Sleet is rattling the windows, but inside Rebecca’s Girls School (For Boys), all is warm, soft, and pink as a rose. Carole, the sole student this Saturday, is taking Maiden Voyage-Beauty 101, which the syllabus describes as two and a half hours of “intensive femme focus and formation and finding the look for you.” The class, “specially designed for the girl-on-the-go,” lists at $225, plus equipment: Rebecca’s offers breast forms, corsets, and hip pads. Hip pads are flat eye-shaped pillows, larger versions of the “cookie” that fills out a Wonderbra. They slide into four slots on a sort of anti-girdle—it adds, rather than subtracts—extending from waist to mid-thigh.

A self-described “full-figured gal,” Carole fluffs up only his top half. He has brought his own breast forms—surprisingly heavy silicone bags with sculpted nipples—and situates them in his black bra with a lean and a tug. Matching panties peep from below a Santa spread of belly as he steps into a semiformal skirt and blouse, and matching jewelry.

Carole walks on the femme side with the help of Rebecca, the proprietress, and Anna, a “cosmetics consultant.” These three do not reveal their real names, Rebecca and Anna because they are married to cross-dressing men who are not “out.” Carole will describe himself only as a single heterosexual who works out of his home.

After he’s dressed—except for stockings and pumps—Carole is led to the makeup room. Rebecca and Anna ease him down onto a chair, into the frame of a mirror surrounded by hot white bulbs. The space around him is like the fantasy bedroom of a 9-year-old who will eventually escape the Midwest to be a gay fashion designer. Satin slips, sequined gowns, and ’50s photographs of women in bullet bras and girdles obscure the walls; pink plush carpet covers the floors; panties and garters pile up alongside copies of Vogue, Elle, and coffee-table makeup books. A lamp shaped like a ballerina wears a little tutu.

Rebecca offers Carole lipstick shades “from soft orange to a really deep plum” in a voice as soothing as hot tea. She kneels on the floor to do the pedicure, while Anna prepares Carole’s face for foundation. Carole stretches like a cat while the pretty tag team moisturizes him. “In male mode,” he says, “you never get this done for you—get your hair done, have people play with your face and your feet.” Anna paints, then blends a complex stratum of goop on Carole’s eyelids; she brushes a reddish-orange foundation onto his cheeks. (Orange tones are best for disguising stubble.) Carole squints hopefully into the mirror, Rebecca and Anna’s faces flanking him. The three commence the timeless female ritual of self-deprecation and reassurance.

“My eyes have too many wrinkles,” Carole laments.

“No, they don’t; you have beautiful eyes,” Rebecca murmurs. “And a really nice brow, not prominent at all.”

Rebecca is a demure femme, sexy with no sharp edges. She models lush, curvy womanliness to her male students as she lavishes it on them, like Snow White with adoring new charges (Transie, Pansy, Sissy, Femme…). Her establishment, a sort of charm school for cross-dressers, peddles acceptance and pampering, and has found an eager market in D.C.’s large transgender community: Rebecca’s Girls School opened its doors in upper Northwest in late November and has had a steady stream of customers from the start—one advertisement alone netted 50 responses, and the school’s new Web site is bustling.

Besides Rebecca and Anna, the staff comprises two additional makeup consultants, two hairdressers, a counselor who discusses the “feminine mystique,” and a resident photographer. All but the photographer are women, or, as they call themselves, “genetic girls,” or “GGs.” The courses include shopping or dining outings, which, for some students, mark their first ventures out in public dressed as women. Rebecca brings the remade girls into a small network of stores, restaurants, and nightclubs that are friendly to transgenders and do their best to guarantee a field trip free of hostility and ridicule.

Many of the school’s customers, including Carole, belong to the TransGender Education Association (TGEA), the D.C. area’s largest support group for transgendered people. The term covers—and the group accepts—cross-dressers (who are usually straight men), drag queens (generally gay men), and pre- and postoperation transsexuals living full time as the opposite sex. Most of the people in the last group have switched their identities from male to female (or, in subcultural parlance, “M2F”).

TGEA strains to protect its members’ privacy; its bylaws specify that members must not acknowledge each other if they happen to meet out in their man’s world. TGEA’s officers screen callers extensively before telling them where meetings are held. The first test question, says Debbie, TGEA’s president, is “How long have you been dressing?” If the caller replies, “I just started,” Debbie suspects a spy, because most real cross-dressers begin pillaging their mothers’ drawers between the ages of 4 and 8.

At TGEA’s Halloween party and meeting, held in a plain social room of a suburban church, minutes are read, the upcoming holiday dance is plugged, and sundry announcements are dispensed. About 20 men wearing wigs, dresses, and heavy makeup perch awkwardly on folding chairs. About a third of them sit next to their wives or girlfriends. It’s not a fabulous sight—more Monty Python than La Cage aux Folles. Only a few members have dressed for Halloween, the drag holiday of the world. Debbie wears an Elvira wig, dress, and fishnets; membership director Yvonne has come as Monica Lewinsky in a blue dress, beret, and kneepads. The group’s secretary, Sara, a tall, slim, postop male-to-female transsexual, wears the wittiest costume: Her Redskins jacket, baseball cap, and fake swagger are the only manifestations of what the Pinnacle, TGEA’s prim newsletter, calls “Gender F@#$.”

Several male-to-female transsexuals turn up at TGEA’s meetings, but most of the group’s 70 or so members are heterosexual married men who occasionally slip into female get-ups. TGEA currently counts no female-to-male transsexual members, but that constituency has its own support groups, among them the American Boyz, a national organization based in Elkton, Md. “AmBoyz,” says its Web site, serves “Butches, F2Ms, Transmen, FTVs [female transvestites], Gender Outlaws, Transsexuals, Drag Kings, New Men, Boychicks, She-Bears, Shapeshifters, Transfags, Tomboys, Passing Women, Amazons, Tranny Boys, Intersexuals [those with nonstandard XY chromosome sets, including hermaphrodites], Female Guys, Bearded Females, Tranz, Boss Grrls, Transgenderists, Sirs, and our Significant Others, Friends, Families, and Allies….”

Popular wisdom holds that tomboys generally have an easier time in the world than sissies. “Drag kings,” or women who impersonate men, have sneaked into the mainstream more easily than male cross-dressers because, some gender theorists contend, they do not pose as great a threat to the social order. A man who would relinquish his ascribed power in society by “becoming” a woman, this school of thought holds, disturbs civilians incalculably. Women who dress as men aren’t viewed as necessarily moving up in the social hierarchy: Celebrities such as Marlene Dietrich, Lily Tomlin, Grace Jones, Annie Lennox, Crystal Waters, and Julie Andrews in drag have registered in the public imagination as safely, cutely kinky. And those women, in turn, paved the way for today’s It Boy/Girl drag king Gwyneth Paltrow, who owes her Oscar to her mustache.

Male cross-dressers bitterly point out that women can and do wear men’s shirts, pants, shoes, and coats with impunity. Pamela Anderson recently wore boys’ underpants on the cover of the strenuously heterosexual Esquire. All of which prompts men harboring an inner Barbie to ask—as Ed Wood did before them—must one little piece of silk underwear make a man a pervert?

Attempts to explain the enigma of cross-dressing have hardened into cant: “I’m at peace when I’m dressed”; “It’s not about sex”; and, most frequently, “Sex is between the legs and gender is between the ears.” Many cross-dressers echo the rationale of Debbie, whose real name is John: “As a male, you have to be tough, and I come from a family where girls were cuddled, so you associate that nurturing with being dressed,” he says. “When I feel unloved and alone, the urge to dress increases.”

Rebecca’s husband, Sandy, says he tries to spend several days a week en femme as Sandi, or somewhere comfortably in between. Sandy meets me at Rebecca’s Girls School as Sandi, who’s as striking and soft-spoken as his wife. He’s 6-foot-3 and rail-thin. He wears high-waisted jeans and a tight scoop-necked T-shirt over small breast forms. His gray hair, which he ties in a ponytail when he’s Sandy, falls loose halfway to his waist.

Cross-dressing, he says, brings him closer to his personal best. “I think women are the chosen people,” Sandi declares. “I think the Creator did a much finer job with women than with men. Women are more insightful, more spiritual, more attuned to the details of life.”

Debbie says he undergoes a psychic transformation when he sheds the clothes of a retired colonel with two ex-wives and three kids. “Debbie is more creative, and John is more controlled,” he says. “At a tear-jerker movie, Debbie will allow herself to cry.”

Men, some folks believe, are more “visual,” meaning they respond more intensely to what they see than do women. Supporters of this notion point to the pornography trade; the cosmetics, plastic surgery, women’s magazine, and beauty industries; the gyms full of buff gay men. Cross-dressing, it happens, is a largely visual practice—a literal way for men to see their feminine sides.

At TGEA, cross-dressing is not the kind of outré exercise you’d expect from having watched Paris Is Burning. Most of the cross-dressers in TGEA transform themselves into respectable matrons, mainly because they are a conservative bunch: Besides Debbie the ex-colonel, two others at the meeting are “in law enforcement” and many others are feds living in the suburbs. When they dress as women, they seem to express their belief in a genteel femininity as reflected in the fantasy world at Rebecca’s Girls School. Their vision couldn’t be further from that of drag queens, who exaggerate a whole other set of female virtues: bitchy, shallow, and cheap.

By affecting a ’50s gentility, these heterosexual men in dresses claim to be keeping the focus off their sexuality. TGEA director Tammy, a big-shouldered fellow who stands 6-foot-4 and wears dark lipstick, explains his femaleness as asexual. He nervously smooths his slim skirt and says, “Being female is a state of mind, and I become so overwhelmed by the experience that I don’t have sexual feelings.”

Sandi insists that he doesn’t cross-dress to attract anyone, because he’s married. “In my male drag,” he says, “I like to be in style, make a personal statement—and that’s not about attracting women. And I’m not trying to attract men when I’m dressed, because I’m not gay.” At some level, however, femaleness involves becoming the object of desire, which confuses him. “Two years ago,” he says, “I was sure I was a heterosexual cross-dresser. But then I saw this guy looking at me and I said, ‘He’s cute.’…The more I examine myself, the less I know.”

Throughout history, women have adopted male personas to work or fight or make art. Cross-dressing for some of these men is analogous. Tammy, a cop, believes cross-dressing helped push him toward a macho, demanding position in his career—the J. Edgar Hoover profile of a transgendered person. “Proving that we were OK was important, so many of us became overachievers,” explains Tammy. He’s been dressing since he was 4 years old; as an adult, it has become a break from his position of power.

“A lot of people in the male-to-female transgender community will tell you, ‘This is my vacation. This is how I relax. This is how I detox,’” says Sandi, who runs his own communications business. He calls cross-dressing an opportunity to “lay down the sword that men have to carry through life.” Sandi explains that if he’s forced into a contest at work, “I can slam dicks with the best of them, and sometimes I have to do that…but I hate it….And after an ugly, shitty contest like that, I am so disgusted at the dehumanizing, demoralizing manner by which it had to be accomplished that I need to get away for a while and dress.”

Gender dysphoria—the state of being a woman trapped in a man’s body or vice versa—is not a pathological condition but a “natural aberration,” writes psychotherapist Carl Bushong, director of the Tampa Gender Identity Program, a treatment facility in Tampa, Fla. The number of people who experience gender dysphoria is in dispute; estimates, he reports, run as high as 3 percent of the population. Occasional cross-dressing “treats” some gender dysphorics, but a mere vacation from the birth gender is not enough for all of them. Those who would become transsexuals must take a one-way trip into uncharted territory.

Definitions of the phenomenon have taken strange turns over the past few decades through the revisions of the Diagnostic and Statistical Manual of Mental Disorders (DSM), the official handbook of mental illnesses published by the American Psychiatric Association. The DSM spells out the diagnoses that mental health workers must use to be reimbursed for their services by insurance companies. The 1980 edition, the DSM-III (the first not to include homosexuality as a mental disorder), added a new diagnosis: Gender Identity Disorder of Childhood, the criteria for which included preference for the other gender’s clothing and “intense desire to participate in the stereotypical games and pastimes of the other sex.” (Writer Phyllis Burke, in her book Gender Shock, presents several cases of tomboys and sissies needlessly hospitalized and “treated” under the new diagnosis.)

For the DSM-IV, published in 1994, the phrase “of Childhood” was eliminated, and, in an odd twist, the malady became the diagnosis transsexuals needed to receive hormones and sex-reassignment surgery (SRS). Under the widely accepted standards governing such surgeries, candidates must first live as the intended gender for a year and be under the care of a psychotherapist, who signs his or her consent. Those “Benjamin standards” are named for Harry Benjamin, a New York endocrinologist who coined the term “transsexual” and legitimized the idea that surgery, not therapy, could be the appropriate treatment for gender dysphoria.

Some advocates have since dropped off the bandwagon. The Johns Hopkins School of Medicine was a trailblazer in transgender studies and SRS, but stopped performing the surgeries in 1979, says Peter Fagan, director of the school’s Sexual Behaviors Consultation Unit. The decision came in response to studies showing that most people were not happier after their surgeries. Several studies found, for example, men who expected to be treated better as women and were completely unprepared for the hostility they provoked as transsexuals. Fagan, a clinical psychologist, does not dispute the existence of gender dysphoria but says that his “therapeutic aim would be to confirm the biological gender” rather than to surgically reassign.

Fagan’s method would not have satisfied Sara, TGEA’s secretary, who spent her first 40 years as Peter. “A large class of us feel we might be more content in a female body,” Sara tells me when I meet her at the first TGEA meeting I attend. “We’re like cross-dressers, but instead of eroticizing the feeling of wearing women’s clothing, it’s the feeling of wearing the female body.”

One paradox of people who experience gender dysphoria is that they protest the tyranny of gender roles but spend much of their lives pursuing membership in some gender or other—even if it’s one they’ve conjured in an acronymically infested jungle somewhere between the “M” and “F” boxes. Their identity depends on some acknowledgment from the same society that has made them outcasts.

Author Leslie Feinberg tries to explain defining oneself across the violently patrolled gender border. She is a genetic woman who looks like one of Martin Sheen’s sons on the jacket of her book Gender Warriors, wherein she writes: “I am transgendered. I was born female but my masculine gender expression is seen as male. It’s not my sex that defines me, and it’s not my gender expression. It’s the fact that my gender expression appears to be at odds with my sex.”

Feinberg and her fellow radicals argue against a dyad of gender in favor of a continuum. Sara explains how she never fit in the “blue” category, even though she was a man who liked sex with women. “Identity is based on feedback of other people,” Sara observes. “You see yourself as a female, but you have a penis, so what does that mean?” Of her journey to womanhood, she says, “I wasn’t making my body match my brain. I was finding out.”

Sara meets me at an unpopulated coffee shop, where I try to get her story in chronological order. We loop and digress so much we haven’t even gotten to the sex-change operation when it’s time for me to go to a friend’s gallery opening. I ask Sara to come and look at the art in Georgetown, then finish talking over dinner. We separate at one point, and I watch people squint inquisitively as they talk to the 6-foot-tall woman with the quick wit and the confusing skin. Sara’s cheeks look as soft as any natural woman’s, but around her eyes, it’s subtly, attractively leathery. I know by now that she’s primarily lesbian but likes male attention, so later I comment encouragingly on a fellow I’ve seen chatting her up. “Puh-lease,” Sara laughs. “That guy was painfully gay. Gay men love me now; I’m unthreatening or something.”

Growing up as Peter, he liked science, sports, and girls. Today, Sara is defensive about her lack of gender dysphoria. “People find it hard to understand why I would want to change when I was relatively comfortable as a boy,” Sara says. “I didn’t want to dress up in frilly clothes.”

Unlike some of the TGEA cross-dressers I talked to, Sara doesn’t see women as superior creatures, and in fact she speaks scornfully of “girly-brained” women. She initially refuses to describe such a brain but finally obliges: “helpless, dependent, not learning about sports or cars. Not curious about how things work.” She flaps her hands near her shoulders and squeaks like Betty Boop: “‘I don’t understand how they work—I just drive them.’”

As a teenager, she says, she envied girls their desirability. “I was drawn to women, but during sex I’d start to visualize being a female….My defenses would break down and I’d like them on top and I’d be imagining them having the penis.”

Like many transsexuals these days, Peter had his conversion experience in cyberspace. He joined America Online in 1995 and soon was having cybersex as Trina or Gina. The male-female ratio was favorable, and being pursued by men was as thrilling as Peter had dreamed. In 1996, he began using the Internet to research hormones and sex-reassignment surgery.

Sara has worked for the last 13 years as a cartographer in a federal agency that she calls “a guy kind of place.” Peter’s physical transition started with hormone shots in late 1996, and around that time he told his supervisor that he’d be “going through some changes.” In June 1997, impatient to push the process along, Peter came to work in a skirt. When he went to the ladies’ room, a woman called security, and Peter had to explain the transition he was making. Sara imitates the security guard responding robotically, like a graduate of sensitivity-training boot camp: “‘We don’t discriminate on the basis of sexual orientation,’” Sara recalls. “I didn’t bother to explain to him that it’s not orientation, it’s actually identity.”

Soon thereafter, Peter picked his new name, which became official in August 1997. He chose “Sara” because “it was simple, and I wanted to be a regular girl, to seem normal. I didn’t want to be called Desiree or something….I associated ‘Sara’ with women who were not really femme, but educated and level-headed.”

When he first began taking hormones, Peter’s hair got finer; his face, breasts, hips, and ass fattened up; his muscles got smaller; and his chest hair fell out. He could get an erection up until surgery but suspected he was infertile several months beforehand. He considered saving sperm, perhaps to fertilize another woman, but didn’t. “I used to want kids when I was in my early 30s, but not anymore,” says Sara.

We move to a seafood restaurant, and Sara switches from wine to Bloody Marys. She describes her vaginoplasty, which took place in Portland, Ore., eight months earlier, while she’s knocking back a dozen oysters.

“First, they remove your testicles, and they throw them into a compost heap,” she begins. Her doctor is renowned for building vaginas that can have orgasms—a 75 to 80 percent success rate. His technique is to scrape out all the internal erectile tissue in the penis and use the head of the penis to build the clitoris. He inverts the outer part of the penis and stuffs it into a cavity between the intestine and pubic region. The labia are created from scrotal tissue.

Sara plans to get a second operation, called a labiaplasty, for aesthetic reasons, in a year or so. That procedure will create inner labia and a hood for the clitoris, for what she calls a “gynecologist-can’t-tell” look. Before that, she needs electrolysis so that the tissue that folds over doesn’t have hair.

A new vagina is like a gigantic piercing that will close in on itself without a starter dildo. “You have to dilate every day, using phalluses of various thickness four times a day for the first month, then twice a day for the three months, then once a day for the next three months,” Sara explains.

Sara’s experience suggests that hormones lie much closer to the core of gender difference than genitals do. Estrogen and progesterone, as most women will attest, can be emotional slavedrivers, and in her previous incarnation as a man, Sara didn’t spend a lifetime getting used to the stuff. She’s logical and linear one minute, volatile and scattered the next. Tears fill her eyes several times during the interview. She’s taking higher doses of hormones than a postmenopausal woman in an attempt to “feminize faster,” she says. “I want a body like Michelle Pfeiffer.” Chasing the dream with hormones renders her as mercurial as a woman during puberty or menopause.

Sara’s love life has not been great during the transition. “I know the rational question is ‘Why would I give up my penis if I liked being with women?’ but I visualize myself as female.” The last time Peter masturbated before surgery, Sara now says, “I thought, ‘This may be the last orgasm I ever have.’” (So far it is, she says, but she hasn’t given up trying.)

She says she’s a lesbian, but wonders: “What lesbian would want me?” She tried sex with a few men when she was in transition before the surgery. “I liked it OK, but they were all bottoms and didn’t want to penetrate me,” she sighs.

Sara ticks from one explanation to the next for her journey, then leans toward me and says conspiratorially, “We haven’t even talked about the masochism of it all. I think, sexually, there’s a desire to be punished, and part of that is the illusion of what women are. That they’re there to be the sexual object and there to be the punished object. It all kind of goes together….There’s a degradation aspect of it, of giving up control. Part of the whole transsexual experience is to live that fantasy of spreading your legs and being fucked.”

Receptiveness, both literal and metaphorical, is seen as a female faculty by people from every gender. In her charming memoir Conundrum, British transsexual writer Jan (né James) Morris describes how she’s a more sensitive receiver as a woman—in terms considerably more prim than Sara’s. “My moods and conditions are more variable now… In a curious way my inner sensations show on the outside—and set the postman smiling too. I don’t believe men feel this instant contact with the world around them; for me it is one of the constant fascinations and stimulants of my new condition.”

Besides that heightened sensitivity—perhaps in response to it—Morris, a travel writer, found herself less interested in “great affairs” after her SRS. “My scale of vision seemed to contract, and I looked less for the grand sweep than for the telling detail. The emphasis changed in my writing, from places to people.”

For Carole, Maiden Voyage-Beauty 101 at Rebecca’s Girls School seems as big a journey as a sail to Australia. As Anna and Rebecca praise and indulge him, he smiles, laughs, and touches them more and more. A warmth and ease he did not walk in with animate him when he cross-dresses. I realize Carole is living the universal fly-on-the-wall fantasy of knowing how the other sex interacts—in this case, experiencing the sisterly company of women.

But the vulnerability and corresponding trust in a women-only setting is only part of the tuition package. Carole’s third hour at Rebecca’s prepares him for his road show: the walking lesson. Carole, who’s serious enough about passing as female to be considering electrolysis, has been going out as a woman for four years. It’s long enough to know the importance of walking.

A woman walking down the street is working it whether she wants to or not. Men who don’t know her tell her to “Smile!” as if it were a civil right, and passing a construction site can be like running a gantlet. Charm schools long before Rebecca’s have taught girls to walk properly, keeping them aware that it’s never just locomotion. For cross-dressers, the male gaze is a pass-fail test, with stakes ranging from embarrassment to physical danger.

Rebecca sends Carole across the sitting-room floor several times, appraising his gait through slitted eyes. She directs him into a higher pair of heels to help push his pelvis forward and shift his weight back. Carole still swings his arms too much, and his lower half is too stiff. Rebecca walks close behind several times, her hands pushing Carole’s hips from side to side. Then they promenade with Rebecca pulling down and back on Carole’s shoulders, to still his arms and better present the bosom.

Carole tries again on his own. “Smile,” Rebecca commands. Carole bares his teeth in obedience, but the smile soon spreads to his eyes, then to his body. He talks excitedly about his outing to a club that night. He’s starting to get the hip swinging down and begins to beam genuinely. In his enthusiasm, though, he forgets to mince. As he gets steadier on his pumps, his strides get bigger and his arms start swinging. Rebecca reins him in by handing him a purse. “Do I use my left or right hand?” Carole asks.

Next comes the sitting lesson. “Don’t spread your arms over the back of the couch. Women don’t do that,” Rebecca scolds. Rebecca shows Carole a couple of ways to sit—the legs-crossed sink and the ankles-and-knees-together descent, with the butt eased down at an angle. Rebecca says the hands should “protect the vulnerable areas. If the legs aren’t crossed, then put your hands together over your lap.” Carole tries to stay daintily contained as he lowers his bulk down and up, over and over.

Finally, he stops for a bathroom break. He laughs and tells me on his way in, “In this area, cross-dressers have been known to cheat.” Carole will talk small, walk small, and sit small, but lets us know that in the ladies’ room, he’ll be standing tall. CP

Art accompanying story in the printed newspaper is not available in this archive: Photographs by Darrow Montgomery.