gash of Sam’s ass as he nibbled the back of Sam’s neck to talk. “Your
first time baby doll, this might hurt. But it’ll get better I promise.” He
crooned as he pulled his hips back and pressed the head of his cock to Sam’s
ass.
 
“Want it.” Sam cried out and Dean pressed forward, slowly and steadily, no
matter how much his body screamed at him to take, he was aware of how he could
hurt his Sammy. When he was fully seated he let out a breath against the damp
skin on Sam’s neck.
 
“My babygirl still okay?” He asked between smeared kisses.
 
“Yes, Dee, c’mon fuck me like you mean it.”
 
Dean pulled back onto his knees and gripped Sam’s hips as he let loose, fucking
Sam like they were both going to die if he didn’t. The sounds coming from Sam’s
throat were intoxicating. Even if he wasn’t pent up; even if he hadn’t wanted
this for longer than he could admit, Dean would be ready to come sooner than he
wanted.
 
“Feel so good baby. Made for me; you were just made to take my cock like this.
Fuck, Sammy.” Dean groaned as his hips jumped forward and slammed into Sam as
fast as his hips could stand.
 
“Come in me Dee. Wanna feel it. C’mon.” Sam turned back and whined at him and
that was it. Dean’s whole body seized up as he pulsed and came in Sam’s ass. He
pulled out with a wet squelch and turned his blurry eyes to Sam’s pink and
fucked out hole to watch his come trickle back out.
 
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