When Your Wife’s Bra Won’t Fit You

Inside Miss Vera’s Finishing School for Boys Who Want to Be Girls, where anything goes except for your real name.

Photography by Matthew Salacuse

Behind Manhattan’s Port Authority Bus Terminal lies a grimy, litter-strewn block of brownstones where a half dozen bums have camped outside an abandoned storefront. The tableau is like a mote of Old New York dust suspended in the neon beams reaching west from nearby Times Square. Since the late 1990s, the New York–based group Crossdressers International, or CDI, has maintained an apartment here.

For its roughly 30 key-holding members, the CDI headquarters serves as a support group and a locker room. There are two rules: no photography and never reveal your male name.

In the entry hall of this low-ceiling garden apartment, there’s a stack of pigeonholes for passing along communications and sometimes love notes to other members. There are two sofas and a television in the living room, a shelf for unwanted clothing, and a bulletin board with announcements and resources. The periphery is lined with lockers and stacks of luggage; members pay a fee to keep their wardrobes here and can come and go as they please.

I’m first introduced to Karen — nervous, small, balding, with a close-cropped horseshoe of hair and a deep, husky voice. She’s standing wigless in a skimpy dress, shuffling through her locker, and won’t look me in the eye. Pointing at my voice recorder, she whispers, “I can’t be on tape. I can’t have people recognizing my voice.” She slips by me, shoulders bowed, to the bedroom, where she stands on a paper towel to put glitter polish on her toenails.

Karen is single, without children, and works as an accountant. “I wish people in my office could see me look like this,” she says. “I’m so boring and dumpy at the office.” She carries two cell phones and uses a back entrance to her apartment building that allows her to ferry her female clothing in and out without the doorman or neighbors seeing. She says she goes out in a dress four or five nights a week, far more than anyone else here tonight — save for Jen, the current president of CDI, and her girlfriend, Michelle, who live full-time as women.

They met through CDI and have been dating a few months. Jen’s story sounds a little apocryphal: She says she became transgender under “very rare” circumstances. “Mine was an accident because of prostate cancer,” she tells me, adding that things became “quite bizarre,” amid the hormone therapy she was receiving during treatment. “I got saturated with estrogen, and that’s when I discovered it. I have not known my whole life like most of the girls in here. Before I was diagnosed, I was pretty much asexual.”

Dues also help pay for things like CDI’s weekly dinner parties, including the one hosted on this recent Wednesday evening. The other eight diners gathered around the card table live outwardly as men except for the handful of times a month when they change how they dress. They’re all sexually attracted to women or to other cross-dressers. They have wives and children. Many have grandchildren. Everyone is around retirement age. They have a taste for skimpy dresses, short skirts, high heels, heavy makeup, and the kind of glittery accessories that usually appeal to teenagers.

“For as long as I remember, I’ve had gender identity issues. About 11 years ago, I was very suicidal,” says one member, who has grandchildren and who asked not to be identified by name. “I started living a double life. I’ve invested 40 years in my marriage. I’m successful at work. I don’t want to walk away from that. My wife has a really hard time. It really turns her off.”

Nancy is a longtime member. She’s not dressed tonight and looks a bit like Jerry Van Dyke with a manicure. “You dress, you go to Macy’s, you go to a Broadway show,” she says. “I’ve been married 34 years. I love my wife. I can’t [fully transition]. It’s not going to happen.”

“The gays aren’t too pleased with us because they think we are like Punxsutawney Phil — you come out on Groundhog Day, and then you go back down the hole,” Nancy adds. Many cross-dressers rely on gay bars as places to feel safe in public, yet that’s usually where the association ends. Nancy claims CDI’s application to take part in New York’s annual LGBT Pride March has been continually rejected in recent years, with organizers telling her each time it was filed too late.

Another member, Donna, echoes a sentiment heard over and over. “I came to it more through a fetish for high heels, boots, leather. But at this point in my life I’ve realized that becoming trans is not an option, so I will be a cross-dresser.”

SLIDESHOW | INSIDE THE SCHOOL

And a gentle Midwesterner named Joan — with the kind of voice that’s good for telling stories around a campfire — says, “My wife doesn’t want to see me dress, but she will offer makeup

advice. She’s unhappy every time I go out.”

Veronica Vera, known as Miss Vera, is a prominent mentor on the cross-dressing scene and the only biological female in the room.Part of her mission is to help wives understand and embrace their husbands’ cross-dressing desires. Raised as a Roman Catholic in New Jersey, she pursued a career on Wall Street, then one in pornography and sex journalism, before founding Miss Vera’s Finishing School for Boys Who Want to Be Girls in the early 1990s. It bills itself as “the world’s first cross-dressing academy,” and still operates out of her Chelsea apartment.

Before the term transgender gained traction in the ’90s, all trans people were regarded as transvestites, or cross-dressers. Now, though most cross-dressers put themselves under the trans umbrella, the mainstream trans movement is not always eager to claim them as its own. The term retains connotations of perversion and fetishism.

“They are the inconvenient truths of the trans movement,” Miss Vera explains.

Still, as long as there’s been a New York, there have been cross-dressers in the city. One of the earliest colonial governors, Edward Hyde, also known as Lord Cornbury (who served from 1702 to 1708), reportedly spent half his life in women’s clothing, opening the 1702 New York Assembly dressed as Queen Anne and making a hobby of hiding behind shrubbery while in women’s clothing, waiting to pounce, shrieking in laughter, on passersby. A portrait of a man with a five o’clock shadow, dressed in white gloves and a blue dress, hangs in the New-York Historical Society and is

believed to be Lord Cornbury.

Around the time her finishing school started, Miss Vera’s husband, Robert, an openly gay man, had just died of complications from AIDS. There was a tabloid, The Transvestian, serving the cross-dressing community and a couple of specialty clothing stores had opened. The film Tootsie had been released a decade earlier.

“There’s a scene in Tootsie where Dustin Hoffman is walking alone in this crowd. That’s what they wanted,” Miss Vera recalls of her earliest clients.

Her first was a 38-year-old government attorney from Texas who described his femme self as a 21-year-old “airhead” named Jamie Sissyribbons.

Miss Vera is warm and matronly, with a cheeky side. She has the assured airiness of someone who thinks a lot about spiritual matters. We’re sitting in the school’s main room, which looks like the inside of a bottle of Pepto-Bismol. The words cherchez la femme (“look for the woman”) are scrawled on the blackboard. Her second husband, Stu, who recently passed away, had two female personas, Misty and Nurse StuRonica. A snapshot of Misty, laughing and wearing a short purple dress and a red wig blowing in the breeze, hangs on the wall.

“A lot of people who come from the straight world would really like their wives to be more in charge of them,” Miss Vera says.

The school, which conducts individual consultations, employs a dean of high heels, dean of cosmetology, and dean of voice, among others. A two-and-a-half-hour session is $550; prices increase incrementally to $3,000, for the two-day Femme Intensive, with extended stays available.

Miss Vera is showing me a stack of student applications, where prospective enrollees are asked to describe their femme personas.

“At home, Carly is guided by a beautiful wife who she loves to please. In business, she’s a smarty-pants scientist and entrepreneur,” reads one. Students check off from a list what best describes their female side. Options include “sissy maid,” “sexy vamp,” “whorish slut,” “mommy’s little girl,” “conservative librarian,” and “pregnant.”

“I identify all the cross-dressers who come here as transgender because their feelings are very deep. It’s not just a fetish,” Miss Vera says. “Sometimes the way they access this part of themselves goes hand in hand with masturbation, and they feel very sexually charged. And these are people who sometimes then transition, and then sometimes after they transition, because of the hormones, their sex drive goes down.”

Certain radical feminists are pushing back against all this gender kumbaya.

Elizabeth Hungerford, an attorney living with her wife outside Boston, co-authored a controversial letter to the United Nations in 2011, addressing language in gender identity laws, specifically seeking to protect sex-segregated spaces from people who may use gender to override sex.

“Being a woman is not just dressing up. It reduces being a woman to a costume, rather than a lived experience that spans many years,” she tells me. “The hyper-femininity, the exaggeration, the caricature of what is stereotypically associated with women — I do find that offensive.”

Hungerford is familiar with Miss Vera. She thinks her heart is in the right place, but “according to her school, in order to be a woman it’s very important to be able to walk in high heels,” she says. “I would disagree.”

Miss Vera invites me over to meet a student arriving from Orange County, Calif. He’s 55 years old, straight, and single, and he’ll be spending close to two weeks at the academy, forking over a tuition just south of $10,000. (This is below the normal rate. He received a partial scholarship in return for performing secretarial duties, which Miss Vera said he executed with immense enthusiasm.)

“Blissful euphoria,” he says of the first time, in February 2011, when he left the house in women’s clothing. “I was definitely born male. Now I like the flexibility of making gender fluid.”

The man is silver-haired, charismatic, tall, and broad. Even sitting in a negligee while having his face done, he appears, psychologically, in full-on male mode until the wig goes on.

“Did you notice the immediate transformation?” asks the dean of cosmetology, stepping back. “It’s always like that with the students. It took me a few times to get used to it.”

I had noticed, both days I spent with this student. As soon as the wig is in place, there’s a different person in the room. Her name is Ginger: energetic, flirtatious, confident, something of a bimbo. (Ginger describes herself as “as a classy executive.”)

I had also picked up on what Miss Vera described as the student’s “pussy hound” nature. As a man, Ginger has had his share of girlfriends, and many have known about the cross-dressing but have stopped short of embracing it the way he would like. He loves women, and not in a lewd way. He loves being around women. He admires them. He loves lesbian porn. There isn’t a gay bone in his body.

But now I feel Ginger’s gaze fall on me.

“In the process of my cross-dressing,” she says, “I definitely want to have sex with a guy.”

I feel like this is directed at me.

“I want to know what it’s like to be a full femmie bottom,” she says.

During Ginger’s stay, Miss Vera is a constant chaperone for brunches, shopping, and bar crawling. Later they are going to a cross-dressers’ sex party in Midtown and invite me along. Admission is free for ladies and cross-dressers but $100 for men. “You’re welcome to come by the school and borrow a dress,” Miss Vera says. (Tempting, though ethically muddy.)

Perhaps Miss Vera’s most imperative role for her students is therapist. “A lot of people who come here feel like their femme self is their best friend, their protector. There are a lot of trust

issues involved,” she says.

We’re watching Ginger slink down an imaginary catwalk with Julia, the dean of high heels, a willowy girl from Eastern Europe. As they stroll, Ginger’s wrist is too errant, her hips too swishy, her laugh shrill. But this is, of course, why she’s here.

“If I’m never in a relationship again, fuck it. Who gives a rat’s ass,” Ginger says. “Because this other stuff has now become more important to me.”