My First Time Playing Girl

Before the World Wide Web, there were Telnet chatrooms, and that is how I first came out to the world. The internet afforded a high degree of anonymity, and I was very concerned about how being outed would affect my family and job. It was exhilarating to talk with other trannies, but also men who were interested. I had adolescent experiences with men and boys in the past, but I wanted sexual experience feeling feminine as a transvestite. I didn't always want this. In fact, the idea was given to me by a girlfriend who, after seeing me dressed up, said, "Don't you want to be fucked by a man? That is the most feminine thing you can do." I wasn't sure how I felt about it, being new to the whole crossdressing experience. In retrospect, she may have been probing to see if I had any homosexual inclinations. I have had bottom sex with men, but don't enjoy it as much as when I am playing girl, where I can be a submissive and receptive sissy.

Through another 'girl' I met online, I learned how she met men. She said they participated in the chatroom. She introduced me to someone, and I set up a meeting with a guy in a town I visited on business. We corresponded in the chatroom and agreed on a time and place. I signed off using the name Chris, which could go both ways on the gender spectrum. I rented a motel room in the suburbs near my office and carefully chose the outfit I was going to wear. It was a simple, cute mid-thigh dress, heels, pantyhose (crotch removed), a wig, and makeup. I was flushed with adrenaline and anticipation as I cleaned up and shaved my chest and legs. I carefully applied makeup and finally put on the wig. I didn't look too bad, but I was concerned he would not find me attractive. When the time arrived, I was dressed and more than ready.

This being a weekday, the guy showed up after work. His name was Bill, and he was a rough, working-class man, but I didn't care--I wanted to be desired and used for his pleasure. We chit-chatted for a while, me drinking wine--he had brought beer for the occasion. He told me what he did, although I can't remember what it was. I asked if he did this kind of thing often, and he replied, "No." I asked if he found me attractive, and he said, "Yes." The conversation was not flowing, and I imagine he was as nervous as I was.

After a while, I decided to make the first move as I reached over and stroked his thigh. He responded by unzipping his pants. I got on my knees, gently freed his rod from the confines of his pants, and, for the first time as a girl, experienced a man's penis in my mouth. He was very hard and enjoying my attention, but I wanted to experience real penetration as a woman would. I asked if he wanted to fuck. He said, "OK, but you get on top and do all the work." Fine. He put on a lubricated condom. I straddled him, still dressed except for the hole in my hose. I then reached back and guided his dick to a position near my waiting hole. What followed was my trying to wrestle his cock into my virginal, tight ass. Finally, I got it in, and girl, did it hurt! Undaunted in my quest to feel like a woman, I started to rock back and forth on his dick until the pain subsided, and he eventually unloaded in the condom.

He got up and left, and we agreed to get together again. The next day, my anus was feeling not unlike when one passes a rather large bowel movement as I sat through a day of boring meetings. Most of that day, I was daydreaming about doing it again. I didn't feel shame or guilt--only desire, and I was happy to have discovered a way to realize my fantasies. I remember wondering if I came across to my colleagues as different than I was the day before because I felt different--liberated. Did it show?

OK, check that one off the to-do list. Bill and I got together once again, but I was gaining confidence and thought I could do better. With increasing confidence in my appearance, I went to an 'alternative lifestyle' bar and was hit on by a guy. I remember thinking, this is just too easy--put on a dress, heels, and lipstick, and go to a bar where a man buys you drinks and takes you home. We went back to my motel, only to find out that he couldn't get it up. This was an often-repeated phenomenon--men thinking trannies would take men who couldn't get it up. I was also to find that just as many men wanted to be on the bottom. I told them if they wanted to bottom: shave your legs, pluck your eyebrows, and wear uncomfortable shoes. What a complicated world we live in.