Posted originally on the Archive_of_Our_Own at https://archiveofourown.org/
works/834549.
  Rating:
      Explicit
  Archive Warning:
      Choose_Not_To_Use_Archive_Warnings, Underage
  Category:
      M/M
  Fandom:
      Supernatural
  Relationship:
      Dean_Winchester/Sam_Winchester
  Character:
      Sam_Winchester, Dean_Winchester, implied_OC
  Additional Tags:
      Virgin!Sam, experimenting, handjob, blowjob, Fluff
  Stats:
      Published: 2013-06-08 Words: 2824
****** Questioning ******
by SixSevenNate
Summary
     Highschool!Sam set when they were younger, Sam comes to his big
     brother when he's questioning his sexuality. Dean assists him in
     figuring it out
Notes
     Sorry if theres a lack of the letter C, my keyboard is wonkey.
     PS this is my first post to AO3, so sorry if I do something wrong!
"Questioning?"
The question was simple, not a scoff of disbelif like Sam had thought--it was
more of a question, like Dean didn't hear him right. The teen shifted on the
bed, sitting across from his brother with at least a few feet of space shared
between them on the ragged blood red blanket. Dean's head cocked to the side as
he looked at his little brother, who was shaking like a wet dog. Sam rung his
fingers together on his lap and looked up at Dean.
"Questioning." Dean repeated. Sam nodded his head.
"I-I" Sam studdered, looking helplessly at Dean in his attempt to explain. He
blew air out of his lungs and looked down again. "Yeah."
Dean felt a little frushtrated. Sam knew he could talk to him, why was he
getting choaked up? "C'mon Sammy, spit it out. Explain."
"Well...ah...there isn't much to say." Sam muttered. "I...I like girls, but I
think I like boys too. More so than girls." he said, still shaking.
"Could be a big bad bisexual like yours truly." Dean said, a grin breaking
across his lips. "You really do take after me, don'cha?"
Sam grinned bashfully and looked down again. Yeah. He did take after Dean a
lot, yet he wsn't completely sure. Dean could just go out on the street and
seduce any stranger who walked past him, Sam though...he was somewhere between
puberty and non-puberty, tall with a mascular jaw, but everything else was
scrawney and his voice squeeked when he spoke every so often. Dean was...Dean
was a man, and he knew exatly how to prove his sexuality. Sam envied him for
this.
"So what made you get to thinkin' kid brother?" Dean asked, leaning closer like
a girl at a slumber party about to hear a juicy piece of gossip. "Any nice
pieces of ass in that school of yours?"
"Shut up." Sam blushed.
"Sammy's got a crush!" Dean jeered "What's his name?"
Sam shook his head. "Not telling."
Dean just smirked cockily and sat back, putting his arms behind his head so his
shirt shifted up slightly. Given the conversation, this made Sam uncomfortable.
Dean shifted his shirt down and looked lazily at Sam. "Anything else you want
to confess to me Sammy? Not a virgin anymore? Took the last cookie?"
Sam shook his head. "NO\o but...I have some questions."
"Hit me."
Sam looked down for a seond, ringing his fingers again like he did when he was
nervous. "Is it different kissing guys?"
Dean thought for a second. "Well, depending on the person, their lips are
usually thinner and agressive. At least in the boys I like."
"Too much"
"Shut up I'm giving you advice." Dean hissed "If he's more of a 'fem, he'd
probably be a gentile kisser. The more macho the rougher...usually. Then theres
friction playing" Dean grinned cheekily "That makes kissing very fun."
"Friction play?" Sam asked.
Dean held up his hands, balling his fists but keeping his index fingers up. He
rubbed his index fingers together slowly in an obscene gesture, Sam got the
picture right away and perked up a little. "Oh. Dry humping you mean?"
"So you know a little." Dean chuckled.
"You teach me it. You should remember."
"I taught you how to do girls, y'know, since I felt bad for you being a virgin
and all."
Sam furrowed his eyebrows. "You taught me how to 'do girls' by shoplifting a
DVD of Busty Asian Beauties and narrated the whole way through." he shuddered,
he had never been so uncomfortable in his life.
"Well its not like I really had anything to demonstrate on, now did I?" Dean
said, crossing his arms.
"Ew." Sam said, picturing Dean getting a blow up doll to "demonstrate"....or
worse.
"'Course Sammy, if you'd like, I could show you some things I know." Sam went
red as a wicked grin spread across his brother's face. "You'd learn...well."
"Thats..." Sam felt his fae grow hot, "Thats incest! Wrong!" he spluttered.
"C'mon Sammy. Don't act like you've never at least thought about it."
He was right. Sam had thought about it, a few times just to pass the time, fall
asleep of get himself off when nothing else came to mind. The thoughts were
pleasing, imagining Dean's stained and calloused hands wrapped tightly around
Sam's dick, sliding up and down gently while he sucked on just about everywhere
else on Sam's scrawny frame, his muscular body pressing against him, moaning
his name "Sam...Sammy..."
"Sam!"
Same looked up and realized he'd been staring off into space. "Yeah! Yeah.
Sorry. Uh...maybe once or twice."
Dean smirked. "You little cockslut. You were just thinking about it, weren't
you?" he leaned forward, getting uncomfortably close to Sam. "I could make some
of those dirty little thoughts ome true, Sammy, but you gotta let me. I can
show you the whole nine yards if ya like, but you have to let me." the last few
words came out in a whisper as he crept close and closer to Sam, who baked away
a little bit with his cheeks turning red, and he suddenly understood how Dean
could get so many girls--and boys--to jump right into bed with him. Those eyes,
thick lips begging you be kissed and/or fucked, the way he almost loomed over
you, Sam felt himself melting even if there was at least 5 inches left between
their faces. He reached up and swiped Sam's bangs out of his eyes gently, green
meeting green as Dean kept leaning in.
"You suck." Sam whispered.
"Is that a command?" he chuckled.
Sam leaned in so their lips met, his face almost on fire as he slowly sucked
the sides of Dean's mouth. His lips were softer than he'd ever imagined, and it
felt great...beyond great. Great and deliciously wrong. When Sam pulled away
from him he glanced up at Dean "don't tell Dad."
"'Course."
Sam slid off the bed and slipped off his shirt and jeans, leaving him in only
his boxers. Dean watched, still sitting on the bed while watching Sam strip
bare. "Keep your undies on." he said. "I'll just be walking you through."
"Are you gonna-?" Sam's voice trailed off as Dean held up his hand and smirked
again. "Alright." he climbed back on Dean's bed and knelt by him, still shaking
despite being with the one person he trusted the most. Dean leaned over to Sam
and pushed him onto his back, leaning over him and putting his head in Sam's
neck. He wasn't sure what Dean was doing until he felt gentle sucking on his
neck, sending tingles on pleasure down south to the forming lump in his boxers.
"D-Dean" he breathed, reaching around and putting his arm around Dean's side
and clutched his back "It feels so weird." he murmured as he trailed the
pressure down his neck and along his collar bones, nipping occasionally and his
whiskery stubble rubbing against his skin. Dean pulled off Sam's neck with a
pop-ing noise, causing a nice deep red bruise to flare up. "See that? That's a
hickey." Dean said, trailing his finger over the red mark, smearing his saliva
along it. "It's usually used to show ownership, like putting your name on a
drawing or whatever pansy-ass stuff you do at school." Sam nodded and took note
of that.
Dean slid his hands up the sides of Sam's body, his rough fingers bumping
against Sam's ribs that stuck out slightly, not yet blanketed by muscle like
Dean was. He pressed his thumbs against the small brownish nubs of Sam's
nipples, rolling them in between his thumb and index finger. Sam moaned,
rolling back his head a little as he enjoyed the pressure. Dean smirked and
dragged his tongue across the right one, then blew air onto it making the skin
scrunch up and become more sensitive, also causing Sam to yelp. "Dean!"
"Like that?" he asked.
Sam nodded. "Bite me." he said softly "literally. I want to see what it feels
like."
Dean did so, gently he ground his teeth against the hard nub, just enough to
get a reaction out of the younger Winchester--a groan, long followed by a
slight intake of air. Dean smiled in spite of himself. Sam seemed to like this.
"Kinky little son of a bitch."
"Look whose talking." Sam shot back. "What else can you do?"
Dean slid back up the length of Sam's body, swinging his legs over so he
straddled his hips, leaning down he trapped Sam's arms above his head and
kissed him deeply, adding tongue this time and he rocked bak and forth. "You
mentioned dry humping erlier" he said between kisses, giving Sam another long,
tongue filled kiss "this is how you do it." Sam groaned inwardly, his eyes
fluttering closed in ecstasy as the cloth rubbed up against his cock,
pratically sending sparks going. "Oh god it's like you're fucking me already."
Sam whimpered. Dean shook his head and held Sam by the sides, kissing him
again. "You really are a virgin aren't you?" he chuckled. Sam nodded and begged
him not to stop, Dean however had different plans.
He slowed to a stop, earning a whine of protest from his brother who bucked his
hips up to keep going, but Dean put his hands down on his pelvis to make him
sit still. Sam obeyed, watching Dean slide off of him through half-lidded eyes.
Dean smirked at the small dark pre-come spot Sam made, seeing his cock twitch
under the fabric. "Ditch those" he said, snapping the waistband of the dark
green underwear. Sam obeyed, bending his legs up to pull them off of himself as
Dean reached over into his bedside drawer and pulled out a bottle
of...something. Sam spread his legs open to see what Dean had. He turned bak to
him and held up the purple bottle, beaming slightly. "Lube." he said "a gay
man's best friend."
"I thought you weren't doing anything with your...y'know." Sam said, pointing
at Dean's crotch with his foot. Dean looked down and laughed. "Oh no, not yet.
But I can use something just as good." Dean popped open the cap of the bottle
of lube and squirted some on his fingers, rubbing them together then spreading
it over the crack of Sam's ass. He squeeked at how cold it was, shuddering as
his legs twitched causing Dean to have to put his hand on his pelvis again.
"Speaking of cocks, damn Sammy." he commented, taking a hold of Sam's erection
"I might just fuck you after all."
Sam chuckled and swayed his hips at Dean. "Please start now." he asked, pushing
Dean's hand off his cock and spreading his legs more. Dean smirked in amusment
again at his kid brother's friskyness for him. He liked him like that, spread
wide and displayed out in front of him. He lowered his fingers to Sam's hole,
pressing his index finger to his hole, tighter than a pulled on knot. Sam
moaned and pushed against Dean's fingers "Dean please!" he hissed, grinding his
hips down into the bed, trying to get friction against his fingers. Dean pushed
in a little harder, slipping past a couple rings of muscle that caused Sam to
cry out. He rubbed Sammy's thigh with his free hand, reassuring him that it
would get better soon. "This is...well you can take a guess." he saw Sam was
too busy breathing to answer "it's fingering. And its a good way to find a
certian area that would make the manliest of men moan like a whore." Dean
dripped more lube into Sam's hole, helping him open a little more so he could
fit another finger in his kid brother. "if I could just figure out..." he
crooked his fingers and turned them in a circle, watching Sam's expression as
he did so. Sam suddenly bucked up and moaned in pure ecstasy, loud enough to
wake the dead. "There we go." Dean laughed, pressing his fingers to the spot
again, making Sam's back arch and cry out. "DEAN!"
"Like this huh?" Dean said, able to add another finger he pressed all three
fingers down and rubbed against Sam's prostate. Sam, who was now withering and
leaking everywhere, moaned Dean's name over and over again, followed by a spew
of sounds somewhere between "aw" and "ah" that chimmed in Dean's ears like
music. However, he didn't want to alert the neighbors and make them suspicious,
Sam was being a little too loud. Without another thought, Dean leaned over Sam
and kissed him, starting to thrust his fingers in and out of Sam's asshole
rapidly, letting him moan into his mouth as his tongue twitched against Dean's.
Sam wanted to grind against Dean so badly, get some kind of attention on his
neglected cock when Dean suddenly pulled out and slid off of him. Sam whimpered
at the loss.
"Don't worry." Dean said, shifting down so he sat between Sam's legs, running
his hands over his thighs. God, he was more amazing looking than any kind of
fucked-up fantasy he had ever jerked off to. Dean pressed his mouth to the
inside of Sam's thigh, slowly sliding his hand up the length of Sam's cock.
"blowjobs." he said, leaving a hickey on Sam's thigh then went to suck Sam's
balls into his mouth, rolling his tongue between them then letting them go with
a pop. "What you need to do first is rub, then play around a bit with your
mouth until they're dripping. To be fair though--you were already leaking
before you got your clothes off." he wrapped his fingers around the base of
Sam's dick and liked the clear stream of liquid off the head, running his
bottom lip against his skin as he went. "Your dick sucking abilities depend on
two things. One-" he drew his lips up and down his length again "your lips,
two:" to Sam's surprise, Dean slowly went down his length, swallowing it into
his throat for a ouple seconds then sliding it bak out "how far you an go."
"You have no gag reflexes." Sam giggled.
"Exactly why I'm great at this." Dean said, starting to suck again. He didn't
go all the way down again, but he went half way and used his hands to fill in
the rest, which still made Sam buck and moan, coming hard in his brother's
mouth to the point where it dribbled out of his mouth and onto the blanket. He
looked up at Sam's completely blissed out expression, his eyes only slightly
open and his mouth gaping as he gasped in air, sweaty bangs sticking to his
forehead. Dean wiped the tangy fluid off his cheeks, using his mouth to clean
Sam (and himself) off, his tongue working like a dog. Sam reached down and
lazily stroked Dean's head, trying to pull him up for a kiss but he wasn't
strong enough. Dean climbed over him again and pressed their lips together,
letting this kiss linger for a bit. Sam tasted himself of Dean, and it was
okay.
"Dean." Sam said suddenly, breaking off. "I want to taste you."
Dean raised his eyebrows, like he hadn't understood the request. "What?"
"Pull down your pants, I want it. Please." Sam looked so innocent the way he
said it, all fucked out but still wanting it. "Its only fair."
Dean nodded slowly, rolling to the side so he could slide his pajama pants down
his thighs and kick them off to join the rest of Sam's clothes. Sam reached out
to stroke Dean's cock, watching the small flow of pre-come already dripping
from it onto the bed. Dean swung his leg over Sam's middle again, straddling
him in just the right spot where Sam ould suck him. He leaned his head forward
and took Dean in his mouth as far as he ould go, bobbing his head bak and forth
as fast as he could trying to get him off. As good as it felt though, Dean
didn't want Sam getting a crick in his neck. He pushed Sam's head back on the
pillows and jerked off, holding Sam's head still as he came closer and closer
to the edge. Sam held his mouth open for him just as Dean came, admitting a
long groan as he shot into Sam's mouth, he squeezed his eyes shut to keep from
getting any in there.
"Holy shit, Dean!" Sam said, turning his head to the side to wipe off his face
with his hand.
"Hows that for facial?" Dean laughed, falling back onto the mattress next to
Sam, who nodded as he sucked the last bit into his mouth and swallowed loudly.
"Still questioning, Sammy?"
"I definitely like guys." he said.
"Good." Dean said. "I do too."
~FIN
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