I was 18 and it was totally unplanned. I tried the doing the straight thing throughout high school (thanks to a strict church upbringing), but I never got past second base with any of them. I was always timid and never really interested. The entire time I was chatting with an older top and exclusively beating off to gay thoughts.
I had a messy breakup with my then girlfriend and said fuck it. I messaged the top saying I wanted to suck his dick. We met at his work after hours in one of the stalls in one of the public, family bathrooms. While happily sucking my first cock, he casually told me to turn around and spread my knees apart. I definitely hadn't planned on getting fucked.
Next thing I know his hands are on my hips and he's spitting on my asshole while pushing his dick into me. It was surreal in the moment. This was the mid-90s. No prep meds. The city I lived in at the time had, per capita, the highest STI rate among gay men in the US. Of course, I had no condoms because it was only going to be head.
A million thoughts race through my mind while he took my virginity especially knowing that he was raw and that he was going to cum inside me. When he finally came it was the greatest and the scariest thing in the world for me. As I was starting to get up, he goes, "Don't worry. I had to get tested for my health insurance." It seemed like the strangest thing to say to someone.
By the time I drove back to my apartment, the anxiety had disappeared and I just wanted him to fuck me more. I messaged him telling him that, and he stopped by my place on his way home to deposit another load. I knew I was hooked. He was also the person that introduced me to the one bath house we had in the city.