Work Text:
Puberty is hard.
Especially when you're Sam Winchester and your older brother is oddly obsessed with it. Not that Sam noticed really, but he was a little weirded out when he turned twelve and Dean kept giving him skin mags. Some new, some old with pages sticking together. After carefully prying those pages open, Sam found that a lot of them featured slender brunette women. Not that he really understood why the pages were sticky, he just figured maybe Dean looked at these while he was eating and it was simply sauce and grease smeared over it, but he could tell that these pages were 'used' most often.
With them being on the move all the time, it was hard for Sam to get a proper education. He was in and out of schools, which he was a little happy about, considering each school he went to he ended up being made fun of, called a freak. But the other part of him was upset that he was being taken away from his learning, and socializing. With this, Sam severely lacked knowledge of human anatomy and bodily functions. Thank God for his big brother showing him porn, how else would he learn?
Just a week after Sam's birthday, Dean had sat him down on the end of one of the odd-smelling motel beds, and popped a tape into the player. Sam was about to complain that "This movie has terrible acting" before the woman in the video took her clothes off. That was the first time Sam's body had a reaction he didn't quite understand yet. And it only got worse with the more inappropriate media Dean would show him.
Which is why tonight, when he's certain his brother and father are going to be gone for at least two days, he settled himself onto this week's motel bed and got busy. His face burned slightly as he chose a random magazine from the literal pile Dean had provided him with, flipping through until he found one with a woman he found especially good looking. Dark hair, beautiful eyes that Sam can't discern if they're green or blue -- what with the poor motel lighting and the fact his vision is blurred with shame and arousal.
His nervous eyes darted to the door for the hundredth time that minute , worried that John and Dean would just happen to return right as he started. When nobody came in, he took a breath and started shuffling out of his pants, and his Spiderman boxers that were getting too small for him, but he wasn't quite ready to let go of. He looked at his hard cock, only feeling his face get hotter at the sight. One time, he'd walked in on Dean while he was peeing, and of course his curious eyes wandered and he got a glimpse of his big brother's dick. It was soft, of course, but still bigger than Sam's was. Poor Sammy wondered if his own cock would get as big as Dean's.
Once he snapped out of his weird trance, he started stroking himself slowly, looking at the image of the woman on the page. It felt okay. Sam didn't realize it'd feel a hell of a lot better if he got it wet first, obviously. Not that this was his first time trying this, no, he'd tried before. He just didn't understand it, so he'd get confused and frustrated and just give up. He knew he was doing the right thing, he'd watch the men in those videos do this right before that weird, stringy liquid would come out. With all of his 'failed' attempts, he was starting to wonder if only grown-ups were capable of having that happen.
His gaze kept darting between the magazine and his cock. He was waiting for that liquid to come out. He's already getting frustrated again. His hand tightened around himself and his eyebrows furrowed together, but his face quickly relaxed when he realized it felt better now that his hand was more firmly gripping his dick. Sam started to go faster, and he got so excited when he saw a tiny drop of liquid forming at the tip. Unfortunately, that was when the door opened. It was Dean.
Sam froze before he tossed the magazine away from himself, frantically trying to drag the too-tightly-tucked motel blanket over his crotch. "I'm sorry! I'm-- I thought--" God, he was starting to cry .
"Heyheyhey, Sammy, Sammy," Dean shut and locked the door behind him as he raced over to the bed, cradling Sam's wet cheek in his dirtied hand. "It's okay. Why you cryin'? You were having fun, right? Sammy, that's what the magazines are for." He gave a breathy chuckle at the end, hoping his smile would soothe his baby brother.
Dean is doing a good job of comforting Sam while his brain fries itself over the fact he just walked in on him jerking off. As much as he wanted to obsess over it, that would have to wait, because he does want Sam to stop crying. He feels kind of awful that he interrupted, but simultaneously oh so grateful. Dean thinks for a moment that maybe there is a God. Though, that doesn't make sense, because if there was, he probably wouldn't be encouraging this... Whatever.
"I was having fun, yeah, but-- De, 's embarrassing..." Sam hiccups, his big wet hazel eyes staring at Dean. He does think, though, at least it wasn't John. Oh, shit. John. "Wait-- where's Dad? He's gonna see me crying n' get mad, crap--!" His clean hand flies up to his face to quickly wipe away his tears.
"It's alright, Sammy, Dad's still out. He won't be back for another few days, 'kay?" Dean's hand pet Sam's hair out of his face. "You looked like you were mad at it when I came in, dude, what was goin' on there?"
Sam let himself relax when he heard that their father wouldn't catch him crying. But then he felt embarrassed all over again when Dean mentioned what he was doing.
"I-- I was trying to get the stuff to come out. Y'know, the... the white..." Dean felt his chest ache when he realized just how innocent Sammy still is. He didn't even know a single word for semen.
"That's called semen, Sammy. But don't call it that when you're with a girl, you call it 'cum' then." What? Dean Winchester is no teacher, okay?
"..Oh. Well, I was trying to get it to come out, like in those videos you show me. But I couldn't. It was kinda working, I think, but then you came in..."
"Sorry. Hey... I can teach you. How to make it come out. It's actually really important, I think you need me to teach you." Dean has almost never felt so dirty in his fucking life. He feels like a total and complete scumbag. But he isn't stopping himself.
He felt even worse when Sam agreed with nothing but trust in those cute little puppy-dog eyes. Dean nodded and went to go wash his hands. If he had to teach him hands-on, he didn't want his hands to be covered in filth from the hunt he'd been helping their father on. When he came back into the room, he could have fucking passed out. His little brother Sammy, now uncovered, lying there and waiting for him. He still looked shy, but he wanted it. He wanted Dean to teach him. If only it was with pure intentions...
"Alright. So, you had it. Go ahead n' put your hand around your cock again." Dean sat on the end of the bed, fighting hard to keep his hands in his lap rather than touching Sam. Once Sam had done what he was asked, Dean continued. "Nice. You were missing a step, though. Too dry, it feels a million times better when it's wet. That's why when you get with a woman, you gotta get her pussy wet first before you touch her, remember that."
Sam almost asked why you would have to get a woman's cat wet before you have sex with her, but then he remembered the words Dean would mumble to him as they'd watch porn together. He did note that, though, for a later date.
Dean wanted to spit on Sam's cock and lubricate him like that, but he felt like his brother would think it was too far, so he went for the safer option and fished the small bottle of lube out of his duffel bag. He grabbed Sam's small wrist, pulled his hand away from himself for a moment, just to put a fair amount of the lubricant into his palm. It wasn't a lot, considering Sam's size -- he is only a kid, after all -- but it definitely got the job done. Dean's hands gripped his thighs harder than ever before at the pleasured noise Sam let out at the feeling. That would play on repeat in his mind for the rest of his fucking life.
"Feels good, Sammy? Talk to me." He hoped his little brother didn't realize the sudden gruffness in his voice when he spoke again.
"Y-Yeah. Feels better. It--" Sam was cut off by a pathetic, high pitched noise ripping from his throat when his cock twitched in his hand. He sped up, his chest rising and falling quickly as he started to pant.
Dean could recognize that Sam was getting close. He was proud of his little brother for reaching his very first voluntary orgasm (as opposed to the involuntary ones he had in his sleep without even realizing, just waking up to his boxers all sticky). And he was the reason for it, in a way. He was present for it. All because John got angry at him and kicked him off of the case so he got to come back early. The butterfly effect, or whatever the hell.
"Dean, I don't-- why's it--" Sam couldn't even form a sentence due to the pleasure building up as he fucked his fist. He was a little worried about the feeling of his orgasm coming up, only because he'd never felt it before. He was aware he could just stop to ask Dean what was happening, but it felt too good, he almost physically couldn't stop.
"Feelin' good, Sammy? Keep going, don't stop now." Sam wasn't looking at Dean, his eyes closed long ago from the pleasure, but if he was looking at him, he'd catch him palming himself through his jeans that'd gotten uncomfortably tight since the minute he walked back into this God forsaken motel room.
Dean just couldn't help himself. He felt like such a dirty, disgusting pervert -- and he is one. No normal person does this. No normal person would have been waiting for a moment like this, thinking about it for years. He wanted to pull his own cock out of its restraints, make Sammy jerk him off with his soft, small hands, but that would have to wait for another time. Right now it was just about Sam and his pleasure only.
When Sam finally felt that white liquid he'd fantasized about seeing in real life and not just those weird videos Dean showed him, he smiled. That made Dean come in his pants like a... Well, like Sam had been doing without realizing. Watching the genuine relief and excitement on his baby brother's face when he realized he'd reached such a goal was the hottest, yet cutest thing he'd seen in his entire life. He could die happy now.
Sam remembered that he could stop now that the white stuff -- semen, he now knows it as, thanks Dean -- had come out. He whimpered as he peeled his sticky hand away from his twitching cock. His blurry eyes opened again, first landing on his crotch. He was slightly disappointed in the amount that'd come out, since in the videos he'd seen, it would usually be way more than that. But he knew he did it right, because it was Dean that taught him how to do it. Speaking of, once he pulled his eyes away from the mess he'd made all over himself, he looked to Dean.
Sam had never seen Dean like this, face flushed, plump lips parted and wet, and his usually bright green eyes suddenly... Dark. Predatory is the right word, but Sam doesn't know that. Maybe a few years down the line, when he's smarter and understands the world and people better, he'll find out just how wrong this all is. How awful it makes Dean. But maybe he won't care when he finds out, because Dean is still his big brother, right?
Dean was in a little bit of a trance, but when he came to, he smiled at Sam a little. When Sam smiled back, so proud of himself, so thankful for Dean teaching him, this almost felt right. Like he didn't just do something so disgusting that he'd probably consider putting a gun in his mouth for later.
He told Sam to stay there and he'd clean him up, so Sam didn't move. When Dean returned, he was holding a wet towel and came to wipe the stickiness from his little brother's hand and crotch. There was a wet patch Sam noticed at the front of his big brother's jeans, and he almost thought that maybe Dean had semen come out too. But that's impossible, he wasn't touching himself, right? So he cluelessly chocked it up to Dean having accidentally splashed some water there and it made a conveniently placed wet spot.
Dean was about to walk away to change out of his clothes that were now not only dirty from the hunt cut short, but now he'd jizzed in them, too. But before he looked away from Sam, he started pulling up his Spiderman boxers.
"You still wear those things? Sammy, I st--" No, don't tell him they're stolen. "I bought those for you when you were seven."
"Spiderman is still my favourite... They are getting really small though. Do they come in bigger sizes..?" Sam asked as he moved to grab his pants from the end of the bed. Dean almost forgot to answer as he caught the sight of the Spiderman boxers hugging Sam's cute little ass so tightly it seemed like they would burst.
"Uh-- probably, probably. Yeah. I can check. Batman's cooler."
"No he's not!"
"He is! You just like Spiderman 'cause you're a freakin' nerd!"