I had always been curious about men. By fifteen I had been with my first girl but I didn't enjoy it, perhaps it was the fact we were both young and inexperienced but I didn't find myself attracted to her.
The summer I turned eighteen, I had been perusing craigslist awhile but finally decided to post a M4M ad. It was intended to just chat and see how I felt about men, even though I had been sexually curious for a long time.
An older gentlemen, 54, messaged me. His name was Charles. He was very sweet, unmarried, just looking for someone to talk to. I had a suspicion that he wanted more but I was young and lonely, and incredibly curious.
Everyday for the next two weeks we messaged one another. He kept an odd schedule as I did, so after work I would send him a message on AOL (I feel old now!) We would stay up until two or three in the morning getting to know one another.
I'm a fairly old soul so the two of us really clicked. Then, one night, we started talking about sex. He asked what I wanted to try, what my boundaries were. I told him I wanted to try bottoming and topping, oral, kissing, most normal things. I wasn't too experienced with kinks yet. We talked about this until daylight. He was gay all his life, which was difficult growing up in the small communities we both lived in. I asked him if he would be willing to teach me a few things. He responded with caution, the age difference. Talk was one thing, actually doing it was another thing entirely.
The next couple days were back to our normal chats; talking about life, politics, our communities. Then he asked if I still wanted to come over. I was shocked! I said that I would adore that!
We planned for Thursday night, it was a Sunday night we talked (I believe). I asked if I need to bring anything, a change of clothes if I want to stay the night.