Posted originally on the Archive_of_Our_Own at https://archiveofourown.org/
works/840589.
  Rating:
      Explicit
  Archive Warning:
      Underage
  Category:
      M/M
  Fandom:
      Supernatural
  Relationship:
      Dean_Winchester/Sam_Winchester
  Character:
      Dean_Winchester, Sam_Winchester
  Additional Tags:
      Crossdressing
  Series:
      Part 1 of The_Skirt_Thing
  Stats:
      Published: 2013-06-12 Words: 2645
****** Moving Your Body So Brave And So Free ******
by jackles67
Summary
     Dean finds a skirt in Sam's bag and Sam wears it for him.
Notes
     unbetaed.
Dean’s torn between pride and disbelief - his little brother got laid and the
first he hears of it is finding the girl’s clothes - which, by the way, nice -
 in Sam’s duffel when he’s looking for a sweatshirt. The anticipation of Sam’s
annoyed “Deeeaaann” tips the balance and Dean stuffs the skirt into his own bag
before stuffing himself down into a corner of the couch to watch fuzzy tv while
the space heater croaks out a thin stream of hot air and the smell of burnt
carpet. They better go somewhere warm next. Florida. Texas. Fucking Arizona,
whatever. 
Sam comes home late and Dean had a whole thing planned, he was going to tease
the every-loving shit out of Sam, make him turn tomato red and maybe even
wrestle like they never seem to do anymore, but he clearly underestimated his
own sense of betrayal. 
“You had sex?” Dean’s a smooth guy. This is not smooth. This is an awkward,
stilted question that, for what it’s worth, has Sam blushing furiously behind
his too-long hair. 
“No, Dean. Told you I’d tell you all about it when it happens.”
“Then why do you have chick clothes in your bag?”
Sam’s eyes fly to the still-open duffel sitting on his bed and his mouth is
opening and closing but nothing’s coming out. Dean suddenly doesn’t want to
know, doesn’t like anything that leaves Sam, of all the snot-nosed know it all
loud mouths, speechless. He’s opening his mouth to apologize when Sam whirls
around to glare down at him and the anger written into every line of his face
twists it up, turns it into something Dean doesn’t often have aimed at him.
He’s kind of scared - Sam’s smaller but he’s fucking ruthless when he fights
for real. 
“Don’t you ever go through my shit again, Dean.”
And that’s that. 
***
That’s that until it hits Dean, something like 36 hours later, that the skirt
might have been Sam’s. Like, Sam’s. 
“Oh,” Dean breathes, turning wide eyes on Sam, who’s staring out the window of
the Impala, cheek pressed to the glass. He’s still angry - Dean knows Sam can
hold a grudge like fucking no one else, just hasn’t had it held against him
yet, or at least not like this. Dean doesn’t know how to deal with it so he’s
acting like everything’s fine, trying not to wince when Sam throws him dirty
looks every few minutes. “You wear it?”
Sam doesn’t startle, doesn’t need any kind of context to that statement, just
stares out the window for a moment before answering. 
“Seriously? A day and a half to reach that conclusion? 
“Really? I’m a freak in every other aspect of my life, why not in this one?” It
sounds like a well-rehearsed line, like something Sam tells himself to make it
okay. Dean laughs. 
“Dude, wearing a skirt does not qualify you as freaky. I’ve seen some - “
“Not making me feel better, Dean.”
“What about the people you wear it for? They must like it, right? They call you
a freak?” It occurs to Dean, belatedly, that the answer might be ‘yes’. 
“I don’t wear it for anyone else.” Sam sounds scandalized by the idea and Dean
wants to laugh. 
“C’mon, you don’t want someone tellin’ you how pretty you look in that thing?”
It’s mostly a joke but he’s curious too. It’s a nice skirt, pleated on one
side, some pink and orange color like salmon. Coral? Something like that. Dean
still has it, which is weird but not as weird as trying to give it back would
be. 
This time Sam keeps quiet and Dean sneaks a look over at him. He’s blushing,
like, hard. His eyes are fixed on a spot in the middle distance, staring
straight out the window, head tilted to keep his bangs in his face but Dean can
see the angle of his cheekbone, a strip of tanned neck and both are red like a
bad sunburn.  
“Dude.” This has to be the weirdest thing be giving advice to your kid brother
about. “There’s nothing wrong with your skirt and there’s nothing wrong with
having someone tell you what a pretty girl you are while you wear the damn
thing.”
“Boy.” 
“Huh?” Dean’s eyes are back on the road but he can feel Sam watching him,
steady and intense like he does sometimes. 
“I want someone to tell me what a pretty boy I am.” It’s a confession,
whispered and all and Dean feels like this is the part where he should laugh,
tell Sam it’s fine, tell Sam there are probably thousands of people just
waiting to be offered the chance to do just that - except now he’s imagining
the trucker they just passed, or that lady who served them coffee at the diner,
or the girl two years older than Sam who watched him for the entire three weeks
they were at their last school, sitting on their bed in a crappy motel room and
telling Sam how good he looks. 
See, Sam gets his need to prove himself fulfilled by school, gets his need to
rail and fight fulfilled by Dad, and from what Dean can tell, he gets whatever
needs his teenage hormones have pumping through his body fulfilled by his right
hand. Everything else, Dean takes care of. Dean doesn’t know what the hell kind
of need this qualifies as, but fuck if some stranger’s gonna be the one giving
it to Sam. 
“I could do that.” Dean’s voice comes out rough and too serious, all traces of
humor wiped away by twisting uncertainty in his belly. 
“You could - “
“I mean, I bet you do, Sam. I bet you look real good in that little skirt,
always had real long legs.”
This is the part where Sam should tell Dean to shut up, tell him to shut the
hell up and never mention the skirt again, tell him he sounds like an idiot and
this isn’t what Sam meant and he doesn’t want it from Dean anyway. Sam’s
silent, still staring out at the fields that haven’t changed for hours, still
blushing. 
“We could try it. See if it’s… see if that’s what you…”
Sam jerks his head, enough of  a nod to settle the snakes in Dean’s stomach for
all of five seconds before it hits him that he just offered to watch his little
brother wear a skirt and tell him how good he looks in it. At least he won’t be
lying - he’s aware of Sam’s body in the same detached kind of way he’s aware of
his own - it’s the box his favorite person comes in, the wrapping that doesn’t
really matter - but he can appreciate that it’s very nice wrapping. It has nice
legs.
***
He leaves the skirt on the ugly floral bedspread while Sam’s showering and
doesn’t stick around long enough to see his reaction, slips into the bathroom
as Sam’s stepping out. He intended it as an easy out for Sam but as he’s
staring at his foggy reflection in the glass, it hits him that he’s going to
walk back out and find Sam wearing… a skirt. Or maybe not a skirt. Or maybe
nothing but a skirt. What does he usually wear with it? They should have
discussed this more. 
Sam’s standing awkwardly by the bed. His face is flaming red, hair still wet
and curling around his ears and neck, bottom lip caught nervously between his
teeth. He’s wearing the skirt. 
He’s also wearing a tight t shirt, too tight, something Dean’s never seen on
him. It rides up a little, reveals a thin strip of flat stomach just above the
top of the skirt. That fucking skirt.
It sits snug and low on his hips, tight to his body until it just barely flares
out. It’s short enough that the creamy pale part of Sam’s thigh is revealed and
Dean was right, his legs do look awesome like that, right down to the sheer
white socks that come up to just past his knees. 
Sam shifts his weight from one foot to the other as Dean lets his eyes travel
up and down, lingering on that exposed line of belly, on the way the skirt
doesn’t quite sit the way it would on a girl’s hips, the way it doesn’t lie
flat over the space between his legs. 
Sam wipes his palms on the pink material, smoothing it down against his thighs
and drawing it tighter across that telltale bump and Dean lets out the breath
he didn’t know he was holding.
“You wanna turn around, lemme see the rest?” Dean asks, making his way over to
the bed. He sits back against the headboard without taking his eyes off Sam. 
Sam does it, turns slowly and as soon as he’s facing away, he squares his
shoulders, arches his back a little and the back of the skirt is tight, fabric
pulled taut over Sam’s ass but sticking out below it, not quite managing to
follow the curve to his thighs. There’s space there, space for a hand or -
“What do you usually do now?” Dean asks when Sam’s completed his circle, eyes
fixed on the carpet. 
“Dean.” There’s a new kind of whine in Sam’s voice, not his usual plaintive
“Dean”. This one’s more like a plea. 
“Just tell me.” Gotta make sure Sam gets what he needs, make sure he doesn’t
want to go to anyone else for this. Ever. “If you, uh, wanna. You don’t have
to.”
“I - I jerk off.” If Sam turns any redder he’s going to spontaneously combust.
Dean knows the feeling - there’s something burning under his skin, something
ticking like a time bomb behind his ribs. 
“How?” He doesn’t know how he’s keeping his voice steady when all the air in
the room is gone. “Wanna show me?”
Sam freezes for a moment, long enough for Dean’s eyes to catch on the way the
front of his skirt is being pushed out. Sam nods and takes a step towards the
bed, finally meeting Dean’s eye. It’s a defiant look, a dare, but underneath it
Dean can see Sam’s fear like a neon sign. 
It hits him that this is brave, what Sam’s doing. This isn’t risking his
internal organs, the pulse in his throat, on a hunt that might leave him
mangled and bloody - this is risking Dean, risking everything they are and Dean
is suddenly, ridiculously proud of Sam. For showing Dean, for trusting Dean
enough to show him. 
“I do it on the bed. On my knees, pretend someone’s bending me over and…”
Apparently the rest of that sentence isn’t going to make it past Sam’s clenched
teeth. That’s okay, Dean can work with what he’s got. He slides off the
mattress and gestures for Sam go ahead, watches as Sam kneels in the center of
the bed and bends until he’s on his elbows, back arched obscenely, face hanging
inches from the scratchy blanket. 
It occurs to Dean that he hasn’t been fulfilling his end of this bargain. 
“Fuck, you look good like that.” Once the words are out, it’s like something
unlocks in his chest and it all comes pouring out. “Look so perfect, so fucking
pretty in that little skirt, bet you’d have guys breaking the door down if they
saw you.” Dean circles the bed, stands behind Sam and fuck, there’s his little
brother’s perfect, bare ass. 
It’s possible this is getting a little out of hand. 
“No panties, huh Sammy?” Sam makes a little choked sound in the back of his
throat and shakes his head, one hand dropping to his cock. Dean shifts until he
can see it - one of Sam’s hands wrapped tight around the base, not stroking,
just holding on. “Maybe next time I’ll get you some, pretty pink ones to go
with that skirt. Maybe see if I can make you come in them, get them all sticky
and wet.” 
Sam whimpers and his knees shift further apart, head dropping to rest against
the bed while his hand starts to move on his cock, one long squeeze from the
base to the tip, a quick slide of his thumb over the head before it slides back
down, slick and easy now. 
Dean comes back around to get a better look at Sam’s face. Still burning pink,
eyes screwed shut and lips bitten dark, parted around a series of gasps and
pants that has Dean’s cock jerking against his zipper. Jesus. 
“Tell me what you’re thinking about.” The words are out before Dean has a
chance to think them through and the second he hears them there’s a fierce
surge of jealousy spiking through his veins. “You thinking about someone
touching you? Pushing your skirt up and fucking you with it up around your
waist?”
A little twinge of worry reminds Dean that he doesn’t actually know if Sam
wants to get fucked, if that’s part of this, but Sam moans and nods against the
bed, hand moving faster now, hips rocking down into his fist. 
Dean’s just starting to think Sam’s not going to answer when his eyes fly open
and find Dean’s, black overtaking hazel, a desperate, reckless light in them. 
“Thinking about you,” Sam gasps and it’s a punch to the gut, the Impala
cresting a hill too fast, weightless. “Your hand up my skirt, makin’ me wear it
in the car, makin’ me ride you. Wanna - wanna be good for you.”
Fuck.
“You wanna be a good boy for me? Want me to make you take it, want me to bend
you over and pull your panties down, fuck you so hard you can’t sit for a
week?” Dean’s mouth is completely out of his control, filth pouring out while
he palms his dick hard and watches Sam, watches his body curve and arch like
Dean’s actually doing it, actually fucking him.
“Fuck you’re so hot like this Sam, wearin’ that skirt for me, being so good for
me.”
Sam lets out a whimper that has Dean pretty sure he’s going to come in his
pants and he really doesn’t care, doesn’t even unzip his jeans because Sam
looks like he’s about to lose it and Dean can’t take his eyes off him for even
a second. 
“Dean - oh god - Dean, I’m gonna - “
“Yeah, c’mon Sammy, let me see you come like that, fuck, do it.”
Sam comes with a strangled moan, hand flying over his cock while the other
grips the bedding, his body twisting and jerking, skirt shoved up by the
movement, face screwed up in pleasure. The sight is enough to push Dean over
the edge, hips shoving up against his own hand, knees nearly bucking at the
pleasure drawing up through him, pulsing hot and thick into his boxers. 
He half steps and half crumples onto the bed where Sam’s lying on his side,
inches from the wet puddle of come in the center. He looks… perfect, hair
mussed in every direction, face still flushed red, chest heaving and skirt
still rumpled up to reveal his sticky, softening cock. 
His eyes are slitted, fuzzy gaze on Dean’s face, the only hint of nervousness
the way he tugs his skirt down to cover himself. 
“Was that - ” Dean starts, clears his throat - Jesus, he sounds like he gargled
with Drano this morning. “Was that okay?”
Sam nods and curls toward Dean, contorting his body to avoid the come, and Dean
stretches out an arm to wrap it around his skinny shoulders, tugs him in
closer. 
“What do you say? Panties next time?” Dean tries for playful, but they both
know what he’s really asking. 
“Mmhmm. You have to buy ‘em though.”
“‘Course.” Dean grins, braces for the elbow his ribs are about to receive.
“Anything for my pretty little brother.”
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