For years I described whatever we had as a ‘romantic entanglement.’ It wasn’t a relationship, but it wasn’t nothing. It was…indefinable. I don’t know if, even now, I can pin down exactly what we were. This was good and bad. One of the issues, early on, was that I expected things from him I probably shouldn’t have. I expected him to treat me like a boyfriend, even though that’s never what I was to him, nor he to me. I think these deluded expectations are why I thought losing my virginity to him would be something special.
It wasn’t. Does everyone romanticize the first time they had sex? I did for years, and then I started really thinking about it...it was basically awful. We planned it. Ugh. That speaks to every neurotic bone in my body!! We planned it! I planned when I would lose my virginity... I feel like my whole sexual existence is starting to make sense. l had gone with him to a club, drank, not too much, but...a bit—obviously he drank too. In fact, he drank a lot. So much so that I had to drive us to his house—30 minutes away, knowing the whole time we would have sex once we got there. While I may not have been wasted, I probably shouldn’t have driven—I was 19 with alcohol in my system for God’s sake! If that wasn’t bad enough, once we were on the highway, this asshole fully reclined the passenger seat, so he could take a nap—a mother fucking NAP. I can’t help but think this was not the optimal way to lose one’s virginity. Isn’t it supposed to be magical? Shouldn’t I be driven in a chariot instead of driving myself in a Honda Civic? Shouldn’t I be wooed by the sweet sounds of jazz—or at least Janet’s Velvet Rope album—instead of the deafening rattle of a deviated septum?! Shouldn’t I feel safe and secure instead of unsure of which exit to take? I guess it’s pretty appropriate that the lead up to my first sexual experience would be weird...I mean, look at what’s happened since... On one hand, he could have been resting up to make sure he had the energy to give me a solid dicking-down, but, after knowing The Asshole for some time, I can guarantee this was NOT the case—his ass was tired. Period. And while he got his beauty rest, there I was driving my sleeping top to this inevitable rite of passage. It was not hot. There were no vibrations, or romance—nothing to make you excitedly unsure of the next step. There was no throw-down or childish abandon. It was so...mundane. I wonder if this single night has subconsciously shaped my entire sex-life. Maybe this is why I live in constant pursuit of something spontaneous, situations that feel exciting in the moment—but ultimately fizzle into disappointment.
Once we arrived at his house, I had to wake him up. Charming. We went inside where he poured us another drink and we sipped our poorly mixed, aggressively strong cocktails under harsh fluorescent lighting in his kitchen—awkwardly making conversation. I leaned against the island littered with mail while he stood across the room at the sink filled with dirty dishes. I tried my best to be flirty, but even at that young age I knew I didn’t have to work for it—we’d both already decided what was going to happen next. And as soon as the ice cubes clinked the bottom of our glasses, he led me down the hall to his bedroom.
It was happening. Now I’d been in this room before, but under very different circumstances. This used to be his sister’s apartment. Since she and I are very close, I’d been here countless times—but never for sex. Clearly. Because of this, there was something very unsexy about this particular room. However, the whole apartment didn’t feel that way to me. When I was in high school, The Asshole and I would secretly hook up in a room down the hall. Everyone else would be sleeping, and we’d crawl into bed and explore each other’s bodies. It was magical. I wish I had lost my virginity on one of those nights...but life isn’t like a movie, I guess. I should feel lucky I had those nights at all. They were beautiful and riddled with passion—a stark juxtaposition to the night we were having. I wonder if things would have been different if I’d led him to that room instead… Minutes inside the bedroom and I was on my back, knees to Jesus, taking in the sterile atmosphere—trying to quiet my mind… Good GOD, why is the light on? There is way too much light. Did he mean to leave the light on?
Why do people leave the lights on when they’re having sex? I get SOME kind of light, so you have a relative idea of where you’re poking and prodding things—but unless the both of you are in peak physical shape…I can’t see the reasoning behind it. I mean…things fold and tuck and wobble and hang. I just can’t help but feel like dim lighting does a service to all parties. Though, he had a leg up in that department. Years earlier he’d gotten unnecessary lipo and pec implants.
I know. They look good, though.
Maybe that’s why it was even more important the lights weren’t angrily beating down on me. We weren’t approaching this from an even playing field. I had yet to begin working on my pectorals...or really, anything for that matter. And my anticipation of this sharp, forcefully penetrative act was so intensified by every light in the room, its stark outline of our current situation—of my situation—it overwhelmed me.
I was hardly his first, and, the more I’ve thought about virginity, I think that’s best. I suppose there’s something beautiful about two young, fumbly gays trying to figure out how butt sex works, but there are some logistics involved that require a learned professional—at least if either party is interested in the bottom enjoying himself. I just wish he’d learned more about lighting during all the field testing he’d participated in.
I watched as he expertly spread lube in and around my area. I was so tight and nervous. It was going to take an act of Congress to get me to relax—but I tried. I tried to take deep breaths and open myself to this man I’d been infatuated with for years. And it worked, at first. I heard the distinct sounds of the crinkly plastic begin to stretch and pull on his dick as he opened me for the first time.
And then, like the fire of 1,000 suns, I felt an angry burning unlike any other I’d ever experienced. It felt like a hot poker was violently stabbing at my asshole!
This can’t be gay sex!!
“Holy Fuck—stop, stop, stop.”
“I just...that can’t be right. Something about this really doesn’t feel good.”
“Ok, don’t worry. Why don’t we try you on top. Here—I’ll lay on the bed and you can control it going in.”
I didn’t have any idea if this was going to work, but whatever we’d been trying had ceased all viability—so I thought, why not?! He crawled next to me on the bed and lovingly gave me a kiss as he guided my body onto his. It felt sexy and safe. It reminded me of the nights we’d spent down the hall.
This was better.
I adjusted myself as I reached back and guided him into my recently accosted hole.
Ok, you can do this. You drove him all the way here for this exact purpose. You’ve been looking forward to it. You’ve got this.
And then, I sunk back onto his hyper-lubed dick. It was painful at first, but I was determined. I winced the further he probed into me. I couldn’t do it. The pain flung me forward until I was bracing myself on his chest—against his hips that were bucking into me. I finally found his mouth and leaned into the warmth of his kiss, hoping it would save me.
Something started to feel better. I don’t know if it was the child-like love I was falling into, or if my anal cavity was finally embracing this intruder, but I started to relax into the idea of having a dick up my ass. All that said, I didn’t love it. It still felt adjacent to a red hot baseball bat being banged and prodded up my hole. I couldn’t quite get the hang of how I was supposed to steady myself. I suppose the point is to sit all the way back and bounce on it? But there was no way I was in a position to sit back, much less bounce. So, I did my best to prop myself on his chest while I let him poke around in there.
Things were going well for a while—I was hating it and he was thoroughly enjoying himself—until I lost my balance with one particularly aggressive thrust. Because of the excessive lube, I slipped. I tried to grab ahold of anything I could. In this case, his pecs were the only real option. I grabbed onto them, desperately, in an attempt to keep from violently face planting. And, in theory, this would have worked—but the damn lube! My grab turned into a treacherous slip-n-slide and I spastically grab-slid my way all over him.
Though awkward, I did manage to avoid a violent head butt. I didn’t have long to revel in my triumph, though. As soon as I’d stabilized my parade of awkward, I heard a scream like I’ve never heard before—or since.
I readjusted myself on his chest to get a better look at him—to see if I could get a better idea of what was going on. He screamed louder. WTF?!
He grasped his chest.
What was happening? Was he having a heart attack? He wasn’t THAT much older than me!!
“You...you twisted my implant.”
And then he threw me off his dick and hobbled to the bathroom as I tried desperately to keep from falling onto the floor.
I...didn’t know this was a thing! I didn’t know you could mess up someone’s pec implant! Holy hell! Was he going to be ok? Was I going to have to take him to the hospital? Was I going to get to finish?
He slowly emerged from the bathroom—silent, but he seemed ok. He held his hand up to my mouth to keep me from speaking and lovingly put me on my back. After some thrusting and heavy breathing, it was done. It wasn’t a total disappointment, but I had no interest in rallying for a second go of it—even if he’d been able.
I guess it was my fault? I can’t imagine what it would have felt like to have my pec implant twisted in my chest. Yikes. I’m sure I wouldn’t have been able to finish after an incident like that, but even without the lackluster ending I can’t help but think the entire situation was...serviceable at best. However, the further I got from the moment, the more I started inflating what had happened, romanticizing it. I started confusing those secret trysts we had during my high school years with that weird, stilted night.
It was this conflation of the past that would keep driving me back to him. It would inspire me to look the other way when he rejected me for other men or, worse, drugs. I loved him in my own fucked up way because of my misremembering of that night. With time, I’ve begun to see him for who he is, and while I can’t say I’m GLAD I twisted his tit...I’m not saying that, in the end, he didn’t deserve it.