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?

The Serious Shemale

Instead of short shorts...what if my latest fashion purchase was referred to as  "sea-level-rise-induced-by global-warming" hotpants...would I then begin to be taken more seriously?

Instead of short shorts….

….What if my latest fashion purchase was referred to as “sea-level-rise-induced-by-global-warming hotpants,” would I then begin to be taken more seriously?  Not that I pretend to be a real intellectual or anything, but still….

Why don’t people take us shemales seriously?  Is it because we’re perceived as boys who just want to be bimbos?  The truest and most authentic of bimbos who’re only interested in and motivated by sexy, dolled-up clothes — and, of course, sex itself?

But “regular” transsexuals — those who follow through on SRS (sex reassignment surgery) — are often treated with the utmost dignity and respect.  (That is, obviously, except among Philistines and homophobes!)

Not only are transsexuals like Jan Morris (the travel writer and essayist) and Jennifer Finney Boylan (the English professor and author) greeted with respect, even awe — but also are considered intellectually serious thinkers worth paying attention to.

Part of the reason, of course, is that shemales are often associated with porn and prostitution.  While I personally have never done porn, I readily confess to having worked as an escort (just a euphemism for prostitute!)  But getting paid for sex (or often simply my companionship) did not deter my intellectual curiosity.  To the contrary, I read more now — and am better-informed — than I’ve ever been.  And each of my clients was like a richly nuanced character in the very greatest novels and/or a deeply layered case study in the most intense Freudian psychoanalysis.

My mission, then, is clear.  It’s simple.  You can guess what it is!

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 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.

Shemale Sampler: What Men Like

No wonder men desire me! I desire myself!

No wonder men desire me! I desire myself!

“A woman’s vagina is a scary place for a guy to understand,” a Trannychaser named Chris tells me. “But because he has a penis, a guy knows what makes it feel nice. A girl like you has both a penis and breasts, so I’d feel less pressured because I would know what I’m doing.”

Even more experienced guys express this same sentiment — a mixture of fear and loving of the opposite sex — to justify their attraction to shemales, foreign but familiar. “Men fear the inability to bring a woman to orgasm. We can never be sure,” says Mike. “But when a t-girl comes, it’s obvious, even if she’s embarrassed, as some are, of that male part of her body.”

Plus, according to a correspondent named Victor, “T-girls don’t come with all that perplexing emotional baggage of genetic girls that men can never explain. I don’t find beauty in the male form. But, unfortunately, I relate better with males. With a t-girl, subconsciously I’m probably thinking here is a guy who looks like a girl.”

So it’s a guy thing, so much so that so-called tranny-chasers are sometimes defined as latent homosexuals. That’s the conventional wisdom. But it’s not so simple. In my experience, these men are definitely women-lovers, attracted to the feminine, at least a man’s idea of the feminine, while sexually repulsed by masculinity. If latent anything, they’re wannabee t-girls themselves, although I’ve only had a couple of guys actually admit to this uncomfortable self-knowledge.

“Being with a transsexual is not gay, because the transsexual’s femininity provokes the initial attraction. It is not a man’s cock; it is a woman’s cock,” proclaims a self-described “43-year-old married man with two great kids.” Certainly, from my own transsexual point of view, he is the kind of man I find most attractive — legitimizing me as a woman, since he prefers to fuck me rather than the real cunt back home. Indeed, most of the men I “date” — a large enough sample, I’m sure, to be statistically valid — have been married straight guys.

“All men at some point want to suck their own dick, but we can’t, most of us,” laments another married man named John. “As men we have been raised to think sucking dick is gross, and gay. However, when we see a beautiful t-girl in a heavenly woman’s body, it just might be all right to suck that dick. And to fuck that booty or even submit to anal penetration.” Asking his wife to fulfill his fantasy with a strap-on dildo, John says, “would freak her out.”

Fantasy: that’s the recurring key word in the male vocabulary defining their attraction to girls like me. First, we ourselves are phantasmal — deceptive, or illusory, women. As such, we can make any forbidden male fantasy come true. “It’s a fantasy of mine to have done to me what I have done to woman my entire life, consume them sexually,” says Ralph. “Oh, to have a beautiful, full-lipped woman throw me down on the bed and just start ravaging my body, all the while growing inch by inch until it’s proudly sticking out of her panties. It’s a complete surrender, I guess. I never have given a second look to any man, but I would take her dick in my mouth and just go to town. That image I have of being fucked by a woman is enough to get me rock hard.”

Integral to the fantasy is the assumption that shemales must be purely sexual creatures, combining the come-hither desirability of the most brazenly alluring woman with the unquenchable lust of the horniest man. So says Lawrence: “From a very early age, I think it’s fair to say that most men are taught that things like high heels, long painted nails, and porn-star-looking makeup are sexy. I can’t remember the last time I saw a t-girl who was not sporting all three of these little ideals. Why stick with boring everyday women when you can have super-glamorous, fantasy women who actually make a point of putting as much thought into what shoes to wear as the girl next door does into her pension plan?”

Indeed, why else would a transsexual go through such a painful, time-consuming, and expensive transformation, except to attract and please men? After all, we know what men want, because we were once men ourselves! We know that the mere glimpse of a woman putting on lipstick is incredibly sexy. She is advertising herself, making herself ready and receptive. Being a shemale is so self-absorbed and time-consuming, there is time for nothing else except making yourself ready.

That’s the male assumption, and yes, to the extent that male desire validates us as the females we long to be, an assumption grounded in truth. And so we do indeed craft and creatively package ourselves into the supreme sex object, the embodiment of sinful lust, insatiable in our desire to be desired by men. I am desired, therefore I am. With exaggerated femininity and all its fetishistic accruements — big boobs and a finely sculpted ass, not to mention painstakingly applied makeup and suggestive clothes — we advertise that we’re ready and willing and “want it.” Indeed, want it as much as any man.

“That willingness to make an effort, the attention to detail, the openly sexual nature of their look and their attitude,” drools an admirer named Jim. “They embody the ultimate fantasy woman.” Another long-time admirer, Allen, gushes: “Transsexuals attract me because they have declared their femininity and in taking on the ‘weaker sex,’ by implication, their submissiveness. Not that I’m a dom, but I love the fact that they have chosen to be vulnerable, making themselves available to being used by men.”

“Then you have the thrill of everyone thinking you are going out with a really gorgeous girl, but they don’t know she has a penis just like you!” says a long-time shemale fan who identifies himself as Smidsy. Of course, sinful secrets and edgy risk-taking provide a spark to any sexual relationship.

Sometimes I think I’m like one of those life-like, blow-up women dolls that lonely men make love to. As a fantasy, I’m not real. I’m a simulacrum, a virtual woman. (Virtual: one of my transsexual sisters once said, “I wouldn’t have ever existed without the Internet!”) Since I can never be an authentic woman (even with SRS), I become an exaggerated artifice, more feminine and seductively alluring than any real woman can ever be. Shemales are to women as Las Vegas is to Paris or Venice.

But this much is real: I want what every woman wants — not just to be desired, but to be loved. I want romance and flowers. And so my favorite tranny-chaser fan mail comes from Gilbert, who says: “It doesn’t matter what’s between your legs. It’s all about whether you really fall for someone. True love.”

True love for an untrue woman? Maybe, just maybe, Gilbert is on to something. Any student of romantic love knows that the most enduringly passionate love requires obstacles. Think Romeo and Juliet. Think the adulterous affairs on daytime soap opera. And think of that medieval romance of Tristram and Isolde. Since she was already married to King Mark, Tristram laid his sword between their two bodies, his and Isolde’s, as they prepared to sleep together. I am Isolde, and what’s between my legs is Tristram’s sword.