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?

Becoming a Shemale Hooker: Chapter 1

Today’s flaneur doesn’t even have to leave home but can just “stroll” around the Internet. For an uninhibited woman like me — whose self-esteem can too often be measured in the height of my fuck-me high heels — staying glued to a computer screen is no fun at all, however.

I want to be seen as much as I want to see others. Without their eyes validating my sex appeal — my very sense of self! — I sometimes wonder if I’d even exist. I might as well be dead. Validation comes not simply with the male gaze, but most especially with the cocks that I make hard.

So it is that when you’ve had sex with as many men as I have, it’s hard to go anywhere without spotting a familiar face. Of course, across the ocean, in faraway cities, it’s highly unlikely they are the actual guys I have known…and been oh so intimate with. But occasionally they can certainly look alike — sometimes scarily so — so much so as to cause me to do a double-take, catch my breath, and feel, against my conscious will, the memories flow.  Not unlike the way an old tune suddenly coming on the car radio can transport you backwards, time-traveling — making yesterday even more real than today.

Take the apparition I see now at the coffee shop while I’m sipping my latte and my eyes glancing up from my laptop:

The ugly, old guy sitting at the cafe table not talking to the unhappy woman sitting across from him (she must be his wife).  He looks exactly like my very first trick!  How extraordinary.

How can I ever forget him?

I can still feel the fear as I drove to the rendezvous that spring evening.  I was wearing precisely what he had instructed me to wear when he booked the “date” — long, elegant jacket; with matching short, tight skirt; strappy high heels (of course); flesh-colored pantyhose but no panties. “Absolutely do not wear any panties!  Do you understand?” His insistent voice on the telephone, hoarse and heavy, really did frighten me.

I must continue this journal entry later as I, in the here and now, have another date, yet another, totally different man to please and so please me.  But I will say this for the moment: I’m no longer frightened…..

Why, O Why???


You Say You Love Me: This Unhappy Hooker Wants to Know Why

This was not my intention: to become a freak. All I wanted was what any girl wants: to grow into as normal and natural (not to mention beautiful) woman as possible. But something happened — or didn’t happen — along the way, to make my coming of age story have anything but a fairy tale ending. Not that I don’t have plenty of adoring Prince Charmings (maybe too many, moralists might say). It’s just that the girl of their dreams is not exactly what I had in mind for my body.

Most girls, I know, would love to be loved for their imperfect selves. No need to worry about making yourself over according to some impossibly high, unachievable beauty ideals. Plump or skinny, naturally blonde or happily highlighted, short legs or tiny breasts, you are accepted (wouldn’t it be wonderful?), indeed even loved, warts and all.

But, you see, I’m not like most girls, for my wart is a penis. Once, like any normal male-to-female transsexual, all I wanted was wart-removal surgery. That’s why I took up escorting — simply to pay my bills for the never-ending electrolysis, collagen injections, and estrogen therapies, not to mention breast augmentation and browbone reduction and Adam’s apple shave, plus save enough for the cash-upfront sex-change operation itself. But now that I’ve got the money, I’m no longer sure I want a facsimile cunt. I’m afraid I would lose all my clients. They wouldn’t love me; they’ve told me as much. Right now, I’m special.

“A chick with a dick? an incredibly sexy babe with that something extra…38C-28-38, plus 6 inches, cut….” That’s the way my escort service Web page advertises, quantifies, and objectifies me. I have to turn away clients, I’m so overbooked. Most of my business is repeat. One even sends me flowers and pretends he’ll leave his wife for me if I’ll forsake escorting and promise to love only him.

Could any girl, even a genetic girl, ask for anything more?

I tell my psychiatrist this when I have to explain why I keep postponing my final surgery.

“Don’t worry,” he says, “you’ll make a very desirable woman.”

“Will you promise to fuck me, then, after I have the operation?”

He stammers. I make him blush.

“See, no one will want me! I’ll just be another aging cunt.”

His blush gets more crimson, and I can tell that psychology, in the final analysis, is no help. For my fundamental question is perhaps too grandly philosophical: what is the nature of desire, the pull of Beauty and Truth? When I’m layered in makeup and clad in fashionably sexy thigh-high boots, macro-minis, and cleavage-revealing, nipple-protruding camisoles, I seem to have the seductive Beauty part figured out. As for Truth, maybe being transmogrified into some kind of mythological creature — half-boy, half-girl were-woman — provides a sufficiently perverse angle of vision to understand finally and fully the meaning of life?

Angle. What angle? Atrophied to the point of permanent limpness after years of hormone therapy system shock, what remains of my penis is not worthy of the name. It’s good for nothing but peeing. When it stirs at all, it acts like a clit. That’s the idea, of course, and I practice with a vibrator. And when I finally do come, there is no come. My shrink applauds me: I am the best candidate for genital conversion surgery he’s ever had, since I’ve already figured out how to achieve a female orgasm. Even for many of the most expertly carved post-ops, it remains forever elusive.

My escort service owner tells me just the opposite. Like most pimps, he’s not into positive reinforcement. Instead, he gruffly tells me what I must do:

“Look, honey, you’ve gotta be fully functional. Even supposed straight clients demand it.”

“But I don’t want to be a genderfuck. I just want to be fucked like a girl.” I almost cry.

He ignores what I say and hands me a bottle of Viagra. He’s not kidding. “Take one pill fifteen minutes before each appointment. You’ll surprise yourself.”

So much for my dream of being a real woman. And so much for philosophical Truth. It all comes down to physiology in the end. In my case, physiopathology, which the dictionary defines as “the study of bodily dysfunction caused by disease.” If my addiction to castrating, penis-shriveling estrogen leads to dysfunction and my gender dysphoria is some kind of disease, or sickness surely, do men love me simply for being a medical marvel? What other conclusion can I draw?

By the same logic, you, too, must be sick — to be interested enough to be reading this essay. Oh, you’re just curious, you say? That’s what all my first-time customers say.

So you tell me: Why in the world are we she-males, or T-girls, such a turn on? Why? I want to know. Like you, I’m curious. Go ahead and use me. I just want to know. It’s research for my book deal. Once I’m a celebrity, “fully functional” will be needed no longer. People will love me for the real-life, anatomically correct doll I was meant to be.