I’ve never really thought of myself as a big hairy ape before.

But then I’ve never had to shave my legs before. Or my armpits. Or my arms. Or my chest. Or my knuckles. Or my toes. Although I stop short of a Brazilian bikini wax, I believe the shaving process has already afforded me a deeper understanding of what it means to be a woman. Of course, I also realize that most women don’t have wall-to-wall shag carpeting on their inner thighs. With hair this thick, you may as well use a spoon as a razor. Still, a lifetime and a few dulled Mach IIIs later, I’ve transformed myself from a hairy ape into ... well, a relatively hairless ape.

Already, I’m starting to see problems.

Standing naked in my friend’s bathroom, an expanse of rapidly stubbling flesh before me, the prospect of my becoming a woman is beginning to seem as plausible as John Ashcroft joining the ACLU. My neck alone, which can only be described as "Venturian," is like having man stamped on my forehead. Also, my walk — my lumber, my lope — has about as much feminine grace as a sumo wrestler trying to step on an ant. And that’s before I’ve opened my mouth. Though not endowed with what you’d call a booming voice, I’m no Edith Piaf, either. Finally, there’s the, ahem, equipment. I’ll spend an hour spooning the hair off my knees, but I will not be tucking anything into any little abdominal cavities, thank you very much.

Miss Vera, advised of my misgivings, is unmoved — she’s heard it all, and seen it all, before. She’s dressed lumberjacks in bridal gowns, construction workers in baby clothes. She’s had a professional wrestler, Vietnam vets, a Hasidic Jew who refused to shave his bushy beard. ("We gave him a veil and turned him into an Arabian princess," she says. "We do our best to heal Middle East relations.") One student had a neurological disease that made him vibrate. Another had a Howard Hughes–like aversion to being touched. Those clients, Miss Vera says, posed a far bigger challenge than I ever could.

Even so, heading over to Miss Vera’s studio, I cannot help but be gripped by a kind of dentist-appointment apprehension. Upon entering the studio — frilly, lacy, and overwhelmingly pink — my apprehension is replaced by something more akin to angst. In a few hours, I will be wearing a dress, lipstick, ruffly undergarments. Does this make me — not that there’s anything wrong with it — gay? According to the Boston-based transgender magazine Tapestry, 75 percent of transgendered men are heterosexual. The majority of Miss Vera’s clients, she tells me, are straight, and many of them are married. Furthermore, how about those Patriots?

"Hello, Miss Vera," I say, sounding like Charlton Heston as Moses. Vera — large of chest and arched of brow, with a head of thick, immaculately coiffed hair — calls to mind the kind of woman who might work in a high-end jeweler’s shop (only it’s my jewels she’s going to be fiddling with). She immediately displays that odd mixture of affability and severity that had so unnerved me on the phone. Within a half-hour she has told me I have a "nice ass" and chastised me for saying "Yeah" instead of "Yes." Though she insists that "we don’t spank, no matter how much they beg for it," you get the sense that Miss Vera might be capable of doling out some pretty effective corporal punishment. "Kneel down here," she says, leading me to a small shrine, "and repeat after me:

"I dedicate myself to release

all of the juicy female energy inside of me.

I place my trust in Miss Vera

and the deans of the academy,

and I thank myself for this gift."

The use of the word "gift" here is no accident. According to Miss Vera, all men, even those not given to wearing skirts, could benefit from her classes. "Men are generally out of balance," she says. "They are in emotional straitjackets, unable to get in touch with the feminine aspect of themselves. What I associate most with femininity is tolerance, sensuality, and pleasure. To take these elements and move them back into the male persona, I think, will lead to a happier, healthier, sexier human being. I’m not saying I want to grab every man and put him in a dress, but I do think it would be helpful."

Miss Vera goes on to add that many first-timers come to her classes with the am I a sissy? question rattling around their heads. Her answer is yes — and that’s a good thing. "A lot of men are uptight about their maleness," she says. "But if you face your fear that you are the biggest sissy in the world, if you embrace your sissyhood, then you don’t have that fear any more and you become more of a man." She adds, "It takes balls to be a lady."

This may well be so, but, in the world of cross-dressing, balls are also something of an impediment. This fact becomes patently clear when I find myself in a closet with Miss Vera, naked, struggling to squirrel my package away between my legs. "If ... I ... can ... just ... get ... it ... hmmmff," I say. "Hnggrrrgh!" Having tucked and stuffed to the best of my abilities, I must now attempt to hold the whole shebang in place with a stiff G-string-like contraption — a "gaff." "Put your leg in there," says Miss Vera, gaff in hand. I lift a leg and — sproing — it’s time to start the tucking process over again. "Hnggrrrgh!"

At some point during this cramped and sweaty game of Twister, Miss Vera and I manage to install the gaff — which, to my dismay, is cut so low that a dark spume of pubes flourishes over the rim. I wouldn’t mind, but there is a cameraman present, Brent, who is here to film the proceedings for New York’s Channel 13. As I emerge from the closet, Brent and I exchange troubled glances. He, apparently, is none too keen on the idea of filming a half-naked, half-shaven man, and I am none too keen on the idea of being filmed as one. Finally, to sighs of relief all around, Miss Vera hands me a pair of blue lace panties and a matching camisole. It’s not much, but it’s something.

There is, I am starting to discover, a world of difference between being a woman and being a man becoming a woman. For one thing, relatively simple tasks like putting on a pair of stockings or buckling a pair of shoes are made considerably more complicated when you have a pair of testicles jammed between your legs. Unfortunately, I come to this realization under the watchful gaze of an increasingly impatient Miss Vera. "Fasten them," she says as I fiddle with the tiny buckle. "Keep your legs closed!" Easy for her to say — she doesn’t have a game of mahjong going on in her underpants. "Unghh!" I say, fastening. "Unghh!"

When I’ve buckled my shoes, and wiped away the tears, I am instructed by Miss Vera to parade up and down the room a few times so she and her Dean of Cosmetology, a plump and pretty blonde named Miss Deborah, can get a look at me. "Head up!" sings Miss Vera. "Back straight!" I glance over at Brent, who seems to be suppressing a smirk (he wears this expression for much of the evening). But it’s not only my sense of dignity that’s taking a beating. Walking in high-heeled shoes — like everything else about the transformation process — is much more difficult and painful than it sounds. Wibble-wobbling across the pink rug, I feel like a circus act — half clown, half daredevil: step right up! Behold the ankle-snapping walk of death! "Okay," says Miss Vera moments before I crumple to the ground, "let’s get her makeup on."

Already, I have become a her.

Or have I? As I sit in the makeup chair, Miss Deborah peers over the top of her glasses and leans in until her face is inches from mine. "Hairs!" she says. She may as well have said "Rat!" Miss Vera emits a little sucking noise of disgust. No lady, after all, would consider a thatch of nose hair an acceptable part of her beauty ensemble. Even though I spent God knows how long de-furring myself earlier, the nose hairs have, in the words of Miss Vera, "put a fly in the ointment." This is why learning to be a lady is so elusive — you cannot improve at it simply by trying harder. It’s like learning to be left-handed. Or learning to like the music of Barry Manilow.

Even so, I am not going to get much sympathy from Miss Vera, who has suggested to Miss Deborah that the offending bristles be plucked (I’m starting to have my doubts about her). Mercifully, Miss Deborah opts instead for the scissors. "You should have removed these before you got here," she says — snip-snip. Having exorcized the nasal hairs, Miss Deborah finally starts in with her makeup routine. "Don’t blink," she says as she jabs a pencil toward my eye. This is going to be a long night.

As a boy, I used to love watching my mother apply her makeup. There was something calming about the way her hands moved easily over her face, dusting her cheeks with powder, tracing the lines of her eyes with thin, sure strokes, gently running the tip of a lipstick between the corners of her mouth. The whole process couldn’t have taken more than a few minutes. In direct contrast, Miss Deborah’s effort to transform my face is a prolonged, insanely elaborate process involving a wide array of brushes, pads, prodders, puffers, dabbers, rubbers, flakers, and scrapers. Lipstick is applied and reapplied. Spidery eyelashes are fastened. Fake nails are glued. A blond wig is jammed on my head. Finally, Miss Vera bastes me with perfume — rendering me not only odorous, but also, I suspect, flammable.

And then the moment of truth. "Take a look," says Miss Deborah.