No two men, it seems, touch a woman’s breasts in quite the same way. I learned this fact recently at a bar in New York’s West Village, where, in the space of an hour or so, I had my breasts prodded, twiddled, tweaked, squeezed, cupped, and, finally, patted. "Hey!" I barked at the guy who had given my left boob a there-there. "It’s not a dog!" In retrospect, maybe I should have been a bit more discriminating. "Touch ’em," I kept saying. "Go on, have a feel."
I should point out that I’m not usually given to this kind of behavior. For one thing, I don’t usually suck down three gin and tonics in the space of 20 minutes. For another, I don’t usually have breasts. And what breasts they were, too — pert, perfectly shaped, straining against the material of my knit-and-glitter Lord & Taylor evening gown. "You look gorgeous," said a fellow grinning from a nearby table. And I believed him — at least until I tottered off to the ladies’ room and took a look in the mirror.
To say the creature who greeted me was a mess would be a gross understatement. I looked like I’d had a hand grenade lobbed at me. Rills of sweat had made a moon map of my foundation; mascara formed Rorschach splotches on my cheeks; a fake lash hinged from my left eyelid, like a spider dangling from a light fixture. With trembling hands, I tried to press the lash back into place, only to have one of my long red fingernails ping into the toilet bowl. "Shit!" I hissed in a very un-ladylike fashion. "Shitting shit!"
A few minutes later, I was perched on my barstool again, my legs splayed at a 45-degree angle, my crotch a matter of feet from the face of the "you-look-gorgeous" guy. In all honesty, he couldn’t possibly have been turned on by my Sharon-Stone-lighting-a-cigarette moment (chances are it made him want to take up the habit). Undaunted, I burped, hiked up my fake ass, and ordered another G&T. Some lady I turned out to be.
My journey into womanhood started out promisingly enough. To assist with my transformation, I’d enlisted the services of Veronica Vera, the best cross-dressing coach in the business. As founder of the New York–based Miss Vera’s Finishing School for Boys Who Want to Be Girls, Miss Vera has stuffed more bras, fluffed more wigs, and tucked more testicles than she can count. Her school is widely considered the foremost cross-dressing academy in the US. "It’s the only cross-dressing academy," Miss Vera corrects, in a singsong tone laced with rather daunting severity.
Er, yes, Miss Vera. Sorry.
Besides presiding over the world’s only cross-dressing academy, Miss Vera is also the author of two books, the most recent of which, Miss Vera’s Cross-Dress for Success: A Resource Guide for Boys Who Want to Be Girls (Random House), was published earlier this month. Though primarily a how-to manual, Cross-Dress for Success is also a kind of manifesto. "Each of you is a messenger," Miss Vera writes, "a Mary Kay rep changing the face of humanity."
The book also, however, has a passage that reads, "At Miss Vera’s academy we offer complete makeup training with our expert deans," reminding readers that there’s a commercial side to all this. Indeed, when Miss Vera starts discussing her future dreams — "The show, the movie, the Home Shopping Club!" — she sounds like a gender-bending Martha Stewart.
A former porn star, prostitute-rights activist, and sex journalist (and a genetic woman, by the way), Miss Vera founded her academy in 1992 to, as she puts it, "keep myself in pantyhose." Today, she employs 10 "deans" — a Dean of Deportment, a Dean of Voice, a Dean of High Heels, and so on — and offers courses in ballet dancing, body building, cooking, flirting, music appreciation, and female genitalia. For $585, you can walk into Miss Vera’s studio and, a few hours later, walk out looking like Cher, Diane Sawyer, or, if you’re anything like me, Courtney Love after a Jim Beam bender. Those prepared to stump up $3995 can spend an entire weekend being pampered, prettied up, and prepped in the dainty arts. Given the school’s average of four students a week, there seems little chance that Miss Vera will be running out of pantyhose anytime soon.
"I was in the right place at the right time," she says, "with the right idea."
And yet cross-dressing, of course, predates Miss Vera’s academy. According to some, men have been wearing women’s clothes for as long as they’ve been wearing anything. "Cave paintings and artifacts found in Cro-Magnon and early homo sapiens settlements," asserts the online magazine TGWorld, "show transgendered figures." But then Cro-Magnon man didn’t have the likes of RuPaul, Dame Edna, Eddie Izzard, and Miss Vera to bring cross-dressing to the masses. Today, transgenderism is undergoing something of a revolution. The old ideal of the shame-faced hubby tugging on his wife’s panties in the cellar is rapidly being undermined by a spirit of openness — even celebration. As one local transgender activist puts it, "Fewer and fewer of the girls are in hiding."
But it’s not only places like New York and Boston that are seeing what Miss Vera describes as "a dramatic and significant increase" in the number of male-to-female cross-dressers. "We get students from all over," she says, "from the teeniest towns to teeming metropolises. Just look around: your postman, your lawyer, your florist — trannies are everywhere."
According to TGWorld, the percentage of men who wear, or have worn, women’s clothes is "quite high, perhaps as high as 50 percent." More conservative estimates put the figure at between three and six percent. "I calculate that to be six million adult males," says Miss Vera. "That’s a sizable student body right there." While no truly reliable figures exist on how many cross-dressers there are in the US, Miss Vera is confident that the numbers will continue to grow. "Transgendered people are changing the face and the body of society," she says. "To me, this is the most exciting thing that’s happening nowadays. Just the idea that people can change gender is really quite amazing."
This sort of pioneering spirit is evident throughout Miss Vera’s new book. "Welcome, gender explorer," she writes in its introduction. "Today is the perfect time for you to become the kind of woman you want to be." Even though she goes on to instruct her readers to "pop your testicles into their little abdominal cavities," I find myself more and more intrigued by the idea of becoming a Miss Vera Girl. By the time I discover that Miss Vera has a fake ass named after her — "The Veronica" — I am sold. I give the academy a call, and a week later find myself driving into New York City, listening to "YMCA" on the radio, wondering whether I’ll need to shave my legs.