My First Time

My First Time: “Your roommate is here. What’s up with that?”

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It was 1985.

I was 18 and new to college. I wanted to go off and be away from home. It was Vermont, a small town and it was August. My dorm roommate seemed pretty cool. Jay was from a nearby town and was very social. I, on the other hand, was shy and still trying to decide if I was gay or straight.

On a few occasions, he asked me to go out with him, but I told him I was really into girls. So I would pass. He asked if I was gay and I honestly said, “I’m not sure.”

One Friday night, I had just finished my job at the campus food center and went back to the dorm. It was about 11 or so, and I jumped into bed and was passed out. Sometime during the night, I heard Jay come in with one of his girls. It was obvious that they had been drinking and the two of them just jumped onto his bed. They really didn’t notice right away, I kept still while trying to sneak a peek at the activities.

After they had both got naked and were on the bed, his date noticed me in bed and stopped. I could hear her say, “Jay, your roommate is here, what the fuck is up with that?” I didn’t move. Jay answered her by saying not to worry about me and they went back to their business. A few minutes later, someone is poking me and waking me up. It was Karen. She was accusing me of being some kind of perv or something by watching them in the room. Jay stops her and say, “Hey, the kid is no perv. Hell, he’s not even sure if he likes girls or guys.” Yikes, thanks for blurting out that bit of news. Karen asked me if I was gay. I responded by saying I don’t know. Suddenly, she pulls me out of bed, as she’s saying, “Let’s find out.”

Here I am, laying on the floor looking up at my roommate and his girl, both naked looking down at me. In a really quick move, Karen drops my sweatpants and there I am, all boned up and exposed.

“Wow,” she says, “I think maybe you do like girls…” and she grabs my cock. I remember he hand was warm and felt really nice. She held on for a while, then yelled, “Switch.” Next thing I knew, Jay was grabbing onto my dick. That felt really nice too. So nice, I felt myself getting harder as he started to stroke it. “Wow,” Karen yells, “You are gay, or maybe bi.” The rest of the night we all spent in Jay’s bed. I had my first boy=boy kiss and Karen convinced me let Jay fuck me. Didn’t really take much convincing though, as he stuffed my new ass, Karen jerked me. It was heaven and a night to truly remember. Karen eventually disappeared during the semester, but Jay and I had a great first year in college.

— Male, 18, Vermont