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Sam wouldn’t call their sex life boring in any sense of the word but they weren’t all that out there either. Hell, their whole sex life was one big illegal thing already which kind of made it kinky and taboo all by itself.
Still - they had tried a few things, liked a few things, hated a few things and all that. Like that one time they had tried out the whole semi-public thing and Dean had been so tense at the thought of anybody seeing Sam in a way that only Dean was allowed too that it had been almost impossible for either of them to get off in the end. (Or the one time where Sam had (jokingly) suggested for them to switch roles and Dean hadn’t even thought about indulging him - had just put Sam in his place which made sitting a little awkward the next day)
Living on the road, motel after motel and nights in the Impala in between didn’t afford them too many luxuries to indulge in or space for unnecessary supplies anyways.
Which was why Sam hadn't expected tonight to be anything special - he hadn’t even expected sex at all if he was honest.
Dean had surprisingly looked at him with a hunger like they hadn’t eaten dinner already and even though Sam hadn’t expected it, he was on board pretty quickly. There was no research to be done right now and no urgent case or business that needed attending to so it was no hardship to strip and indulge his brother for the rest of the evening.
—
Ass up, face down. Dean’s favourite position to put him in, loving the vulnerability of Sam not being able to see what was going on, just needing to trust Dean.
Dean groaned when he dropped to his knees behind Sam, the mattress dipping. Sam was about to ask what Dean had planned for tonight when a hand came down on his ass, cutting his words off with a grunt.
His brother chuckled darkly behind him, his other cheek receiving the same treatment.
“Dean-” Sam complained breathlessly.
“Yeah,” Dean just said and Sam could hear the stupid grin in his voice.
Dean spanked him again before he moved on, grabbing Sam’s cheeks and pulling them apart, his thumbs pulling at his rim immediately. Spit landed on the furled hole a second later and Sam grumbled, uncomfortable with the feeling. Dean rubbed it in, pushing his thumb inside with the little lubricant his spit provided.
“Been shopping, Sammy,” Dean mumbled, nipping at the reddened flesh.
Sam tried to turn towards Dean but was stopped by a hand pushing down his upper back, pressing his chest to the bed to keep him in position.
“Love how eager you are, Sammy but don’t worry, we’ll get there.” Dean’s now free hand stroked along Sam’s side once, before he spanked his ass again.
Sam managed a few moments of letting his brother do what he wanted before he spoke up again. “Dean-”
“Alright,” Dean said, and the tone let Sam know that Dean was getting impatient too, probably too keen to try out whatever he had bought.
Thankfully Dean had also brought lube, though it still made Sam squirm when Dean poured some of the cold liquid on his crack, some dribbling down to where Dean’s one thumb was still pulling at his rim.
He hissed slightly at the feeling but Dean didn’t allow him to move away and the constant rubbing of Dean’s fingers made the lube warm up rather quickly. Dean’s thumb slipped in deeper with the added slick, making Sam moan.
“So desperate already, aren’t you, Sammy?” Dean asked, slipping a second finger inside and hooking them inside to pull Sam’s hole apart.
Sam’s hips canted forward a little as Dean started to pull and push at his hole.
“Got bigger things planned for you,” his brother told him, slipping a third finger in a little too soon.
It was a little uncomfortable but it only spurred Sam on and he wanted more, too intrigued by Dean’s promises. He pushed back onto Dean’s finger, taking them deeper.
“Yeah, c’mon Sammy, fuck yourself on my fingers, c’mon,” Dean groaned, “love it when you’re this desperate so soon.”
There was a part of Sam that wanted to do the exact opposite, stop moving and let Dean do the rest but Dean’s fingers had found his prostate and he couldn’t resist the sparks of pleasure, rocking his hips again and again to chase the feeling.
Dean added a fourth finger, stretching him apart further and Sam whined at the stretch. “ ‘m ready, Dean, please.”
“You sure?” Dean asked and his amused tone made some alarm bells ring in his head but he ignored them.
“Yes, please,” Sam repeated.
Dean chuckled again, his fingers leaving Sam’s hole, and gripping his leaking cock instead, stroking him a few times until Sam was about to blow his load already. His brother knew him though and pulled back just at the right second to edge Sam.
Sam slumped into the bed a little more until there was something distinctly not flesh and blood nudging at his hole.
He tensed up a little but Dean reprimanded him to relax and slowly but surely Sam did, letting the toy - he suspected a new dildo - inside.
Sam had suspected the wrong thing when the silicone thing - a ball Sam now knew - entered him easily. There was a second of panic until Dean pulled at something and Sam could feel the ball inside him being tugged at.
“Are those-?” Sam asked, biting off a yelp when Dean pushed a second ball inside quickly. “Fuck, are those beads?”
“So smart, college boy,” Dean confirmed, pulling at the string again.
A finger circled the furled rim around the string before Dean pushed a finger inside alongside it, feeling and pushing against the ball.
Sam groaned at the strange feeling, his muscles clenching down at the new intrusion. Without much warning Dean pushed another bead inside Sam, the size increasing and making him moan, swaying forward as his body sucked it inside.
“Jesus, Sammy,” Dean groaned, hands constantly touching him, moving and pulling at the string. It made the beads move inside Sam, one pressing against his prostate and he whimpered.
Sam didn’t know how many more there were but knowing his brother he was going to take all of them tonight, one way or another and he was glad when his body readily accepted the next one too, the strange, partial fullness a new feeling.
“Two more, Sammy,” Dean told him as he pushed another silicon bead against his hole. His hole opened slowly, almost accepting it until Dean pulled it back again. The push and pull repeated too many times for Sam’s liking and his whines increased.
Sam knew he could take it, but Dean didn’t let him, letting the ball slip out again. There was a weird pull when Dean let go of the string in order to grip his dick that had slightly flagged. His cock perked up immediately, pre-cum leaking from the tip as Dean stroked him a few times, squeezing and pulling at the sensitive flesh.
“Please, Dean,” Sam moaned, moving his hips back and hoping that Dean would get on with it and just fuck him properly.
Dean slapped his ass again, tutting at him. “Pushy,” he muttered and let Sam’s dick go, letting it sway uselessly beneath him again.
Without any warning Dean pushed the second to last bead inside Sam, his hole stretching wide before swallowing it up and it punched a moan out of Sam. He rocked forward, one of the balls resting against his prostate and every movement made him tremble and moan again.
His brother slapped the other ass cheek again, making Sam buck and groan and whine. “Last one, Sammy.”
“Yeah, okay-” Sam agreed breathlessly, well and truly at Dean’s mercy with how his body was already reacting to the beads inside him.
Dean thankfully added some more lube to his hole, pulling at the string lightly before pushing it back inside and taking some of the lube with it. The last ball was rubbed across his aching and heated hole then, smearing the last of it around until Dean began to push it inside.
It was big, bigger than most of their other toys and the stretch was just on the right side of uncomfortable.
“So pretty,” Dean mumbled from behind him as he forced the ball to spread Sam wide, keeping it so it sat just inside him at the widest point.
His brother played with it then, pushing it inside, pulling it out - all the while Sam was shaking his head, rubbing his cheek along the pillow as the nerves in his sensitive hole were rubbed raw.
One last push and his body was finally allowed to swallow the ball, the pressure and feeling of fullness nearly enough to send Sam over the edge as he groaned loudly, tears leaking into the pillow below him.
“Don’t come,” Dean told him sternly, a hand clamping down below his balls and Sam sobbed at the tight grip, nerves beginning to get overstimulated.
“Please,” he blubbered, voice muted by the fabric.
Dean circled his rim with his fingers, pushing the balls deeper inside, increasing the pressure inside him. He tutted again and Sam knew he was shaking his head. “Too tight, Sammy. Can’t fuck you like this.”
A sharp tug at the string brought the last bead back to Sam’s entrance and he could only imagine the way his hole looked now. Wrecked and red and raw and he felt like he was gaping already, showing some of the silicone too.
His body released the last two beads in rapid succession and the noise Sam made was more than just humiliating, a cross between hurt and ecstasy too.
“Now,” Dean commented, letting the string go again and this time the blunt force against his sore hole was hot and giving and certainly not silicone.
Sam wanted to protest, demand Dean to take all of them out before he fucked Sam but Dean had already pushed inside along the string and making the remaining beads move to accommodate the new intrusion.
He bit down on the pillow, the taste chalky and of cheap detergent but it was the only way he wouldn’t let the whole motel know what they were up to. Even though Sam wasn’t quite so sure what they were up to anymore either, his skin feeling too tight and his nerves on edge, so desperate.
Dean bottomed out before Sam even registered him really entering and the feeling was unlike anything he had experienced before. His prostate was stimulated constantly, the shifting beads - moved by Dean’s thrusts - left him breathless.
“Dean-” Sam managed to moan and it must have sounded pathetic enough to affect his brother.
“Come for me Sammy, c’mon,” Dean finally encouraged and he didn’t need to tell Sam twice.
One of the beads caught Sam’s prostate just right and he dipped forward again, face pressed deep into the pillow as he came without a hand on his dick. His cock spurted beneath him, wetting the mattress with his cum.
“Holy shit,” Dean hissed and thrust in a few more times before he bent over Sam too, his orgasm overwhelming the older Winchester too. Dean nipped at Sam’s shoulder as he rutted against Sam’s ass, cumming deep inside his little brother.
..
Dean pulling out was uncomfortable and Sam wasn’t able to swallow his whines as Dean finally pulled the anal beads out, each ball leaving him making him feel relief but also a sore-nearly-painful feeling.
Sam slummed forward, not caring that the wet spot was underneath him now.
He was left alone for a moment and he tried to breathe deeply, willing his heart rate to go down again.
Rationally Sam knew that the thing touching him next was a wash cloth but he flinched nonetheless.
“Did so good, Sammy,” Dean praised him.
Despite the overwhelming exhaustion and soreness and Sam not quite being sure that he had liked it enough to repeat it, the words still made him glow and feel warm, at least enough to maybe think about indulging Dean some more.