Passing 101: The Strut

catwalkJust forming the word, saying the syllable, sounds sexy, doesn’t it?  Strut!

Back in the days before ubiquitous computer screens, when people used to go outside occasionally, you could always tell a man from a woman just by the way they walked.

Walk is the wrong word.   To be a desirable woman means to strut.  A man who wants to “pass” as a woman must therefore know the strut; not to know means he will be “read.”  Being naturally tall and slender helps.

To see it: a confident and elegant woman’s tantalizing strut — the actual word in alluring action — can make the most ancient and decrepit of men cry.  The tears are tragic; for the lustfully alive legs and hips creating the strut may be seen but never again, as in their virile youth, possessed.

So it is that to feel it — to actually do the strut yourself – is indescribable.  Maybe that’s what makes it so impossibly hard to master.  If no words exist, how can an ignorant would-be woman ever be taught?

That was the primary reason I enrolled in modeling school – to learn to strut.  Once upon a time “educational” places like this used to be called a “charm school,” and I wanted to learn all the other secret feminine charms, of course.  But how to walk – to strut – was my main motivation.

Everyone was surprisingly welcoming.  No one said I didn’t belong.  Maybe they were afraid some macho boyfriend of mine would sue on my behalf for sex discrimination?  Whatever…. The tuition for the six-week course was the best investment I ever made.  Cosmetic surgery is costly, but learning to strut is priceless.

Even now, after so many years living “full-time,” I don’t always have the steps down.  The strut may be a learned movement, but once learned, it must be as natural as breathing.  If I become too self-conscious, I can look like I’m on a fashion catwalk: my arched back becomes exaggerated, my gait too slow and long, my wiggle just a bit too wiggly.

But when your hips are undulating just right, your stride feeling like a glide, and the very clicks of your heels making heads on the street swivel, you know you’re in the groove…you’ve got the strut down pat.  With eyes fixed straight ahead, mobile device hand-held to your ear (especially if you’re not really talking with anyone!), the experiences you absorb as practitioner of the strut are like no other.  Truly, you see the world differently.

But mostly the world sees you…envies you…desires you.  You’ve got the strut.

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 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?

“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.

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….

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.

tristan3

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.