Actions

Work Header

Show me how, please ?

Summary:

Sam comes home from school one evening and accidentally walks in on Dean jacking off, he then becomes curious which leads to him beginning to explore himself, with Dean’s help of course.

Dean is 16, Sam is 12.

Work Text:

Sam raced from the bus stop, his almost too big back pack flopping against his back with every step. He couldn’t wait to get home and tell his big brother about his day and the new friend he had finally made.

Sam struggled a bit when it came to popularity, so he was very pleased to have finally hit it off with someone, especially since Dean halfheartedly teased him about being 12 years old with no friends.

Once Sam reached their small brick home, he was nearly vibrating with excitement as he entered and toed off his sneakers. He dropped his backpack beside the door and headed for his and Dean’s shared room in order to wait for his brother to get home since the high school dismissal was a bit later than the middle school.

He opened the bedroom door only to quickly realize his brother was already home. Sam furrowed his brow and was just about to speak up to ask why he was home already when a low moan left his brother’s parted lips.

Sam’s breath caught in his throat and he couldn’t quite tear his eyes from the situation before him. Dean’s freckled cheeks were painted a gentle pink, his head was tilted back against the headboard exposing the flushed skin of his neck, his lips parted ever so slightly- Sam hadn’t ever seen Dean like this and he was confused as to why his stomach felt like it was doing somersaults.

Dean hadn’t realized Sam had entered the room so he continued to pleasure himself, sliding his fist down the length of his shaft and groaning as his hips bucked up into the pressure of his fist.

Sam gawked at his brother, allowing his eyes to travel down to Dean’s lap where his hand was wrapped tightly around his hard member, precum glistening against the flushed tip.

Dean shifted slightly to make himself more comfortable only to open his eyes and quickly realize that he had company.

“God damn it Sammy !” Dean yelped, clambering to pull his jeans up and cover himself. “You should’ve knocked.” Dean grumbled, pulling a pillow to cover his lap.

“It’s my room too.” Sam huffed, walking over to climb up onto Dean’s bed. “What were you doing anyways?” Sam questioned, furrowing his brow. Dean felt his face burn hot with embarrassment. “Don’t play dumb Sam.. you know what I was doing.” Dean answered, shifting slightly to not be sitting so close to his little brother as he felt it was awkward to discuss and be sitting close enough to have their legs touching.

“I know you were touching yourself.. but why ?” Sam questioned innocently. “Why was it so hard?” He added, staring up at Dean. Dean cleared his throat. He had come to the realization that Sam really didn’t know much about sex or anything related quite yet, after all Sam had been a fairly innocent child despite being in public school.

“Jesus Sammy.” Dean breathed out, throwing his head back against the headboard with a gentle ‘thunk’ and a defeated sigh. “You really don’t know huh?” He squeezed his eyes closed as if mentally preparing himself for the conversation he was about to have.

“When you go through puberty it gets hard.. sometimes for no reason… and you can make yourself feel good by playing with it…” Dean explained, toying with the edge of the pillow that rested in his lap.

“Mine gets hard sometimes but I don’t touch it very much.” Sam answered, rubbing his hands against the thighs of his jeans. “It’s hard right now.” He added nonchalantly. Dean nearly choked at Sam’s admittance.

“Sammy, you’re not supposed to tell me that.. you’re supposed to take care of it while you’re alone… like In the shower or something.” Dean answered, continuing to fidget with the hem of the pillowcase.

“I don’t know how to make it feel good though.” Sam answered, placing his hand over the small tent in the crotch of his jeans. Dean let his gaze travel to the younger boy’s hand before snatching his attention away and mentally cursing himself for even looking at Sam that way.

“You just gotta find what feels good for you… play with it and see if you like it fast, slow, hard, whatever makes it feel good…” Dean tried to explain as Sam furrowed his brow in thought.

“What do you like?” Sam questioned, spreading his legs further apart to make himself more comfortable. Unfortunately for Dean, that meant closing the gap he had purposely put between the two boys on the bed.

“Uhhh..” Dean’s cheeks flushed. “I’m not sure we should be discussing this Sam..” he answered earning a frustrated groan from his younger brother.

“Can you just show me then? I don’t know how to make it feel good.” Sam asked nonchalantly. Dean chewed on his lower lip, contemplating whether he’d be okay with crossing a line at this point. His brain was screaming no but his dick was doing the exact opposite.

After what felt like an eternity of silence, at least to Sam, Dean finally removed the pillow from his lap to reveal his tented jeans.

“You can’t tell anyone I’m showing you how to do this, got it? “ Dean warned. Sam nodded quickly.

“Okay…” Dean breathed out as if to collect himself. “You gotta undo your jeans and pull it out of your underwear.” Dean instructed, unzipping his own jeans and pushing them down to his mid thighs. He hadn’t buttoned them back up earlier when He was in a rush to cover himself so he could skip the first step himself.

Sam lifted his hips and slid his jeans and boxers down to just above his knees in one swift motion. His hard prick sprang free, smacking against his lower belly from the sudden motion and earning a gentle gasp from his lips.

Dean’s mouth went dry at the sight before him: his baby brother, cheeks flushed a gentle pink, bare pale thighs, his hard little cock nudging against his belly.

“Good… “ Dean breathed out, reaching down to free his own now throbbing cock from the restraint of his boxer briefs.

Sam licked his lips at the praise, allowing his eyes to flicker from Dean’s face to his lap and back.

“Here.. take some of this.” Dean instructed as he reached to the bedside table to dig in the drawer and retrieve a small bottle of lube. He squirted some onto his own flushed member and moved to drop a nice sized glob on Sam’s as well.

Sam shuddered as the cool goo slid down his shaft. He watched carefully as Dean used his hand to smear the lube across his own member before attempting to mirror him.

“This will help it not get raw from friction burn.” Dean informed him, tucking his lower lip between his teeth as he slowly started to stroke himself like before.

Sam nodded slowly, watching as Dean started to stroke himself. His stomach still felt like it was cutting flips and he couldn’t help but stare as Dean played with himself.

“C’mon Sammy.. you try it.” Dean encouraged, flicking his wrist to toy with just the head of his member. A gentle breathy sound left Dean’s throat and Sam found himself biting his lower lip nearly hard enough to taste blood.

He wrapped his fist around his own member, stroking to smear the lube like Dean had done to himself moments before. He gave long slow strokes, watching the way the lube glistened beneath his hand with each movement.

Dean leaned his head back against the headboard allowing his eyes to flutter shut as he began to stroke his full length once more.

Sam furrowed his brow attempting to match the pace Dean was holding on himself. It felt good.. better than any time he’d touched himself before but not quite as good as Dean seemed to be feeling.

Gentle breathy groans were leaving the older boys lips & his breathing was picking up. Sam could see his thighs tense every so often and he found himself wondering why it didn’t feel that good to him.

Dean felt Sam still beside him and he lifted his head to see what had happened. “What’s wrong Sammy?” He questioned, stopping his own movements.

“Just doesn’t feel that good.” Sam frowned, using his hands to cover himself as suddenly felt very embarrassed to be exposed.

Without thinking, Dean knocked Sam’s hands away from himself and wrapped his hand around his brother’s shaft. Sam’s hips stuttered and he failed to bite back a surprised moan.

“D-Dean..” Sam stammered out, swallowing thickly. “I’m gonna help you.” Dean responded, glancing up to lock eyes with his brother. “That okay?” He questioned carefully. Sam nodded feverishly. “Yes.. p-please.”

Dean smirked. “I mean.. I could just let you figure it out on your own.” He teased, laughing gently at the furrowed glare from the younger boy.

He slowly drug his fist up and down, watching Sam’s reaction to judge what the boy liked and didn’t. Once he found a speed and pressure the younger boy seemed to really enjoy, Dean stuck with it matching the pace with the strokes he offered himself with his other hand.

After a few minutes Sam’s breathing had become labored and his thighs were trembling. He was doing his best to stay quiet but gentle moans managed to escape every so often.

“D-Dean!” Sam croaked out. “F-feels like I’m gonna pee…”Sam warned, trying to squirm from his brother’s grasp.

“It’s okay Sammy, relax…” Dean chuckled, flicking his wrist to toy with the younger boy’s head.

“Uunngghmmyygodd dddeannn..” Sam groaned as thick white ropes of cum coated his belly and Dean’s fingers.

Just the sound the younger boy had made alone was almost enough to bring Dean to the edge. With a few more pumps of his hand Dean was cumming alongside his brother, stroking them both through their orgasms.

With a satisfied groan, Dean fell back against the pillows. After he caught his breath he reacted to the bedside table and grabbed tissues to wipe his hand and belly clean.

“How was that?” He questioned. Sam smiled sleepily. “Very good..” he yawned, scooting down to lay next to his brother in the pillows. Dean grabbed another few tissues to clean Sam’s belly too. Tossing them into the trash, Dean then shifted to wrap his arm around the younger boy and pull him in to cuddle.

Dean wasn’t usually much of a cuddler so Sam would definitely enjoy as much of that as Dean would offer. He snuggled against Dean’s bare chest and sighed contently. Dean smiled, resting his chin on top of Sam’s head.

“Can we do that again sometime?” Sam questioned, failing to suppress another yawn.

“We will talk about it later, just lay here for now.” Dean answered, tangling his fingers in his brother’s hair. Sam nodded softly and used his hand to trace gentle patterns on his brother’s skin.

Dean knew this was something that probably shouldn’t have happened but he didn’t want to freak Sam out or himself (more than he was already beginning to for that matter). He sighed softly choosing to focus on the warm, comforting embrace of his brother rather than the mistakes he had just made.

“I made a friend today, D.” Sam hummed sleepily against the older boy’s chest.
“That’s great Sammy.” Dean whispered, placing a gentle kiss to the top of his head once he was sure the younger boy had fallen asleep.