I'm not sure why I said yes. I think I was still in shock when he led me into his bedroom.
I had woken up befuddled and bemused to find my roommate sitting on the foot of my bed. I was tired and at first I tried to stay asleep – was he mad about the dishes or something? It could wait until morning. Then I realized what he was saying, and there was no more sleeping. His proposition was simple: we would mess around, nothing too intense, just hands and maybe mouths. He never used the word bros, but it was implied all over the place. Just a couple of bros, helping each other out when there's no women around, no big deal.
I was in my mid 20s, depressed, low self-esteem, and generally feeling lost in life. I was desperately lonely. I know now that I am bisexual, and I am proud of that, but at the time I was pining for women. The problem was, I was busy self medicating and hiding from the world in a haze of beer and weed. I had no idea how to meet women, let alone how to talk to them. I had messed around with guys a few times before, with little success, although there had certainly been moments that hinted at more possibilities. Still, at best I felt indifferent about the prospect of sex with men. I knew that if I went to the larger cities there was a gay culture and gay hangouts where guys would hook up, but it held no appeal for me. (I once gave my gay friend a hand job, partly out of curiosity and partly out of sympathy. I still remember him coming all over my hand in great gushing spurts. It didn't bother me, but it didn't feel sexy either – I was more concerned with how I was going to get it cleaned up.)
My roommate was older than me by a couple years, and he was very libertarian and pro gun. He didn't like the democrats, this being the the Clinton years. He was muscular and capable, good with tools and cars and fixing things. (Did I mention he had broad shoulders, muscular arms, and shoulder length brown hair?) He hunted and fished with great proficiency and skill. He had girlfriends on and off in those years, although I thought they tended to be a little trashy. From time to time he had echoed the general homophobic stance that was the norm for our culture. So I was completely blown away by this proposal from such an unexpected quarter.
From the beginning, he made it abundantly clear that he didn't want anal sex. I don't know if he found the idea gross, or if it was simply too gay. I think a little bit of each. Just a couple of bros having a good time, hands and maybe mouths, nothing too serious, right? I didn't know it at the time, but when I crawled in his bed, my body had other ideas.
How did it start? I remember him coming in my mouth, huge bursts of salty strangeness going over my tongue to be dutifully swallowed. I remember my legs on his shoulders, his weight on top of me, straining to get inside me, giving me intense pain and intense pleasure all at once. But all that was later. That night it was awkward and fumbling and uncertain. I think at first I was just going through the motions, not really feeling aroused. I would've gone along with anything, to be honest. Not just to be accommodating, which is my nature, but also because of the strangeness of it all. The idea that he would proposition me, that I was in his bedroom, divesting my clothes and taking his dick in my mouth – and later another way – it was too surreal to be true. But it was also intensely flattering. As we fumbled through that first strange mutual exploration I felt like I was in a dream.
The question of what to do – how to use our hands, our mouths, our bodies on each other – was new to us. I think we tried a little sucking, but it didn't do much for me. But when I climbed on top of him and started rubbing my ass against his bare crotch, I started to feel something more. I had no agenda and I wasn't trying to get him to fuck me. I just kept rubbing because it felt good. Soon I felt him pushing back, grinding insistently underneath me. He dick became greasy, and I started rubbing the head of his penis directly on my private, secret entrance. It was incredibly pleasurable. Suddenly he stopped me and stood up – was something wrong? He looked at me strangely, like he didn't understand what he was experiencing, and he said, "I want to fuck you." It was almost a question, and I think it surprised him as much as it did me. Suddenly, I wanted him inside me like I have wanted nothing else in my life. All pretense of avoiding anal went out the window. There was no question, that dick had to go in my hole ASAP. He went under his bathroom sink and came up with a bottle of hand lotion. Not the best thing, but given our ignorance and desperation, it could have been worse.
I wish we'd known what we were doing. It hurt a lot more than it needed to. Not just that first time, but every time we did it. I guess we thought pain was normal and eventually things would get loosened up and it wouldn't hurt anymore Or maybe we thought the pain was just the price that had to be paid. Since then, I have explored my body and I know we could've done a much better job – better for both of us – if we hadn't been so completely clueless. But we did well enough given the circumstances.
Sex with him, that night and every time it happened, was the best sex of my life. It was transcendental and transformative. For the first time, I knew what it was like to walk around in the warm afterglow of the night before.
In the culture I come from, being receptive to a man like that was supposed to be degrading and humiliating. It made you a "bitch", less than a man. To actually want it – to enjoy it, to give it willingly and to derive pleasure from it – was unthinkable. But the truth is, it made me feel more masculine, not less. It made me feel manly. It made me more comfortable and accepting of my body and what it wants. I was proud of what we did, and I wanted to tell the world, or at least to tell someone. But I promised him I would keep it a secret, and I always have.
There was never any question that our relationship was anything other than purely physical and entirely on the down low. He didn't like it when I talked about how much I liked what we did – it made him uncomfortable and I think he was afraid I would develop feelings and demand a public acknowledgement or something like that. That would have been unthinkable for both of us. But in his bedroom, he always treated me with kindness and respect. He never made me feel like less of a man for wanting him inside me. I was called back to his bed, again and again, by a lust I can't explain even now. I can't say I wanted a relationship with him, but the sex was so intense I wish it had never stopped.
Eventually we moved on in life and lost touch. I still fantasize about him. A couple of years ago I broke down and looked him up on Facebook. He accepted my friend request but never responded to my messages – which I kept completely above the board, with no mention of our former trysts. Then I found his twitter account, and I found out he retweets a bunch of alt-right nut jobs and pro-trump accounts. I think I can safely say getting back together in any capacity is probably off the table. But then I remember him, lying on his bed wearing nothing but a bathrobe, waiting for me without a spoken invitation, knowing I would come, crawling across him in the dark, touching him with my lips, wrapping my legs around his hips. And the answer is always yes. Yes, I will, yes.