My First "Real TS Encounter"

September 2007

Alright, so I’m going to put into writing the story of my very first “Real TS Encounter.” This was back in 2007, so I’m going to do my best to remember as much detail as possible. However it’s been nearly a decade, so we’ll see how it goes.

I had be watching “Shemale” porn for about a year at this point. I wasn’t too much into it, it was something I watched every once in a while. There were only a handful of TS Porn Stars that I liked (or even was aware of) like Danielle Foxxx, Vicki Richter, Joanna Jet, TS Jesse and perhaps a few others I can’t really remember. Danielle Foxxx was my favorite, and I’m pretty sure she was the one who got me into TS Porn at that point.

In July of 2007, I’d somehow figured out that Craigslist had a t4m section. I wish I could remember how I discovered that, but I’m not sure. Regardless, I would often browse the t4m section to see who was out there. I replied to a few ads but either didn’t get responses or didn’t respond myself if I got an email back.

Once September 2007 hit, I knew I wanted to make this happen. So I went on Craigslist again, and I started emailing back and forth with a TS Woman from Brooklyn. She was 40, I was 18. We sent a handful of emails back and forth, and after a few days of this, exchanged phone numbers.

We spoke on the phone a few times over the next few days, and the last phone call ended with tentative plans to meet on a Monday evening around 9:00. So Monday came around, and we spoke again to confirm the plans for that night. I happened to be in New Jersey that day/evening, and so around 8:00 pm, I started making my way towards Brooklyn.

I get to Brooklyn around 9:00 pm and I park my car. It’s hard to remember exactly, but I’m going to guess and say that I was pretty nervous. Not in a scared about going into a stranger’s house kind of way (although yes that too) but more-so I just didn’t know what to expect. I’d loved women my whole life, I didn’t know what to make of the idea of hooking up with a Transsexual (especially one twice my age). I was nervous about if I would regret what I had done, if my life would be different after this, if my sexuality is no longer straight, etc.