My First Transsexual

One of an army to come!

Eventually, via owning and running an escort advertising agency and website, I’d become acquainted with a virtual army of transsexuals. But that’s not how and when I saw my first shemale. Ironically, it was on the road in a band. Allow me:

Once upon a time, she males weren’t in vogue nor part of mainstream culture like they are today. Most people didn’t even know that transsexuals existed! The year was 1974. And the place was Richmond, Virginia when I glimpsed my first trans woman. The circumstances? Let me dial back those 40+ years to explain.

After graduating from college with honors and attending graduate school for a hot minute, I decided to punt the academic world — and my fellowship — to pursue a career in music. But being young and dumb and having no clear picture of exactly how to succeed in my new pursuit, all I really wanted to do was go on the road with a band…see the world…and hopefully, eke out a living in the process.

And so every Wednesday, I would pick up The Village Voice (an alternative weekly in New York City) and cull through the “public notice music” ads looking to somehow hook up with a road band — or at least some kind of work to pay the rent.

Initially, I found dribs and drabs of junk to tide me over. But eventually, through dogged determination, I finally hit the road about a year and a half later with “The Jamissohn Scott Revue,” in what was called a “show band” back then.

Though it got a little better as my year with the outfit went by, at the outset, the band would travel by car on a moment’s notice wherever our agent sent us. The jobs entailed playing six nights per week…four or five sets per night...for the lofty sum of $180 for each band member! Once having found the club in whichever city to where we’d been dispatched, we then had to hustle up some rooms at the local flea bag. That usually cost $30 per man for the week! And it was at The Capitol Hotel, the dump we found in Richmond, that I saw my first shemale!

Upon hearing our destination (Richmond), I was totally stoked. Being a big Civil War buff, the prospect of playing in the capital of The Confederacy was much more appealing than working in Rochester and Syracuse NY, Springfield, Mass., and South Amboy, NJ…our four previous locations.

The engagement was at The Jester Club, an irony for sure given that the clown who owned the joint wrote us rubber checks, and that week stood as the only occasion during which we actually never got paid. But that’s not the point. The week was certainly not a total loss in retrospect. I dragged my roommate around to all the museums…and the girl who fronted the band ran into a carny who invited us to his little piece of road heaven. And that carnival was something from another world.

They had the clown sitting atop the big tub of water baiting people with insults so they’d buy balls to try to hit the target and dunk him! They had actual bear rasslin’ (though the bear was declawed), and a funky strip show with nasty black girls with attitudes and a bunch of old black musicians playing “The Stripper” as the ladies gyrated for the crowd (though they didn’t actually strip). And the carny even had a couple of freaks, too! And we’re not talkin’ hippies who smoked a lot of pot — if you get my drift.

Well anyway…back at the flea bag, Ravioli (my roommate) and I were listening to the latest tunes of the day one afternoon. If you wanna know how long ago this was…I gotta describe the scene. Way back then, cassette players were brand new. And while the drummer had one for his own entertainment, Rav and I were still old school vinyl. Hence, we actually traveled with a milk crate full of our favorite albums, a turntable, a pre-amp and a Fender Champ practice amp. I jury-rigged all the components together and BAM! We had music! I know it sounds ridiculous but that’s what it was! All the elements had vacuum tubes and the unit actually had a clear crisp sound.

I can remember that at the time, our favorite song was “Only So Much Oil In the Ground,” by Tower of Power. Ironic to ponder that given the current state of affairs. Talk about a band ahead of its time!

Whatever…one afternoon, I ducked out of the hotel to score a little food and there she was! MY FIRST TRANS LADY… a black shemale inhabiting the room next to ours. So I got the sandwiches and came back to tell Ravioli what I’d just seen.

It really was not a very momentous occasion. We both knew the hotel was full of geezers and welfare cases and what not. So it came as very little surprise that an androgynous and gender fluid individual would be mixed in with all the miscellaneous nuts and bolts. Nobody lost any sleep or jerked off to the thought of that very first tranny. Or at least, I didn’t!

To finish the story…on the last night of our gig, the clown of an owner handed us each a check for the week. The rest of the band split on that Saturday night, but I convinced Rav to stay in town till Monday morning to cash our fucking checks. And of course, the checks were worthless as I’d suspected all along, and we never got paid. But it wasn’t a total loss. Instead of heading back to NY (we had our first week off in two months) on I 95, Rav and I went back on The Skyline Drive, a very beautiful glimpse at nature. Plus I went to all the museums in Richmond…attended a real live country carny and saw my first tranny.

I remember each and every stop we made that year I stayed with that band, and thinking back, Richmond was not one I’d rather we’d missed even though we got ripped off. In fact, it was the single most culturally enriching experience of the year. So who gives a crap if I never got paid? That week made for a lifetime memory.

Once I quit that band and settled in New York’s East Village to further pursue my fate, I came to discover a tranny bar just around the corner from my apartment. And then when I became a cabby, she males were no stranger to my back seat. And finally, when I got a job selling escort ads? Trannies galore!

It’s interesting that my music, cab-driving, and then ad-selling careers had one common thread: Transsexuals! Go figure!