First Time With a Shemale

I was living in LA and pretty fresh out of school, not to mention pretty naive in the peripherals of human sexuality. I'd been with a few girls growing up, but nothing ridiculous. I liked going out with my buddies, and we'd drink and there was the occasional recreational use of ummm, how should we say... party favors.

I liked my share of porn, and as I had just gotten my first computer, I finally had the resources at my fingertips to do as much online porn surfing as a young man could handle. And it was only a matter of time with all the stuff out there that I would stumble upon shemale porn. I'd never seen anything like it. Here were beautiful looking women, very feminine but instead of a pretty little pussy, there were these dangling cocks hanging between their legs. I was utterly fixated, and I've been hooked ever since. Don't know what it is, but there's just something about t-girls that completely fascinate me.

So I would look at the pretty shemales from time to time, jack off, and wonder what it would be like to be with one for real. Well, this went on for a couple of years, just looking at the online stuff and continuing to date real, genetic women. But then I entered a period where I wasn't seeing anyone regularly, and my fantasies about shemales began to become even more fixated.

I had just joined an online site for dating, and it was a little more risque than the usual dating site, almost a bit "swingerish" in some respects. There would be gatherings and all kinds of sexuality getting thrown around, althought to be honest, I didn't participate in much of that, though I did go on a few dates, and did manage to get lucky a few times. Well, one night I'm perusing the chat room on the dating site, and it's the same ol' usual dialogue, until a new person logs in. I certainly didn't recognize the name, but her quick profile read that she was a woman, so of course I immediately clicked on her name gaining access to her full profile.