Dean stared at the ceiling, humming happily as the cell pressed against his ear buzzed. He was sprawled on top of the covers of a hot Louisiana motel, wearing nothing but a pair of boxers and waiting for Sam to pick up the phone. He’d be in Sam’s room in a week, but that wasn’t nearly soon enough.
The phone stopped buzzing as Sam picked up. “Dean?”
“Hey, little brother.” Dean stretched on the bed. “How’s Stanford?”
“Good, I got into all the summer courses I wanted to take. Everything on track for your visit?”
“We’re all good.” Dean rubbed his palm over the front of his boxers absent-mindedly. “Wish I was there right now.”
“Yeah, me too. I’m getting tired of sleeping alone.”
Dean chuckled. “Thought you were sleeping with half the school, Sammy?”
“You know what I mean.”
“Yeah. I miss you too, kid.”
There was silence from the other end for a moment. Then Sam cleared his throat. “Hey, Dean, speaking of that... some time when you’re visiting, do you think you could try... um...”
Dean grinned and squeezed his soft cock eagerly. “Mmm, try what, Sammy?”
“...Do you think you could try bottoming?”
Dean’s hand froze mid-jerk and he gave the ceiling a perplexed look. He licked his lips, his face starting to heat. “Uh... lemme make sure I heard that right... You want me to bottom?”
“Yeah. Don’t get me wrong, I love riding your dick. And the mutual blowjobs are awesome. But, you know, I like topping too.”
Dean was pretty sure his brow would be stuck in a permanent furrow after this. “Uh, don’t get me wrong, Sammy, but I thought... you know, I thought you liked being pushed around and ‘owned’ or whatever.”
Sam laughed. “Dean, I’m not asking you to be a submissive for me! Just a bottom. I still want you calling the shots and pushing me around.”
“Just...” Dean gestured. “With your dick in my butt.”
“Yeah. I’d like it a lot.”
Dean rubbed a hand over his forehead and managed a smile. “Well fuck, Sammy, if you like it, we’ll give it a try.”
“No rush. I want you to like it too. And, uh... if you want to do it on this trip, it would be a good idea to practice a bit before getting here.”
“Practice?” Dean’s eyes widened. “Oh. Practice.”
“If you’re really not into it, we don’t have to—”
“Nah, nah, I’ll at least give it a try.” He grinned. “You make it look pretty fucking fun.”
Sam chuckled. Then he sighed. “Hey Dean, I’ve gotta go to a night class now. But I’ll see you in a week?”
“A week,” Dean confirmed. “Love you, little brother.”
“Love you, Dean.”
Dean hung up and stared at the ceiling again, thinking. His hand, resting casually on his groin, slid down and crept between his legs, just behind his balls. Dean pressed his lips together and gave the ceiling a thoughtful look.
Dean thought about what Sam had said for the entire next day’s drive. By the time he checked into his next cheap little motel, he’d resolved to give “practicing” a try.
He’d seen the size of his brother’s cock, and the thought of getting that monster inside him was intimidating to say the least. But maybe just one little finger wouldn’t be too bad. He had a week before he had to worry about Sam’s dick.
First, there was cleanliness to attend to. Sam’s ass was made of candy and rainbows as far as Dean was concerned—he’d licked it out the last time he’d visited, and fuck he’d enjoyed that—but Dean wasn’t so sure about his own rear end. It seemed to Dean that his ass would probably be a regular old ass with all the standard assly unpleasantness. So he made use of the motel shower and cleaned himself very thoroughly before he did anything else.
Dean stood in front of the mirror as he dried himself off, thinking. When he was dry, he turned around and took a good look at his own ass. It wasn’t something he spent a lot of time staring at. He guessed it looked fine. Dean reached back and cautiously spread his hand over one cheek. He gave it a squeeze. Yup. Definitely an ass.
Dean chewed his lip nervously and tried grabbing his ass with both hands, still looking at it in the mirror. Then he spread it.
“...Oh.” Dean’s cheeks went red. That was a view he wasn’t used to seeing on himself. He’d seen it on girls and his brother, but... fuck on a stick, that was his hole.
...How the fuck was he going to fit Sam’s monster cock in that tiny little hole?
Dean let out a deep breath and let go of his ass.He walked naked out of the bathroom, flopped down on the bed, and found he’d run out of excuses to put this off.
Hesitantly, Dean lifted one of his legs and slipped a hand behind his balls, biting his lip and making a thin noise when his fingers brushed over his hole. He’d never really touched it before. It wasn’t the same as rubbing his finger over Sam’s hole. For one thing, Sam always kept everything down there shaved-smooth, and Dean had never bothered. And Sam’s hole always relaxed eagerly around anything pressed against it, but Dean was pretty sure he could compress coal into a diamond with the sheer power of his ass right now.
Oh yeah, and touching Sam didn’t involve feeling every little tingle of a finger rubbing against his asshole. That was a significant difference.
Sam seemed to absolutely love it when Dean fingered him, so there must be something enjoyable about it. Dean heaved out a deep sigh and leaned over the side of the bed, dragging his duffle bag over. He rooted around until he found the lube, then squeezed out a generous amount onto his hand. It would be just like fingering Sammy, right? Lots of lube, gentle movements at first, starting with one finger... only Sammy wasn’t actually there and he was about to slide a finger into his own ass.
Dean took a deep breath and tried to psyche himself up for this while the lube slowly melted on his hand. He thought about what Sam’s face looked like when he was being sucked off. The flushed cheeks and the hazy eyes the wet, open lips with that pretty pink tongue just slightly hanging out as he gasped and panted... Dean thought about being spooned up behind Sam and jerking him off slowly, Sam squirming against him, helpless with pleasure.
From there, it was easy to imagine the overwhelmed look that would be on Sam’s face when he was squeezing inside his brother.
Dean let out a long, slow breath and lifted one of his legs again, smearing the lube behind his balls. He hissed. It was cold. And now the crease of his ass was all wet and slippery and it felt weird as hell. Dean closed his eyes and blew out a breath, smearing the rest of the lube over his soft cock and giving it a few tugs. He thought about Sammy sprawled out naked on a bed under him. He remembered the way his brother submitted to every touch, begging for more breathlessly. The image alone was enough to make his body relax and his cock start to swell in his hand. Dean kept on gently jerking himself off as he pressed a finger gently against his hole again.
...Oh. It felt... better when it was wet. Weird, sensitive, really damn embarrassing, but also somehow better.
For a split second, Dean caught the mental image of Sam lying between his legs right now and licking his lips. Dean’s hand clenched around his swelling cock.
“Fuck,” he breathed to himself. “Okay. Fuck. Fuck.” Dean clenched his teeth and tried to relax as he teased the tip of his finger into himself. “Fuck!”
It was weird. But not bad. Dean pushed in a little further, and the lube seemed to suddenly kick in because the next inch slid in without any resistance. Dean gasped at the ceiling. “Oh fuck me...”
He’d been expecting it to hurt, but there was no pain at all. Just the odd, perplexing, kinda thrilling feeling of having something inside him. Dean tried moving his finger and tensed with a squeak at the resulting sensation. Was this what it felt like for Sam when he was fingered? God, no wonder Sam got all limp and breathless and submissive. Dean got a sudden memory of bending Sam over his desk and ramming every inch of his thick cock into his little brother. Jesus fucking christ, how did Sam do it?
Dean took deep breaths, jerking his cock lazily as he got used to the sensation of having something in his ass. It was weird, but... whenever he started to lose himself in a fantasy and jerk his cock faster, he’d clench around his finger and... wow. That was a different thing right there.
Dean let his hand slip off of his dick suddenly and reached for the bedside table, his lube-slippery fingers grappling for his phone. He picked it up and looked at the time. Sam was probably in his night class by now. Dean’s fingers moved over the keypad as he typed out a text one-handed.
fingering my ass for you
He sent it to Sam and dropped the phone on the bed, returning his hand to his cock. He tried moving his finger and had to muffle his moan in the pillow. He wasn’t getting it very deep, he knew that, barely a knuckle. Dean rolled onto his side and reached behind himself, pressing a finger into the slick crease of his ass and sliding it in. Dean gasped into the pillow. Oh fuck, that was deeper.
The phone buzzed. Dean grinned as he picked it up and looked at the text.
Dean held his tongue between his teeth as he typed back an answer.
yeah and i think i like it
This time when Dean dropped the phone back on the bed, he tried moving his finger in and out, like it was a cock. He bit his lip and whined. Oh fuck. How was he supposed to be aggressive and dominant with something slicking in and out of him like that?
The phone buzzed. Dean picked it up and laughed breathlessly as he saw Sam’s answer.
you fucker i’m about to take a test with a boner
Dean grinned and typed back.
naughty boy, punish yourself later
Dean put the phone aside and slipped his finger out gently. Fuck, he felt all... loose and wet and sensitive now. He thought briefly about how much more wet and loose and sensitive he’d be if Sam had just come in his ass, and his cock twitched.
...His body seemed to be more on board with bottoming than he was expecting.
Dean cautiously tried nudging two fingers at his hole. As he started to tease them in, he winced. Fuck, how did two measly fingers feel so big? He felt stretched and he’d barely gotten them in. Dean pushed a little farther and gasped as he got the first knuckle in. Oh fuck. He’d seen Sam take so much more than this, but right now he felt completely stuffed with just these two fingers.
And christ, he was tight. He could feel the squeeze of his own body around his fingers. God, Sam was going to love feeling that around his dick. He’d blow his load in fucking minutes.
As if in response, the phone buzzed. Dean picked it up and swallowed at Sam’s reply.
yes sir, of course sir
Fuck. Domming his little brother while bottoming was starting to look a lot more plausible.
Dean didn’t make it to Stanford within the week. He got held up in Arizona by a haunting in the very hotel he tried to stay at. It took him three extra days to identify the ghost, track down its remains, and properly destroy all of them.
But every night before he passed out, even if it was five in the morning and he was dead on his feet, Dean took at least a minute or two to play with his ass a little. Not jerk off, not stretch it open. Just play for a few minutes before falling asleep.
And each time, it felt a little bit more awesome.
When Dean had checked into a motel just a day out from Stanford, he sprawled out on the bed and lubed up and managed to get three fingers stuffed inside himself before he came all over his own chest.
Dean got a call from Sam the next morning as he was preparing to check out of the motel. He flipped the phone open and held it against his ear with his shoulder as he pulled his pants on.
“Hey, Dean. You on the road yet?”
“Not yet. Something wrong?”
“No, I just realized that I should have said some other things before. I didn’t even ask if you were interested in subbing. I’m not sure how good of a dom I’d be, but I’m willing to give it a try—”
Dean chuckled. “Nah, I like being in charge, Sammy. Don’t you worry.”
“Whew, okay, that’s a bit of a relief. So the other thing was... speaking of domming and subbing... um, I don’t know if you want your first time to be, you know... not kinky?”
Dean outright laughed at that. “Uh, first time, Sammy?”
“You know what I mean. I wasn’t sure if you wanted it to be... special.”
Dean paused in the middle of putting his pants on. “Look, Sammy... every time with you is special. Kink or not.” He grinned and stood up, zipping up his pants. “Besides, I’ve got some great plans for what to do to you, and I’d hate to put those plans off—”
“Okay, yes, you’ve sold me. Kink it is.”
“Atta boy.” Dean grabbed his belt off the bed and started putting it on. “Don’t get off today, little brother. I want you pent up for me.”
Sam was disappointed about the three day delay. He would have been happy to hear that Dean got to Stanford a half hour earlier than he’d expected, but Dean didn’t give him a call. Instead, he found the class that he knew Sam was in and waited, out of sight, for the class to end.
It was about ten minutes before the doors opened and students started filing out. When Dean caught sight his brother’s familiar shaggy hair and tall frame, he smiled. Sam started walking away, oblivious, no doubt heading back to his dorm to wait for Dean. Dean indulged himself in a glance at the seat of his brother’s tight-fitting jeans before silently following him.
Sam hummed a little, cheerful and absent-minded, but didn’t so much as glance behind himself as he walked briskly back to his dorm. Dean held back a snort. Kid was out of shape if he didn’t notice he was being tailed. Dean waited until Sam was in front of his dorm door and rooting around for his key before silently stepping close to his brother and grabbing him from behind. He pressed a rough hand over Sam’s mouth to muffle his shout of alarm, his other arm pinning Sam’s arms by his sides.
“Hush, little brother,” Dean whispered in Sam’s ear, making his struggles falter. “No screaming or I’ll gag you with something more than my hand.”
Sam muffled Dean’s name through his hand, letting out a groan as Dean’s arm loosened and he slid his hand up Sam’s t-shirt. They were still out in the hallway and anyone could walk by as Dean’s hand groped around under his brother’s clothes. Dean let his hand wander down, past Sam’s tense stomach to his pants, finding his little brother’s already swelling erection and giving it a squeeze.
“Time we put that big cock of yours to use,” Dean murmured against Sam’s neck. Sam’s back arched and he moaned loud enough for the whole hallway to hear. Dean kept his hand over Sam’s mouth while he rubbed the front of Sam’s jeans slowly, feeling his brother stiffen against his hand. “You gonna open the door?” he asked softly, “or do I have to fuck you out here in the hallway?”
Sam reached a shaking hand into his pocket and managed to find his key. He fumbled with the door while Dean sucked on the side of his neck and rubbed him through his pants.
“That’s it, good boy...” Dean groaned and nipped at Sam’s ear, starting to undo his pants, still covering his mouth. “You gonna behave for me?”
Sam nodded as he opened the door, his cock stiff and aching as Dean reached into his pants and rubbed it through his boxers. Dean herded Sam inside, finally taking his hand off of Sam’s mouth so he could close the door.
“Dean,” Sam panted, “oh fuck, Dean—”
“Thought you’d like this,” Dean purred against his neck. He squeezed the bulge in Sam’s pants. “Get on the bed and strip, slut. I’ve got plans for this big dick.”
“Oh fuck—” Sam practically dove for the bed, already pulling his shirt off before he flopped down on it. He started undoing his pants without looking at them, watching breathlessly as Dean grinned and shrugged out of his jacket.
“You been a good boy, Sammy?” he taunted as he dragged his shirt up, watching Sam’s movements falter and stop.
“Y-yes—h-haven’t touched myself, sir—”
“Good.” Dean tossed his shirt to the floor and began walking over to the bed as he undid his pants, watching Sam struggle out of his own. He had to swallow when he saw Sam’s thick cock spring out of his pants and flop against his tense belly. It looked a little bigger than he remembered.
“Touch yourself now,” he commanded as he yanked his belt open.
Sam swallowed and wrapped a hand around his cock, sliding his palm loose and quick over the warm skin. He kept his eyes on Dean, not bothering to hide his open desire as Dean stepped out of his pants and walked naked to the bed.
Sam looked like a fucking wet dream, his long legs splayed out over the bed, one hand eagerly tugging his fat dick while he panted up at Dean, face flushed and hair tousled, waiting obediently for orders. Dean smirked.
“So good at putting on a show, Sammy,” he taunted. “We could make a lot of money if we put you on a stage.”
Sam whined and his hips jerked up into his hand.
Dean climbed onto the bed, smiling as he crawled over his brother. Sam swallowed and laid back on the mattress, still tugging his cock. “Oh god oh god—”
“Yeah, that’s it, lie back for me, Sammy.” Dean kept crawling up the bed until he could bump his cock against his little brother’s lips. Sam moaned and licked the head, staring up at Dean with big hazel eyes.
“Fuck, such a slut...” Dean groaned and grabbed Sam’s hair, pushing him down. “Lower, baby. Eat that ass out.”
Sam eagerly shuffled down the bed, licking his way down Dean’s shaft and over his balls—fuck, some time Dean would have to get Sam on his knees and make the kid worship his balls for a good hour or so—before nuzzling between his legs. Dean grunted, but kept a firm hand in Sam’s hair to encourage him to keep going. God, it was weird having someone down there, seeing everything and breathing against him in warm puffs, peach fuzz brushing against his skin. Sam grabbed his brother’s ass and spread it, moaning a little as his lips pressed over Dean’s hole.
“A-ah, that’s it...” The first warm, wet touch of tongue made Dean’s whole body go tense. “Oh fuck yes, Sammy—”
Sam’s tongue was lapping over him, and damn, this was nothing like a wet fingertip. It was silky soft and Sam just kept moving it, licking Dean’s hole like it was the best thing he’d ever tasted, moaning against him. Dean choked down gasps, his heart pounding. It was weird and seemed like it ought to be embarrassing, but it felt fucking good. Dean shifted to get comfortable, sitting back on his brother’s face and rubbing his cock slowly while Sam ate him out.
“Yeah, that’s a good boy... use that pretty tongue, Sammy, I want it buried in me.”
Sam groaned and Dean gasped when he felt something wet and slick teasing him open. “Oh fuck yes, that’s it, good fuckin’ boy—”
Sam’s tongue probed into him, hungrily licking him out with deep, slow thrusts. It made Dean dizzy, made his cock leak as he slowly rubbed it. Sam was looking up at him with hazy eyes, and Dean didn’t have to turn around to know his cock was twitching.
“Like that, Sammy?” he panted, rocking his hips and riding Sam’s tongue. “Like eating out your big brother?”
Sam whined and his hips bucked into the air. Dean grinned and leaned over the headboard, keeping his ass on Sam’s face while he reached into the bedside drawer.
“Now, where do you keep the rope...”
Sam made a startled, eager noise against him. Dean groaned and rocked his hips down.
“Fuck, such a good mouth...”
He somehow managed to dig the lube and a fair bit of rope out of Sam’s dresser without having to pull away from that sweet tongue. He had to stop for a moment and remember how to breathe when Sam sucked on him, nipping at the sensitive skin before plunging his tongue back in. Dean was breathless by the time he managed to straighten up with the lube and the rope. He grabbed one of Sam’s wrists and Sam whined when it was dragged up to the bedpost.
“We’ll have to keep you trussed up for this, Sammy,” Dean murmured, slowly grinding his hips down against Sam’s face as he bound Sam’s hand to the bedpost. “You’re such an eager slut, you’d probably get excited and thrust without permission.”
Sam groaned and submissively brought his free hand up to the other bedpost, still licking his brother out as he waited for it to be tied.
“Uh-uh, Sammy, that one stays loose.” Dean chewed his lips and rocked forward onto Sam’s tongue. “You’re gonna need it.”
Sam groaned against Dean’s hole.
Reluctantly, Dean lifted himself off of Sam’s mouth, rubbing his thumb over that flushed, wet lip while Sam panted up at him. “God, Sam... You look so fucking good like this...”
Sam licked his lips. “F-fuck, Dean, d-do that to me more often.”
“Oh, I’m not close to done with you, baby.”
Dean turned around and crawled down the bed, still holding the rope. He grabbed one of Sam’s legs and brought it to the bedpost, leaning over, keeping his knees apart. Sam let out a desperate groan behind him.
“Oh holy fuck, Dean—”
“Like the view?” Dean smirked over his shoulder and sat down, Sam’s thick cock fitting neatly into the crease of his ass. He ground his hips forward, feeling that hot, veiny length rub against his hole. “You got me so nice and wet, baby.”
Sam cursed and pressed his hips up against Dean’s, his cock twitching. Dean kept his ass planted right where it was while he slowly tied Sam’s ankles to the bedposts, one at a time. Sam’s shaft felt so smooth and hard and hot against his hole, sensitive and twitchy when he rocked his hips against it. It was almost tempting to just ride his brother’s cock like this, jerking off while he ground down against that dick until Sam came with a scream.
Maybe some other time.
Dean turned back around and crawled up to Sam’s face again. He bumped his cock against Sam’s slick mouth, painting a smear of precome over his bottom lip.
“Open up, slut,” he teased.
Sam obeyed with a groan, letting Dean sink into his mouth. Dean let out a long breath as he watched his cock disappear inch by inch into his brother’s mouth. He didn’t try to work in the whole thing. Instead he lazily slipped the first few inches in and out of Sam’s mouth, making it nice and easy for Sam to suck on him.
“You’ve got the sluttiest mouth, Sam. Looks so good getting fucked. Doesn’t matter if it’s a cock or an ass... fuck, we gotta bring a girl some time so I can watch her grind off on your face.”
Sam whimpered around Dean’s cock, nodding up at him. Dean grunted as he reached for the lube bottle, still making shallow pumps with his hips.
“Gimme your hand, Sammy. Can’t just lick out my virgin ass, you gotta finger it before you stuff your cock in there.”
Sam’s hips bucked again and he held his hand out for lube eagerly. Dean squeezed a generous glob onto Sam’s fingers and Sam reached around to smear it over Dean’s hole.
“F-fuck—” Dean chewed his lip, putting the lube bottle away and gripping the headboard while he rocked his hips up and down, fucking his brother’s face. “God yeah...”
Sam was rubbing his hole, teasing it. Dean groaned and thrust down hard into Sam’s mouth when that finger started to nudge into him. Sam gave it a little twist, slipping it into his brother’s ass slowly and smoothly, letting out horny little noises around Dean’s pumping cock.
“That’s it,” Dean groaned. “Oh fuck yes, there’s a good boy...”
Sam kept whimpering around Dean’s shaft. He must be painfully hard, must want to get off so badly. Dean grinned breathlessly down at Sam as his brother fingered him.
“How’s that ass feel, Sammy? Nice and tight?”
Sam muffled an affirmative, sucking Dean’s cock hungrily. “Mmm-hm!”
“S’gonna feel nice squeezing around your dick, isn’t it?”
Sam whimpered desperately and tried to suck more of Dean into his mouth.
“All big and thick inside me, that nice hot cock... mmm, put in another finger, baby.”
Sam complied in a rush, pushing more lube into Dean’s hole as he slid his second finger in. He pumped them in and out and Dean had to stop his thrusts for a moment so he didn’t come in Sam’s mouth.
“Oh fuck, Sammy—harder—”
Sam pushed in a third one and Dean whined, his knuckles whitening against the headboard. Sam was stretching him out so nice, getting him so slick and wet...
“F-fuck!” Dean pulled himself out of Sam’s mouth, panting and watching his cock rest against Sam’s gasping lips. He reached back to grab Sam’s wrist and slid the fingers out carefully, slamming Sam’s hand down next to the bedpost.
“Gonna fuck you,” he panted. “Gonna ride that big slutty cock.”
Sam choked as Dean bound his hand to the post. “Oh god oh god oh god—”
As soon as Sam’s hand was tied, Dean shuffled down the bed so he was straddling his brother’s hips, rubbing his ass back against Sam’s precome-slick cock.
“Gonna take it nice and slow, Sammy,” Dean hissed viciously. “Wanna see you writhe.”
Sam squirmed under him. “Oh god, please, please—”
Dean reached between their bodies and grabbed Sam’s cock, giving it a tug and grinning when Sam shouted in pleasure under him. “Needy,” he accused, lifting Sam’s cock so he could rub the head of it against his hole. Sam chewed his lip and whined, and Dean let out a pleased moan.
“Ooooh, that does feel nice.” He rubbed Sam against his lube-slick hole, feeling the heat and smoothness of that thick head. “You’re so wet for me, little brother.”
Dean grabbed his brother’s neck, forcing Sam’s wide eyes to meet his.
“Don’t. Move.” He bit each word out and Sam nodded fearfully.
Dean straightened up, splaying one hand over Sam’s broad chest and pressing himself gently back against the head of his brother’s cock. Sam’s chest was already heaving under his hand.
“There we go...” Dean hissed as he relaxed and the head of Sam’s cock began to nudge inside. “Ah, fuck, big boy...”
“D-Dean, holy shit...” Sam swallowed visibly as Dean pushed his hips down just a fraction of an inch. “Oh fuck, I c-can’t believe you’re doing this—”
Dean tried to breathe slowly so he could relax. Fuck, he had been starting to get comfy with three fingers, but he was pretty damn sure Sam was thicker. He hummed and rolled his hips in a slow circle, feeling Sam’s cockhead slick around his hole.
“Mmmm, I think I’m gonna take my time with this, Sammy. What do you think?”
Sam made a noise close to a sob when Dean lifted off of him for a second before pressing back down. “Oh g-god, Dean, fuck, I wanna be in you—”
Dean clucked disapprovingly. “Naughty Sammy. That’s not the proper answer.”
Sam whimpered, trying to find words. “...Y-you should fuck me as s-slow as you want, sir.”
Dean grinned and sunk down just a little farther, letting a little more of Sam’s cockhead nudge into him. “That’s a good boy.”
It took another thirty seconds or so of slow breathing and gently pushing himself down before Sam’s cockhead suddenly slipped into him, bumping past the tight ring of muscle. Dean’s fingers dug into Sam’s chest and he gasped.
“Oh fuck—fuck you’re big, Sammy—”
“D-Dean—” Sam gasped and his hands fisted in their bindings when Dean sunk down another inch. “Oh holy fuck Dean—”
Dean let go of Sam’s cock and braced both his hands on his brother’s chest, humming in pleasure and sinking leisurely down onto his brother’s thick shaft. He’d never felt this filled with fingers, it was incredible. Dean hesitated when he got Sam as deep as he could, digging his fingers into his brother’s chest and moaning.
“God damn...” He panted down at Sam, rolling his hips slowly, watching his brother squirm. “You make a nice dildo, Sammy.”
“D-Dean, oh god—”
Dean stroked his hand over Sam’s heaving chest. “Tell me how feels, baby, tell me how nice that virgin ass is.”
Sam whimpered, his whole body shaking as Dean rolled his hips again. “D-Dean, god, you’re so t-tight, s-so fucking tight—you look so hot, god, just want you to fuck me into the mattress—”
Dean bit his lip and lifted his hips slowly, feeling Sam’s slick cock start to drag out of him. His eyes fluttered closed and he groaned. “Oh god that’s nice...”
He could feel Sam’s cock throbbing inside him, hard and needy. That was the fucking hottest part of this, knowing his brother was stuffed inside him. Dean’s own dick was leaking, oozing slick drops that dribbled down his length. He groaned as he squeezed a hand over it. The resulting pleasure made him clench, and Sam gasped in response.
“Oh god oh god—”
Dean panted as he sunk down again, a little deeper this time, before sliding up Sam’s shaft until the crown of Sam’s cock tugged at his rim. That shifting movement, fuck, his little brother filling him up and pumping slowly inside him—
“G-god, Sammy—” Dean sunk smooth and easy down Sam’s dick while Sam made the most delicious noises, needy choked gasps like he couldn’t handle all the pleasure he was feeling, like each new inch that Dean took was startling and painfully arousing.
Dean bit his lip when he felt his ass press down against Sam’s hips. “F-fuck, baby, got the whole thing in me—”
“D-Dean, g-god, if you move any faster I’m gonna c-come in you—”
Dean’s breath hitched, his cock twitching in his hand. “Gonna spill your load without permission, Sammy? Gonna come balls-deep in me like the needy slut you are?”
Dean’s precome was dripping onto Sam’s heaving chest with every rapid jerk of his fist. His hand was shaking where it was splayed over Sam’s pectoral muscle.
Sam whimpered, his hips lifting just a fraction of an inch, pressing his cock hungrily up into Dean. “O-only if you say I’m allowed, sir.”
Dean cursed and his back arched when he came, so hard and fast it startled him. The orgasm made him squeeze around Sam, feel the thickness of Sam stretching him open, and Dean choked as another pulse of come made his cock jerk in his hand. Sam was staring up at him with unadulterated wonder and lust, his mouth open.
Dean let out a long breath, letting his wet cock fall against Sam’s come-splattered belly. He could tell immediately that he wasn’t up for riding Sam’s cock any more, though he hadn’t been riding it all that much to begin with. Dean licked his lips and braced himself on Sam’s chest again, dragging himself off his brother’s cock slowly.
“You’re a good ride, Sam. Nice slut.”
Sam chewed his lip and whined when his cock popped out of Dean, resting against his stretched, wet hole.
“Think you deserve to get off, slut?” Dean asked, grinning.
Sam seemed to be struggling to submit any more than he already was. “Oh g-god, sir, please, please let me come, I’ll be so good for you I’ll do anything—”
Dean purred and let Sam’s cock fall against his belly, sitting down on it, rubbing his sensitive hole over the thick, veiny shaft. “You’re already so close, aren’t you? You really loved getting to dip your cock in a virgin ass.”
Sam writhed when Dean rocked his hips back and forth, rubbing over his dick. “G-god, yes, yes—!”
Dean shifted forward a little more, slipping his slick hole over the twitching head of Sam’s cock, humping down onto it and watching Sam come apart under him, melting into shivers and moans and frantic, breathless begging.
“Oh god, th-thank you, sir, you feel so good, sir—”
“I’m gonna have to practice with that big dick,” Dean murmured, flicking his thumbs over Sam’s nipples as his hips worked. “Gonna have to ride you every day until I can get you to come inside me—”
Sam bit his lip hard to muffle a scream as he came. The slit of his cock pulsed hot and wet against Dean’s hole, drenching it, thick and warm and sticky. Dean hummed with satisfaction, waiting until Sam had stopped shuddering before lifting himself off.
“F-fuck...” Sam was still breathing hard as Dean stood up on the bed. “God, you’re fucking incredible...”
Dean cocked an eyebrow and turned around, showing Sam his ass and pulling a cheek aside so Sam could see his come-splattered hole. Sam made a noise like he’d been punched in the stomach.
“Look at the mess you made,” Dean taunted.
Sam swallowed and nodded dryly. Dean huffed and knelt over Sam’s face, looking down over his shoulder.
“Clean it up.”
Sam held his tongue out eagerly, groaning when Dean sat on his face again. He laved his tongue over his brother’s ass in long swipes, cleaning up the come and shuddering under him. Dean closed his eyes and let out a happy sigh, grinding down on Sam’s tongue, feeling it soothe his used hole.
“Love how obedient you are, Sammy. Such a good boy for me.”
Sam muffled his agreement.
Dean sat up when he felt clean, crawling off the bed, watching Sam lick his lips and grin.
Dean laughed. “Damn. Look at you.”
Sam squirmed on the bed, still smiling innocently up at Dean. “Will you untie me now, sir?”
Chuckling, Dean walked over to the headboard and started undoing the rope. “Yeah, let’s get you cuddle-ready.”
When Sam was untied, Dean flopped down onto the bed next to him. Sam straightened up to grab some tissues off the dresser, but Dean urged him back down onto the mattress. “Uh uh. I got this, Sammy.”
Sam grinned down at his brother while Dean shuffled down the mattress, kissing Sam’s chest, licking up drops of come as he went. He dragged his tongue across Sam’s stomach in long strokes when he got to his own long, sticky white streaks. When he got to Sam’s cock, he gently suckled come off the head and the soft shaft, planting wet little kisses over everything he cleaned. Sam rubbed his hand over Dean’s hair lovingly, eyes closed in bliss while his brother licked him clean.
“So was it special, Dean?” he asked sleepily.
Dean chuckled. “Told you, Sammy. Always is.”