
Posted originally on the Archive_of_Our_Own at https://archiveofourown.org/
works/426936.
  Rating:
      Explicit
  Archive Warning:
      Underage
  Category:
      M/M
  Fandom:
      Supernatural
  Relationship:
      Dean_Winchester/Sam_Winchester
  Character:
      Dean_Winchester, Sam_Winchester
  Additional Tags:
      Feminization, Crossdressing, Sibling_Incest, Fingerfucking, Teaching,
      Comeplay, Dirty_Talk
  Collections:
      Weecest
  Stats:
      Published: 2012-06-07 Words: 1726
****** A passion for learning ******
by queerly_it_is
Summary
     Sam asks for Dean to "teach him" how to please a girl. So Dean gives
     a hands on demonstration on finger fucking.
Notes
     Written for heard_the_owl over on LJ.
 Sam has that twitchy, nervous look that says he really wants to ask Dean
something, but is all shy and embarrassed about it.

As a good big brother, Dean is obligated to help him out.

“Y’know Sammy; if you wanna take me to the prom, all you gotta do is ask.”

Doesn’t mean he isn’t gonna be a dick about it, o’course. At least Sam stops
squirming all over the tiny motel room furniture, little bitch was making it
hard to think.

“If I wanted to take you to the prom, I’d have to drown myself in holy water.”
Not even the slightest pause between the blushing and the bitchface.
Impressive.

“Oh, I’m hurt Sammy, you don’t think I’m pretty?” Pouting, batting his
eyelashes at his brother across the room.

Back to blushing now, then. Interesting.

“Dean. Do you. Could you maybe.” Stammering, way he always does when whatever
he wants to ask is about sex. This oughta be good.

“C’mon Sammy, you can’t say it, you shouldn’t be doin’ it.” Trying to sound
smug and all-knowing, rather than pissed at the idea of Sam going off and
finding someone to do sexy stuff with. Dean’s right here, for fucks sake.

“Howdoyoufingeragirl?” All one word, like if the kid gets the question out fast
enough the blood won’t reach his face. Doesn’t really work.

“One more time there, Sammy?” Dean knows exactly what he said, just kinda wants
to hear Sam say it again. He ignores the epic sigh and roll of fox-slanted
eyes, focuses on the way he licks his pretty pink lips instead. Best part of
hanging around Sam; there’s always somewhere fun to look.

“How. How do you finger a girl?” And Dean’s gotta give him credit; only one
pause and eye-contact all through the question.

“Why d’ya wanna know that Sammy?” Something low and dangerous - predatory - in
the question “You got some sweet little thing you haven’t told me about?” Sam’d
better say no; Dean doesn’t like hitting girls.

“No!” Embarrassed again, and Dean relaxes a little. “I just. Bethany Maynard;
from that school back in Kanas? She kinda. She wanted me to.” Some meaningful
hand gesture, and Dean reminds himself driving straight back to Kansas to kill
little Miss Maynard would be wrong. “And I didn’t really know how to, you
know.” Really blushing now, but Dean supposes it’s only natural.
 Sammy did just turn fifteen today, after all.

“Ah, okay. Well, not to worry Sammy, big brother’ll help ya out.” Way more
innuendo than he meant to put into that, but Sam doesn’t seem to mind, way he’s
wriggling on the chair again.

“’Course, only real way you’re gonna understand the material is with a proper
demonstration.” Sounding less like a teacher and more like a porno actor, but
fuck it.

He crosses to his duffel, digs right to the bottom where he hopes he still has
the - yes. It’s a miniskirt. It was gift from a freaky little number a couple’a
states back; Terry, Tricia, something with a ‘T’, Dean doesn’t remember, s’not
the point, anyway.

Sammy’s gonna look awesome in it.

“Dean, what. C’mon man, no way.” He’s trying to hide the hitch in his breath,
but Dean knows every tell his baby brother has; knows he’s got him on the hook
now, just waitin’ to be reeled in.

“Gotta do this right, Sammy.” He says, as much seriousness as he can muster
with this much blood moving away from his brain. “Can’t have my little brother
not knowing what to do if his lady’s in a skirt, now can I?” Yeah, ‘cos that’s
why Dean’s doin’ this.

He flings the tiny little garment at Sam, all but shoves him into the bathroom
so he can change, reminder of “No underwear, Sammy!” shouted through the wooden
door.

He goes back to his duffle, pulls the lube from the side-pocket, yanks the top
sheets off the nearest bed, sits, and waits. And waits.

“C’mon Sammy, only got three days before Dad gets back.”

“I look stupid, man.” Faint reply from the bathroom. Dean seriously doubts
that.

Sam walks outta the bathroom, and every bit of blood in Deans body floods into
his dick so fast he actually gets light-headed. Jesus fucking Christ.

Sam is naked, except for the little green skirt; long, long legs bared up
nearly to his crotch, lithe, compact muscle and caramel skin everywhere, hair
flopping in his face, chest heaving slightly with every breath, teeth clamped
firmly onto his lower lip.

Dean tries not to come, right then and there.

“Lookin’ good, Sammy.” Voice like he’s been chain-smoking, Dean holds out a
hand and Sammy walks over, quiet and meek, which really doesn’t help. He stands
between Dean’s legs where he’s kinda slumped back on the bed, and Dean runs a
hand from the waistband of the skirt up as high as his arm will reach,
fingertips barely reaching Sam’s shoulder.

Other arm going ‘round Sam’s waist, Dean tugs and gets his baby brother
underneath him, spread out on the bed. Coltish limbs everywhere, bulge clearly
showing under the skirt, dark, secret place between his legs.

Fuck.

The snick of the cap on the lube gets Sam’s eyes on his, pupils seriously
blown, breath coming harder, deep-red staining halfway down his chest.

“S’okay Sammy. Gonna take care of you.” Running one hand up and down Sam’s left
leg - reminds himself about waxing, for next time - he squeezes a decent amount
of lube into his right palm, and tries to remember how to talk.

He’s supposed to be teaching Sam, after all.
 “First thing you gotta do, is relax her a little.” Runs his non-slick hand up
Sam’s thigh, under the skirt, feels the muscles relax as his breath pushes out
in a broken sigh.

“Always start slow, just ease her into it.” Slick finger circling the tight
little place between Sam’s legs, bypassing his more than half-hard cock
altogether.

Sam is playing a girl right now, after all.

The muscle relaxes, quicker than he’d expected - sudden flash of Sam doin’ this
to himself in the shower making him groan - and his index finger slips in to
the first knuckle.

“Fuck, that’s it Sammy, open up for it so nice.“ Sam moans, eyes squeezed shut,
dick totally hard now.

Finger working in a little deeper, Dean uses his other hand to spread Sam’s
legs wide as he can “C’mon baby boy, know what you want, know just what you can
take.” Doesn’t register half of what’s coming out his mouth now, just talking
for the way it makes Sam wriggle on his hand.

“Fuck, there ya go, that’s one all the way in, Sammy. How’s it feel, huh?”
Fingertip pressing hard against that spot inside.

“S‘fuckin‘ good Dean, God.” Hips pushing down into Dean’s hand, impressive
bulge twitching beneath the skirt.
 “You want another one, Sammy?” Running the tip of his middle finger around
Sam’s pucker where it’s stretched and clenching a little.

“Yeah. C’mon Dean, I. I want it.” Pleading broken with high-pitched whines as
Dean slides a second finger straight to the middle knuckle.

“S’right, Sammy, gonna stretch you all out, get this little pussy all wet and
messy for me.” Fingers fucking in and out, Sam opening up so sweet, hottest
fucking noises coming from his throat.

The squelch of lube is audible as Dean presses around his brother’s rim with a
third finger, and knowing that Sam likes the burn as he’s forced open just that
little bit too-quick almost makes him wanna stuff Sam all the way full, watch
him try to take it just for Dean.

He’s aware it’s not really about the girls, anymore.

He really needs to see, he suddenly decides, flips the skirt up above the
waistband. Sam’s fucking perfect cock leaves a wet blot of precome against the
almost-rough material as it slaps toward his belly, red at the tip and so so
hard. Pretty as that is, it’s nothing compared to the sight of Sam with three
of Dean’s fingers buried up in him. Fuck he’s a sexy little bitch.

“So pretty like this Sammy, spread out and fucked open, fingers in your little
cunt. God love it don’t you.” Angling to hit Sam’s prostate just right with
every thrust, Dean watches as Sam squirms and pushes his hips down into it.

“Perfect little slut when you’re begging and all broken open. Fucking made for
this, baby boy.” Hand moving faster, harder, seeing if Sam can come without a
hand on him. Judging from the way he’s leaking like a busted faucet; precome
drooling from the almost-purple head of his dick, thin string of it connecting
his cock to the fabric of the skirt, Dean’s pretty sure he can.

“Your so fucking wet Sammy, little pussy dripping.” Twist of fingers, shudder
running from Sam’s hips all along him, dick twitching and leaking everywhere.
“You gonna come baby? Gonna come on just my hand, thinkin’ about my cock.”
Particularly hard thrust, and Sam flies over the edge; come shooting up his
chest and landing on his neck, his stomach, the skirt.

Dean fucks him through it, hand slowing a little, getting Sam to ride the
orgasm out while his other hand fumbles at the button on his jeans, shoves them
down his thighs and pulls his cock out. He withdraws his fingers, Sam making a
noise of what Dean’s gonna go ahead and call dissapointment, and jerks himself
off with the warm, wet slick still covering his hand.

“Gonna mark you up Sammy, get my come all over you.” Getting close already, way
too long trapped in his jeans while he focused on Sam.

“Yeah” weak croak, throat working as he swallows. “Mess me up, Dean.” Fuck that
is it. He shoots over Sam’s legs, his cock, some mixing with the mess already
on his brother’s belly. He watches his come run down behind Sam’s balls,
joining the shiny-wet covering his thighs and leaking out of him where he‘s all
loose and open.

He runs a hand through the mess, spreads it into Sam’s skin. Drags him up and
kisses the breath out of him, tasting and savouring the sweet flavour of his
mouth. Need for air forcing him back a little, he presses his forehead to his
brother’s, speaks low and soft.

“Happy birthday, Sammy.”
Please drop_by_the_archive_and_comment to let the author know if you enjoyed
their work!
