Dirty Little Secret

tampon trainer Serendipity! Think of how many splendid things happen in life because of serendipity! Sort of like Kismet…. So much better and more romantic than mere biological necessity….

I remember it as if yesterday, every detail, told and retold in my mind so often that it’s become myth-like in my creation: the first time, the very first time, I bought tampons!

Why, oh why, would a “special girl” like I ever need to buy tampons?  Wrong question.  As with any unnatural act or unspeakable practice, it has very little to do with “need.”  Rather, the correct frame is this: Why would I WANT to buy tampons? And the answer to that is really quite easy:

It happened in my early days of transitioning, always watchful that I wouldn’t “pass,” when one afternoon I was pushing a shopping cart full of necessities at the local grocery store and caught out of the corner of my eye an older woman staring at me. I didn’t acknowledge her gaze, but, instead, pretended to read the various yogurt labels in the refrigerated display case.  She continued to stare as I pushed the cart toward the check-out.  The quickness of my gait no doubt betrayed my nervousness…and confirmed her doubts.

And then…and then…I happened to spot the display for Tampax   Without really thinking, I found my hand casually reaching for a super-sized box and dropping it in my cart.  A few more steps brought me to the check-out lane, and the stalker had vanished.

Of course, once I got home in the privacy of my bedroom, since I had paid for them, I had to try them out — using the only hole I had. I’ll mercifully spare you the details of my initial experimentation, but….

I became addicted.  I bought boxes and boxes of tampons, testing all makes and sizes.  I would go through five or six tampons a day. To feed my addiction, I bought tampons at any store that sold them, so that the clerks at my neighborhood grocery wouldn’t think I had some kind of serious gynecological problem.

For an anal sex virgin, as I was then, the Playtex “Gentle Glide” — yes, most especially the aptly named Gentle Glide! — provided perhaps the friendliest rectal dilator possible for bottom training.  It opened the way or primed the pump (which is the better metaphor?) for butt plugs and ever bigger dildos and, yes, of course, eventually, the real thing.

And more, so much more: I found that having a tampon inside of me, underneath my panties and hose, when I went out on a date made me feel so much more naturally, womanly receptive — for the real thing later that evening.  And just like a real woman getting ready for the real thing — before I would let his hard cock enter me — I would excuse myself to go quickly to the bathroom, to make myself ready.  After discreetly disposing of the tampon, I never felt so clean — my butt-pussy, that is.  But the moisture-absorbing tampon also made it feel unusually dry, of course, so I would always be prepared by bringing ample supplies of lubricant in my purse.

There!  Now you know just about all my dirty little secrets.

But not quite all….

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?

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 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…..