Becoming a Shemale Hooker: Chapter 2

callgirl3“Don’t wear any panties!” The scary, heavy-breathing voice over the telephone kept commanding.

How could this be? What was being asked of me? A male-to-female transsexual not wearing any panties?  That’s like a cappuccino without any foam…skinny jeans without fuck-me boots….  Why, I had spent all my life working up the courage just to wear panties!

It was as if he were asking me to cut off all my hair, which I had so religiously cultivated over the last couple of years…or commanding me to smear my impeccable makeup into the face of a clown….

But he would be paying me for my time, during which I would be expected to do exactly what he wanted of me, so I had to do what he asked, right? This wasn’t at all what I had bargained for when signing up with the well-established local escort service as their newest (and therefore presumably hungriest) “fully-functional” shemale hooker.

Marvin, the founder and owner of the escort service, seemed to take a special interest in “the new girl” and tried to reassure me:

“Mr. Jackson is a regular client. He always wants to check out the new girls. If you do what he wants and he likes you, it’ll be a regular gig. And that can be very lucrative.  He tips extremely well.”

“But he doesn’t want me to wear any panties!” I protested.

“Believe me, he’s totally harmless…. You’ll see. He’s kind of pitiful, actually.” Marvin then held my hand, as it were, by gaming out the scenario in which I was to be the leading lady:

“Mr. Jackson is an older gentleman who owns his own business. As you drive into the parking lot, he’ll be watching from his office on the second floor. I think he even has binoculars. The idea is for you to be very femininely, professionally dressed as if arriving for work, yet underneath having your male genitals hanging out. He apparently gets his kicks from knowing what no one else knows watching you….

“If you look like a drag queen or you can’t pass, he’ll send you away. He might give you a tip, but he won’t pay for the full one and half-hours.” Marvin paused. “Don’t worry, baby, you’ll do fine.”

Still, I just couldn’t imagine getting all dolled up and not having the most basic feminine foundation securely underneath. How could I look and feel feminine if my nuts are swinging while I sashay across the parking lot? Admittedly, the flesh-colored pantyhose that Mr. Jackson had instructed me to wear would hold things somewhat in place. But without tightly tucked panties, there might well be a decidedly unfeminine bulge against the tight skirt I had also been instructed to wear.

It would take 30 minutes or so of driving in the evening rush hour to reach Mr. Jackson’s office in a suburban business park. The traffic was made worse by a heavy rain. I was dressed exactly as instructed, sans culotte. But tucked, like a security blanket, in my purse by my side on the front seat was a brand-new pink pair of Victoria’s Secret bikini briefs, a nice and snug size six.

When I got lost — just like the good bimbo I was striving to be! — I seriously considered turning the car around and telling Marvin I just didn’t feel right about things. Perhaps he would let me try someone besides Mr. Jackson as my very first John? But I knew Marvin well enough to know that he was all about the money, that Mr. Jackson was one of his most valued regular clients, and that my cowardice would no doubt be a career-ender.

I often wonder how my life now would be different if I had in fact turned around that rainy spring evening — and not kept going down the (rush-hour-clogged) road of becoming a shemale hooker?

About Joy Saint James

Day job in Big Banking. Elsewhere I'm @ScholarlySlut, whose essays and erotica have appeared in various print anthologies and websites. Email: joy.st.james@hotmail.com.

3 responses to “Becoming a Shemale Hooker: Chapter 2

  1. Aaron Boy

    yeah. this story is awesome too!!!

  2. tittiesbootyshaftnovaj

    I don’t mind being whatever you want to call me/Hi(e)m(r). I don’t want another thank you note to write so for those of you who see this thanx again for the handjob.

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