The first threesome I had started as a fling with a local transvestite. Dave and I were having a drink, just socially, and he bought me a couple drinks, which I tried to politely refuse, just because I felt bad that I was broke and didn't want to take advantage of him. He jokingly told me not to worry about it, so long as I promised him my first gay encounter would be with him. I laughed and told him it was far too late for that.
Obviously that night I went to bed with him. It wasn't because he had bought the drinks, but once he knew I was interested in men as well he began working very hard to seduce me, and the truth was he hadn't really needed to try. I like sleeping with men, I find men attractive, but I find transvestites and transexuals so much more attractive than the average man. I like feminine qualities, and I like cock.
That was a great night. The next evening I was having coffee with an ex-girlfriend. Our break up had actually been hard on me, and the reason I had gone out drinking in the first place. She had already moved on herself, and we had decided to be friends, and she was very excited to see me with hickeys on my neck. When she found out they were from a man though she got more than a little excited.
This girl, Lisa, like a few others I had known (but never accommodated) wanted to see two men together in person. Thinking about me and this other man together really got her excited, and it wasn't long before she begged me to call him up again and take her with me. I was a little conflicted, and this was certainly going to complicate my "friendship" with this ex-girlfriend, but how could I resist. I called the guy up, and he happily agreed.
Just a couple nights after my first encounter with him I found myself once more in his bed, between him and my ex, as he started to stroke my cock.