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Dean hasn’t seen Sam naked since they were kids.
Sure, they’ve grown up in each other’s pockets and there have been plenty of times when they’ve undressed in the same room or partially stripped to tend to injuries, but this is the first time Dean has allowed himself to actually look at Sam’s body in well over a decade. This thing between them – the messed up, forbidden thing lurking beneath the surface of their relationship to which they’d recently decided to say fuck it, let’s do it – has finally opened that door for the both of them.
They’re both carelessly throwing off their clothes when Dean looks over at Sam hungrily, only to be stopped in his tracks by the sight before him. Sam freezes when he realizes that Dean is staring.
“What?”
Dean shakes his head, eyebrows raised in surprise. “Dude. Do you honestly think I’m letting you put that in me?”
Sam’s dick is huge, embarrassingly so. The thick shaft is red and angry with arousal, pronounced veins leading a path down its considerable length to the slick mushroom head. Heavy balls hang beneath the base, which is adorned with a neat patch of dark hair.
Sam blushes and shies away, self-consciously putting one hand over his crotch. “Oh, uh. Yeah. All right.” He shuffles his bare feet on the carpet, at a loss for what to do.
Dean eyes him and prods, “Seriously, has no one ever told you you’ve got a fucking porn star dick?” He’s too distracted right now to care about inflating Sam’s ego. Knowing Sam, he probably won’t take it as a compliment anyway.
“Um. Yeah. I mean, some girls have had an issue with it at first. But…” he trails off, peeking behind his hand to look down at his erection like he’s never considered it before. “It’s not that weird, is it?”
Dean purses his lips and sighs. Leave it to Sam to whip out the puppy dog eyes right along with his giant cock. The kid is impossible.
“Geez, Sam. You’re the only guy I know who could think having a big dick isn’t the most awesome thing in the world.” Sam still looks sheepish, so he continues, “No, Sammy, it’s not that weird, all right? Just…don’t expect to put it anywhere near my ass any time soon.”
Sam smiles and nods. “Okay,” he agrees earnestly. “We can do other stuff.”
And they do. That first time, Sam fucks in between Dean’s thighs from behind and Dean can almost believe it’s the real thing. Sam’s eager for it; he thrusts forcefully into the tight space created by Dean’s clenched legs and kisses him from where he lays spooned up against Dean’s back, stroking Dean’s cock in time with his thrusts forward. He whines into his big brother’s neck when he comes and there’s not a part of Dean that wishes their first time could have been different.
The second time they have sex, Dean pushes Sam down onto the bed and grinds their naked cocks together, trying the whole time not to think about how much smaller Sam makes him look by comparison. Dean’s dick isn’t anything to be ashamed of, but goddamn. This could give anyone a complex. Sam distracts him from his dismaying thoughts when he reaches down between them to stroke them both and uses his other broad hand to pull Dean closer so they can watch each other come with their foreheads touching.
Sam lets Dean fuck him the fifth time. Dean takes a long time opening him up, because Sam’s never done this before and he’s nervous. Dean is hyper-aware of every twitch in his brother’s muscles when he pushes in achingly slow, searching for signs of discomfort. Sam takes it like a champ, though, and it isn’t long after that tentative beginning that he’s arching and groaning with each of Dean’s thrusts. Dean makes sure Sam comes first.
It’s just about two months after their first time when Dean asks Sam to fuck him. They’d been slowly working up to it for weeks. Dean had taught Sam how to prep him, Sam had stretched Dean open with his fingers more times than either of them could count, and they’d gone through enough lube to stock a whorehouse. After a solid two months of sex in various positions, Dean feels a lot more confident in both their abilities to execute this permutation successfully.
Sam’s lubed and fingered him for ten minutes before Dean gets antsy.
“Fuck, all right. Will you come on and fuck me already, Sammy?”
“Hey, you’re the one who’s scared of my dick.”
“Am not!” Dean shoots back. He sounds like a petulant child, which is made more disturbing by the fact that he’s lying naked on a motel bed with his brother’s fingers in his ass. Sam chuckles but moves to obey. He removes his fingers and lubes them again so he can slide his hand over his cock, slicking it up thoroughly. He inches closer so he can line up with Dean’s ass.
“Any day now, Sammy,” Dean says as he lifts his ass in the air.
“God, will you calm down? I’m getting to it.”
He spreads Dean’s cheeks with one hand and uses the other to guide his cock into Dean’s wet hole. He pushes tentatively forward, but the head won’t slip in. After spreading Dean’s cheeks further and re-gripping his dick, he pushes a little harder and manages to get the slick crown inside the tight heat of his brother’s body. Sam’s pleased groan almost drowns out Dean’s grunt of discomfort.
“Shit, Dean. Are you okay?”
Dean scoffs. “Fine, Sam. Keep going.”
Sam moves the hand on Dean’s ass up to the small of his back so he can massage the muscles there while he slides the rest of the way in. Dean remains quiet through the process, but the muscles in his back are tight. Bottoming out, Sam pauses to examine where their bodies are joined.
Sam’s cock is practically throbbing inside the tight ring of Dean’s stretched, red hole. It doesn’t look like it feels nearly as good for Dean as it does for Sam.
“Dean?”
“Hmm,” Dean groans softly through closed lips.
“Is it – how does it feel?”
“Well, Sammy,” he sighs, “it feels like I’ve got a baseball bat shoved up my ass, thank you for asking.” He tries to laugh it off, but the strain in his voice is evident.
“It’s nowhere near – ” Sam stops himself before he can continue because arguing about his dick while it’s currently inside of his brother can not end well. “Okay,” he breathes, trying to hide just how desperate he is to fuck in and out of the sinfully tight pressure of Dean’s ass. “I’m going to pull out now.”
“Woah, hey!” Dean’s hand shoots back to rest on Sam’s thigh. “Don’t go anywhere.”
Sam furrows his eyebrows. “But you said…?”
“Yeah, I said you’ve got it in. Don’t go taking it out before I can even give it a shot.”
“Okay.”
Sam holds his hips as still as he can while he leans over to grab the lube from where he’d tossed it on the other side of the bed. He dribbles some onto his fingers and warms it between them before massaging it around the edges of Dean’s stretched hole.
Dean hisses but doesn’t protest the treatment. Feeling the unmistakable sensation of Dean’s hole clenching even tighter around him, Sam offers, “It’ll hurt less if you relax.”
Dean huffs in annoyance. “Yeah, I know. I’m the one who taught you all this, remember?”
And it’s true; Dean did teach Sam all about the wonders of anal sex. Dean’s the one who’s done this before, but he doesn’t seem to be reacting to it in the way either of them expected.
“I’m just trying to help.”
Dean breathes deeply and says, “I know.” He shifts his hips minutely underneath Sam’s steady weight. He hums.
“Try something. Move a little.”
Sam obeys. He pulls back just a slow centimeter or two, bracing himself for Dean’s cry of pain. All he gets is another grunt and a “keep going.” So he pulls back a little more and takes the opportunity to slather more lube onto the exposed part of his shaft. At Dean’s prompting, he pushes gently in again.
“Heh,” Dean chuckles nervously. “I’m alive.”
Sam smiles down at him and does it again, just a tiny little thrust, and it’s not nearly enough to get him off but it’s something. He watches and listens to Dean each time he moves, building up a gentle pace of shallow thrusts eased by the generous reapplication of lubricant. When Sam reaches under them to grasp Dean’s cock, he’s disappointed but not surprised to find it soft. He uses his lubed up hand to stroke it, hoping to get Dean’s body interested again, but Dean pushes his hand away.
“Leave it.”
Sam sighs but doesn’t argue, and he stops his slow thrusts shortly after because they both know it isn’t going to carry either of them over the finish line tonight. Sam pulls his persistent erection out of Dean slowly, wincing in sympathy at the sight of his brother’s gaping hole. Dean shudders once they’re no longer joined and drops down to lie boneless across the bedspread. Sam’s forehead crinkles and he twiddles his thumbs while glancing down at his still-hard cock, unsure of how to proceed.
“Can take care of that for you,” Dean says. He’s lying on his front, the pillow muffling his words.
“You don’t have to.”
“Want to.”
Sam shuffles guiltily up to him and leans down to kiss his freckled shoulder. Dean turns his head and looks up at his brother with a warm, tired smile on his face. He moves to roll onto his back but reconsiders when he winces at the ache in his ass, ending up on his side facing Sam, who’s still kneeling awkwardly in front of him.
“Do I look like an invalid to you?” Dean demands. “Get down here and be my little spoon.”
Sam smiles weakly and complies. Once he’s settled in, Dean reaches around him to grip his cock and stroke it expertly. He knows everything there is to know about getting Sam off like this, and it isn’t long before Sam’s coming noiselessly.
Dean wipes Sam’s come off of his hand perfunctorily and pulls them together with a strong arm over Sam’s chest. Sam shuts his eyes and says, softly, “I didn’t want it to be like that. I didn’t want to hurt you.”
Dean shakes his head and shushes him. “I know. Don’t be upset,” he tells him as he trails his calloused palm down Sam’s chest and over his abdomen. He kisses the back of Sam’s neck and strokes his fingers through the line of hair trailing from Sam’s belly button to his groin. His lips curl into a smirk.
“Practice makes perfect, right, little brother?”