Where it happened: Car
I was working at a supermarket while in highschool. An older guy from school saw me walking home from work one night and offered me a ride. On the ride home, we got to talking. He parked the car in a local park and we talked for an hour or so. He finally mentioned that he was gay and asked if I would like to have have my dick sucked.
I thought about it and said I would like to try it. I pulled out my dick and Bruce gace me my first blowjob. The warmth of his lips felt awesome. After a minute or two, Bruce asked if I would like to try it in his butt.
We went to the backseat, he sucked my cock and left a lot of spit on it and bent over. It took a few tries, but I managed to get it up his butt. I inserted it too quickly, and Bruce had to tell me to go slower. I finally got it all the way in. It felt nice and warm, but I could not cum and Bruce kept asking me if I was almost done, so I pulled out and jerked off. Bruce took the cum in is mouth and spit it put the window.
Bruce wanted to do me in my butt, even offering to go to an all night drug store to get some Vaseline, but I refused.
A few nights later, Bruce was cruising around and stopped by my work and offered to pick me up when I got off shift. I agreed. When he picked me up, he asked me if I wanted to do anything, maybe try it in the butt. He said he had condoms and Vaseline, so I agreed. I asked if it hurt, and he said “it relaxes”.
We drove around and finally found a place that was clear. I placed a condom on my dick and told Bruce to bend over. I placed a little Vaseline on the tip of my dick and slowly inserted my penis into his butt. I thrusted and put my hand around his dick to jerk him off a bit, but he told me he didn’t like it. So I continued to fuck him. This time he asked me if I was “almost done” once. I came fairly quickly, and the condom broke. Bruce did not seem to care though.
Then I bent over for Bruce. Bruce had a fairly large, curved penis with a big head. He unrolled a condom on his dick and positioned my ass very low. He slowly inserted his dick into my butt. I remember the head of his penis slowly stretching my asshole open. It hurt a bit, but the pain subsided when the head finally popped in. He stopped and I said “start pumping” So he slowly thrusted into my ass. I remember the feeling of not being in charge, having no control, as Bruce fucked me. It didn’t really hurt that much, but it felt wierd. Bruce began to stroke my dick, but it felt too intense. I told him to stop. I asked him if he was almost done…and I don’t remember him responding. Bruce finally came, pulled out of my ass and threw the condom out the window.
We fucked a few more times after that. Once the condom broke and really hurt my ass. Antoher time, we had a messy accident.
I also fucked another guy, shortly afterwards, who had a smaller dick, so I didn’t mind taking it in the rear so much. I usually topped first, then he would fuck my ass afterwards.
I had no feelings for the guys I did it with, but the sex did feel good, and after I got used to it and relaxed, anal penetration began to feel rather good.
Today, I am a happily married man, but I still remember the first sexual experiences in highschool. I won’t do it with another guy again, as I respect my wife too much.