We’re looking for stories about the first time you had sex. Email with 500-1000 words. (Don’t worry, we won’t print your name — but please do make sure to include your gender, where you were, and how old you were.) Submissions may be edited.
He was seventeen and lived in his parent’s basement. We both played guitar and jammed together a lot. Even though I looked like a girl who wore oversized band t-shirts and cargo shorts every day, he was into me. I was surprised, but fifteen-year-old me thought he was the coolest person alive because he could come and go as he pleased and had a car. I was so into him.
At this point in my life I had never touched a penis. I had never had one in or even around my mouth. I had seen plenty in porn. Hard, potentially dangerous flesh that seemed so far away, so alien. I had no comprehension of what it was going to feel like the first time I interacted with one, but I was equal parts terrified and excited to find out.
We drove around our small town for hours in his champagne-colored Honda Accord, grabbed Dairy Queen, then eventually parked in the lot of a playground we had both been to as kids.
We talked about metal-core bands between kissing. As the chorus to “Angel of Death” peaked, he said, “I wish I had a condom right now because I want to fuck you so bad.”
I smiled bashfully, nearly forgetting to breathe.
He leaned back for a moment in the driver’s seat, biting his lip, then eyed me saying, “You know bro, there’s other ways to do it that don’t require protection.”
With that statement, fifteen-year-old me was thinking, “this is my moment.” It was time to touch a dick. We moved to the back seat and he immediately pulled down his shorts and boxers, bare ass to the car interior. For a second I felt some form of shock, I was overwhelmed with the concluding anticipation. His penis sticking straight towards my face, my mind just went blank.
Distraught by my inaction he said, “try licking it like a lollipop,” and as creepy as that line sounds, it was helpful to have any form of direction. I popped him in my mouth and was immediately confused by the temperature and texture of his skin. It was not at all as I had expected. Something in my brain had made a connection between the visual stiffness I had seen in porn and rigamortis. I imagined something cold as steel and unbendable. This was much better. I was incredibly envious.
Finding my post-mortem hypothesis disproven, I continued, with no real grasp of technique or execution. It occurred to me, catching my first up-close glimpse of a ball sack, this was the only time he had ever been in someone’s mouth, so regardless of what I did or didn’t do, with no comparison, it was probably going to seem like the bee’s knees.
Years of practice jerking himself must have created some sort of muscle memory to every porn he had ever seen. He grabbed me by the shoulders enthusiastically, and within seconds I found myself stretched across the length of his backseat, the interior cold against the back of my arms.
He said, “don’t worry, I’ll just pull out.”
Fifteen-year-old me nodded with a mix of sudden hormonally-driven bravery and complete reckless abandon. Parts of my brain were calculating percentages based on every Health class safe-sex video I had ever seen while my body simultaneously began shutting down all pathways to logical thought.
Ten seconds later, I had one foot on the driver’s car seat and one on the armrest of the back door. My boxers were thrown to the ground and then, he was in. Female-bodied people will often comment about pain the first time they were penetrated. In full and complete honesty I can say I didn’t experience physical discomfort. I did, however, feel this overwhelming sense of invasion. Like a fortress had been compromised in a war I wasn’t fully aware I was battling.
I could feel him thrusting in and out, every so often looking down at me and asking, “what’s up?” which I took to be his version of, “are you okay?”
I had heard first times for male-bodied people didn’t typically last long, that they climaxed quickly, but about ten minutes later I distinctly remember him saying, “dude, you should flip over and let me do you from behind.” This is how we communicated, even in this situation, “dude,” “man,” “bro”.
He grabbed me by the hips and it felt better than the first position. He went on for a bit longer, then without hesitation, went right for the gold— “your ass look so nice man- I want to stick it in.”
And I’d figured, we’re already here, may as well. It was what I wanted, even if I was too timid to admit it at the time. Pain does not begin to describe anal sex without proper lubrication, but I took it. Because, when in Rome, or when in Honda Accord, or whatever.
That’s what did it for him. He said, “I’m going to cum on your ass bro.” Keeping his promise, he pulled out before he came. The warmth landed on my bare backside.
Something about that moment made me grasp the gravity of the situation, the real true gayness of what was occurring in that car. A man losing his virginity to a man who was also losing his virginity to a man, in a relationship perceived as heterosexual.
He slumped back, breathing heavily, while I cleaned-up with my own boxers. We sat quietly for a few minutes letting the rest of the Slayer album fill the air.
I had gone from giving head for the first time to having unprotected anal sex in a matter of thirty minutes. I wasn’t sure whether to feel terribly disgusted or be completely impressed with myself.
“Dude, that was amazing,” he finally said with an exhausted smile.
I smiled back, deciding right then to never regret that moment.