The story I'm about to relate is technically my first time with another man. I say that because, when I was younger and learning about my body, I had a friend who liked to experiment as well.
And, happily, he later became the first man I had sex with in the more literal sense.
To start, my friend Jim and I have been best friends since we were in grade school. We did everything together growing up - riding bikes, reading and swapping comics, going to the town swimming pool, sleeping over at each other's house. As we got older, we even double-dated.
But, between the time we were playing with our 'Star Wars' action figures and the time we started to go out with girls, we were curious about the changes in our bodies. We 'borrowed' our older brothers' Playboy and Penthouse magazines and went off to his or my basement to see what was what.
A few years later, we 'discovered' real girls as opposed to the two-dimensional kind. And, by the time we were seniors, we were lucky enough to both lose our cherries. With the same girl but at different times.
College came along and we ended up going to different schools. I stayed near St. Louis while Jim went to California. We saw each other at breaks and over the summer but only spoke occasionally during the year.
The second summer we were home, we were going out to hang with some friends. On the way, he seemed edgy and asked if I'd drive around for a while. He seemed to want to talk but, knowing Jim, it might take time to come out. I asked but didn't pressure him, he'd tell me when he was ready. We were close enough that there were never any real secrets between us anyway.
Finally, he told me he wasn't a virgin any longer. I looked at him, wondering what he was talking about. I knew that. I knew the girl he'd fucked the first time. When he finally explained, I felt a bit like a moron. He hemmed and hawed for a while then finally told me he'd slept with a man. And it was not a one-time thing. I found myself pulling over to stare at him.
He turned pale and mumbled something. I asked what and he said, "I guess we aren't friends anymore."
I hugged him and said that was ridiculous. He was more like a brother to me than my own brother. Then I asked him about what had happened.
As he told me, with only the barest of details, what happened I realized I wasn't surprised. But, deep inside, I had to admit to myself that I was disappointed his first time wasn't with me. When I realized that, I was dumbstruck once again.
The rest of that summer, and the summers and breaks that followed, were pretty uneventful. We got together, hung out by ourselves and with our friends, went to concerts and movies - the usual stuff. Jim's new lifestyle - he had eventually told me that women just weren't exciting to him anymore but men were - never really came up.
Well, except for the moment he told his parents. While they were initially upset, they came to realize Jim was still the same loving son they had raised. Fortunately, his parents, while good Catholics like mine, aren't too narrow-minded. They came to accept his alternative lifestyle. And pretty quickly too.
After college, we both ended up working in different parts of the country. I was lucky enough to stay close to home and got my own apartment. Jim ended up in the New York area - Long Island specifically. We stayed in touch by phone and he visited often enough that it was still kinda like our college years.
And I admitted my fascination of male sex - to myself. I would go to bookstores in the Central West End and buy magazines with pictures and stories in them. These became a major source for my solo sexual escapades. (I wasn't ready to go to adult shops for gay videos - that was more than I had the courage to try at that point. And the internet wasn't quite as 'sophisticated' as it is now.)
I never explored that aspect of my life outside of very personal, very secret fantasies. Neither Jim, my folks, Jim's folks, my girlfriends, or anyone else would've suspected my lurid dreams.
Finally, I made what I thought was a big mistake when Jim was home for a visit. We were in a bar and I had just enough to drink that I mentioned it to him. And the fact that I often had the image of Pete (his college lover whose picture I'd seen once) with his dick up Jim's ass. As soon as I said it, I regretted it.
Fortunately we were in a semi-private booth and no one else heard me. Jim had, of course, but didn't say anything for the longest time. Finally he asked me why I'd waited so long to tell him. I admitted I was scared - scared of my feelings and desires and scared of society's attitude.
Turned out he was upset because he had just started a relationship with a man he'd met in NYC and it was developing well. He asked me, "If I'd asked you last year to have sex, would you?"
I told him yes but then seeing how that seemed to hurt, I added, "I think so. I'm not sure. It's all so new."
We talked long into the night about this. He admitted he wanted to have sex with me but he couldn't while he was involved with Steve, his new lover. I agreed and said I wouldn't either while I was involved with Becky - a girl I'd been seeing for a couple of months. After that, the subject never really came up again during his visit.
A few years ago, during one of our long-distance phone conversations, Jim asked me if I wanted to try something new. I agreed and we began to have phone sex a couple of times a month.
The first time, we arranged a time to do it and I was lying on my bed, naked when he called. The pattern repeated with Jim or I doing the calling after pre-arranging a convenient time for both of us.
The first few times, we told each other stories - fantasies. My favorite was telling him what I pictured him doing the first time. It had become pretty involved considering how little he actually told me about how Pete had seduced him. He enjoyed telling me about the first man he seduced. These and other stories were more exciting than anything in any magazine and I came every time. And I came a lot.
Soon, we began to describe what we'd do to the other as we stroked ourselves. This was just as hot, if not hotter, and we always seemed to experience orgasms at virtually the same time. Just hearing him moaning and breathing as he climaxed would get me off and I'd end up moaning with him.
We also used private email accounts to share stories, links, and images. Soon, I was sitting up at my computer, masturbating with my best friend as we shared the same gay sites on the web. While not as comfortable as laying in bed, it was very exciting to be looking at the same pictures or reading the same stories while we jerked off.
More than once, I'd come so hard, I ended up having to clean the monitor.
A year or so later, Jim began to plan a trip home the following summer - his first since we had begun our long-distance trysts. We discussed this and what it would mean to see each other in person for the first time since we began long-distance sex. We agreed that we would not allow it to interfere with our friendship regardless of our fantasies and long-distance jerk-off sessions.
The possibilities were there for us now that both of us were single again. He'd broken up with Steve about the same time Becky and I had split. In my case, it had nothing to do with Jim but was just the gradual withdrawal in a relationship that wasn't meant to be. (I later learned the same happened between Jim and Steve which was a huge relief to me. I never want to come between anyone if I can help it.)
