Conservative Men in Conservative Dresses

Heterosexual crossdressers bother almost everyone. Gay people regard them with disdain or affectionate incomprehension, something warmer than tolerance, but not much. Transsexuals regard them as men "settling" for crossdressing because they don't have the courage to act on their transsexual longing, or else as closeted gay men so homophobic that they prefer wearing a dress to facing their desire for another man. Other straight men tend to find them funny or sad, and some find them enraging. The only people on whose kindness and sympathy crossdressers can rely are women: their wives, and even more dependably, their hairdressers, their salespeople, their photographers and makeup artists, their electrolysists, their therapists, and their friends.

Drag queens (gay crossdressers) make sense to most of us. There is a congruence of sexual orientation, appearance, and temperament: feminine gay men dressing as women for a career, like RuPaul, or less lucratively, as prostitutes, or to express their own sense of theater and femininity. (Barney Frank as a drag queen makes no more sense, intuitively, than Dick Cheney.) Actors whose most famous performance is as a female, like Barry Humphries's brilliant and textured Dame Edna or Flip Wilson's one-note gag of Geraldine, don't puzzle us. Tootsie and Mrs. Doubtfire and the boys in Some Like It Hot don't puzzle us; they're just men doing what they have to do to survive, learning a nice lesson about the travails of womanhood and giving one on the benign uses of masculine self-esteem. Even the crossdressing women of history, from Pope Joan to Joan of Arc to America's jazz-playing Billy Tipton, from Little Jo Monaghan the cowpoke to Disney's adorable Mulan, don't puzzle us; they chose to live as men because they couldn't otherwise have the lives they wanted.

Every fall, hundreds of heterosexual crossdressers come to Provincetown for Fantasia Fair, an annual event since 1975. They come to attend seminars on self-esteem and lectures on Your Feminine Self, to accompany their wives to support group meetings, and to pay for photo sessions of themselves "en femme." They come to walk up and down Commercial Street, to eat in the Governor Bradford and Fat Jack's, simply to be and be seen in public dressed as women. Provincetown seems like a pretty safe place for them, and it is, but even here there are looks and chuckles, and there is no sign that any of the residents, gay or straight, recognize these men as people with whom they have much in common. The gay people do not say, "Oh, you're a straight man who likes to wear a dress? Welcome aboard!" And the straight men do not say, "Well, except for the dress thing, you're just like me. Howdy, pardner!"

Heterosexual crossdressers—straight men who have not only a wish but a need to wear women's clothes and accessories—manage to be marginal among heterosexual men, marginal among other men who wear women's clothes, marginal in the community of sexual minorities, and completely acceptable only to fetishists, who accept anyone who says they belong.

Many heterosexual crossdressers never come out of the closet, not even to their wives; they spend their whole adult lives dressing in secret, ordering size 20 cocktail dresses from catalogues, with only the mirror for company. Others tell their wives after ten or twenty or thirty years of marriage, sometimes because they've been caught wearing her clothes, sometimes because the clothes have been discovered. (The revelation that he himself is the "other woman" is a staple of crossdresser histories, and although the husbands say that their wives were relieved, it's not clear to me that they were, for more than a minute.) Second wives usually get told sooner, and as with other matters, third wives tend to know everything there is to know before the knot is tied.

But a lot of these men want to crossdress outside their bedrooms, driven by loneliness, by unmet narcissistic needs (all dressed up and nowhere to go), by risk-taking impulses (it's not hard to grasp that a forty-five-year-old, two-hundred-forty-pound former Marine strolling through the Mall of America in full drag is consciously courting risk). They go to get-togethers in Kansas City, in Pittsburgh, in Seattle, all over America. They make forays into malls in pairs, and they go to tolerant gay bars in small groups. They browse in the Belladona Plus Size Shop of Beverly, Massachusetts, and they hang out at the Criss/Cross Condo in Houston, which offers the Empress, Princess, and Duchess packages for a twenty-four-hour getaway as a woman. They go to weekly or monthly meetings, of six or ten or twenty guys, at the Paradise Club in Parma, Ohio, at Long Island Femme Expression in Ozone Park, at gatherings of the Central Florida Sisters of Kissimmee. There are crossdresser groups in Nashua, New Hampshire, and Trenton, New Jersey, in Springfield, Missouri, and Allentown, Pennsylvania, and throughout the Bible Belt. There are enough crossdressers in Arizona to support chapters in Phoenix and Tucson. A man who crossdresses and needs to be seen crossdressed can go to conferences like Provincetown's Fantasia Fair or Atlanta's Southern Comfort or the Midwest's Fall Harvest, or take a cruise aboard the Holiday, a Carnival ship offering a four-day trip to Catalina out of Los Angeles, happily hosting twenty-five crossdressers and their spouses amidst the other thousand guests.

Sometimes the wives wish to come, to support their husbands and enjoy the trip, or to hang out with other wives, like golf widows or wives in Al-Anon. Some come because their husbands need them to. "I don't mind, but really, if he could learn to do his makeup properly and fasten his own bra, I'd rather stay home," one woman told me at Fall Harvest 2000, in St. Louis. (Later she called to say that she had bought her husband a home video guide to makeup for men and a magnifying mirror, and that she was resigning as his dresser. "He can ask one of the other guys to hook his bra.") Happy wives are everyone's favorites, but happy or cowed, enthusiastic or grimly accepting, the wives at all of these functions are simultaneously important objects of much public appreciation and utterly secondary to the men's business. The world of crossdressers is for the most part a world of traditional men, traditional marriages, and truths turned inside out.

I am on line to board the Holiday and my antennae are up. So far, I have seen three large families, one Filipino, one African American, one mixed Caucasian and African American. There are lots of couples in their twenties, some with six suitcases, some with small gym bags. There are several pairs of well-dressed women who are clearly travel agents. I keep scanning the crowd for the crossdressers, but no one stands out.

As I make my way to my small room on B Deck, I wonder what to wear to dinner and a preliminary cocktail party in the suite of my hosts, Mel and Peggy Rudd, both blond, heavyset Texans in their sixties. Peggy has written a number of books on crossdressing, the best known of which is My Husband Wears My Clothes (PM Publishers), and was formerly the director of SPICE (Spouses' and Partners' International Conference for Education), an annual workshop that "focuses on spouses' and partners' issues, communication skills and relationship-building" for wives of "ordinary heterosexual men with an additional feminine dimension." I've met the Rudds before. I've traveled to Texas to interview them, stayed at their home, woken up in their astonishingly sunny and beribboned guest room, and walked down to the breakfast nook past a phalanx of posed photos: the Rudds with Ronald Reagan, the Rudds with both Reagans, the Rudds with George and Barbara Bush. At breakfast, Peggy said to Mel, "Oh dear, we should have taken down all those pictures of us with famous Republicans before Amy got here." Mel smiled. "Oh, I think she's a true liberal, she won't mind about the Republicans."

I waffle about what to wear for nearly half an hour. Outside my door, the men are coming down the hall in twos and threes. Finally I decide that silk pants and a tank top and sandals is right—right for the level of dressiness of the dinner (which I have overestimated) and right for my own social and appearance anxiety (which I have underestimated). When I walk into the little party, the Rudds hug me and introduce me to everyone as "Amy the writer." Some men flinch, although the Rudds have told everyone to expect me. Tory, a good-looking young man from Mexico, shakes my hand: "Hello, Miss Amy." His aunt and his cousin and his girlfriend, Cory, are on this trip, his first time crossdressing in public. Tory and Cory, with their romantic banter, his devoted relatives, and his final painstaking and successful transformation from Antonio Banderas to Daisy Fuentes, become the darlings of our group; they make everyone feel better.

I meet the rest of the guys and their wives. The men—to whom I will refer in print as "he," and to whom I refer in person when they are crossdressed as "she"—are not drag queens, hardworking perennials like Pearlene the Size Queen and Big-Boned Barbie, not actors, not Vegas female impersonators. They are most definitely not gender-benders of any kind, not Marilyn Manson, not Prince. They are more like Mrs. Attanas, my formidable fourth-grade teacher, a big, tall lady with a bolsterlike bosom, thick legs, sensible pumps, hennaed hair, and twin spots of rouge on her cheeks. I meet a happy, long-married couple, Steve and Sue, who look alike whether he's crossdressed or not. I meet Harry, who is always somewhat crossdressed (women's jeans, women's sneakers) but never flamboyantly; his appearance is that of an effeminate man, and he doesn't bother with a femme name or seem to have any of the common need for a more feminine presentation and feminine affectations. I would have thought that this might be easier for his wife than a husband who calls himself Lulu, spends hours in the bathroom on his face, and parades around the living room in a strapless lavender tulle dress and matching fuck-me pumps, but it's not.

"I love him," she tells me later. "I love him, but I don't want a man who is excited by the idea of being a woman. We have two kids, he's a great dad, a good provider, but I want a man who's comfortable with masculinity. I don't want to be sisters . . . or lesbians. If I wanted a woman, I would have found one by now. But . . . there's all the other things that are good." And he tells me later, with great sadness, "She is the most supportive person in the world, and this is a terrible thing for her. We work on it, we struggle." He stops and gathers his defenses; throughout the cruise he will condescend to the men with femme names, the men who insist on hours of makeup, because he sees himself as "evolved," free of the trappings and compulsions of crossdressing. "All couples struggle, they fight about money, about sex. You can't tell me they don't. This is no different." He looks out at the ocean. "This is different, I know, but I refuse to let it ruin our lives."

At dinner I am seated at a table anchored by Peggy and Melanie (as Mel calls himself when en femme), in nearly matching vibrant floral prints. To my right are Tory's aunt and cousin, who speak almost no English, and next to them is a very attractive woman, Lori, a Lee Remick look-alike, husband nowhere in sight. To my left are Felicity and his wife. Felicity is a large, hunched man, made up in a conventional, slightly stiff manner. He looks like a librarian, or perhaps the strong-minded wife of a minister, and he is, in the rest of the world, a Southern Baptist minister from the very buckle of the Bible Belt.

"So, you're the writer. Well, I'd say you pass pretty well," Felicity tells me. I smile pleasantly, as if I am not offended, as if I didn't think he intended to offend me. "Well," he says heartily, and then he clears his throat twice and stares at my silk pants. "You gals just get to crossdress all the time and no one says boo." He sounds furious that life is so easy for me and so hard for him, but because he is a minister, and even more because he is dressed as and representing someone named Felicity, he cannot be direct or angry; he has to try to convey a serene and gracious femininity regardless of his feelings and the oddness of the setting, which is as hard for him to do as it would be for me. And his wife is beside herself, tight-lipped, hands clasped; she is a Christian woman doing what she must, and as much as she might wish it otherwise, what she cannot be is pleased.

On the other side of me is a man in his late sixties, recently retired as a senior partner in a white-shoe law firm in the Deep South. He looks great. He looks like a Neiman Marcus matron, right down to his Chanel slingbacks, and although he seems a bit out of place, it is only because the cruise is so downscale and there are twenty-year-old guys clumping around the casino in their NASCAR jackets, baseball caps, and hiking boots, as if a nice shirt and a pair of slacks would be way too much trouble.

At first I thought that the matronly look so common to straight crossdressers reflected some weird attachment to the mother, that the image they wished to present was that of their own first woman—hence the heavy foundation, the blue eyeshadow, the big pearl button earrings. I no longer think so. That same look is common among their wives, and among lots of middle-aged women not much interested in changing fashions.

Most crossdressers, and almost all married crossdressers, live lives in which they are not crossdressed. They don't take female hormones, they usually don't have electrolysis even if they would like to (many express the wish to wake up and find themselves without facial, arm, or leg hair, but their wives are opposed), and they are not regular readers of Elle, Vogue, or even Ladies' Home Journal. They cannot easily put together a natural, believable female appearance. First, you need beard camouflage to flatten and disguise the stubble, then powder over that and foundation over that, and sweating is a big problem. (Jim Bridges, a transformation guide and guru, creator of the Bridges to Beauty 2000 and Hollywood Makeup Secrets videos, which are offered at his boutique in California and through his booming Internet business—"Can't tell you who in the House of Representatives, can't tell you who in the NFL," he says to me while putting false eyelashes on a John Deere salesman at Fall Harvest—counsels a quick swipe of antiperspirant on the upper lip and at the hairline. Crossdressing is not only anxiety-provoking and arousing, it is also warm under the wig, the corset, the padding, the pantyhose.) You need the foundation for smoothness and for color, and by the time you add lipstick and a wig, if you're a man you get that overdone crossdresser look and if you're a woman you get Joan Collins. A pronounced face requires pronounced makeup for balance, and after the false eyelashes and even the most subtle contouring of the wider jaw, the thick brow, one can look beautiful or ridiculous, but one cannot look like most of the women around.

My tablemates look like more attractive versions of the photos I've seen in the personals sections at the back of crossdresser magazines. I flipped through thirty issues of Transgender Tapestry and saw a lot of men who looked bad, like every joke and caricature of a crossdresser: the big shoulders, the jagged makeup, the prom dresses or JCPenney crushed-velvet tube dresses. Some looked mentally ill and possibly dangerous. I saw a few beautiful women, very often transsexual, as it turned out, but occasionally just crossdressers blessed with the right shape and the conventional proportions, narrow shoulders, small hands. And then there were always a dozen crossdressers who looked like pleasant, average women: librarians, day-care providers, schoolteachers, not staggering, not intense, not lovely, but perfectly ordinary, pantsuited, sensibly shod middle-aged women. I have met crossdressers whose presentation is just this side of Christina Aguilera, and I have met a fifty-year-old Midwestern engineer and a sixty-year-old born-again Christian CEO and a forty-year-old police captain, all of whom dress exactly as they would if they had been born to the distaff side, in clothes both contemporary and appropriate, whether Gap or Escada or Dress Barn. Anatomy may not be destiny, but it certainly lays a hand on our options.

Age is a great help to crossdressers. It is, for us all, the great androgynizer; the skin softens and sags, the secondary sex characteristics shrink and fade, slacken and thin. I have seen far more convincing crossdressers over sixty than under. Except for the guys whose height and build make it impossible for the world to construe them as female (and this is a problem for very tall and muscular women, as well), by sixty, crossdressing men have undergone the inevitable softening of the face and chest, the diminution of testosterone, and have enough practice and enough confidence to make very passable grandmothers of themselves. Not surprisingly, the amount of time that many crossdressers spend en femme triples after they retire. They can crossdress when they want, and many of them want to a lot.

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Excerpted from Normal by Amy Bloom. Copyright © 2002 by Amy Bloom. Excerpted by permission Random House. All rights reserved. No part of this excerpt may be reproduced or reprinted without permission in writing from the publisher.