My first Transexual

This is a true story, told as closely to how it actually happened as my old memory will allow.

Back in the mid-1980s, I was newly divorced, beginning to explore my bisexual interests, and very, very horny. I had seen some TV film loops in adult bookstores (usually while getting my cock sucked through a gloryhole), had bought and enjoyed TV stroke books, and had done a little crossdressing in panties. I loved the silky feel, and enjoyed fucking my ass with a small dildo while watching TV porn videos in my living room.

I was on a business trip to San Jose CA, just down the road from San Francisco, and as usual on these trips, was touring the sex businesses and looking for fun. In one of the adult bookstores I picked up a copy of The Spectator. I don’t know if they’re still in business, but in those pre-internet days they were the San Francisco version of Screw Magazine, with stories, ads for adult businesses, and ads for prostitutes of all types. I read through it back at the hotel, and found some very interesting ads from TVs, Transexuals, and crossdressers. I was really excited, and jerked off looking at the ads.

The next night I took the Spectator and headed out for SF to see what I could find. Using the ads as a guide, I hit a couple of adult bookstores, stroking myself to the movies in the video booths. I got a couple of offers from guys, but wasn’t interested in a quick suck in a small booth. I stopped at a little bar to have a drink or two to gird my courage, and perused the ads in the back of the Spectator. There were a couple of TS ads that looked promising, and I got some change from the bartender and went to the phone in the back of the bar. I’m sure he knew what I was up to, and I’m equally sure he didn’t care. I made a few calls, said thanks, but no thanks to ones that didn’t seem to have the attitude I was looking for. After a few tries, I talked to one “girl” (I’ll use the feminine from now on) that seemed like just what I wanted. We talked for a few minutes, I mentioned what I was looking for and asked about location and rates. She gave me directions to a convenience store a short ways from her place and told me to drive there and call again.

I had another drink while I made up my mind to go through with this, paid my tab and headed out. Getting in my rental car I drove to the directed place and called again from the pay phone in the parking lot (remember, this is pre-cell phone too). She answered immediately, and gave me directions to her place, only a block away.