Crossdressing For Dollars
By: William, Dollar Bill
Tags: Education, Crossdressing, Inspiration, Culture, Transgender

Crossdressing For Dollars

Where’s Victoria?

Joey Velasquez — Pixabay

Before I scored my job selling escort ads for Action magazine, I wasn’t entirely unfamiliar with the trans world. I’d driven a cab in New York City for years. And not only did several shemales grace my back seat — but the garage where I worked was located in the meatpacking district of the Big Apple, a location where shemales sold their service. So at 5 AM when I exited the garage and walked to the bus stop, street girls populated the boulevard right next to the bus stop.

But still, I didn’t know all that much about the culture — a reality that changed drastically when I was hired by Action, and directed to sell to all the shemales whose ads graced the pages of Screw magazine. My boss’s publication boasted just 3 shemale ads. Screw had 72! And Action’s owner wanted a full-court press on the 69 who weren’t forwarding their money to him. You get the idea!

The same day Joe (the boss) hired me…he also hired a transsexual telemarketer to call all those ads in Screw. The plan was for her to set up the sales calls…and for me and another salesman to hit the pavement and close the deals.

As a trans person herself, Chris (the telemarketer) had no problem setting us up with multiple appointments all over Manhattan and the outer boros. And one of my early sales calls involved a ride out to Astoria, Queens to visit a girl named Victoria.

The pre-war building in what was then a provincial neighborhood was nothing to write home about. This wasn’t the glamor capital of the world. But when I was buzzed up and entered Victoria’s place, my eyes lit up with anticipation. There were four shemales awaiting my arrival to see what this new paper they’d never heard of was all about. It looked like I could sell a bunch of ads!

Curiously, the individual who let me in was a very good-looking gay man who introduced himself as Mario. I thought little of it at the time, what with being fairly hypnotized by all the girls and the possibility that I’d sell multiple ads and really score points with the boss!

So I go through the whole sales spiel about how my boss’s customers will be suit-and-tie newbies who’ll cum in 30 seconds and tip big. All of which is why they want my Action clients.

Sure enough, two of the girls decide to buy ads and fork over their money. I didn’t hook all four but hey! Two was pretty good. After all…they were taking a flyer on an unknown paper. I’m not sure even the best sales guy could have done better.

Still, I gave it one last try (to sell another ad), and asked “where’s Victoria?” I’d suddenly realized that the girl to whom I’d been dispatched was nowhere in evidence! Maybe she would come out of a bedroom and buy a last ad.

Not hardly! Mario, the good-looking gay guy who’d let me in, was in fact, Victoria! He lived his normal life as a gay man — but dressed in drag to turn tricks! Silly me!

Fortunately, Mario didn’t cop an attitude at my being so green to the scene. And nobody said “Listen, you dumbbell! Give us our money back and get the fuck out of here!” So it was all well and good. I’d learned a lesson the easy way.

As time went on, I became much more familiar with the culture and well-aware that a significant portion of my transsexual clients were actually transvestites. Ya know…men in women’s clothing and mascara. No hormones…no surgery…and such. Just a cute dude in a dress.

But I’ll tell y’all what. A couple of my crossdressing clients had me fooled. I thought they were pre-op transsexuals. But when I saw them out of their dresses and falsies, they were clearly men. They just had cute/petite bodies and good legs. Once a crossdresser has that, he can work and make money as a shemale no problem. Just so he looks like a girl, trans fans are all in on what lies underneath the skirt!

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