Disclaimer: I do not own Supernatural or any characters, nor am I doing this for any kind of profit. There would be a lot more gay sex on screen if I did own them.
Author's Note: Extremely quick thing I came up with. It sucks, I know, but I had to get it out of my head. Also, this was unbeta'd so I apologize for mistakes made.
The first time that the thought had ever crossed his mind was when he was in the locker rooms of one of the hundreds of high schools he'd attended. Dean had only decided to try out for the school's dodgeball team because it seemed like the 'it' sport to play there—something to say to the girls to get their panties around their ankles quicker—that, and he needed a distraction from watching Sam twenty-four/seven. He needed some sort of social life that didn't include showing his brother how to take apart and clean a revolver. So, Dean had joined the school's dodgeball team and Sam had joined some Latin club (Dean couldn't resist teasing his younger brother about being a nerd when Sam had decided on THAT club out of all the ones the school offered).
One practice, Dean had been last—or so he thought—to leave the locker rooms after his shower. As he rounded the corner, he ran into one of his teammates, Thomas Anderson, who'd been heading towards the showers. Thomas was a pro on the court with his deadly aim and knack for dancing around on the field to avoid the red balls that tried to assault him. However, that wasn't what Dean noticed in that moment. What he'd noticed was just how tiny beads of sweat slid down Thomas' bare chest, the way his hair clung to his flushed face, and the fact that those lips would look much better after they were bruised from a quick make out session against the horrendously painted metal lockers. The thought froze him into place as Thomas gave him a warm smile, apologized for running into Dean and then continued his journey towards the showers. It wasn't until the showers had turned on did Dean dare to breathe. He didn't like guys, no matter what other parts of his body tried to say. The young hunter just chalked it up to having a long day and nothing but the company of his hand in his bed lately.
Weeks passed and soon Dean and Sam were once again at a new school. He'd paid Sam twenty bucks to go see a movie just to get him out of the hotel room so he could have some alone time with the smoking hot blond (who was captain of the cheer squad, he reminded Sam when the boy had tried to protest). One thing had led to another and the girl was under him, writhing in ecstasy as he finally put the condom in his wallet to good use. Feeling himself near release, Dean closed his eyes as he kissed her, none-too-gently. With his eyes closed, he pictured those lips weren't Tanya, the hot blond, but Thomas, the dodge ball-playing-stud. It was this that brought Dean over the top, Thomas' name on his lips. Thankfully, the cheerleader hadn't heard him, but he quickly shooed her out of the room, panicking somewhat. He'd just reached his orgasm by thinking of his former teammate.
That night, Dean drank an entire flask of holy water just to make sure he wasn't possessed.
Years passed before Dean thought of another man like that. Sam had gone off to college leaving Dean and John to hunt on their own. Dean was hunting down a vengeful ghost in Arkansas while John was hunting something called a rakshasa in Tennessee. With the ghost taken care of, the younger hunter had decided to hit the bar to celebrate. It had started out innocently enough, whiskey being downed one glass after another while he spoke with a rather good looking guy (Dean found he couldn't tear his eyes away from the male's lips) who looked to be about his age. The night turned into a blur and Dean woke the next morning, naked, lying in a foreign motel room next to the male he'd been talking to at the bar. Once more, Dean panicked, running out of the room with his stuff. He thought he was safe when he got to the safety of his own motel room, until the male—Lee Roberts, he said—called his cell. Dean couldn't believe his drunken self had not only slept with another guy, but had given him his number too. An argued conversation on the phone helped Dean to realize several things: first, he had slept with the guy. Secondly, he had been on top (thank god, he thought). Thirdly, maybe he wasn't as straight as he thought he was.
That was what had started Dean's experimenting.
Whenever he and John split up to work on different cases, Dean worked to get his case done as fast as possible so he could spend the remaining time working out this newfound pleasure. He still liked women (he was pretty sure at least), but he was coming to realize he liked men too. He was definitely a hit at gay bars, finding at least four or five men that came up to him or bought him drinks from across the bar, so it was never hard for him to take his pick. After a string of one night stands, he'd found he preferred men more of his build than chubby. He also had decided that while short hair looked better, longer hair was more fun to play around with. He preferred brunettes to blondes and he liked when they were around his height or taller. Dean had finally gotten comfortable with this lifestyle when John left. When John left, Dean went to find Sam and put his experimenting behind him for now—that wasn't something he wanted Sam to find out.
Once he and Sam had been on the road for a while, hunting down their father, he got that itch. Sure, he'd hit on plenty of girls since their little 'adventure' began, but this was a different itch—and one he was dying to scratch. Occasionally he stole Sam's laptop when they split up for their investigations, hoping that just a quick search of some gay porn site would sate him before he deleted the history from the computer, erasing any evidence that Sam might come across. Soon, that wasn't enough and one night when Dean was positive that Sam had been dead asleep, he made his way to the local gay bar, picking up a guy and heading back to his place for a quick romp between the sheets. The next day, Sam had questioned why Dean seemed to be practically glowing, curious as to what he missed while he slept. Dean had simply responded that he'd gone to the bar and met a cute brunette and that was where Sam had cut him off, not wanting to hear more about his brother's sexcapades. Dean was grateful for quick dismissal, deciding it couldn't hurt to do this more often
This was how it was for what seemed like forever—Dean sneaking out when Sam was fast asleep and scratching his itch to be on top of (and sometimes under) a smoking hot guy. He still kept up appearances around Sam; hitting on the hottest girl at the bar and sometimes sleeping with them, kicking Sam out of the hotel just to make sure Sam saw that he was actually sleeping with a girl. However, more and more, his thoughts were focused on men and not women. The problem with this (because he'd already determined that if he was gay then, well, he was gay—nothing else to it) was the fact that he had a smoking hot, tall, brunette living with him day in and day out. Which, when Dean thought about it, this probably wouldn't have been a problem … If Sam wasn't his brother. It was wrong. More wrong than wrong. Yet, Dean found himself, more times than he'd like to admit, in the shower stroking himself to the thought of Sam—his Sammy—on his knees in front of him, lips on his dick, sucking like his life depended on it; or Sam throwing him down onto one of those dingy hotel beds, paying the quarter for the magic fingers and then plowing him into the mattress. It was these thoughts of screwing his brother (or letting him screw him, honestly he didn't care) that Dean knew had really damned him to hell and he wasn't coming back, which was another reason that offering his life in return for Sam's was something he could do without blinking.
The following year had been torture. Dean had wanted to confess everything to Sam, to tell him how he felt about him—how his love for Sam went further than just being brothers. How he always felt that little flutter in his chest whenever someone made some sort of off comment joke about them being lovers before one of them politely corrected that they were, in fact, brothers. Of course, it wasn't something he could just drop on Sam before he left him alone on Earth, so Dean kept silent.
What Dean hadn't planned was to come back. Hell was … Well, hell. There were no other words for it and he'd never wish it on anyone (unless they really deserved it—you know, mass murders and the like) but he had never planned on returning. His first thoughts were that Sam had brought him back, just the thought of seeing Sam again set his heart fluttering once more. Nothing compared to when he saw Sam once more in that hotel room.
"I know … I look fantastic, huh?" Dean had told him, when in truth; Sam had been the one to look fantastic. More than fantastic. Then they'd shared that hug, in which Dean could feel every muscle under the other's back and it brought back those feelings he'd kept buried.
All Dean wanted was to bury himself in alcohol. Maybe pick up a guy (or two) and just party back in someone's hotel room. He wanted to forget the feelings he had for Sam and just go back to before he started thinking about his younger brother sucking him off or other lewd acts. Fuck! Sam didn't even know he liked guys! A week of being back had only ended up with him reuniting with Bobby, thinking dirty thoughts about his brother constantly, meeting Castiel, and finding out that God had brought him back for who knows what reason. It was really too much for him to take in at once.
It was one late night when Dean stumbled in, drunk off his rocker. He was giggling as he stumbled around in the darkness, tripping over the tacky coffee table that was made of bowling pins to go along with the room.
"Dean … ?" Sam grumbled as he rubbed his eyes, turning on the lamp to try to see what his brother was doing. "How drunk are you, Dean?"
"'m not drunk, Sammy!" Dean responded, a grin on his face, not particularly caring that his clothes were disheveled and he was wearing some other guy's bright pink polo.
"… Uh huh. Nice shirt, stud."
Dean glanced down, a confused look on his face before he grinned. "Innit?"
"I'm not even going to question why you somehow have a new shirt. It's definitely not from a girl and I really doubt you found a twenty-four hour mall open—"
"Sammy!" Dean said, stopping him, trying to put on his most serious face as he moved over, nearly tripping over the shoes he'd just taken off. "Sammy … I gotta tell y' …" He hesitated a moment and it seemed as though he was on the verge of hurling before he continued. "… I like guys, Sammy. Hot guys."
Well that had been somewhat of a shock to the system for Sam. "I-It's okay, Dean … You know that I'd never think of you different or anything. You're my brother, Dean," Sam reassured the elder. He'd known plenty of gay guys and really, it had never bothered him. He might've even checked out a few videos just to see what it was like.
"No! No, Sam … I like hot guys …"
"Yeah, no … I got that, Dean …"
"… You're a hot guy …"
He honestly had no idea what to say. Of course he loved Dean, but they were brothers. That was so far from the right thing, it left him speechless. The next thing that he knew, Dean was leaning in and their lips were connecting. Dean tasted like the cheap liquor he'd drank all night and whoever that shirt belonged to. Sam found himself wanting to get rid of the other male's taste and replace it with his own. His attitude about the whole 'we're brothers' thing changed so quick, it made his head spin. Dean was his, just like he was Dean's. Quickly, Sam pulled Dean atop him, never stopping their fevered kisses, working at his clothes as quickly as possible—making sure to rip that pink eyesore that he'd throw out tomorrow morning—wanting Dean to be just as undressed as he was.
"Fuck … I love you, Sammy …" Dean groaned against the other's lips as Sam rolled his hips against Dean's.
"… I love you too, Dean …"
The next morning, Dean woke up to a throbbing headache. He ran a calloused hand over his face to try to wake himself up more before he realized he was lying next to a rather warm and naked body. Silently begging the God who'd saved him from Hell for the face that was connected to this torso to be hot, he slowly looked up before his eyes widened. "Sammy?" Dean croaked out, which earned his naked brother jumping up quickly, knife in hand, looking around for whoever was assailing them. Once Sam realized that no one was there except the two of them, he looked at Dean confused.
"W-What the hell happened last night?" Dean sputtered out, trying to keep his eyes above Sam's waistline.
"Well … You … Came back last night drunk as hell … Said you liked guys—hot guys—and that … I was a hot guy … And well … One thing led to another …" The younger male ran a hand through his hair, putting the knife down on the night stand as he grabbed his boxers, tugging them on. "… Sorry, I know … we probably shouldn't've—"
"Sam … Its okay. So long as … you really wanted to do that?"
"'Course Dean. You're my brother. I love you more than anyone else."
Dean thought over the other's words before flashing that classic Dean Winchester grin, "… I love you too Sam."