
Posted originally on the Archive_of_Our_Own at https://archiveofourown.org/
works/455805.
  Rating:
      Explicit
  Archive Warning:
      Underage
  Category:
      M/M
  Fandom:
      Supernatural
  Relationship:
      Dean_Winchester/Sam_Winchester
  Character:
      Dean_Winchester, Sam_Winchester
  Additional Tags:
      Underage_Sex, Top!Sam
  Stats:
      Published: 2012-07-10 Words: 787
****** How Many More Times ******
by myoldsupernaturalaccount
Summary
     The first time Dean lets Sam fuck him, instead of the other way
     around. Sam is sixteen.
Dean loved Sam.  Dean loved fucking Sam, his little ass clenching hard around
him as his brother moaned like a five-dollar whore and drew him deeper with his
ankles locked behind Dean’s waist.  Dean loved being on top.
Dean also loved Sam’s cock.  It was beautiful, thick and long and especially
large on Sam’s lanky sixteen-year-old frame, and Dean couldn’t stop thinking
about feeling it inside him.  He fantasized about Sam fucking him when he
jacked off in the lukewarm motel shower, one hand twisted behind him to get two
fingers inside himself, but it wasn’t ever enough.  Dean wanted more, and he
resolved to get it.
Sam was on top of Dean almost as soon as they got inside the room after the
endless car ride from the high school, all soft lips and roaming hands, and he
tugged Dean down to the bed on top of him, shedding his clothes and immediately
trying to get Dean’s hand between his legs, searching for his fingers to prep
him.  Dean grabbed his wrist with one hand and pressed the other flat against
Sam’s chest where the fabric of his shirt gapped open, half-unbuttoned.
“Stop,” he said firmly, stomach twisting as Sam’s expression turned confused-
hurt, and then his brother’s lips were parting in a little “oh” of
understanding as he flipped them over so Sam was lying across Dean’s chest and
Dean’s legs were splayed wide around him.
“Fingers,” Dean reminded the stunned Sam, and that snapped him back to the
present, a slow smile spreading over his face as he kissed Dean again and wet
his fingers in his mouth.  Dean bit his lip in arousal at the memory of those
pretty pink lips around his cock instead of long, slender fingers, but then Sam
was pressing those long, slender fingers inside him, two at once, which burned
a good burn that he pushed back against, lifting his hips up the mattress to
give Sam a better angle, his head falling back against the pillows.
Sam’s confidence grew by the moment, kissing over Dean’s chest, mouthing at his
nipples and smiling every time his older brother gasped or moaned.  He began to
tease, dragging his fingers in and out, scissoring experimentally, until Dean
was all but writhing beneath him, whimpering unashamed little pleas for his
baby boy to please fuck him already, please, please, oh God please.
Dean always insisted they use a condom, because who knew what he might have and
he didn’t want his Sammy catching whatever it was, and he was pleased that Sam
remembered that rule.  Sam’s fingers were clumsy as he fumbled the condom on,
taking way too long as far as Dean was concerned, but soon enough he was trying
to get into a good position as Dean propped his own hips up with pillows - he
knew Sam liked to fuck face-to-face the best.
Sam grit his teeth and groaned as he carefully eased himself in, again taking
way too long, but Dean was tight, very tight.  Dean felt like he was splitting
in half by the time his baby brother was seated entirely inside him.  It felt a
million times better than his fingers ever did.  He yanked Sam down for a kiss,
fingers tangling in that stupid shaggy hair as they breathed hotly into each
other’s mouths.  Dean rocked his hips, urging Sam to fuck him already, and his
brother seemed to get the message, starting slow, almost like he was afraid to
hurt Dean, but with more encouraging moans and hair pulling from Dean he got
into it more and more, until their hips were slamming together with every hard
thrust.
Being a sixteen year old boy, it didn’t take long at all for Sam to climax,
gasping against Dean’s neck as he came hard inside him.  Dean didn’t care that
he hadn’t come yet.  This was for Sam.  It was always for Sam.
Sam, however, did seem to care, because almost as soon as he’d pulled out and
thrown away the condom he was wrapping his long palm around Dean’s dick,
stroking him with a trembling hand.  It wasn’t the best hand job Dean had ever
gotten, but it was Sam, and Sam was smiling against his lips and his cum soon
dripped over Sam’s lovely fingers.  Dean was only dimly aware of Sam wiping his
hand on a bunch of tissues and then he was curling up against Dean’s side,
slender limbs tangling with Dean’s.
They were silent for a long time, eyes closed, hearts matched beat for beat,
and then Sam spoke.
“I’m gonna fuck you every time I can get you alone,” he declared.
Dean laughed.  “We’ll see about that, baby boy.  We’ll see.”
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