Posted originally on the Archive_of_Our_Own at https://archiveofourown.org/
works/2340911.
  Rating:
      Explicit
  Archive Warning:
      Underage
  Category:
      M/M
  Fandom:
      Supernatural
  Relationship:
      Wincest, Weecest_-_Relationship, Dean_Winchester/Sam_Winchester
  Character:
      Sam_Winchester, Dean_Winchester
  Additional Tags:
      Masturbation, Voyeurism, Anal_Fingering, Anal_Fisting
  Stats:
      Published: 2014-09-21 Words: 1800
****** Curiosity Doesn't Necessary Kill ******
by FarTheSuperFan
Summary
     Sam Winchester is a curious kid, and Dean Winchester is very
     promiscuous.
Notes
     Sam is underage, around fourteen.
See the end of the work for more notes
Sam Winchester was a curious kid. Always had been and, considering the way he’d
been raised, he had every right to be. It would sometimes get on Dean’s nerves,
though; occasionally he’d feel as if Sam was interrogating him, or just trying
to annoy the holy hell out of him with the constant observations and
questioning. “How come we don’t have a mom,” “Why do we always have to move
around,” “Where’d dad go?” It took some getting used to, but Dean eventually
figured out the best ways to answer these types of questions: usually with a
witty retort, or some kind of partial-truth answer. He never told Sam the whole
truth about who they are and what their Dad does, though. He wanted Sam to be a
kid just a little while longer, wanted to protect him and keep him safe. When
Sam started asking questions about how to talk to girls, well, Dean was always
comfortable with those sorts of questions. Hell, he was comfortable rattling
off about at least a dozen answers to every sex and romance question Sam had
asked him. Dean was comfortable answers every sex question, except one.
“You want to know how to do what?” Dean asked.
“How to make…you know…masturbating…more satisfying,” Sam replied.
Dean stood there, in the middle of this week’s grimy motel room, eyeing his
little brother. Of course Dean knew how to make masturbating more satisfying.
He picked up little tips and tricks along the way while hooking up with various
women of all ages and sexual experiences. This one Texan bar tender that had
served their dad at some local diner opened him up, quite literally, to the
stimulation of his prostate. It was weird at first, and caught him completely
off-guard, but he was too immersed in the pleasure it brought him to stop and
question the twenty-something waitress. It was the most satisfying sex he’d
ever had, and he continued that practice by himself almost daily. But telling
Sam all of this…well, Sam might be disgusted by Dean, and Dean just couldn’t
live with himself if his brother thought he was a freak and refused to even
look at him. That was the worse case scenario, of course.
“What? They don’t teach this in sex ed, Sammy?” Dean replied sarcastically,
with a look that, very poorly, tried to cover up his discomfort.
“Dean, I’m serious.” Little Sammy, always so serious.
Dean hesitated for a little bit, shifting his weight between his feet. He
looked briefly around the room, seeming a little too interested in the patterns
of the uselessly thin curtains and the odd stains that littered the grey couch.
After a few moments, he sighed and rolled his eyes, closing them before meeting
Sam’s.
“Okay, listen. There is this one thing that I do sometimes. But you can’t freak
out. I swear if you freak out, I’m –”
“Dee, just tell me,” Sam interrupted, annoyed. He knew his brother had a
reputation of being promiscuous. In fact, Dean practically made sure Sam knew
the details of each one-night stand, to the point where Sam felt as if he had
watched the scenes Dean described, instead of feeling like he was listening to
a story. While he waited for Dean to speak again, Sam’s eyes never left Dean’s
face.
“Don’t ask me how I know, but…play with your ass occasionally, you know, like
when you’re rubbing one off in the shower or something.” Dean’s answer was not
at all what Sam expected. Sam wasn’t really sure just what he was expecting,
but that certainly was not it. As embarrassed and uncomfortable as Dean was, he
studied Sam’s face, looking for any signs of disgust or rejection. Instead, he
saw Sam’s brows furrow together, a quizzical expression crossing his still
delicate teenage features.
“Play with my ass? How?”
“Jesus, Sammy, you can google that! You don’t need me to break it down for
you.” Dean turned away, embarrassed. But he knew from previous experience that
Sam was going to keep prying unless he got a direct answer.
“I can show you, if you want,” muttered Dean, barely opening his mouth to speak
the words. “If you’re really interested, I can show you what I do.” He couldn’t
resist those puppy dog eyes Sam threw at him.
Sam was breathless as Dean began stripping off his shirt and shedding his
pants. Sure, he’s seen his older brother naked before, close quarters and all
was part of the lifestyle, but this felt different. All of these new feelings
Sam was experiencing went straight to his quickly hardening dick. He proceeded
to watch closely, forcing himself to breathe as Dean slowly, almost teasingly,
removed his boxers. With his clothes now in a pile on the floor in front of
Sam, Dean turned and walked slowly to the bed, trying not to smile as he felt
Sam’s eyes on his ass, and lied down on his back.
When he finally remembered that, yes, he did have full control over his body,
Sam cautiously followed Dean into bed, sitting on his knees in front of Dean’s
spread legs. Dean wasn’t much for exhibitionism, but he laughed under his
breath when he saw Sam seated in front of him. He mumbled something, and then
closed his eyes, slowly getting himself in the mood. It was in this moment that
Dean figured out he definitely has stage fright.
Dean circled his nipple with the pad of one of his fingers, slowly and gently
at first, then began to pinch it. Small moans managed to escape from his mouth
as he bit his bottom lip to quiet himself, and couldn’t stop himself from
rolling his hips. Sam shuddered and almost couldn’t resist grabbing his hard-on
through his jeans. He knew that his was a big step for Dean, and he didn’t want
to distract him; he wanted Dean to stay in the moment as if his little brother
wasn’t even there. Both nipples were red and hard now, and Dean continued to
move down his body, ghosting over the area right above where his treasure trail
was the thickest. Dean was really sensitive there, on his lower belly, and it
tickled just barely running his fingers over it. He grinned subtly and took his
dick in his hand, flicking his wrist to the very top of his penis, lathering
the rest of his member in pre-cum. A high-pitch moan came out of Sam, who froze
as soon as the sound left his mouth. Dean’s eyes fluttered, but he refused to
open them and acknowledge Sam.
He worked his dick faster now, slicking his fingers in enough pre-cum to
provide lubrication. The hand that was previously stroking his dick moved down
to his ass, being replaced by his other hand. Dean treated his ass like he did
his nipples, circling his tight entrance and occasionally dipping a finger in,
moaning. Sam blushed and palmed the hard member in his jeans, never taking his
eyes off of his older brother. After quite some time, Dean began fucking
himself on one finger, excess lube causing the most obscene and delicious
noises imaginable. Squeezing his eyes tighter, Dean inserted another finger,
thrusting them in and out ferociously, moaning like a whore. Dean’s been
fingering himself for a while now, ever since that waitress back in Texas. By
now, he’s figured out what he likes, what he doesn’t, and how to nail his
prostate to create the most blinding orgasms without even laying a hand on his
penis. Once, while Sam was at school and John was away on a hunt, he spent the
entire day fingering himself. He especially loved fucking himself without lube,
loved the wonderful pleasurable burn it created. Dean also figured out that the
necks of empty beer bottles provided even more pleasure than his own fingers.
They could go deeper than his own fingers ever could, and could stretch him
wider.
“Oh, god,” Dean moaned, rolling his lips and scissoring his fingers. He had
abandoned his dick by now, not purposefully though. He was just too caught up
in the sensation of rubbing against his prostate to focus on his dick. Besides,
playing with his ass provided much more pleasure than stroking his dick. Three
fingers in now, and he already felt so full. Wanting to provide a show for Sam,
he attempted four. Dean had never done any more than three, so he used his free
hand to grab the lube from under his pillow and squirt it on his fingers
generously, still avoiding Sam’s face.
“Oh, fuck. God dammit, oh my god, ahhhh,” Dean yelled, shoving a fourth finger
in his ass to accompany the previous three. “Yes, yes…fuck, yes!” Dean’s face
contorted and he bit his lip. He wasn’t really sure when he put his fifth
finger in, but he felt the extra burn and fisted himself faster. “Shit, oh my
god. Fuck! Yes!”
Sam was transfixed by the sight of Dean’s entire fist in his own ass, and it
was just too much for him to handle. Without even thinking, Sam yanked his
zipper down and grabbed for his cock underneath the elastic of his boxers.
Shuddering when his hand wrapped around his dick, Sam practically screamed a
chant of “god fucking dammit, oh my god, Dean, Dean, yes! Dean!” Coming with
Dean’s name on his lips, he looked up at his older brother, who was looking
right back at him intently. Dean’s face was red, and his hair stuck to his
forehead. He looked fucking wrecked. Dean continued to fuck himself with his
fist while looking at Sam, without even blinking. He came with a scream,
continuing to shove his fist in and out until the last drop of come landed on
his chest.
Breathlessly, Dean watched Sam come down from his own high, all red-faced and
sweaty, just like his older brother. Sam crawled up next to Dean, leaving his
previous position from in between Dean’s legs. For a minute, both of them were
quiet, trying to control their breathing.
“Holy shit,” Dean finally breathed, breaking the silence.
“I know,” Sam agreed. “Thanks, for showing me that, Dee,” he said, contouring
himself against Dean’s solid, strong figure. Dean brushed the hair out of his
baby brother’s face.
“You’re welcome, Sammy. But don’t go using up all the hot water in the shower
now that you know this. I need my own alone time, too, you know.”
Sam shot him a look. Not quite a bitch face, like Dean expected. There was
something hopeful in his eyes, something clouded with lust. Something that said
Sam wanted this to continue, to go further. Dean was screwed. “Jerk,” Sam
grinned, nudging his brother lightly.
“Bitch,” Dean smiled.
End Notes
     This is my first time writing fanfic. Comments appreciated!
Please drop_by_the_archive_and_comment to let the author know if you enjoyed
their work!