In the 90s, the way chatrooms worked was usually either on AOL or Yahoo, and there would be rooms for transgendered people. There were also Yahoo groups that were more populated. You could actually meet people and not some bot.

It was another late night of chatting, getting on cam, and showing my goodies 🙂
There was one night though that someone lived not terribly far. Maybe 20 minutes away. He wanted me. He wanted me bad. I was still pretty new to this. I had everything to dress up, of course. But he was a panty boy. He told me stories of how he liked going to the pharmacy to buy pantyhose an the clerk would look at him knowingly. He liked it. He also told me he was 7 inches. He wasn’t. But when you’re new at this, and itching to go out and play, you’re bound to be less picky. That was the case here.

I drove out in the late night. I changed into my outfit in the car. I got to his place. He lived alone upstairs. We chatted. He wasn’t pushy. He liked the way I looked. He was in his dark sheer pantyhose with his cock showing through. I rubbed it. It was hard. Maybe we watched a little porn together, I can’t remember. Eventually, I got down and sucked his cock. After a while, I stopped. We chatted some more. He told me that he once had a cross dresser girlfriend and showed me a picture. She was beautiful. That she had slept over, etc. Other days after this, he would contact me and he wanted me to be his girlfriend, go to the movies, go to lunch, etc.

This was many years ago, and my old account is long gone, having been hacked. I don’t know what happened to him. He is probably still jerking off in pantyhose. I’m not really into panty boys, but if I saw him, I’d probably turn his pantyhose wearing ass into a panty and bra wearing girl.

– Miss Patricia