Firsts - Sam and Dean

[reggie11]

Rating: NC17
Genre: PWP
Characters: Sam/Dean
Word Count: 5320
Spoilers: Small spoilers to the beginning of season 4.
Warnings: Wincest, references to canonical character deaths.
Disclaimer: I own nothing but my own words and imagination. If I did, this would have really happened.
Author’s Notes: This is my first time writing slash and Wincest. I'm so nervous I've bitten off all of my fingernails *runs and hides*. This is part three of my Firsts 'verse but each story is stand alone and if you don't like het you may not want to read parts one and two. Part one was Dean's first time and part two was Sam's. This chronicles their firsts together.

Part 1: Dean
Part 2: Sam

The first time anything happened between them was three months after Jessica’s death. It wasn’t even really sexual – more like grief management.

Sam had barely slept since Jess died and when he did he was plagued by nightmares. Dean knew because he was always startled awake by Sam waking gasping for breath or calling out Jess’s name. He also hadn’t cried since the last day he spent in Palo Alto when he had taken flowers to Jessica’s grave to say goodbye. Dean was at a loss as to how to help him. Every time he tried to get Sam to talk about it he was shot down with a withering glare.

But for the last week or so every time Sam came out of the shower he was in an even filthier mood than before and dug into his grief just a little bit deeper. Dean also heard him masturbating in the middle of the night – or at least trying to – and then instead of the grunt of release he would hear a quiet whine of frustration and then Sam would toss and turn all night worse than before. He was pretty sure he knew what was wrong. For some reason Sam had gotten into his head that touching himself was somehow betraying Jess. Like release was something his mind wouldn’t let him have or enjoy.

Tonight after listening to what must be Sam almost rubbing himself raw he thought maybe, just maybe, he could do something to help. Best case scenario, Sam would get some release and with it some sleep – worst case scenario Sam would punch him in the face and even that might give Sam some sort of relief from his pent up frustration.

Sam was on his side facing away from Dean’s bed so Dean got up quietly and made his way over and sat on the side of Sam’s bed and put his hand on his shoulder.

“What the fuck, Dean?” Sam startled and looked mortified but instead of moving away Dean scooted closer until he was almost spooned behind Sam. “Shh, I’ve got you.” Then he took Sam’s hand in his own and brought it back down to Sam’s erection. “You need this. Let me help.” Sam’s back stiffened but he didn’t push Dean away so he took that as permission and started to stroke Sam with both their hands whispering in his ear, “Come on Sammy, it feels good, just let it go.” He could hear the hitch in Sam’s breath that at first he thought was arousal but then he realized Sam had started to cry. “Just let yourself feel the sensation, Sammy,” he sped up the strokes, “Let it go, just let go.”

When Sam came with a shudder it was like the floodgates opened and he began sobbing in earnest. Dean wrapped himself tighter around his brother and with his clean hand stroked through his little brother’s hair. “That’s good Sam, let it all out.” He stayed there, holding his brother tightly until the sobbing subsided and Sam finally drifted off to sleep. When he was certain he wouldn’t wake him he slipped quietly from the bed, washed his hands and face in the bathroom and climbed into his own bed. He didn’t think his brother would appreciate him still being in the bed with him come morning. It didn’t feel wrong or strange to have pretty much helped his brother jerk off, it felt like he’d found a way to help him get some much needed stress relief. Even though he hated to see his baby brother cry, he was pleased that he finally had. The grief process was going to be long but maybe this would be the first step. Sam slept the whole way through until late morning and he didn’t have any more nightmares that night.

Neither of them mentioned it the next day but there was no real discomfort between them either.

It happened again a couple of times over the next few months. When Dean could sense that Sam was being overwhelmed by so much grief and anger he was afraid Sam may explode or collapse from it.  They never looked at each other and Dean certainly never touched himself – the only acknowledgement was a brief look of gratitude from Sam the next morning and then it was swept back under the rug like so many other things in the Winchester’s lives.

Things changed a little between them when, one night, when Dean was sure Sam was sleeping he took himself in hand enjoying the long slow glide of his hand on his cock. He’s not even sure what made him turn his head but when he did he saw Sam’s eyes open, watching him. It’s not like they’d never heard each other rub one out before, they were always living practically on top of one another growing up it was just another fact of life. They’d seen each other naked so often it was routine, seen each other’s morning wood and overheard each other quietly come in the dark but this was different – they’d never actually watched. Sam blinked when he realized he’d been seen and started  moving to roll away but Dean held his eye contact and kept going. Dean couldn’t really figure out what exactly it was that was happening but once they locked eyes it didn’t take long before he was coming – and coming hard.

From there it stepped up to one of them starting to jack off and if the other was awake they would start too. Although they remained in their own beds and not a word was spoken, they would bring themselves off watching each other. It wasn’t something that happened frequently. If it had one or the other may have really started freaking out over it. It was just something that happened sometimes and Dean chose not to question it too much whenever he thought about it.

Then after the Rawhead, Dean had almost died. Sam was frantically trying to find anyone, anything, to save his brother. The grief from Jessica’s death was still too raw and his whole life had always been wrapped up in his big brother. The thought of losing him was shaking his world to pieces. The visit to Roy may have healed Dean but the guilt of knowing someone else had died in his place was almost too much for Dean to bear. The night he said goodbye to Layla he felt like his newly mended heart was being ripped in two. How was he supposed to live with this burden? He was angry at himself and he was angry at Sam, even though he knew that had their positions been reversed he would have done exactly what Sam had. Neither of them had known but in Dean’s mind that still didn’t let him off the hook.

When Sam found him crying and shaking with guilt all of his own reserves were shattered. All of the grief for Jess, the fear for Dean’s life poured out in torrents of tears. He held Dean tightly telling him over and over that he wasn’t sorry Dean was saved until Dean was holding onto Sam with the same fierceness. Whether it was adrenaline or proof of life neither of them knew, but the sobbing and the holding became a frantic grappling and rubbing as both men dry humped one another to completion. They hadn’t really laid hands on each other and there certainly wasn’t anything like kissing but both knew, as they lay beside each other sweating with come in their boxer briefs just getting their breath back, that  a line had been crossed.

Once again, it wasn’t spoken of but both made sure that if they needed to jerk off it was done in the shower, out of sight of the other and Dean picked up even more women than he normally did.

The night they burned their father’s body on the pyre was the first time they touched each other with any real intent. It was also the first time they kissed. The pain was so raw and intense.

After showering off the smoke, both men sat passing a bottle of whisky between them. Sam was an emotional wreck and Dean just felt empty. Sam tried to get Dean to talk but the only word he got in response was Don’t. Dean knew he should comfort Sam but didn’t have the emotional wherewithal to try. He knew he should talk to Sam especially as he was still grieving for his lost love but he had no words. He felt like someone had sucked the life out of him. His father was dead. His father had said the most unimaginable thing to him before he died. His brain had shut down.

When he passed the bottle back he used his thumb to wipe the tears from his younger brother’s face. As he turned to crawl up onto his bed thinking about nothing more than losing himself in sleep, he pressed a kiss to Sam’s forehead and was surprised when Sam grabbed his collar to stop him moving and crushed a kiss against his lips. His own response was even more surprising, he didn’t want to think at all, he didn’t want to feel this emptiness, just wanted to feel. He brought his hand to his brother’s neck and kissed him back. It was no longer just a crush of two mouths together; Dean parted his lips and slid them sensuously over Sam’s. His brother responded immediately by teasing at Dean’s tongue with his own.

This was all so new. Dean had never been with another man and to the best of his knowledge, neither had Sam. He wasn’t sure how far to take this – he wasn’t sure of anything other than the need to feel. Things had been building between them so perhaps it had been inevitable. He couldn’t feel guilty because Sam had kissed him first and this wasn’t about guilt anyway, once again it was about grief.

Dean slid is hand up under his brother’s T-shirt, feeling the hard muscles, so much different to a woman. Sam sucked on Dean’s plump lower lip and started a slow grind into his brother and it felt good. He slid his hand over his taller brother’s ass and pulled him in harder and Sam sighed into his mouth. This wasn’t like the furious, rough dry-hump like last time, it was so much more. Dean didn’t allow himself to think about anything, all he concentrated on was sensation. Sam pushed his hand between them, unzipped Dean’s jeans, slipped his large hand into his brother’s boxer briefs and started to stroke him, all the while sliding hot open mouth kisses down his jaw. Dean arched into the touch and moved his hand to reciprocate. When Sam let out a strangled moan it set a fire in Dean’s blood, he yanked off Sam’s shirt and flipped him onto his back. Grabbing the hem of his t-shirt he pulled it over his head and began taking off his brother’s jeans before removing his own.

When they were both naked, Sam reached up and put his hand to the back of Dean’s neck and pulled him down into a heated kiss, their naked, sweat covered bodies sliding against each other. With hands roaming freely over naked skin, they found a rhythm thrusting against one another, tongues tangling, climaxes building. Not a word was spoken, the only sounds were sighs, moans and harsh panted breathing. Dean came first with his brother just a few stuttering thrusts behind. Both fell asleep with their limbs tangled around one another.

Dean woke early the next day, disentangled himself and packed up their things into the truck Bobby had loaned them to go to the old hunter’s salvage yard. He withdrew into himself, focusing all of his pain and grief into repairing the Impala even though Bobby had told him that he didn’t think she was worth fixing. He knew his silence was hurting Sam, especially after what had transpired between them but he couldn’t deal with losing his father and he really couldn’t deal with what the man had told him. The more Sam reached out, the more Dean pulled away until he exploded and smashed into his baby with a tire iron. He just couldn’t deal and he put himself at an emotional and physical distance from Sam. They didn’t touch each other again until the night after they put down that idiot’s zombie girlfriend. It was much the same as last time – touching, rubbing, kissing, silence and trying to forget.

Then Sam had died. Sam had died and Dean had sold his soul to bring him back and they only had one year left together. Dean had basically gone into self-destruct mode and all Sam could think about, concentrate on, was trying to find a way to save his only remaining family member and the most important person in his life from hell. There was no touching, not until three nights before Dean’s marker was about to be called in.

Sam was frantic and Dean was scared. Sam wanted to spend every single moment they had left trying to find a way to break the deal but Dean wanted to spend what little time he had left with his brother.

“Let’s go for a drive.”

“What, now? You can’t be serious. We’ve got 72 hours to find a way out of this, Dean, we don’t have time to go for a drive.”

Dean looked at his younger brother with his face open and vulnerable, something Sam very rarely saw. “I need this, Sam. Just...let’s spend a few hours, just the two of us.”

Looking at how broken his brother was Sam couldn’t refuse him.

“Okay, let’s do it.”

Dean packed a cooler and they drove for an hour or so and parked in an open field. They sat on the hood like they’d done a thousand times before and watched as the sun sank below the horizon, sipping beer and not saying a word.

“I’ll find a way to save you, Dean.”

“I know you’ll try but I don’t think we’ll be able to stop it.”

“I can’t lose you. I won’t lose you. Please don’t leave me, Dean.”

“I don’t want to, Sam but we have to face facts. We’ve tried everything and nothing has changed. I have to know that you’re gonna be alright, you have to promise me you won’t do anything stupid after I’m gone.”

Sam started to shake and Dean put his arm around him.

“I’m scared.”

“So am I, Sam. Fuck, I’m terrified.” Tears started to slide down Dean’s face and Sam turned and reached up to wipe them away with his thumbs. Dean knew he shouldn’t but he leaned forward and kissed his brother. It wasn’t chaste but it wasn’t passionate – it was tender and he poured as much love into it as he could. “I need...”

“What do you need, Dean?” Sam whispered.

“You, us, I need us.”

“Anything.”

They kissed some more and when the heat started to build Sam broke away and said, “Wait here.” He disentangled himself from his brother’s arms and got an old blanket out of the trunk and laid it beside the car under the stars.
“C’mere.”

Dean went and Sam pulled him gently down onto the blanket, rolling them until Dean was beneath him. He kissed him, licking into his mouth softly. “Tell me what you need.”

“Everything.”

Sam took his shirts off and pulled Dean to a sitting position, tugging his shirt over his head then crushed his mouth to his brother’s and began to rub him through the denim of his jeans. “I want that too.”

He kissed along Dean’s jaw as Dean humped against his hand and then slowly began kissing and licking his way to his older brother’s chest, flicking his tongue against a hardening nipple and Dean hissed and arched into it.

“Sammy.”

“It’s okay, I’ve got you. I wanna make you feel good.” He popped the button and slid down the zipper while kissing his way lower and lower. He started to tug Dean’s jeans down, tapping his hip to get him to lift his hips. He removed his brother’s jeans, boots and underwear and then his own and kissed the inside of both of Dean’s knees before beginning to kiss his way up his thighs. When he reached Dean’s groin, the older man startled and tried to sit up but Sam placed his hand in the middle of Dean’s chest and pushed him gently down.

“Let me.”

“You don’t have to do that, Sammy.”

“Want to.”

He placed a gentle kiss to his brother’s balls making his cock jerk and then licked his way from base to tip, swirling his tongue around the head before swallowing him down.

“Jesus, fuck, Sam.”

Sam hummed around Dean’s cock sending a jolt of pleasure though him and Sam could taste the release of bitter salty fluid on his tongue.

Fondling Dean’s balls, Sam sucked and licked taking more of Dean into his mouth each time until he moved past his gag reflex and Sam’s nose was pressed into the wiry curls of his brother’s pubic hair swallowing around the hard thick length tearing a strangled gasp out of Dean.

“Christ Sam. So fucking good. You’ve done this before haven’t you?”

Sam slid his mouth back up the shaft sucking as he went, releasing his brother with a wet pop answering with a quick, “Yeah,” before diving back down.

Dean’s head reeled for a moment. This was something he never knew and had never guessed about his brother but then all capacity for thought disappeared with the ministrations of Sam’s talented mouth and tongue and far too soon he felt the coil of his orgasm beginning at the base of his spine. When he tugged at his brother’s hair Sam just kept going.

“Gotta move, Sam, gonna come.”

Sam pulled off and used his hand to stroke hard and fast until Dean tipped over the edge and he came with a shout all over his stomach. Sam kissed him deeply while he worked his older brother through his climax until Dean was shoving his hand away from over-sensitivity.

When Dean came completely back to himself he could feel the hard line of Sam’s cock as he rocked gently against Dean’s hip. Not enough friction to get himself off, just the helpless movement of his hips.

He’d never given head before but how hard could it be? “Give me a second and I’ll return the favor.”

But Sam shook his head. “It’s okay, this is about you. What do you need Dean? You wanna rest a while and then fuck me?”

Dean whined at the image that flashed into his mind of being buried inside his brother, being as close as humanly possible to the one person he loved more than life itself. But even though the thought was almost too hot to handle, he didn’t know if he could do it.

“No, want you to fuck me.”

Sam stilled his movement and stopped kissing along Dean’s jaw, murmuring with hot breath into the shell of his ear, “Are you sure? This isn’t some ‘protect Sammy’ bullshit is it? I’ve been with guys before, you haven’t.”

Dean pulled Sam’s head back by the hair gently so he could look him in the eye.

“You let someone fuck you?”

Sam shook his head. “Nah, other way ‘round but I’m cool with it. The only reason I didn’t is because I didn’t trust anyone enough to, but I trust you; you won’t hurt me.”

Dean smoothed the sweaty hair back from his brother’s face.

“Then you’ll know what you’re doing. I want this, Sam. Want you as close as I can get you, want you inside me. It’s not about protecting you,” he said, although that wasn’t entirely true. He really didn’t want to hurt his brother and he had no experience with men and had no idea what to do so that he didn’t hurt Sam. Plus the thought of Sam inside him, even though he was kind of terrified at having his brother’s impressively large cock splitting him in two, was something he really did actually want.

“You’re sure?”

“Yeah Sammy I’m sure. Just...just go easy on me okay. This isn’t exactly small you know,” he said as he palmed Sam causing the younger man to let out a deep moan.

“Yeah, okay. It’s going to hurt a bit at first no matter what but I’ll make it good, I promise.”

“I know you will.”

“We uh, don’t have any lube but there’s hand lotion in the glove compartment and this.” He trailed a finger through the cooling spunk on dean’s abdomen. It’s not ideal but it should work.

“There’s liquid paraffin in the trunk. I use it to clean grease off my hands, it's oil. That’d work wouldn’t it?”

Sam let out a soft chuckle. “Yeah, boy scout, that’d be perfect.”

“Wait. The oil might make a condom break.”


Sam actually laughed this time. “Not gonna use one. I want to feel you.” When he sensed Dean was about to protest he added, “I’m pretty sure you’re careful about where you put your dick, man, and I know you get tested. Anyway if I’m immune to some weird-ass demon virus I’m sure as hell not worried about the clap and shit. Stay here I’ll go get the oil.”

When he returned with the small bottle he saw the frown on Dean’s face.

“You can change your mind, Dean. It’s fine if you’d rather do me. More than fine.”

“No, I want this. Really. Just thinking about...God, Sam. I don’t want to leave you. I’m so scared.”

Tears leaked from the corners of his eyes and spilled down into his hair. Sam threw himself down pulling his brother‘s face into his chest.

“Don’t,” he said, his voice cracking. “I’ll save you, I will. There’s still time.”

He pushed Dean back to the blanket and kissed him ferociously, plunging his tongue into the wet heat of his mouth and biting at his full lips with Dean eagerly meeting every thrust of his tongue.

Sam began kissing along Dean’s jaw, over the column of his throat, down over his pecs until he took the hard nub of nipple into his mouth alternately flicking his tongue and sucking while he rolled the other between his finger and thumb. Dean arched into the touch, his nipples still sensitive from his recent orgasm. Sam trailed wet open mouth kisses down to the splashes of come on Dean’s chest and stomach and began to lick him clean.

“Christ, Sam, so fucking dirty.”

Sam chuckled against his skin. “You taste good.” He continued to lick and just the thought of his brother licking at his come and enjoying it was making Dean’s cock start to twitch in an effort to fill again.

“This would be easier on you if you were on your stomach but I want to see your face, is that okay?”

The thought made Dean’s heart clench painfully and he croaked out brokenly, “Yeah, yeah. I want that too.”

“If you want me to stop at any time just say so, I won’t be mad.”

He opened the bottle of oil and poured some onto his fingers. He spread Dean’s legs and moved up to kiss him again as he gently rubbed his finger back and forth against the pucker of flesh.

“Just try and relax. It’ll feel good. You ever had someone fingers inside you?”

“Yeah, a few times when I was getting head. Just one though.”

Sam tapped his finger against the opening making it flutter and then gently and slowly pushed his long finger inside.

“Don’t clench, it’s just me. Relax, I won’t hurt you.”

Dean willed his body to loosen up and focused on Sam’s mouth as he resumed kissing him while moving his finger in and out, gently tugging at the ring of muscle as he did. It felt strange when he didn’t have a mouth on his dick at the same time and the girls who had done it had only breached him shallowly – Sam was pushing in until his palm was flush with his ass – but it didn’t hurt at all, it just felt weird. After a short time he removed his finger and added another. This time he felt a slight burning sensation which made him grunt. Sam hearing the discomfort curled his fingers forward until he softly rubbed against Dean’s prostate causing Dean to jump and curse.

“Fuck, do that again.”

Sam smiled into Dean’s mouth and did what he was asked. “Feels good doesn’t it? Those girls never touched you there?”

Dean whined and started matching the rhythm Sam set with his fingers pushing back when Sam plunged in.

“Going to add another, okay?”

He crawled down between Dean’s open legs and poured more oil onto his fingers before pushing three of them inside as he took Dean’s cock – which had been beginning to harden from the attention to his prostate – into his mouth to distract him.

Dean couldn’t wrap his head around the different sensations; the impossible stretch and slight burning from Sam’s fingers, the feeling of being too full and the feel of the swirling wet muscle of Sam’s tongue around his cock and began to whimper. Sam immediately brushed his fingers over Dean’s prostate until his breaths were coming in heavy pants, stretching him as gently and thoroughly as possible.

“Oh shit, Sammy. Do it. C’mon, fuck me.”

Sam released his brother’s cock from his mouth and using his free hand, pouring copious amounts of oil onto his own rock hard dick. He removed his fingers and lined himself up against the now loose ring of Dean’s ass while stroking him.

“You ready?”

“Yeah, shit; do it.”

He loomed over his brother’s body, pushing Dean’s legs back toward his chest and looping an arm underneath one to raise it over his shoulder. He leaned forward to kiss him and swallowed the sounds Dean made as he slowly began to push his way inside the velvety tight heat not stopping until he was fully seated with Dean leaving crescent shaped marks with his fingernails in Sam’s biceps. He stilled his movements, fighting the urge to thrust to give Dean time to adjust to his girth and length.

“Jesus, did you swap your dick with a power pole?” Dean winced.

“You okay?” Sam panted, struggling against the intense desire to move.

“Yeah, just...give me sec.” After a few moments he wiggled his hips a little and Sam began to slowly rock before pulling almost all of the way out and gently thrusting back inside. As he started to find a rhythm, Dean adjusted more to the sensation and started to thrust counterpoint to him.

“Dean, God, you feel so damn good,” Sam purred.

He shifted his angle so that he could brush against Dean's sweet spot every few thrusts and both men gave over to the incredible sensations of being lost in each other.

“I love you.” Sam breathed into his mouth before sucking on his bottom lip. Dean thought his heart would burst right there as tears sprang to his eyes once more. He felt Sam’s sweat drip onto his face but when he opened his eyes he realized they were tears.

“I love you too. So much baby boy.”

Sam sped up and nudged Dean’s prostate more often and a little harder causing him to cry out.

“Touch yourself.”

Dean’s hand wrapped around his length and he began to tug and twist with urgency as he chased his release; his expression now one of complete bliss.

“Fuck you’re beautiful, Dean. So goddamn beautiful.”

If he didn’t feel like there were stars bursting behind his eyes he probably would have called Sam a girl but all he could focus on was the almost blinding sensation of his impending second orgasm, rising like a tidal wave.

“Oh God, gonna, gonna...”

And his climax erupted, he threw his head back, all of his nerve endings firing, as he shot thin ropes of come all over himself and his brother.

He clamped down so hard Sam could barely move, feeling the heat of the silken walls flutter and clench around his cock eliciting a strangled cry and then he began to thrust hard and fast, his rhythm quickly faltering and he too threw back his head, crying out Dean’s name as he emptied himself inside.

Sam slumped forward catching himself on his elbows so he didn’t crush his brother and kissed him long and sweet. He rolled to the side, tangling their legs together.

“You okay? I didn’t hurt you did I?”

“Nah, I’m good. Real good. Be better once you remove that tree trunk from my ass, tripod.”

“Oh, sorry.” Sam winced and pulled out as gently as he could, his come leaking out of Dean onto the blanket.

“Eeew, that’s just gross.”

A laugh erupted out of Sam and when he saw Dean’s indignant expression it made him laugh harder.

“You should see your face,” He wheezed out.

“You should see my ass.”

Sam was laughing so hard now that tears were leaking out of his eyes which must have been contagious because soon Dean was laughing along with him. The tension that had been building had made a dam burst and they laughed until they were completely breathless.

When they settled back down it was to a comfortable silence between them, trading slow kisses back and forth.

“I guess we should get back before Bobby sends out a search party.”

“Yeah.”

“This was pretty awesome. Thanks, Sam.”

“Gonna be just as awesome when we switch it up and you do me next time.”

Dean’s face fell and as he was about to say something Sam quieted him by putting a finger to his full lips.

“I’m going to save you. I can’t lose you, it’s not gonna happen. You’ll see. Next time this happens it’ll be you on top. When all of this is over, I wanna feel you inside me. Promise me that next time we do this you’re gonna fuck me so hard I won’t be able to sit for a week.”

“Sammy,” Dean’s voice cracked with raw emotion.

“Promise me, Dean.”

Not knowing what else to say he promised.

“I love you so much.”

“I know.  Love you too.”

They stayed for a little while longer wrapped in each other’s arms savoring each moment, neither wanting to think about what was coming but unable to really think of anything else. When they drove back to Bobby’s it was with their hands linked between them.

ooOoo

After the initial shock wore off and Bobby left to give them some privacy, Sam couldn’t stop touching Dean, running his hands over his face.

“I can’t believe it’s really you. I can’t believe you’re here. I tried so hard and God, I failed you.” Sam began to cry.

“No, no, Sammy. You didn’t fail me. You did everything you could, please don’t cry. I’m here now and I’m not going anywhere.”

He had no idea if Sam would even want him that way anymore. He didn’t know what had happened in the months he had been gone and there had been that girl in the room when he arrived so he didn’t, couldn’t, dare make a move. He just held onto his very large little brother and kissed the top of his head to calm the crying. Then Sam was chasing Dean’s lips with his own.

It had been a long time and so much had happened that he still didn't know about but none of that mattered right now because Sam was kissing him and Dean had made a promise, and he always kept his promises.

Fin