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…..

“A Binder Full of Shemales”

sec4If I can’t make it as a porn star, I’ll settle for being a sexy secretary.

My years working as a high-end escort have well prepared me for this newest role. Classy yet slutty, Bimbo-like but actually probably smarter than my boss (clients), I’ve got the part down pat.

My attitude might seem appalling to feminists. But I’m just so happy to get the job, particularly given the employer’s unconscionable lack of “a binder full of shemales.” (It’s not as if we expect maternity leave coverage or anything.)

Everywhere, Phallic images

brushes makeupTo be perfectly honest: I’m not one of those girls who find all penises lovely. To the contrary, if, for whatever reason, I’m forced to stare and study and contemplate the hard cock so eager to enter me, I begin to wonder: Is it just me, or is this particular penis distinctly unattractive, even unappetizing?

So, no, it’s not the visual aesthetics that excite me. Rather, my cock cravings are all about touch and taste. To hold the hardness in my fingers, to lick and kiss it, to let it slide down my throat, then to feel it enter my make-believe pussy, at first tentatively, thrusting, then deep, thrusting, ever deeper, deep, so deep inside me.

It’s the function, not the form, that counts.

So it is with my makeup brushes. I must have more than a score, all sizes and shapes and textures. To the untrained eye, they sort of all look the same.  But each functions entirely, yet subtly, differently.  To dust powder, you’d never, ever use a contour brush, for example.

Speaking of my contour brush, I must confess that it — even more than the fan-shaped blush brush — is my personal favorite.

The way the bristles are clipped reminds me of the flat-top/crew-cut of a sexy Marine platoon sergeant with whom I once fell in love.  And the very fact that the contour brush is sharply clipped — and not broad and bushy like most of the others — makes me think of a circumcised penis.

The tiniest of my makeup brushes — for eyeliner — also holds a special place in my heart. Its proper use requires an especially deft touch and skilled technique. Which perhaps proves the (larger) point that size does not always matter.

Different cocks, different techniques, different occasions, different needs.  And I get to experience them all in my quest toward truth and beauty!

Sexually Insatiable: Deconstructing a Shemale Myth

20th Century German impressionist interpretation of the Bible's lusty Corinth (Potiphar's wife) trying to seduce Joseph.

20th Century German impressionist interpretation of the Bible’s lusty Corinth (Potiphar’s wife) trying to seduce Joseph.

Women in the Middle Ages were often portrayed as Eve-like temptresses, sexually insatiable. So in the “Decameron,” it is said: “Whereas a single cock is quite sufficient for 10 hens, 10 men are hard put to satisfy 10 women.”

As for today’s lusty shemales like me?  We individually need at least 10 cocks each…probably more…right?

Inquiring minds want to know: Are we shemales really as sexually insatiable as we seem? Sucking cock after cock, bringing each to a cumming climax, yet hardly ever seen to be cumming ourselves. And that gives us pleasure? Is that truly possible? Or are we just playing to type, giving voyeurs what they want — the fantasy image that’s been constructed for us?

As with all myths, some details might not be literally true. But the larger, deeper truth remains. Yes, I guess we’re perpetually horny. At least I am.

It’s a sexual adventure for me just to walk down the street. I don’t have to be dressed provocatively. Just some pumps and pantyhose will do, with a demur short skirt and long jacket: that’s all it takes to feel my hips sway and the firm flesh of my upper thighs rubbing like silk upon one another, each to each. Depending upon the quality of hose, and if my short-heeled pumps aren’t clicking too loudly, I can even hear the delicious swishing.

Maybe it’s because, unlike a “normal” woman, I don’t take sashaying down the street for granted. It’s still new for me: this ability to turn heads just by the way I walk and what I wear. I think it will always be new, this feeling. Let’s hope so! And not just for my sake; selflessly, I know there are so many cocks yet unsucked that I need to arouse.

It’s a powerful feeling that I’m now blessed with — this perpetual arousal, seldom diminished by my own climatic release.

What a mouth-watering paradox: the potency of impotency!    Chemically castrating myself with estrogen, I now have undreamt of power.  Almost absolute power, it feels like; and absolute power corrupts absolutely.  That must be why I’m nothing but a slut.

Shemale Origins: Girly Girl Dreams in a Boyhood Bedroom

girlygurlMy bedroom window looked out — at a safe distance and from the omniscient perspective of the second floor — onto the street. It was not a busy street, but the cars and foot traffic that did pass were enough to enliven the otherwise still life framed by my bedroom casement.

That it was a casement, rather than double-hung, I realize in retrospect, took on great importance. Even more important was that I, at even so young an age, knew — and had wanted to learn — the difference between casement and double-hung. The window treatments for each are so different. Had I been born a boy, a real boy, I’m sure I would have never noticed.

Yes, I was meant to be a girl. And more: a girly girl.  Little wonder that the greatest of women’s literature, from Jane Austen to Virginia Woolf, has always been grounded in the notion of interior space and confinement.

The floor-length mirror screwed to the interior side of my closet door was my closest friend. It had no frame at all, and of course revealed nothing when the door was closed into the darkness of the closet. But when the door was open and I was bold, what worlds it opened up!

With towels and sheets and random fabrics, I improvised and fashioned my own designer wardrobe. I well remember one of my very first creations: a scandalously tiny bikini bottom made from two red kerchiefs, each folded into a triangle and then joined with a square knot at the apex.

Sitting at the edge of my bed, I slid the creation under my butt until the knot was snug in the hole that would become – though then I could only vaguely imagine such sensations – the future happy home for butt plugs, vibrating dildos, and real, hard cock.

After my fingers tied the ends of each kerchief together where they overlapped on my hips, I stood up, admired my creation, and wiggled and gyrated before the floor-length mirror. Such fun!

But I wanted more (don’t we always?).  I – and my creation, my very own bikini – needed to be seen by others. First, I would have to fashion, also out of red kerchiefs, a matching top, though I had no titties yet to fill it. Then, with my costume complete, I spent days and nights practicing and prancing in front of the floor-length mirror.

What would happen if I really did venture outside and let people glimpse me? I had to know.  So one day, when no one else was home, my bikini-clad body snuck outside.  A large beach towel draped around my torso would convey the false impression that I was modest.

A large linden tree’s trunk next to the street, I hid behind.  When I heard a car approaching, I stepped away from the tree so that I could be seen by its occupants and dropped the towel as if I was about to lie down on it to go sunbathing. Then, as the car passed and I could see the people inside staring at me, I feinted surprise, wrapped my arms around my tiny bikini top and even tinier tits, let out a soft squeal, dropped my face as if embarrassed, and quickly baby-stepped away from the street.

Over and over, as I would hear another car approaching up the street, I would repeat the thrilling ritual. Revelation and concealment. Getting the attention of others. Shocking them as if I were an apparition. Exciting them: I could only imagine the intensity of it, but strangely I felt I could feel it, really feel it, the excitement, as if I were they.

But to actually be the bikini-clad and shockingly out-of-place nymph was the most exciting of all.  And so it was that I first tasted the tempting fruits of teasing and seduction. And there would be no turning back….  My closet door with its floor-length mirror, never to be closed again.

gurlygirl

Shemale Schooling: Makeup and Cum Can Mix!

makeupDear Mistress Joy, Your Ladyship:

When men cum on my face, it makes a horrible mess of my make-up. So in order to still look pretty while sucking still more cock, I have to interrupt everything, ruining the romance, in order to run into the bathroom and take valuable time rebuilding my foundation! By the time I return, the cock is often no longer hard. What can I do?

Joy’s Gems (of Wisdom):
If cum on your face is creating a mud-like mess, obviously you’re using a lot of foundation! Which, of course, is necessary if you didn’t start ingesting girlie hormones until after puberty and your electrolysis or laser treatments are still incomplete. (I wonder if the guys giving you facials appreciate how expensive and pain-in-the-ass these treatments are, to eliminate one’s beard to make one’s face more fuckable!)

Anyway, the key variable is not how much foundation you use — but how you apply it.  No matter how much residue roughness you need to hide, you just don’t want to slap and cake liquid foundation all over your face. Remember your makeup basics: Less is more!

Start with a very light base. Don’t smear it all over your face. Rather, apply from the tips of your fingers tapping gently until your face is covered. Then when dry, use a big fluffy brush to dust powder on that first layer of foundation.

Then keep layering and layering and layering: thin coats of foundation followed by dustings of powder. It takes time and patience; but the result is so polished, your feminine face will look like a runaway model’s.

And it will retain that polished look even with gobs of cum all over your face. The trick is not to smear the cum — but to let it dry and cake over your makeup. To prevent huge globs of cum from trickling down your face before they dry, simply dab them with a tissue to remove the excess. Dab!  Don’t rub, wipe, and smear!

Then, to go out in public with subtle spots of dried cum dotting my face — I find incredibly sexy! And all the other girls become so, so jealous. They all want to be shemales!

My Mystery Lover at 30,000 Feet

mile_high_club_stewardess_1__36829_zoomHow can it be? How can it be that the man who gave me the most intense orgasm I’ve ever experienced remains unknown to me? Ah, to be ravished by a total stranger, that’s exciting enough…but more…there’s so much more to the story. Or perhaps I should say “less.”

For he never even touched me! And only afterwards did I see him. I just had to see his face. Who was this “masked” man?

So I tapped him on the shoulder, as we were all standing up in the aisle, after the eight-hour transatlantic flight, to file out of the airplane. He turned his head. I smiled, and mouthed, “Thank you. Thank you very much.” He blushed. Only then, it seemed, did he realize the pleasure he had given me — my phantom pilot.

To fly, to soar, to spread my wings (and legs) — with my phantom pilot at the controls. That’s what had happened high above the dark ocean — maybe Iceland — as the sun would soon rise over the coast of France.

But, actually, my phantom pilot was only nominally in control. I had planned it all, down to the last detail. My pleasure had been premeditated. I knew exactly what I wanted: to make a long-anticipated fantasy come true.

It started with how I decided to dress that day, well before the taxi came to take me to JFK. I usually don’t wear flouncey skirts, but anything too tight might have revealed the bulge in my crotch. The bulge wouldn’t have been from my residual cock (we so-called shemales are well practiced in disguising that!). Rather, it was the sextoy called “The Scorpion,” strapped to the furtherest reaches of my upper thighs. (For a complete description of The Scorpion’s magicial properties, please see earlier blog post “My New Best Friend.”)

I was in control.  I knew exactly what I wanted.  He was totally unaware — just a tool, an extension (literally) of my sextoy.  Man as sextoy: I like that!

mile-high-club-milehighclub-thcfinder

TO BE CONTINUED….