1. I used to ride into school with a guy who lived one neighborhood further out than me. He was gay but we never chatted about anything sexual. I had never done anything other than kissed a girl but I had same sex fantasies I never acted on. When we were riding back one night he started rubbing my thigh. He got very excited when I told him I was 19. His reaction turned me on. He asked if I’d had a girlfriend. I said no. He asked if I ever had sex with a girl and I said no. I was a virgin. He asked if I was ever interested in sex with a guy. I said I thought about it.

He asked what I wanted to try I said I fantasized about anal intercourse and fellatio. I invited him over to my house as my mom was out.

The guy was in his forties. Kind of big but not super fat. Very friendly and easy going. I lived on the second floor in a converted attic. We went up to my room I went downstairs to get Vaseline from my mother’s medicine cabinet.

We got naked and I lubricated my anus with a large gob of Vaseline. I got face down as I didn’t know what I was doing. He put a finger in my anus and I liked the sensation he fingered me a long time then he hooked his arms under my shoulders and drove his penis into my rectum. He said he restrained me so I wouldn’t get cold feet. It was extremely painful for about a minute. Then he started thrusting very slowly. He kept asking me if I was gay. Trying to get me to say I was gay. He kept me in constant conversation. He said I was very loose for a virgin. He said I wouldn’t lose my virginity until he came.

He finally ejaculated and he made a huge deal about it. He was very loud and I was really ashamed. He told me that because I lost my virginity to a man before a girl that I had to admit that I was a homosexual.

We sat there for a while and he asked intrusive questions about how his penis felt inside me. He said that he was very happy that his live sperm was swimming inside me. He said I should be ashamed about how loose my anus was. We had intercourse two more times. He took it very slowly so my legs were cramping but I didn’t want to look like I didn’t know what I was doing.

He was obsessed with getting me to admit that I was gay. Then he asked me to suck him so my experience would be complete. I didn’t even think about the fact that his penis has been in my rectum for hours. It tasted of Vaseline and was slimy at first. It took a really long time for him to come. He told me to savor the taste before swallowing it.

We hung around a little more then he entered me one more time but he stroked my penis and made me come. Then I suddenly got extremely embarrassed and ashamed and started panicking about what happened. He told me that I should calm down that I was obviously a passive homosexual and I should quit whining because my body betrayed how badly I wanted it. He then got very icy and said he had to leave or his partner would wonder why he was late.

I masturbated after he left. My bowels felt very slippery and I thought about how long the sperm would live in my rectum. I didn’t sleep all night.

Amazingly we still rode in together and he took great pleasure in recounting the story every ride and what a good sport I was.