Hi. I was almost 20, in college and curious. This was more than 30 years ago, and there was a single gay bar in the town. I walked from my dorm late at night to the bar, about 25 minutes, went inside but chickened out and left. As I was walking back to the dorm, mad at myself, a guy pulled up in a car. He had seen my brief appearance and asked if I was interested. I had only jacked off one guy before, but I wasn't going to back down a second time that night and said yes. I hopped in the car, and he drove back to his home (he was in his 20s and lived with his mother). He parked in the garage, we got in the backseat and undressed, and he flipped me over on my stomach. He then grabbed a jar of vaseline and lubed himself up. I wanted his cock badly but had no idea what to expect. When he entered me it hurt like hell, and it never really stopped hurting me. But he was fully on top of me and I couldn't move. I don't remember how long he fucked me but he unloaded in my ass with a gasp, and I was thankful the pain was over. He spanked my ass once, told me how great it was and kissed me. He drove me back to my dorm, gave me his number and I ran inside. Before I could get to my room I felt my briefs getting wet. I ducked into the bathroom, looked inside and there was a massive load of cum that had come out of my ass. That turned me on and I jacked off. I never called him again, and it would be years before I took another cock in my ass. But even with the pain, I never forgot that first time and how much since I've craved being a bottom.