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The guilt was eating Sam Winchester alive and it had only been six weeks since his brother sold his soul to bring him back to life.
Sam had always known Dean loved him too much but he hadn’t known all the forms that love had taken until the night Sam left for Stanford and Dean kissed him. Passionately. Frozen in shock for a moment as his brother’s lips moved over his Sam finally recovered enough to put a hand up and gently push the older boy away. Mind spinning out Sam picked up his bag and turned to walk into the bus station without saying a word as he had no idea how to even process the kiss let alone what to say about it, so he just walked away mind completely numb.
When Dean came to get him from school Sam had been afraid that he would bring it up but thankfully Dean never had. Sam still saw it sometimes, the want, the desire, but Dean mostly tried to hide it which was also a relief. He knew it would be better if they talked it out and maybe Sam could understand how Dean could feel that way, but he just couldn’t bring himself to ask so he ignored it as hard as his brother did.
As time passed Sam just watched as Dean buried himself in women and the occasional man while they searched for their missing father and ignored it when the guys would happen to look a little too much like him. Then after John died Dean completely closed himself off for so long Sam was deeply worried, but eventually things between them settled back into their normal and Sam was grateful.
Then Sam died.
Figuring out your brother has incestuous feelings for you is a head trip, but finding out your brother sold his soul to bring you back from the dead is crushing. Gut wrenching, overwhelming, devastating, and enough to break even the strongest person. Finding out Dean only had a year to live before spending an eternity in hell damn near killed him again but it also made Sam start to wonder.
Watching as Dean went through his little bucket list while trying to live his best life with food and sex and killing monsters got Sam thinking as he knew there was one thing Dean wanted more than anything and it wasn’t on that list. Could Sam give that to his brother?
Over the years Sam had gotten used to the idea that Dean wanted him in that way and it didn’t disgust him the same as it had in the beginning, but he still didn’t have those sexual feelings himself. However, he did want to do something for his brother, give him something Dean wanted. Plus, if he gave Dean that maybe the man would start fighting to live and help Sam look for an alternative to just letting the hounds of hell come for him.
It all made sense in Sam’s mind but he didn’t know if he could actually go through with it. If Dean ever thought he was only doing it out of guilt he would never go along with it, so if Sam did decide to seduce his brother then he was going to have to find a way to make it convincing.
Sam figured the first thing he needed to do was learn about gay sex so he started doing research. Sure, he had a basic idea but he knew it would be more complicated than the crude jokes he’d heard in school. Sam read article after article and learned about lube and stretching and the do’s and don’ts of anal sex.
Next, he moved on to finding a sex shop while Dean was out hustling. Buying a ‘training’ plug he started working his ass open when he was in the shower every morning. Sam was surprised to find he quite enjoyed that part and soon worked the ass play into his masturbation sessions. The feel of something rubbing against his prostate was every bit as good as he’d read and he even liked the full feeling of having something stuffed up there which he found out when he bought a small dildo to try.
Sam began watching some gay porn whenever Dean was out so that he could get some visuals and a better understanding of things. He knew porn wasn’t real life and he never got hard from it but it was still helpful. The next step was going to be more difficult. One, he needed to find out if he could do it, have sex with a man. Could he even get it up? Sam hadn’t gotten hard watching the porn but he liked having things up his ass so he was hopeful. And two, he needed Dean to believe he was into guys so the next time they were in a larger city he found a gay bar and went home with a short blond who was hitting on him. The kissing didn’t do much for him but when the guy’s hot mouth closed over his cock he was up and throbbing in no time. Turns out the guy was a bottom so Sam opened him up how he’d read to do and fucked him hard over the man’s kitchen table. Sam left with a smile on his face and a plan in mind.
Waiting for the right opportunity was frustrating and a couple weeks went by where he was more touchy feely with Dean, which raised his brother’s eyebrows but he didn’t say anything. Then it happened. Dean was playing pool with a couple college kids while Sam was at the bar watching when he caught the eye of an older guy across the room. The man looked in his late twenties and had light brown hair and deep blue eyes. Sam could see that he was fit and toned from the muscles bulging under his tee and the shape of his legs.
The guy came over, introducing himself as Ken, and Sam chatted him up while trying to flirt. He wasn’t the greatest flirt at the best of times and knew he was cringy now but it seemed to be doing the trick as the guy was all up in his space and asking if he wanted to go out back 10 minutes into their conversation. Sam threw a look over his shoulder and saw that Dean had indeed taken note of the situation so he said yes and followed the man down the back hall and out the door. Sam swore he could feel his brother’s eyes in his back the whole way.
Ken was on him in a flash, kissing and pawing and Sam tried to keep up as he got his pants open and pushed down. He handed Ken a condom and helped the man roll it down then turned to face the wall, sticking his ass out. Sam was shocked to realize he was actually quite hard and he cried out as Ken pushed a lubed up cock into Sam’s eager body.
It was a fast and dirty fuck with Sam jerking himself off as the man pounded away on his ass. Ken came first but was nice enough to try and keep fucking into him as the guy reached around and knocked Sam’s hand off his dick so he could jerk Sam off himself. It worked and he came all over the wall in front of him. Had it been the best sex Sam ever had, hell no, but he’d gotten there and he was proud of that fact.
When Sam stumbled back into the bar with a hitch in his step he could see that Dean knew exactly what had happened but he averted his gaze and never mentioned it as they headed back to their motel room.
A couple days later Dean finally broke.
“I didn’t realize you were into guy’s?” Dean muttered casually as he stared out the front windshield while driving.
“I wasn’t. It’s a newish thing.” Sam hedged.
“Oh. So, um, you like it?” Dean hesitantly asked with a red face.
“Yeah Dean, I do.” And funnily enough that was the truth. Sure, he didn’t look at guys and get instantly hard but yeah, the fucking part he could handle.
Burying his dick in an incredibly tight hole or having something warm and hard shoved up inside him as he jerked it was all more than okay. Later that night when they hit the bar Dean didn’t leave him to go off and hustle or hook up and Sam let himself hang in his brother’s space, reaching over the other man and letting his arm brush Dean’s chest when he reached for some peanuts on the bar top. Sam heard Dean’s breath catch each time he did it which is why he never bothered to just bring the bowl closer.
“So um, what ah, what do you look for in a guy? Maybe I could help point some out.” Dean asked as he picked the label off his beer bottle.
“Oh, you know, tall but not as tall as me, light brown hair, green eyes and yeah, he needs to have freckles.” Dean’s eyes dilated as he gaped at Sam. “I like them fit too. Wouldn’t want some wimp that would run in the face of danger. And snarky, you know, have some attitude.” Dean’s breaths were coming in little puffs and Sam figured he was hard already. “You know Dean this place is kinda boring, why don’t we grab a six pack and head back to the room?”
Nodding Dean practically dragged Sam out of the bar to the Impala, not even bothering to stop for the beer. As soon as they were through the door he spun Sam around and backed him into the wall where the older man attacked his mouth.
“I didn’t think… after that night at the bus stop, I thought you were disgusted at the thought of us... never thought you’d change your mind.” Dean said as he pulled back to get Sam’s jacket off, then yank his shirt over his head.
“Just needed some time to get there too.” Sam murmured.
Sam pulled at Dean’s clothes as he sucked on the other man’s neck. There was still the voice in his head telling him he didn’t actually want this and it was gross, but he ignored it to suck a hickey on his brother’s shoulder.
Dean ground his bulge against Sam’s softer one which worked to finally get Sam’s dick into the game. And by the time Dean had their pants and boxers off his cock was hard enough to be convincing. The older man immediately dropped to his knees and sucked Sam in with a shocking amount of expertise which had his cock at full mast and throbbing in seconds. Dean encouraged him to fuck his face and Sam slammed his cock into his brother’s eager mouth over and over until he came with a shout down the man’s throat.
Dean got to his feet and kissed Sam with the taste of cum still in his mouth, then walked him over to the bed where he lay the younger brother down and got to work worshiping his body with a warm tongue and soft, plush, lips. It wasn’t long and Sam could feel himself stirring again, which Dean took note of and went back to work with his mouth. As Sam started to harden again the older man pulled off, licking his way down to Sam’s nuts that he sucked on for long minutes before moving even lower. Pushing Sam’s legs up and apart so he could get his face right in there Dean licked a strip up Sam’s asshole then sucked on his rim causing him to cry out with pleasure.
Pushing his tongue into Sam’s ass Dean moaned. Sam had fucked himself open earlier that day so he was soft enough that Dean easily started adding fingers, up to three before pulling them out and hunting for lube. Sam rolled over and got onto all fours as Dean slicked his dick and finally sank into Sam with a long hard thrust. They both moaned at the exquisite feeling and Sam found he really was into this. There was this feeling in his chest of love and warmth and comfort that he’d only ever felt with one other partner, and that was Jess.
Sam could tell that Dean was trying to go slow to take it easy on him but Sam hadn’t done all that prep to be treated like a china doll so he slammed himself back on Dean’s dick and started begging for the man to go harder.
“Come on Dean, I can take it, fuck me already.” He cried out when Dean pulled almost all the way out and slammed back in, then set up a brutal pace that had Sam’s whole body on fire. Sweat beaded his skin as he pushed himself back, meeting Dean’s thrusts, causing the sound of smacking skin and squealing mattress springs to fill the room.
“Oh God Sammy, so perfect, feels so good. Always knew you’d feel like this.” Dean rambled as his fingers dug into Sam’s hips before Dean changed his angle, hitting Sam’s prostate even harder and making the younger man cry out for more, more, more.
Everything inside Sam was building and building and he hadn’t even touched his dick yet. The way Dean was nailing his prostate and that wonderful overfull feeling in his ass and just knowing that it was Dean fucking him gave him this thrill inside his gut he hadn’t felt since the first time he ever had sex. It was all so overwhelming and the moment Dean reached around and touched his dick Sam went off, spurting cum all over the bed below him. Two, three, four more thrusts and Dean frantically pumped his own load into Sam.
Sam lay on the bed trying to catch his breath, a little grossed out at the feeling of cum leaking from his ass, as Dean cuddled up to his side. “Fuck Sammy, that was awesome.”
“Yeah, it really was.” He agreed. It really had been better than he could have ever expected and that was sending him for a bit of a loop. He was only doing this for his brother… right?
Sam told Dean he needed to shower and escaped to the bathroom to clean up and try to get some perspective. Yeah, he had to enjoy it as well or Dean wouldn’t buy that Sam wanted this too but he hadn’t gotten off that hard since he’d been with Jess and he knew that as great as Jess had been in bed it was his feelings for her that had made it as good as it had been. That’s the kind of person Sam was, he wanted to feel a connection with a person before getting into bed with them.
Sam was so lost inside his spinning thoughts that he was startled when the shower curtain moved and Dean climbed into the tub with him. Dean laughed at Sam’s startled reaction then reached out to start running his hands on Sam’s body, supposedly to help him get clean but it wasn’t long and Dean was doing a lot more than cleaning Sam’s dick as the man sucked it back up. Fuck, Sam wasn’t a teenager anymore and he’d already cum twice so he was surprised to feel himself getting hard again.
Then Dean was standing up and spreading his legs as he looked over his shoulder and ordered Sam to fuck him. What was a good brother supposed to do but reach out and start fingering the man open. Pushing inside Dean’s hot, tight body was heavenly. His ass gripped Sam so hard it was hard to move at first but he worked him open with short little thrusts and lots of conditioner and soon he was sliding in with ease.
Oh God, it felt even better than that other guy that Sam had fucked, which he would have thought one ass was the same as any other. But this was Dean. Big strong hero Dean. The man Sam had always looked up to and tried to emulate when he was a kid. The person who had loved Sam and taken care of him his whole life. And the man was letting Sam fuck him against a shower wall. Thankfully the two previous orgasms made it so that thought alone didn’t send him over the edge and end things embarrassingly fast.
Pulling Dean’s ass back further and tilting it up Sam really started to fuck into his brother with fast and brutal strokes aimed to make the man cry out when Sam nailed him just right. On and on he fucked into his brother as the water eventually started to cool behind them. Drilling into him as his hands ran all over the other man, tweaking his nipples and scratching down the man’s chest to finally get a hold of his dick.
“Uh, uh, fuck, uh uh Sammmyyyy” Dean cried out as he came while bucking back against Sam and sending him spiraling into his own intense climax.
When Sam crawled into bed afterwards Dean followed him in and they both fell into exhausted slumbers wrapped around each other in a way they hadn’t since they were quite young. It was actually soothing having Dean so close and for the first time in a long time Sam slept right through with no nightmares whatsoever.
Over the next few weeks Dean couldn’t seem to get enough of him and they fucked hard and often. But Sam couldn’t even blame it all on Dean since he would reach for the older man almost as often. Sam had never had so much sex in his life and was high on the endorphins. When they finally found a hunt it was actually hard for them to keep their hands off each other while working. But Sam didn’t think FBI agents went around groping their partners in public so by the time they’d get somewhere private the need was intense and more than a few articles of clothing got destroyed by getting ripped off.
Even with how much he was enjoying his brother’s body Sam still just thought he was solely doing this for Dean. To make him happy and give Dean what he wanted before… well, before. The first real jolt to this was about six weeks in when they were at some bar between cases and Dean was hustling up some gas money at the pool table. The guy he was playing couldn’t be much older than Sam was himself and was making his interest in Dean clear as they played.
Sam was fuming at the table as he watched his brother work the guy over for over two hundred bucks. He knew he couldn’t just march over there and rip the guys hand off Dean’s arm where he was currently resting it as he said something that had Dean throwing his head back in laughter. Sam’s blood boiled. While they had never talked about what this thing between them was Sam had just assumed they’d be exclusive, that’s just how he was in relationships. But he realized Dean didn’t really do the relationship thing and maybe he didn’t see them that way. But Dean was the whole reason Sam was doing this so did he have the right to demand exclusivity in return?
By the time Dean pocketed the money Sam was a mess of rolling emotions and he stomped over to his brother saying he was leaving, then turned and walked out whether Dean followed or not. He was already outside when Dean caught up to him and grabbed his arm.
“What the fuck Sammy I wanted to get a few more games in? What crawled up your ass?” Dean snarled.
“Nothing.” Sam said as he yanked his arm away. “Why don’t you just go back to your new little boyfriend in there. I’m leaving.”
The confusion cleared from Dean’s face. “Are you… are you jealous?”
“Pfff, why would I be jealous? Not like we said we were exclusive or anything.” Sam huffed as he turned to walk away again. They had come in the car but it wasn’t far to walk back to their current motel. Plus, the night air might help cool his head down a little.
“I didn’t think we had to. But if you want me to say it then yeah, we are.” Dean said as he again caught up with Sam.
“Then what the fuck was that? You made me sit there and watch as you flirted and let that asshole paw at you all night.”
“I was just winding him up to get more money out of him, I figured you knew that. Sam, look at me.” Sam stopped again and turned to face his brother. “Whatever this is with us I’ve wanted for a long time, and I’m in it all the way. That guy in there wasn’t getting any more of my time than what it was taking to get those bills out of his wallet, and I’m never gonna think about him again. But you, you I think about constantly. Every minute of every day. You’re who I’m going home with and who’s going to get to touch me however and whenever you want.”
Sam grabbed Dean’s arm and steered him back over to where they left the Impala, pushing the other man up against the side of the car as Sam crashed his mouth down against Dean’s. The kiss was hard and brutal as Sam let all his pent-up emotion from the evening out. Getting Dean’s pants open Sam reached in and was happy to find him already hard as he jerked it a couple times before pulling off to open the back door and order the older man into the back seat.
“Ooohh Sammy, you make me all tingly when you get demanding.” Dean said as he kicked his boots off and dropped his pants before getting in. Good thing it was dark out here in the parking lot.
Sam slid in behind his brother and Dean was immediately in his lap pulling Sam’s jeans open and his boxers down. Getting a small bottle of lube from somewhere Dean slicked Sam up and sank down onto him in one smooth move. They both groaned at the feel of Dean stretching around his cock as he slowly slid down. It was probably a good thing Sam had already fucked Dean open that morning cause Dean didn’t take any time to adjust before he started riding Sam’s cock like it was an Olympic sport and he was going for gold.
Bucking his hips up Sam slammed up into his brother’s ass as Dean’s head rolled back and he wailed out his release without a hand on him. The feel of Dean’s hole clenching around him and the knowledge that the man had just cum on his cock alone sent Sam crashing into his own climax as he pumped ropes of cum up into his brother’s perfect ass.
Dean stayed slumped down against his chest with Sam’s cock still inside him for several long minutes as they caught their breaths and came down from the high of their orgasms. Sam ran his hand up Dean’s thigh, then up under the man’s shirts that he was still wearing, to lazily trace circles on his back.
“Sorry for getting so mad.” Sam said as he nuzzled into Dean’s neck with his nose, leaving a gentle kiss behind his ear.
“Me too. I didn’t realize what it might look like to you when I flirted back, I’ll keep that in mind next time.” Dean promised softly.
“No Dean it’s okay, I trust you. We just hadn’t talked about it and I got all up in my head and fuck… seeing someone else put their hand on you, even just your arm or shoulder…”
“Hey I get it, if the situation were reversed we both know there’d be blood.” Sam laughed because his brother always had been a possessive bastard, long before they started fucking.
Later on as they lay in bed Sam’s mind kept going back over how worked up he’d gotten. Sam was not usually a jealous person and he’d never acted like that before, not even with Jess. There had been numerous times someone had flirted with Jess right in front of Sam and he’d been secure in the knowledge she wouldn’t do that to him, or if she did she wasn’t the girl for him and he would move on. But with Dean everything was topsy turvey and he didn’t really know what he was doing. There was no rule book on how to date your brother so they’d just have to figure it out as they went along.
Sam still shied away from really looking further into his feelings though. There was this niggling little thought that said a few months ago he wouldn’t have cared who Dean hooked up with so why now? Just because they were fucking or was it more than that? Pushing the thoughts away Sam rolled into his brother’s side and fell asleep.
It was the Broward County Mystery Spot that finally put everything into crystal clear focus for Sam. Seeing his brother die in his arms over and over and over brought things into stark focus. Then living without the man for 6 months as he hunted down the trickster drove it all even further home. Sam was in love with his brother. His cocky, arrogant, reckless, adorable, big brother. How or when that had happened Sam wasn’t sure but somewhere along the way his feelings had gone a hell of a lot further than brotherly and the scary thing was he thought it might have been long before he thought up the plan to give himself to the man.
Once he got Dean as far away from that Mystery Spot as they could get in 12 hours of driving he asked Dean if they could just spend a couple days together before getting back to hunting. Dean happily agreed and they pulled into the next little town they saw and got a room. The first night Sam just slept wrapped around Dean, afraid of letting go and they never even touched each other sexually. It was all about comfort and Sam’s need to get used to having Dean real and alive again.
The second night Sam told Dean everything that had happened both during the never-ending Tuesdays and that fateful Wednesday, after which they got roaring drunk and snuck out to the closed pool for a midnight skinny dip. They ran back to their room laughing their assess off when someone yelled out the window about the noise. The third night Dean lay Sam out and worshiped his body before making slow love to him. Sam let those three little words slip out just before he climaxed but neither of them addressed it afterwards.
Having realized the depth of his feelings for his brother and having experienced the horror of 6 months without him Sam doubled down on finding a way to save his brother. He called Ruby and told her he was in so he started sneaking out to meet her and train after his brother fell asleep. She was trying to teach him to pull demons out of their hosts and not having much luck when she mentioned that drinking demon blood would boost his power. At first he said no, no way. He figured Dean would be against it but after watching his brother wake from a nightmare of being dragged off to hell Sam told Ruby yes.
When Sam finally told his brother about what he was doing with the demon he knew it wasn’t going to go over very well. Dean was not happy. The fight was epic but Dean was as tied to Sam as Sam was to him and wouldn’t leave his brother over it. Sam was deep in research the next time Ruby showed up and he had no idea why he did it but when she was trying to get him to drink more to boost his powers he said it didn’t matter as he’d found a way to kill Lilith on his own. Something flashed in the demon’s face that twisted Sam’s guts up. Suddenly all Dean’s warnings about trusting Ruby were ringing in his head and he spent a few days really thinking on every interaction with the demon and trying to listen to what Dean had been saying from the beginning.
A week later they set a trap and caught the demon. They put her in the panic room that Bobby had just built and the older hunter began interrogating her. By day three Bobby said that she didn’t know anything but Dean stepped in, convinced she was still lying. It took another four days but she finally broke and told them everything. About Lilith and her working in secret to get Sam to drink demon blood because eventually after they broke Dean in hell they were going to start breaking all the seals that locked Lucifer’s cage and the final seal was Lilith’s death which Sam would need to do at a certain place and time. She even told them that the demon blood was to make Sam’s body strong enough to be Lucifer’s vessel when he rose.
After they figured they had every bit of information Ruby knew Sam stabbed her with her own knife and watched the sparks as the demon inside the human body died. Afterwards he felt like 10 kinds of fool for ever believing anything she’d had to say and for the few times he had indulged in her blood. But according to her he had the power inside, he just needed the boost to learn to use it and make him strong enough to kill, so with his brother helping to train him they got back to work capturing demons so Sam could exorcise them with his mind. The freakiest part was it worked. The more he did it the better he got.
Now that they knew what the plan was for Dean the older brother was on board with doing what he could to find a way out of his deal. Being told he was going to start the apocalypse was motivating Dean to stop Lilith’s plans sooner rather than later, although the man still wouldn’t do anything to outright cause the deal to be revoked and Sam to die. But Sam didn’t care, he had finally found what he’d always been longing for, someone to know him completely and love him anyway, and there was nothing that was going to take it away now. He would find a way with or without his brother’s help and he would do whatever he had to in order to keep Dean by his side, where he belonged.
Fin