“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.


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!



First Fuck

reading-is-sexy-earringsFor a “normal” girl, which comes first: menstruation or getting your ears pierced? What if, as in my unfortunate case, the former never happens? Does that mean I’ll never be a woman? In which said case, piercing will have to do.

So getting your ears pierced becomes perhaps the most important rite of passage for special girls like me.

It’s fitting, of course, because being pierced is not unlike getting fucked for the first time. Poking a hole in my earlobe = breaking my imaginary hymen!

But the beauty of piercing is that I got to lose my “virginity” a number of times! The very first time, well before my “Sweet Sixteen,” I cajoled a jewelry store clerk to use one of those piercing guns on me.

The fearful yet pleasurable anticipation was so exciting, I can remember it still. Even more exciting: I wasn’t too young not to conjure up delicious metaphors: the cock-like gun, the darting dildo….

By nightfall, when I had to be back home, I had removed the temporary plugs designed to keep my new holes from healing. And I covered the tiny red spots on my earlobes with makeup foundation and concealer.

No one knew.

And one day no one would know – I could only dream – that I wasn’t really a girl. And I would be fucked for real.  One day.  Yes, one day my Prince would cum.

The Passion of Trannychasers, the Myth of Romantic Love

tristan“When made public, love rarely endures.” Thus spoke “De Amore” (The Art of Courtly Love), written in the 12th Century. This Medieval tome is generally seen as the Ur-text for Western civilization’s notion of romantic love, its unrequited passion and passionate longing. If this love is ever consummated and legitimized, the passion will inevitably die.

Thus we have soap operas making heroes and heroines of those involved in extramarital affairs. Thus we have Romeo and Juliet. And thus we have that Medieval legend of Tristan and Isolde’s forbidden love.

When they sleep, Tristan places his sword between them. True passion needs obstacles, like a sword. When the sword is removed, according to at least one version of the legend, the lovers must drink from a poisoned chalice.

We Tgirls have our own swords, of course.

Maybe that’s why we’re so desirable? There are always obstacles in the way. And our admirers’ love for us is seldom made public.


Just a Cunt, Yes, I Am

Like a horse, I apparently needed to "be broken in."

Like a horse, I apparently needed to “be broken in.”

“Watch where you’re going, you silly cunt!” The man spit the words at me. While texting, I had accidentally bumped into him coming out of a Fifth Avenue Starbucks and apparently almost spilled his latte grande. On the one hand, I found his angry words both deeply offensive and downright scary. But on the other hand, of course, for a want-to-be cunt like me, to actually be called a cunt is always reassuring, even life-affirming.

“I’m sorry, sir.” I batted my eyes. “I truly am.” Those are the words that a true cunt is schooled to submissively say, right? But the teenaged boy still lurking inside me was urging my arms to violently swing my Gucci handbag into his crotch.

Indeed, the lingering hint of male aggression is apparently part of the attraction for so-called shemales — creating a taut, sexualized tension with our feminized features. It took me a while to understand this and learn how to use it.

I had a great teacher. His name was Jay. I met him very early in my transition; I wasn’t even entirely sure then I was a transsexual; I just felt a need to crossdress. His was the very first cock I ever sucked, and it was then that I knew exactly who and what I was.

I remember it was our second or third date and we were doing some serious kissing standing next to his car outside the restaurant. Against my skirt I could feel his hardness growing and bulging against his trousers. My hand, as if it were separate from the rest of my body, slowly slid from around his back and waist down to reach, touch, caress the hardness that my deep kisses had themselves created.

Then, as if I knew exactly what I was doing, surprising myself as much as Jay, I unzipped him and dropped to my knees.

Afterwards,he gave me a critique. But it wasn’t about my oral sex technique; that was just fine, thank you — I had “a natural gift,” he allowed. Rather, I didn’t need to be so blatantly obvious in my oral cravings. “Let the guy be the aggressor,” he counseled. Learning to feint resistance would make any man just want me more.

“I’ll have to break you in,” he announced. That sounded deliciously erotic and exciting, as visions of butt plugs, ball gags, and waist-training corsets danced in my head. And, yes, there was some of that over the weeks and months we dated — not to mention his sometimes loaning me to his friends to fuck.

But mostly what he taught me was simply this: patience and passivity. Those ladylike virtues would reward me with all the cock I ever craved. To be a cunt, desireable and fuckable, I first had to learn to be a lady.

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.