AN: This is a series of minimally related chapters detailing the brothers' explorations into new kinks or sexual experiences with each other. Chapters are labeled by kink.
Warning: This contains lots of sex. Like, this is filthy. Enter at your own risk.
Also, if you didn't catch it in the summary, this is Wincest!
Also, also: I'm a sucker for bottom Dean, so that's something to note too. Most of this is Dean getting all the attention and love he deserves. Sam gets his too, just...have you seen him in the show? He's a fucking top. Let's just say they both enjoy themselves...a lot!
And there's more. Please note: This fic is heavily inspired by many NSFW gifs and pictures. If you'd like to read the version WITH all that, head to my A03 account instead.
Okay, now I'm done. Enjoy!
"Come on, Dean." Sam was lying on his stomach, sprawled out on Dean's bed as his brother fiddled with the handle of his dresser drawer, back to Sam. "You didn't want to bottom at first either. And now you love being split open on my cock." He smirked and watched Dean's ears and neck turn a brilliant shade of red, obvious even in the dim lighting. "What's the harm in trying? You might actually enjoy it." It was hard to keep the desire out of his voice, but Sam knew Dean would only shoot him down quicker if he felt Sam was asking in a moment of horniness.
And yeah, Sam's cock was definitely part of this, but he had thought about this, and a lot of other things he wanted to try, in moments of downtime. He loved being with Dean. There was no question or hesitation there, but with how long they'd been together and how much they trusted each other, why shouldn't they experiment a little, spice things up?
Dean brought both hands up to the back of his neck and laced them, the frustration clear in his stance. He turned to face Sam, features twisted in something between a grimace, a frown, and nervousness. His voice suddenly exploded out of him, hands still clasped at the back of his neck. "You realize where you're talking about putting your tongue? It-It's…dirty!"
Sam almost laughed at how scandalized Dean was, but held it back. He couldn't fault his brother. Rimming was definitely not the most sanitary kink to explore. And Sam knew his brother was skeeved by some things a lot easier than Sam was, something which Sam had always found slightly comical considering their line of work.
Sam rolled up to a seated position and patted the bed, inviting Dean to sit with him. He waited until Dean perched himself on the end, still jittery with restless energy, eyes darting around the room. "Dean. Look at me. I'm not asking you to bend over right this second. We'll take some time to let you clean up and get comfortable."
Dean looked like he was going to interrupt, so Sam rested a hand on his brother's knee and continued. "I wouldn't ask if it was something I was uncomfortable doing. And I'm not asking you to do it to me. Do you trust me?"
Swallowing thickly, Dean nodded. "Then let me do this for you." Sam whipped out the puppy dog eyes and watched his brother crumble.
"Yeah. Yeah, okay." Dean still seemed nervous, but he allowed Sam to kiss him and relaxed into it after a moment.
"So when –" It didn't seem Dean could finish.
Sam smiled and brushed his thumb over Dean's cheek. "How about this. Let's take a nap and then we can go from there. I bought an enema for you, so when you're ready you can use that, and then we can take a bath together to relax and get you focused on other things."
"You bought what? Sam!"
"I know you big brother. I knew you'd want to be completely clean if you agreed to this, so I prepared." He pressed a soft kiss to Dean's lips. "Remember the first time we had sex without a condom? You panicked that you weren't clean enough. And that was just for my dick." Dean flushed red again, trying to pull away from Sam's hold. Sam released him and leaned in to kiss his temple.
Sam smiled and tugged Dean down next to him on the bed. "C'mere. Let yourself relax. You have nothing to worry about." He whispered reassurances into Dean's hair as his brother's breaths evened out against his chest. Sam continued running his fingers through Dean's hair for a few minutes and then finally just held his brother as he let himself drift off too.
When Sam woke up a short while later, Dean was lying in the same position against his chest, but he was awake, fingers tracing unknown patterns on his skin. Sam squeezed his arms tighter and then Dean's gravelly voice broke the silence in a whisper. "Are you sure this is a good idea?"
"Rimming is something I've wanted to try with you for a long time, Dean. Unless you're completely against it and you tell me no, it's something I still want to do."
"But why?" The confusion rang through the question. "I don't get it."
Sam paused before answering, starting a slow drag of his fingers over Dean's back through his t-shirt. He wanted to get this right. "You know that I love you, that I love being with you. There's no doubt in my mind that being with you is the best decision I ever made. And making you feel good is a part of all that. Every piece of you, every reaction I can get out of you," Sam smirked and kissed Dean's hair, "every huff, squirm, moan, it's all amazing and I love nothing more than finding new ways to make you come."
Sam trailed his fingers lower until he was grazing over Dean's crack through his sweatpants. Dean shivered in his arms. "You love when I play with your hole, right? God, you fall apart in my arms and beg me to fuck you every time I finger you. I think having me rim your ass might be even better." Dean muffled a whimper into Sam's chest and rocked his hips.
Sam pushed them both up until they were sitting and then guided Dean off the bed. "Go ahead and get yourself clean. When you're ready I'll run a bath."
It was twenty minutes later when Dean came into Sam's room, red-faced and refusing to meet Sam's eyes. "Ready for the bath?" Dean only nodded. Smiling, Sam gripped Dean's fingers and dragged him back to the bathroom, where he told his brother to undress.
Sam started the water and watched the big tub fill up. The bunker hadn't had a tub when they first got there, but with the help of some angel mojo, they'd managed to get one installed a few months in. It had been a dream of Sam's to have a tub to relax in after a long day and to Dean's surprise, they'd both gotten a lot of use out of it.
In minutes the bathroom had filled with steam and the tub was ready. Sam turned to find Dean standing naked behind him, arms crossed over his chest. Sam quickly shed his clothes and stepped into the water, holding his hand out for Dean. His big brother wouldn't ever admit it out loud, but he loved when Sam held him and the tub had become a place they both enjoyed where Dean let himself be held, Sam's larger frame positioned around him.
Settling into the water, Sam breathed a deep sigh and groaned at the pleasure of steamy water encasing his whole body. Dean sat between his legs and leaned back, giving his own sigh when hot water was followed by Sam's arms in wrapping around his chest. Sam tucked his face into the space over Dean's shoulder and kissed his neck. Dean dropped his head to the side and leaned it back against Sam.
They let themselves soak and just enjoy the heat and each other for a while, Dean resting completely against Sam's chest, his hands resting over Sam's thighs where they were curled around him along the edges of the tub. Every so often Sam pressed lazy kisses to Dean's skin and skimmed his fingers all over Dean's body. A tickle over his stomach and Dean squirmed. A drag over his nipple and Dean bit his lip against a whimper. As Sam caressed a soft line over Dean's cock, the member twitched and bobbed in the water. Slightly lower over Dean's balls and his brother's knees curled up, his legs spreading in invitation.
Sam grazed his teeth over Dean's neck and a full-body shiver shook his body. His brother now sensitive and open, Sam let his fingers drop lower, cupping and rolling Dean's balls before dipping to rub ever so softly against Dean's taint. He sucked in a breath. Dean had shaved while he was in the bathroom earlier. The furl of muscle twitched at Sam's touch and fluttered as he massaged over it, never pressing, just softly skimming in a circular motion.
"Sam," Dean sighed.
"That's it babe." Sam held Dean snugly against his body as his brother's hips tried to lift and seek a harder pressure from Sam's hand. With just a finger rubbing over Dean's hole, Sam had his brother completely boneless, squirming, needy. He kept up the rotation of his finger and let Dean push down against him, just the pad of his finger parting Dean's hole, barely an illusion of Sam inside him.
"Please." It was a murmur, so soft Sam had a hard time hearing the plea.
"Of course Dean. Let me take care of you." Sam kissed Dean's temple again and hit the release for the drain with his toe, letting the water recede around them. After about half had disappeared, Sam helped Dean sit up and climbed out himself, drying off before he guided Dean to his feet and over the ledge. He wrapped a towel around Dean's shoulders and pulled him against his body. "You're so gorgeous. Come on, let's go lay down."
Dean let himself be led back to his bedroom and eagerly laid face down on the mattress, curling his arms under a pillow and dragging it under his head. Sam smiled softly at the sight, taken by how beautiful and vulnerable his brother looked. Dean had a way of retreating into his head in moments like this where he was unsure and couldn't be in control. Since they'd started their relationship, Dean had pushed himself through the moments of panic by doing just this, letting Sam lead and checking out a bit. Sam was proud of him for it, for giving himself the chance to try something new even when he was afraid or nervous.
Climbing up between Dean's legs, Sam soothed his hands over the backs of Dean's calves and then his thighs, massaging lightly over the skin there and then up over the globes of his ass. Sam eased Dean's legs further apart and helped Dean relax back into the near state of bliss he'd achieved in the bath by caressing his legs and back with his hands, letting his brother adapt to his touch.
Sam pressed a kiss to Dean's back and trailed another and another down the line of his spine. Parting Dean's ass cheeks with his hands, Sam continued the line, his lips finally sealing a kiss over Dean's sensitive rim. "Oh," Dean breathed, a soft exclamation, but not disgust or rejection of the act. Sam did it again and felt a small flutter against his lips. Dean was so sensitive here. It was part of the reason he'd thought his brother would enjoy this so much.
Settling himself flat against the bed, Sam kept Dean's cheeks parted and leaned in again, watching Dean's hole twitch as he breathed a puff of air over the area. He heard Dean's breath hitch and then lapped over Dean's hole, the flat of his tongue pressing wide up the length of Dean's crack. Swirling his tongue over the furl of muscle, Sam fought a grin at the squeak that escaped his brother.
At the slight lift of Dean's hips to meet him, Sam dove in, his tongue lapping and flicking over Dean's hole before pressing inside, fighting the tight grip of muscle to reach Dean's inner walls. Even freshly cleaned inside and out, Dean tasted distinctly of his own sweet musk, and Sam couldn't get enough. He jabbed his tongue inside with a pointed motion and repeated it, sucking and lapping. Muffled moans echoed in the room and Sam worked harder, hoping to drive Dean insane with the pleasure.
Bringing his thumb over to rub against the rim, Sam curled it inside and pulled sideways, widening Dean's opening and making it easier to press his tongue in. Dean sobbed and pushed back against Sam's face, desperate for more. Eager to give it to him, Sam eased his other thumb against the side of Dean's hole and again pulled him wide, Dean's hole clenching and fighting Sam's hold on him.
Sam watched Dean throb and then darted his tongue inside, fucking into his hole and carving Dean out on his tongue. His brother was shaking under him, hips lifting back against Sam's mouth, cock hard where it was trapped between his belly and the bed.
Taking a moment just to spread Dean on his thumbs, Sam ducked down to lick over Dean's balls. Dean groaned and again rocked back, seeming to both hump the bed and shove himself into Sam's hands and mouth. Sam spent a minute sucking at the skin of Dean's sac and fucking him open on his fingers and Dean whined. "Sammy."
"I gotcha Dean." Pulling Dean wide, Sam drove his tongue into Dean's hole, lapping at his rim and again fucking him on the long tapered muscle. As Dean rocked his hips, Sam pulled back and sucked at Dean's hole again, this time unrelentingly. Dean cut off a scream and buried his face in the pillow. Hole so sensitive now it was throbbing and twitching under Sam's ministrations, Dean whimpered.
"Please, Sammy! Ah, oh fuck, oh, Sammy." Sam heard the whimpers and dropped one hand to roll Dean's balls as his tongue lapped and jabbed into Dean once more. He felt them tense in his hand and then a sharp cry ripped from Dean's throat as his body shook and his hole clenched down hard, orgasm sweeping through him. Sam didn't let up until Dean was squirming away from rather than into his tongue.
With one last lap over Dean's twitching hole, Sam pulled back and kissed one cheek of his ass. "You are so fucking amazing."
Dean only trembled on the bed in response, and Sam moved up so he could lie next to his brother, pulling him into his arms. Dean curled himself against Sam's chest, eager for the comfort after his orgasm as he usually was. For not being a cuddler, Dean was often the one to crawl into Sam's space and make himself comfortable, especially after he came and Sam was only too happy to oblige him.
Sam was still hard, but at the moment he was so pleased with himself and with the fact that Dean had come mostly on his tongue alone, that he hardly cared. It was a few minutes later, after Dean had time to come down from his orgasm and reclaim his body that he noticed Sam's erection.
"Mmm, let me," he grunted, sliding himself somehow closer against Sam. He curled his hand around Sam's shaft and tugged, twisting and pulling just how Sam liked it. Being so worked up from rimming Dean for the first time, and Sam really hoped it was only the first, it didn't take him long to come. With a good rub just under the head and over the slit on every glide of Dean's hand, Sam came in a few short minutes. He groaned and pulled Dean hard against him, claiming his brother's mouth as the wave overtook him.
As Sam settled back into the bed, head dropping to the pillow, Dean scrunched his face. "Dude," he complained, realizing the tongue that had been in his ass had made it into his mouth.
Sam grinned.