My First Threesome

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.

Dave started just with his hands, drawing my cock out of my pants and making me hard as he nibbled my neck. I was nervous, looking at Lisa, until I saw her face. She was biting her lip and and her eyes were wistful. Within minutes I was rock hard and could feel Dave's lips close around my shaft. Lisa's hand had slipped under her shirt to caress her small perfect breasts. I snaked one hand behind her head, just to feel the skin of her neck and her silky hair in one hand, as my other hand pushed Dave deeper onto my cock.

Soon at my urging Dave swivelled around, pushing his own cock into my mouth as he deep throated me. Lisa's face was very close, watching my mouth encompass his short thick cock. I don't know exactly when my fingers slid into her panties, or when her pants had come off, but she was warm and wet as I slid her clit between my fingers.

I don't know how long we went on like that, I know I came first, and Dave licked my cock as I slid fingers deep into Lisa, probing for secret spots I knew would please her. She screamed and moaned as her own orgasm came, and then I went to work on Dave, sucking and stroking him harder until Lisa got to watch him cum all over my chest, and watch it drip down to my still hard cock.

Dave cleaned me up, and I cleaned him and Lisa, he and I kissed deeply as she watched, and then Lisa and I left. I had grown a few more hickeys though when and from whom I was not sure.

Lisa and I stopped at a playground on the way home, and she confessed to me that she had never been so aroused before. And before I knew it, she was bent over a swing, and I was deep inside her. It was already an incredible night, and that sex in the playground only made it better. I have never forgotten the look of her bent over as her orgasm shook her body, or the light gleaming on her ass as I pulled myself out of her, and came across her bare behind.

I dropped to my knees behind Lisa in that playground and licked the cum from her perfect ass. Something I had never done before. We straightened our clothes and walked to her home, hand in hand, and slept. We would never have sex again, but our friendship finally became comfortable and easy - though to this day I can't explain exactly why.