Posted originally on the Archive_of_Our_Own at https://archiveofourown.org/
works/2228559.
  Rating:
      Explicit
  Archive Warning:
      Underage
  Category:
      M/M
  Fandom:
      Supernatural
  Relationship:
      Dean_Winchester/Sam_Winchester
  Character:
      Dean_Winchester, Sam_Winchester
  Additional Tags:
      Masturbation, Tender_Sex, tender!Dean, Underage_Kissing, Hand_Jobs
  Stats:
      Published: 2014-08-31 Words: 2785
****** Watch and learn, boy! ******
by ElenyasBlood
Summary
     Sam seems to have trouble getting himself off. Dean finds a way to
     help!
Notes
     This is just shameless tender!Dean coaxing Sammy through his first
     real orgasm. uwu
Sam remembered when it happened for the first time. Dean had woken up with his
boxers tented up, a small patch of dampness soaking the faded fabric where the
tip of his penis was pressed against the seam.
“Why is it doing that?” Sam had asked, curiosity rising in his chest along with
Dean's eyebrows.
“Doing what?”
Giggling, Sam had leaned in, reaching out to poke the hard flesh beneath his
brother's boxers with his small fingers just to have Dean catch them up in his
palm. “Why is it being... hard and big like that?”
There had been a dark pink flush creeping up the older boy's neck as he tried
to come up with a proper reply, his fingers squeezing Sam's hand carefully.
“It's because I'm a big boy and... sometimes it happens.”
“When?”
Dean had shrugged. “Now and then. Usually when I'm asleep or... when I wake up,
I guess. Look, I don't know, it's... a big boy thing.”
Beaming, Sam had tried to wiggle his fingers out of his brother's grip, pink
tongue poking out to nervously wet his lips. “Can I touch it?”
“What? No.” Dean's voice had sounded a little bit high-pitched by then, his
clammy palm tightening around Sam's twitching hand. “Of course not. It's not a
frigging toy.”
“But–“
“We're not gonna argue about this, Sammy. I won't let you touch it. It's...
something private and you're... Just wait until you get old enough to have your
own boner. And until then keep your eyes and fingers to yourself, would ya?”
Dean had hated to see his little brother's face fall, but the whole
conversation tasted wrongwrongwrong on his tongue and so he'd let go of Sam
before hurriedly shimmying into his jeans.
“When will I be old enough, De?”
Eyes rolling, Dean had exhaled sharply. “Soon enough. Now go get your clothes
and I'll see if I can find you some Lucky Charms, you little brat.”
And that had been the end of their conversation for the time being.
Time went on and so did the boys and though they never talked about it again,
Sam eventually did get his first hard-on at the age of thirteen and after a
series of particularly confusing dreams.
Waking up at six o'clock in the morning, clammy sheets twisted around his legs
and his hands still clenched in the pillow, he had felt a strange tingling
sensation between his legs, like an itch he couldn't quite put his finger on.
His cock had been strained, aching and touch-starved and there was a smoldering
heat lingering right beneath his boxers, burning through his flesh and setting
his skin on fire. Moaning, he'd tried to get rid of his condition, clumsily
pawing at his crotch, and after a few minutes of fumbling and bucking his hips
he'd spilled into his briefs, feeling sticky and flushed afterward.
It became a regular thing then. Sam would wake up with a boner and with his
skin crawling he'd clasp his fingers around the twitching flesh, squeezing and
rubbing clumsily until the tension would finally bleed out of him again. Biting
his lips, he managed to spill most of the time, but even after a shuddering
orgasm he'd feel somehow empty, unsatisfied and hungry.
Some nights, when Dean was already asleep, Sam would rut against the mattress,
hips thrusting against the plush cushions until the tight, hot feeling
dissolved.
Except Dean was never really asleep in those nights.
 ♦ 
They were stuck in Rufus' Cabin in Whitefish, Montana, two weeks before Sam's
fifteenth birthday. John had left them earlier that week with nothing but a
pile of canned food and a bag stuffed full of weapons and holy water. There
were no books, no TV, no distraction of any kind, and after three days of
staring out into the swampy green of the forest, Sam was ready to crawl up the
walls. Rain was pelting down outside and after three futile attempts to pick a
fight with his big brother, he decided it was time to go to bed.
Several hours and a shit-ton of water relentlessly clattering against the roof
later, Sam awoke with a start. It was still pitch-black outside the fogged
windows and with a groan the boy became aware of the increasing hardness
between his thighs, his cock aching and leaking into his pajama bottoms.
Streaks of pre-come already stained the soft fabric as Sam tugged the waistband
up, snaking his hand beneath.
He still hadn't gotten used to the shape and weight of his cock. Slightly
curved to the right side, it was hot and heavy in his palm, the tip tacky with
pre-come and there was a bed of soft chestnut curls sprouting at the base. The
skin was tight around the strained flesh, velvet-soft and sensitive to the
touch, and Sam felt a moan forming in the back of his throat as he traced his
thumb down the whole length. A shiver ran through his body and after another
couple of slow, tentative touches, he became bolder, more desperate.
Rubbing and tugging, he moved his fingers down, trailing along the vein of the
underside of his cock before following the curve up again, his hips cautiously
bucking up the mattress as he bit his lips, carefully minding his brother
sleeping in the same room. Sam was about to double his efforts in a needy
attempt to get off, when he heard the creaking of rusty bed springs. Panicking,
he felt a blush creep up his neck and chest and with a choked groan he pulled
his hand up just in time to feel the mattress dip under his brother's weight.
“Dean? What are you–“
Dean's voice was low and heavy with slumber when he spoke, his breath warm
against Sam's cheek. “Shh, it's all right, Sammy,” he whispered as he climbed
under the covers with his brother, feet brushing along Sam's calves. “It's all
right, you don't need to stop.”
“I, um, I'm s-sorry, Dean,” Sam mumbled, shuddering at the familiar feeling of
Dean's bare skin against his, their legs intertwining tentatively. “I didn't
mean to, um, wake you up.”
The low chuckle that ensued sent Sam reeling, his whole body involuntarily
curling into his brother's as soon as they were both settled, their limbs
cocooned into the clammy warmth of the blanket. “It's all good, Sammy. I was
awake before you started having fun all by yourself.”
Sam felt himself choke on his breath and he was about to deny Dean's words when
he felt the tip of a warm finger running along the seam of his worn shirt.
“Dean, what are y–“
But Dean's hand was already dipping past the frayed hem, trailing patterns on
Sam's exposed belly. “Shhh, it's all right, little brother. I can help you.”
A shiver ran down Sam's back at the sensation of Dean gently tugging the soft
curls of his happy trail and he barely managed to bite back a strangled moan,
his hips bucking involuntarily. “How d-did you know?” he wheezed, voice rough.
“Heard you having trouble, Sammy. Want me to... to show you how to do it
right?”
Gulping, Sam found himself nodding, and with a soft, shy smile curling his lips
he locked eyes with his brother. Dean's fingers were warm when they traced the
waistband of Sam's pajama bottoms, teasing the boy, making his pupils dilate
and his breath going ragged. Their rhythm was almost playful, the soft touches
sure, and Sam felt himself shuddering against his brother, his body squirming.
“Gotta take your time, Sammy,” Dean murmured, brushing his hand down the curve
of Sam's cock, only one layer of thin, damp fabric separating their burning
skin. “Gotta make it last, right?”
Nodding, Sam swallowed a lewd moan. Dean's fingers were wandering now, trailing
down Sam's cock and softly squeezing his tensed balls through the fabric before
running down his thighs, Dean's whole, calloused palm splayed on the creamy
flesh. Dean took his time rubbing the smooth skin until it was all flushed.
“Make yourself all wet and ready before you start, yeah? Trust me, it'll make
it so much better,” he whispered as pushed his mouth into the crook of Sam's
neck, plush lips only inches away from the sensitive shell of the boy's ear.
His fingers were now at the waistband again, thumbs toying with the frayed hem
and a low chuckle forming in the back of his throat at the feeling of Sam's
impatient movements towards him, those slim hips bucking and writhing beneath
his grip.
“D-Dean, please,” Sam whined, toes curling into the sheets, kicking against the
mattress. “I need... please...”
With a smile, Dean stilled his movements for just a second, savoring the
moment, before he slowly began to push the strained sweats down his brother's
lean body. “Shhh, easy, Sammy,” he cooed half-way through. “I'm here, 'm here.”
And Sam complied, his almost violent, bucking movements slowly easing as he let
his brother drag down the damned fabric. His lower lip continued to quiver,
spilling needy, little moans into the darkness.
Dean took his time getting rid of the pajama bottoms that had been riding low
on his own hips once. Slowly he brushed his hands against his brother's long
legs, feeling the smooth skin of his thighs, skimming up and down his flanks
once the offensive clothing was gone. With his other arm securely wrapped
around Sam's knobby shoulders, he cradled the boy with his whole body, pressing
Sam flush against his chest to not miss a single shudder, not the slightest
little tremor rolling through his little brother's body.
“You okay, Sammy? You good?” Dean asked after a few moments of deafening
silence, his warm breath ghosting over Sam's ear and neck, sparking shivers in
the dark.
Nodding frantically, Sam tried to push up again, feeling his brother's hand
next to his twitching cock as a heavy weight, their scents and heat mingling
beneath the sheets. “'M good, De.”
No further confirmation needed, Dean decided that he had had enough of the
teasing and so did Sam, if his trembling body and the needy moan were any
indication.
“Give me your hand,” he rasped as his fingers kept brushing through the damp
curls in Sam's crotch. “C'mon, don't be shy. No need to anyway,” he continued
as he felt Sam hesitating for the first time since their bodies had entangled
under the blanket. But there was no shame in wanting to make yourself feel good
and with a soft smile he told Sam so.
The boy's nod was slow and his lips curled into a lopsided smile, and he did as
Dean had asked. A shiver ran down his spine as their fingers threaded together,
Dean's broad palm cradling the back of his little brother's hand.
“There,” Dean murmured breathily, “now relax and just follow my movements. I'm
gonna make you feel good, Sammy. I promise.” And with a deep exhale he clasped
both their hands around Sam's cock, their fingers firmly squeezing the hot,
strained flesh.
“G-god, Dean,” Sam moaned as soon as he felt the pressure, the heavy weight of
their combined palms gripping his cock tight. “More.”
“Shhh, it's all right. You want to make sure you're ready to go first, huh?”
Dean chuckled, moving their hands up in a leisurely pace, inching towards the
leaking, pink tip. “C'mon, we're gonna do it together.”
And that they did. Rubbing Sam's palm across the sticky head of his cock, they
slicked up the boy's palm and fingers thoroughly. Relentlessly, they brushed
over the slit again and again, gathering all the glistening pre-come until each
finger and every inch of Sam's hand was covered in sticky liquid.
Shuddering, the boy pressed closer to his big brother. “Dean, 's too much,” he
whined, his lips quivering against Dean's jaw line as he pushed in.
“Nah, little brother, it's all right. You're good, trust me,” Dean murmured,
taking in Sam's heady scent, the exciting mix of clean sweat and soap rushing
through his lungs like an aphrodisiac. “Now, let's get started, shall we?”
Going slow, Dean moved their intertwined hands down Sam's cock, lazily dragging
their fingers over the hot, slick length. It was easy, a familiar movement,
practiced through lazy hours in motel rooms all over the country, and Sam's
cock was beautifully shaped, slightly curved and long and thick. The skin was
silken, hot like burning and smooth under their steadily moving hands.
Breathing labored, eyes fluttered shut and hips jerking desperately, Sam was
already close to losing it after the first few strokes. He had never felt so
strained, his nerve endings on fire. Sweat made his shaggy bangs stick to his
forehead and with a shudder he chased the friction provided by their combined
hands, currently squeezing the base of his cock.
“De, please,” Sam whimpered, tilting his head back to expose the long expanse
of his neck. The pale column of his throat was like an invitation to Dean and
the older boy dipped in, licking a long, hot stripe down his brother's neck.
Pressing a soft kiss into the hollow below his brother's throat, Dean twisted
their wrists. “Shhh, it's okay, Sammy. Relax,” he managed to pant before
feeling a pair of soft, wet lips trailing along his jaw.
Sam's breath was warm and smelled like mint toothpaste and sleep as he exhaled
sharply. “Dean, can I...” he trailed off, whining. With their combined hands
jacking him off, their pace still agonizingly slow and his body almost
vibrating out of his skin, Sam's mouth felt incredibly empty. Not knowing what
else to do, he pressed it against Dean's like they had done when they were
children only this time he hesitantly parted his lips at the sensation of
plush, warm flesh.
Their kiss was just as sweet and slow as their movements. With their hands
twisting and tracing the beads of tacky pre-come spilling down Sam's cock,
their tongues moved just as lazily. Sliding together, chasing each other's
taste, licking deep before trailing a slick path down their chins and necks and
the world was spiraling down, narrowing down on nothing but the feeling of
their combined heat beneath the covers.
“Dean, Dean,” Sam wheezed, throat tight and voice incredibly rough in his big
brother's ear. “'M close, I think.”
Humming quietly, Dean picked up their pace, fingers only slightly guiding his
little brother's hands now. His own cock was painfully hard in his sweatpants,
a damp patch steadily growing bigger in the front, soaking the fabric. But
tonight was all about Sam, about giving and cherishing and so Dean continued to
press warm, tickling kisses down his brother's neck and throat, licking the
sweat from his skin and moving their hands to the sensitive tip of Sam's cock.
It took Sam only a couple more thrusts and a knowing twist of Dean's wrist to
tip him over the edge and with a shout the boy shot his load into the sheets,
hot, sticky come spilling down their entangled fingers. Pulling soft little
moans of pleasure out of his brother's chest, Dean stroked Sam through his
orgasm, his other hand rubbing small, soothing circles in Sam's skin as he
skimmed his fingers down the slim flanks, both brothers slowly coming down from
their highs.
“Shhhh, easy. It's okay, Sammy, shhhhh,” Dean mumbled while rubbing his lips
across the sensitive shell of Sam's ear. “I got ya, shhhh. You're fine.”
And Sam hummed and whined his agreement, erratic movements slowly stilling as
he rode out his bliss. His hair and skin were sticky, his bangs drenched in
sweat and despite the utter warmth Dean's body cradled him in, he shivered. The
sheets felt clammy around their bodies.
“You okay?” Dean asked after a few minutes of breathless silence, nothing but
the sound of their chests heaving against each other in the silence. He was
still holding the boy close, fingers never stilling against the smooth skin.
Sam managed a nod, his smile small and timid. “I... Dean, um... I don't know-”
“Hey, how about getting some sleep, huh? It's still dark outside, buddy,” Dean
cut in, his grip faltering a bit. A rush of air left his lungs and suddenly
their position, and with it the familiar closeness between them, threatened to
become awkward.
Letting his eye-lids droop, Sam nodded, snuggling closer. “Yeah, sounds good to
me,” he breathed before leaning in for a soft, hesitant kiss, just a brush of
lips against lips, their tongues meeting fleetingly.
“Thank you,” he whispered then, smiling sleepily as he pushed his naked body
against Dean's, every inch of tacky, golden skin exposed to Dean's tender
touch.
 
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