I was one of the normal kids. I played football, dated one of the cheerleaders, had friends, went to parties, and picked on the gay kid, Rich. Like every school, ours had the one gay kid that everyone knew about. He had been caught freshmen year making out with another guy, who ended up moving. People took every opportunity to torture him, including myself.
I considered myself to be straight, and had a good sex life with my girlfriend. But, as I was about half way through my senior year, I became curious about how it felt to be on the taking end of sex. I would often tease or even finger my ass while masturbating because I enjoyed the new sensations. I often looked at Rich, the gay kid, and wondered if he had ever been fucked in the ass, wanting to ask him what it was like. I caught myself staring at him in the classes we had together. Even more surprising to me was how often I caught myself looking at his crotch. It seemed like every time I looked at him, he had a hardon, and a big one at that. I always wondered just how big he was. He was not allowed to shower with the rest of the guys after gym, and walking up and asking just wasn't an option.
One day however, everything took a turn for the best. One night I wandered into the movie store, I had just turned 18 and was planning on renting a porno. When I walked in, the first person I noticed was Rich, looking at some older movies. I was feeling daring and went out on a limb.
I approached him, and he tried to avoid me. I finally caught him and said "Hi." I made some small chat, asked him what movie he was getting, just bullshittin' for a while. Then I dove in and asked him if he wanted to come over to my house and watch the movie, my parents were out of town and it was a perfect opportunity for me. After some convincing that it wasn't a plan to hurt him or anything, he agreed to come over. We went back to my house and straight to the basement. We watched the movie, "Oceans 11," very good by the way, then came the awkward silence after we turned off the TV. I went straight for the throat, "Rich, have you ever been fucked?"
He immediately thought I was only poking fun at him, but he eventually loosened up. "No, I'm a gay top, I do the fucking," he answered.
"Have you ever fucked a guy?" I asked.
"No," he responded again "My boyfriend never let me."
"Well how would you like to try it for once?" I asked him. He thought again it was some kind of trick and even tried to leave for a moment.
I convinced him I wasn't joking, I told him how I had looked around online, and was kind of curious about being fucked. He shifted uncomfortably then asked exactly what I was thinking.
"You want to fuck, you're gay, I want to try being fucked, I'm straight. I'm the one with the problem. And the solution is that you could fuck me. But, you can't tell anybody what we do, and as long as you keep quiet, and I like it, we can do it as long as we want." I watched him think for a minute, trying to figure out if I was telling the truth.
"OK," he responded, "I'm up for it." I glanced instinctively at his crotch, the slender pole along his thigh told me he was indeed "up" for it.
"Just remember," I said, "don't tell anybody, or I'll deny it, and nobody will believe you."
"OK," he responded, looking somewhat excited for this opportunity.