Men I Have Known: Chapter 1

Now that I'm respectable, I can reflect....

Looking “respectable” belies my memories….

The turning of the New Year invites reflection; and the thought occurs that time’s passage has, for me, been punctuated not with the ticking of clocks or turning of calendar pages but, rather, with all the different lovers I’ve known.  “Lovers” might be too grand a word, for many of these men I’ve known, when I was escorting, for only an hour or so.  And some I’ve come to know now only virtually, via the Internet.

Whatever I call them, they are someone else’s son, brother, father, boyfriend, husband even.  It’s said that, no matter how intimate, you can never really, really know someone.

So I may not be privy to the day-to-day life of the man sitting across from you at the dinner table right now, but I know his secrets, things you’ll never know.

Take Bukkake Bob, for instance.  That’s what I called him, and not just behind his back.  I made him laugh (not just cum).

All he wanted to do was splash his hot, gooey ejaculate all over my face and titties.  I didn’t have to do anything — not even suck — just kneel there, with my face uplifted and smiling expectantly.  Sometimes I would wag my tongue (this was long before Miley Cyrus’s iconic move) to gesture how much I wanted it, craved it — to feel and taste the splash of his cum.

Once a week, like clockwork, we would meet to perform this ritual, sometimes in my apartment, sometimes in a motel room, sometimes in his huge SUV.

Then one evening, when I had on a lot of makeup (for I was to go on a fancy dinner date with another guy an hour later), I tilted my head ever so slightly just as Bob shot his wad.  So most of what he shot ended up on the floor.

“What happened?” His scream sounded truly anguished.

“I didn’t want to totally ruin my makeup, sweetie.”  I said matter-of-factly.

“Well, you’ve now ruined everything,” he announced, and I never saw him again.

What more can I say?

10 Stupid John Tricks: A Pro’s Pet Peeves

sex worker1.  Like Congressman Weiner (still can’t believe his name!), sexting a picture of your penis…. As if girls care what it looks like! (“Feels like” is another matter.)

2. On the subject of Congress…. Lecturing me about how clever and sexy the House Republicans are.

3. Running my Wolford’s hosiery.

4. Wanting to wear my panties.

5.  Taking my panties with you as a souvenir.

6.  Screaming out your dog’s name when you cum (and we’re not even doing it doggie style).

7.  Telling me to play with a second-hand sextoy that you brought along.

8.  Taking the entire one-and-one-half-hour appointment to cum.

9. Complaining you’ll go limp if you have to wear a condom.

10. Texting your wife while I’m giving you the best head you’ve ever had.

Becoming a Shemale Hooker, Chapter 6

profileWhat’s the hardest thing you have ever had to do?  Learn Latin?  Run to win a 5-K race?  Play hostess at a Black Tie dinner party?  Perform the starring role in your school’s “The Nutcracker?”  Execute a French manicure on your very own nails?

For me, the very, very, very hardest thing is putting a rubber on a limp penis.  I’ve only had to do it once (thank God!), and that occurred during my very first date as a shemale escort.  It was a truly unique skill I developed on the spot.

I could see him go limp as I fumbled in my purse for the condom.  (Have you ever been able easily or quickly to find something in your purse when you need it most, when time is of the absolute essence?)

At first I didn’t think it would be a problem.  All I had to do was lightly brush his sensitive skin with my finely manicured, sexy fingernails, right?   After all, just moments earlier, his cock , though tiny, had been explosively erect.  But that was then; this was now.

Then he had been fondling my own cock, which I preferred to think of as just an oversized clitty.  To be frank, my clitty didn’t like the too rapt attentions of his monotonous, and rather rough, hand motions.  The very tip of my big clitty was actually getting sore; my pantyhose felt like sandpaper.

If I could just make him cum, I would have earned my money, and I could leave.

I pressed the rubber against the head of his penis and clamped the rolled-up sides with my fingers.  Then I took my tongue so that it tasted the rubber tip.  Flicking my tongue, as I so desperately had hoped, gradually stiffened what I held between my fingers — sufficient to gain purchase to unroll the condom.  As it unrolled, my lips parted and slid over the tip and down the ever lengthening, but still short, shaft.

Now my lips and throat and bobbing head could work their gliding magic, and they did.  But, from Mr. Jackson, there were no quickening thrusts and volcanic eruptions, as with a younger man.  Instead, when he came, I heard a barely perceptible grunt and felt the condom inflate like a tiny balloon.  The texture and consistency felt like an over-ripe melon about to melt and get messy in my mouth.

When I left his office, he said a very formal thank-you, and I noticed that all around the walls were hanging pictures of his wife and children and grandchildren (I could only presume, I didn’t dare ask): mute witnesses to the display of his extramarital activities with a shemale.  He must not have cared.

I only cared what he would tell Marvin, my pimp.  Mr. Jackson – I mean Jack (I wasn’t supposed to know his last name) – was one of Marvin’s regulars. What kind of report card would I be given?  I knew it would not be an “A,” because I had dissuaded him from doing what he really wanted – to play with my big clitty.   So was I failure?  Would Jack ever want to pay for me again?  A satisfied, repeat customer?

Or would my very first trick also be my last?

Becoming a Shemale Escort: Chapter 5

secrets7He didn’t try to kiss me.  He didn’t grab my boobs.  He didn’t rip my clothes off, or even undress himself.  Instead, Jack asked me to sit on the edge of the desk and hike my skirt up and spread my legs. He then rolled the desk’s over-sized matching chair toward me and, like an old frayed teddy bear, plopped down in it. His face betrayed a bashful grin as he rolled the chair closer and closer.

I really had no idea what would happen next. But I was no longer afraid, just really curious. So far, at least, if I had to describe him, it would be, as I already mentioned, as an old teddy bear. Gentle but not necessarily cuddly (he was too ugly for that!). And what he was now doing — rolling the chair every closer so that his face was pressed closer and closer to my panty-less crotch — sparked some involuntary whimsy from my lips:

“I feel like my body is a computer and you’re about to start typing on the keyboard!” I laughed.  And he did, too — a hoarse, breathy laugh that tickled my scrotum (yes, his face was that close!).

He nuzzled his face ever tighter against my male genitals, already pressed tight against the flesh-colored pantyhose that he had instructed me to wear. Why he had been so insistent that I wear no panties, I now understood.

If he was expecting me to get hard…well, he would have been within his rights to want a refund. I glanced down and tried to see if he was getting hard — that was all that counted, right? — and I thought/hoped I detected a growing bulge in his pants. Maybe just wishful thinking?

I wanted and needed for Jack to be happy…so that Marvin would be happy…so that I wouldn’t be fired. Most of all, I wanted this moment to be over with, in a satisfactory manner, so that I could feel like I’d actually earned the money. Yes, I wanted to make sure Jack got his satisfaction. Pride in my new identity was at stake.

Against the nylon of my hose, his rough thumb began to make circular motions around the head of my still flaccid penis.  He did it so much and so hard, I was beginning to feel painfully sore and inflamed at the head of my urethra.  I had to change the subject of his attention.

“Let me suck your cock,” I suddenly said.

“With Marvin’s other girls, I always suck their cocks.”  He seemed puzzled.

“Well, give me a chance,” I begged. “You might be surprised. You might really like it. I give really good head.”

Becoming a Shemale Hooker: Chapter 4

callgirl3At first around my waist, gradually sliding down to my butt, Jack’s hand guided me through what seemed like countless doors and long corridors.  The click of my heels and the sway of my hips displayed a confidence I had not yet earned.  Like a virgin acting like a sexpot, down deep I knew I was a fraud, a fake, just a wanabee whore.  It wouldn’t take much to reignite the worries and fears I had felt initially when Jack’s creepy telephone voice was booking our date.

So when Jack ushered me, the nervous Nellie, into the inner sanctum of his executive suite and locked the door behind us, one of my heels snagged the edge of an Oriental carpet. I would have fallen had Jack not steadied me.  All the lady-like poise I had spent months, even years, cultivating quickly melted into embarrassment…and, yes, fear.

“Maybe I should call Marvin…” I stammered and reached into my purse for the cellphone. “… And tell him I’m here.”

“No need to do that, Joyce.”  He handed me an unsealed envelope.  “Put this in your purse instead.”  My fingers opened the envelope and flipped through the bills — four $100’s and one $50.  Just as Marvin — the escort service owner and so, yes, my pimp —  had said it would work!  My estrogen-patch-addled bimbo brain didn’t even have to remember to ask for the money!

What exactly was Jack buying for $450?  I wasn’t yet sure.  That was my appointment rate set by Marvin.  For that amount, the client could have up to one and one-half hours of my precious time.  If the client wanted additional time, it would be at the $300 hourly rate.  Overnight rates could be negotiated.

Everything had to be prepaid, either by credit card over the phone with Marvin or by handing cash directly to me.  If the latter, I would deposit Marvin’s one-third directly into his bank account the next morning at a bank branch most convenient to me.

I’ll tell you more about Marvin later, but at that particular moment I was in awe.  He had thought of everything — as slyly clever as any Wall Street hedge fund manager.  By paying upfront, the client could never be undercover police because that would be entrapment.  And by coordinating all the logistics of the appointment through Marvin’s office, I was reasonably safe: if I didn’t report in by phone in exactly one and one-half hours, Marvin would send one of his assistants looking for me.

Marvin had the address.  He had the client’s phone number, maybe even credit card number.  Marvin knew everything.  My fate was in his hands.  Suddenly I had a glimpse of the legendary power of a pimp:  Marvin had become my God-like protector.

Of course, Marvin at this very moment could not prevent Jack from raping me, killing me, then cutting me up into tiny pieces.  But if Jack was rational, he knew he would never get away with it….right?

Becoming a Shemale Hooker: Chapter 3

callgirl3Just as Mr. Jackson had instructed on the phone (in a hoarse and heavy-breathing voice), I pulled my car into the dark and mostly deserted office parking lot… and headed toward the illuminated place under the lamp-post.  There I was to park — in the spotlight under the lamp-post.  The phallic symbolism — I couldn’t help but smile — relieved at least some of my anxiety.  My next instructions were these:

Turn the car engine off.  Turn on the car’s inside lights.  Look in the rear-view mirror and start touching up my makeup, specifically my lipstick.  Wait for my cell to ring, which it now did just moments after I had deposited my lipliner back in my purse.

“Yes, Mr. Jackson…. Yes, Mr. Jackson…. Yes, of course, I want to make you happy.”   After his abrupt goodbye, I proceeded to do exactly as I had just been told:

Make believe I’m just a normal businesswoman arriving at a real job. Open the car door.  Stay seated, but swivel my legs so that my heels are on the pavement.  Make sure that my skirt is hiked up, so that an observer from the office building can see my crotch.

“Wear no panties!” he had earlier commanded.  Now I began to understand.  And I followed precisely the rest of his instructions:

Pretend I’m unaware of either the observer or the fact that my crotch is showing.  When I stand up, feint surprise that my skirt is hiked up so high; quickly tug it down to mid-thigh; look around, embarrassed, to make sure no one has seen me; then walk briskly, as if late for work, to the office entrance.

Buzzed through security, I then took the elevator to the second floor. There waiting for me as I exited the elevator was Mr. Jackson. I can’t describe exactly the man I had expected as my very first “John,” but he definitely wasn’t it!  And his voice no longer made me tremble:

“You’re beautiful,” he said — the binoculars still in hand that he had obviously used to spy on me arriving in the parking lot. “The agency’s photos don’t do you justice.”

“Thank you, Mr. Jackson.”

“Just call me Jack,” he said, holding the door open for me to step into Suite 210.

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…..

Another Year in Fantasyland: Getting Paid for What You Love to Do!

RISTMA~1“Fantastic!” People often reply when I ask how I look. Or I will say “Fantastic!” when asked how I feel.

It’s a most appropriate adjective for girls like me, whose whole life could be described as a fantasy. And once embarked upon that fantasy – the boy who actually lives the impossible dream of becoming a girl! — I find it hard to reject any fantasy, no matter how flighty, that ever darts into my silly, unpredictable brain.

Take prostitution, for instance. Just about every real woman I know readily acknowledges that she sometimes fantasizes about getting paid for sex. But she never actually acts out the fantasy. “Of course, not!” she exclaims. “I’m not crazy.” Or: “I’m not that sinful.”

But for me, it’s no big deal after the crazy — arguably sinful — journey I’ve already embarked on. That train has already left the station. Or, for a more appropriate metaphor – given everyone’s recurring fantasy of joining the “mile-high club” – the plane has already taken off.

“Selling my body,” as people put it, I’ve never found degrading. To the contrary, it’s validating. Maybe that’s because I’m never really selling my body. I’m just cashing in on a fantasy, not mine but theirs. To the men who pay me, I’m their ultimate fantasy chick.

Not unlike being a Playboy centerfold whose image sparks countless masturbatory fantasies – and fulfillments! The only difference is that the cum splashes and smears glossy magazine paper, while the cum aimed at me is captured in a condom.

Do Shemales Have More Fun?

I am desired, therefore I am.

I am desired, therefore I am.

You catch your boyfriend doing Internet porn. You feel betrayed. But, worse, totally inadequate. The girls he’s been lustfully watching have something you’ll never have. “Women 2.0…special girls with a little something extra,” the porn sites sometimes seductively spin it. Less euphemistically, they more often scream: “Incredibly slutty shemales chicks with dicks…boobs and balls…tantalizing t-girls.”

But no need to worry. Your guy’s not some closet weirdo. Most straight, normally faithful guys seem intrigued, if not sexually turned on by, so-called shemales. They represent the fastest growing segment of the porn business.

Still, you wonder. What’s going on, what’s the attraction, the turn-on? I wonder, too — and I’m a shemale myself!

Back in the day, I would have been just a regular male-to-female pre-operative transsexual — ingesting estrogen and living fulltime as a woman while awaiting the knife, sex reassignment surgery (SRS). That was the traditional narrative of “a woman born into the wrong (male) body” — the feminizing, often arduous journey to become finally “the woman I was meant to be.”

That was then. Now, more and more special girls like me keep postponing the final surgery and opt, instead, to stay suspended in a transitional stage of half-man and half-woman, like some kind of freakish mythological creature. There are always convenient excuses: SRS is so expensive, you know…anyway, I still haven’t finished electrolysis…I want to get adjusted to my newest regimen of estrogen therapy…what money I’ve saved up seems better spent on what people actually notice when I walk down the street — breast implants and facial feminization surgery. When you really stop and think about it, a cunt is just an engineering redundancy anyway, for I have two holes to service cock already. So down deep I know I’ll probably never go all the way, for then I would no longer be special. I’d be just another unattached, on-the-market woman. Too many guys prefer me cuntless, just the way I am.

I am desired, therefore I already am. But what am I exactly, and why am I desired? In order to understand, I wrote a plaintive piece some time back, subsequently posted all over the Internet, and I received literally hundreds of thoughtful responses, love letters — lots and lots of lustful love letters.

I’ll tell you in my next post what I’ve learned.