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    Posted 02.27.04
    Appointment with a Reluctant Transsexual (Portfolio)

    Fran said, "Sit down now." Fran said, "In case any dysfunctional activity happens as a result of this, we're not to blame at all," indemnifying friends who had not yet materialized. "And Maria's the witness." My friend Maria Hong stood there in my apartment and watched Fran rub some makeup into my face that smelled like the old ladies who sat in the back pews at church closest to the restroom. Maria has what Fran is considering obtaining: real breasts and a vagina, for starters. Fran looked at Maria. A beautiful woman like Maria makes it seem so easy: her infectious, fizzy laugh, her knowing self-possession. She walks, but she does not have a gait.

    No one can say why the God Fran often prays to put her in Frank's body. It is a funny place to be if you favor black velvet dresses and high heels. If you asked Fran's neighbors in New Rochelle about him, they would stare at you wide-eyed; they know Frank, the happy, bright-eyed, 5'9" Italian-American C.P.A. with a thick Mt. Vernon accent and thinning, sandy hair, but no Fran. Or not yet, they don't. Frank has that bulbous nose, and got the deep gash under his lip when he wrecked his car on Shore Road when he was 18. It makes him look as if his chin frowns instead of his lips. Frank's eyebrows look witchy -- slight, tapered, and arch -- but Fran's eyebrows look just right. Fran is six feet tall, depending on the fabulousness of his high heels, with long, blond hair and streaks of dark makeup to create cheekbones that aren't visible. He carries a packed black purse in which a man's unkempt wallet lurks, so fat with jagged scraps of paper and notes it won't bend. Fran, not Frank, drives to Manhattan to answer my questions. I am a graduate student in journalism, and about three weeks after I met Fran through friends of friends, he asked me to dress up one night as a girl to go out with him and his transgender friends.

    It was not my idea, but now I kind of wish it had been, although I had no inkling of the deep complexity I would encounter. As a mere example, when I read two books about transgenderism -- Normal: Transsexual CEOs, Crossdressing Cops, and Hermaphrodites with Attitude by Amy Bloom and Crossing: A Memoir by Deirdre McCloskey, an economics professor who used to be Donald McCloskey -- I realized that although in person one refers to a man dressed up as a woman as she, in print, "he" is the norm. Print confers a permanency that conversation does not possess.

    The surgical and emotional journey that would bestow permanent womanhood on Fran is not something he is convinced he is willing to undergo despite his insistence that he was born in the wrong gender. Becoming a woman would probably cause the woman he has been married to for 30 of his 53 years to divorce him, although he desperately wants to stay with her. Like the Applewoods, the protagonists portrayed by Jessica Lange and Tom Wilkinson in HBO's Normal, Fran would like to live as a woman with his wife, but that happy ending seems increasingly unlikely. Three years ago, Frank told his wife that he thought he wanted to become a woman. Frank wasn't entirely certain; she wasn't all that surprised. For many years, Frank worked in retail, and he was always dashing after madcap, get-rich-quick ideas. His wife thinks Fran is yet another example of his flighty pursuit of some ethereal, unarticulated goal. But when they had a daughter 18 years ago, Frank's wife went to work the first year of their daughter's life, and Frank stayed home dressed as Fran. One day Frank picked up his wife at the train station dressed as a woman, and she thought it was a funny and silly thing of him to do -- but temporary. "My mother said I had to deal with it like an addiction," Fran says. "But I told her that it wasn't as easy as that. I wish I could just say, 'Okay, you're right, I'll stop it,' like I did when I was 16 and they caught me drinking."

    In the end, Fran may not be a "high-intensity transsexual," the medical term for people who feel strongly compelled to become the opposite sex, but he did exhibit high-intensity plans for me to dress up as a woman with him. I ignored or deflected his repeated requests, though. I righteously disliked the implication Fran seemed to be making: just because you're gay doesn't mean you want to dress up as a woman "for fun." Then one day Fran happened to be talking about the prickly relationship between gay men and lesbians and transgendered people. "I always thought it was one happy family," he said, until he started dressing as Fran more openly the last several years. Now he says, "We're about as much in the same pond as a duck and a giraffe."

    The Advocate acknowledged the disparity by devoting an issue to transgenderism in May 1999. "Even The Advocate has not been immune to the emotional turmoil surrounding this issue," the editors wrote. "We have had our share of criticism from activists and organizations, both gay and transgender, wondering why the magazine excludes transgendered people by identifying itself only as the national gay and lesbian newsmagazine. Many gay men and lesbians have little understanding of the transgender movement and what it means to be transgendered."

    For now, Fran, who says he does not have any gay inclinations, is more like a straight crossdresser. Amy Bloom notes in her book Normal that straight men who crossdress "bother almost everyone. Gay people regard them with disdain or affectionate incomprehension, something warmer than tolerance, but not much." A transgender activist named Sarah Fox, who founded a now-defunct civil rights advocacy organization called QUILL (Queer Unity Initiative Liberty Lantern), has a Web site in which she addresses the tension between mainstream gays and transpeople, as Fox would say. "Why do members of the larger queer 'family' have troubles with us? Well, I think it's because none of us want to get pinned with stereotypes that don't apply to us," she writes. Fox uses TBLG to refer to transgender, bisexual, lesbian, and gay people; the standard moniker is GLBT. "Gay men, for instance, often don't want to be regarded as wanting to dress like women, so they want to be clear with everyone that they are nothing like the likes of us. I confess I have difficulty understanding why those same men enjoy donning pumps and prom dresses to play baseball."

    "How do you feel about transgendered people?" Fran asked one day, peering straight at me even though he was trying to drive and hunt for a restaurant at the same time. It was a good question. The depth of my discomfort had extended to an egregious habit Fran didn't notice but that I had picked up early in our interviews. I held my reporter's notebook with unusual conspicuousness because it has the word "NEWS" emblazoned across the front of it, and by nonchalantly keeping it front and center, I was able to indicate -- to waiters, to passersby on the street, to no one I actually knew -- that I was accompanying this woman who looked and spoke like a man strictly for disinterested news-gathering purposes.

    I stopped all that the morning we ate at a diner and Fran started telling me about the night he was 17 years old and had gotten into a fight at Buzzy and Dicks, a bar in New Rochelle. There was a big brawl that night, and Frank started fighting with a guy who ended up pushing him through the bar's large glass window. Frank lay there, semiconscious, while the glass that hadn't broken hung suspended above him, a suddenly menacing guillotine. Frank has written about the incident in a rough draft of a book he would like to publish, Dollars From Heaven: 27 Financial Principles and Parables Inspired by the Gospels. Because the bartender, who was the brother of the man who had pushed him through the window, rushed over and pulled Frank out of the window, Frank reminds the bartender whenever he sees him now that he owes him his life.

    At the diner, Fran finished the bar story. As we got up to leave, a man sitting at a table of two middle-aged married couples laughed and said, "I thought it was a woman until I heard him speak," but Fran did not hear him. Having just heard about Frank's raucous bar life and then seen how a stranger felt repulsed by Fran, I can now report with absolute confidence that it is possible to simultaneously feel slightly frightened and fiercely protective of the very same individual.

    I needed to pass Fran's test of gauging whether I was man enough to dress as a woman. For Frank, at least, dressing as Fran certainly is a test. It takes more than a little courage to act upon your need to dress up like a woman when you know you still look like a man. Fran wanted me to literally be in her shoes, and if I could pull it off, I knew that the palpable transgender vs. gay issue that seemed to be creeping into our relationship would dissipate.

    But because I'm a journalist and Fran is my subject, letting him dress me up as a woman was more complicated than bridging the gap between gay and transgendered. I had dressed as a woman only once before, at a Halloween party as Tippi Hedren from The Birds. When Fran asked me whether I wanted to be a blonde or a redhead, "blonde" instinctively popped out of my mouth, but what I was really thinking about was William Finnegan's book Cold New World: Growing Up in a Harder Country. Finnegan lived with and spent several months with each of four families across the U.S. in order to write closely about the people harshly effected by the boom many Americans profited from at the end of the 20th century. "I generally failed to keep my journalistic distance," he confesses in the introduction. "The sheer amount of time we spent together tended to erode the lines between me and my subjects." The same blurring had happened between me and Fran, who tended to ask as many questions about me as I did about him.

    My anxiety about dressing up didn't stem from a fear that I would get beat up on the late Saturday night streets of New York for impersonating a woman, but that I would make a better woman than Frank, who has been working so hard at it. "I've tried to keep one eye on my limitations as observer and analyst," Finnegan writes, "and to reflect, where possible, the densely freighted power relations between me and some of my subjects." Being a prettier woman than my transgendered subject seemed to fall far beyond the limitations Finnegan describes.

    But there is a curious emotional process that happens when a reporter goes undercover. When you're undercover (or under cover -- of Max Factor), it is easier to pretend that the discomfort you feel is not actually happening to you, but to the person you're presenting to the world. My name, Fran said, was Natasha.


    "Get him in the dress, and then worry about the hair," Brianna told Fran at my apartment, the agreed-upon dressing area. Fussed and fretted over, I felt like the baby Jesus at a Christmas tent revival in West Texas, where I'm from, where they'd shoot me like this. In college, Brianna Austin used to be a football player. Now he's a film documentarian and columnist for Girl Talk, a magazine for transgender readers, although she used to be married and has a 20-year-old son. Brianna is a gay man who has been pondering becoming a woman but recently decided to stop taking hormones when he grew to dislike his breasts. Fran is a straight man who would like to become a woman. Brianna's friend Chris was also there -- he's a gay man who dresses up once a week as Chrissy, but only once a week because he "can't handle Chrissy full-time. She's too high maintenance." Chris is a demure, thoughtful man, but Chrissy is a bouncy, flirtatious Amazonian beauty. Maria seemed a little out of place; as the transgender parlance goes, she's a "GG," a real, live genetic girl. Fran had initially asked Maria for her opinion of the particularities of my transformation -- light makeup or dark, for example -- but she didn't really have an opinion. When you're already a woman, you don't sit around thinking about how to pass as one.

    Everyone was standing around watching as I sat at the small table in my apartment having my makeup applied by Fran, who began with a light foundation. "You know Claire, the Wig Goddess?" Fran asked Brianna, who of course knew Claire the Wig Goddess. Brianna knows everyone. Fran said that Claire says it's helpful to mix the foundation with moisturizer and then apply that mixture to the face rather than just the foundation alone.
    "I've never heard of that," Chrissy said.
    "I've never heard of that either," Maria added.
    "I've actually put moisturizer on top of the foundation," Brianna said. Now we all knew who was boss.

    Brianna worked on my lips, and told me to smile real big to make it easier for her to apply the lip liner and the lipstick, a subdued red. It is hard to speak with your lips pinned to your ears, so I was relieved that Maria asked Brianna to tell her the questions that strangers ask her most routinely. Although Brianna doesn't dress as a woman very often, she is quite fearless about doing so. "I guess the common thing that people assume is that everybody that dresses up is gay," she said. "They don't differentiate between the many different factions -- there's drag queens ... cross dressers are something completely different. There's a lot of distinctions between them." And Brianna told a story about going to his favorite gay hangout, a piano bar in Midtown. The regulars there know Brianna both as a gay man in men's clothing and as a gay man who sometimes dresses as a woman. He had first gone as a woman, and then as a man. "They couldn't accept me just as a gay man," Brianna said. "Oh, you're one of them," she recalls them saying. She said, "No, I'm one of you!" One night when she was dressed as a woman, a man came up to her at the bar. "You come here a lot, right?" he said. "I come here all the time," Brianna told him and he could tell that the man was quite nervous about asking the personal questions he so clearly wanted the answers to. Finally, Brianna just said, "Honey, I've had strangers ask me, 'Do you make love like a girl?'
    "That would be hard," Brianna told us.

    Fran worked on my eyes. "I'm just going to stretch your eyelid," she warned, "just to stretch the skin." A good way to buck up when a transsexual is stretching your eyelid is to remind yourself that the pain you're experiencing is sweet compared to the surgical pain of anatomically becoming the opposite sex. "Just keep your eyelid closed," Fran whispered conspiratorially to me so the others couldn't hear. I don't pretend to understand all of Frank's motives for becoming a woman, but Fran was looking out for me. "I'm so afraid of going too hard," she said. "You tell me if I'm going too hard."

    Fran and Brianna sat back and eyed their handiwork. "He should do something light, really light," Brianna said about the tone of the foundation.
    "Something dark," Fran said.
    "Why would you want to do dark with him?"
    "No, just on this part, the lower part. And then up here do white," Fran said, pondering how to slim my jawline, too pronounced to be a woman's.
    "His eyebrows are so thick, you really can't do much with this," Brianna announced. "The Brooke Shields look," Fran decided, working to cast a positive light on my hirsute protusions, which I had previously thought were unremarkable in the extreme. I had established at the outset that there would be no shaving or plucking whatsoever of any part of my person. Still, there were copious offers to pluck my eyebrows.
    "It's not even Brooke Shields because hers were tapered," Brianna pointed out. "We're calling her 'Zorba Girl.'"
    "Have you ever seen Zorba the Greek?" Maria said, to no one in particular.

    Brianna said I could be made into a really pretty girl if they had brought all their equipment with them. "The next time," said Fran, indulging in the assumption that there would be one.
    "He doesn't need much," Brianna said. "Put a lot of mascara on him, make his lips really nice, and a hint of rouge, and he's good to go. Unless we were going to do an outrageous drag queen, but we don't have the supplies for it. The truth is that gay guys, they love to play with this, but they don't want to take us home. They just like to toy with us."


    I could have sworn they were the ones toying with me: The opaque black stockings may have masked my leg hair, but they kept creeping down my legs. By the end of the night, I was tired of yanking them up, and in high heels, my legs wobbled and buckled, as if someone was using them as chopsticks. Not that it mattered, anyway; I failed the lessons on how to walk like a woman, so, in an attempt to obscure my inadequacy, I tried to swing my purse with a wacky, studied nonchalance, like Marlo Thomas in That Girl. The cincher perking up my Kleenex breasts carved indentations into my sides. People think it's cool to do some gender-bending every now and then, but I'd rather be a dweeb. Nothing that requires this much work and pain should be considered hip. Fran had also brought a black skirt and sleeveless top, which was covered by a short sweater. A sassy faux-leather raincoat covered it all. If the dressing committee hadn't decided I looked better as a redhead, I could have pretended I was Glenn Close in her sassier moments in Fatal Attraction.

    I like to think about what Alex Forrest, the character Close played, would have done with a man I met at the Silver Swan, a German-American restaurant and bar in Midtown that caters to the transgendered and their supposedly straight admirers. They gather there because Ina Somera asked them to. This lithe, graceful 53-year-old immigrant from the Phillipines who looks many years younger could easily be tagged as a woman, but he doesn't take hormones and has never wanted to undergo gender reassignment surgery. Sometimes Ina wears a dress to his Saturday night parties, sometimes not, but he never wears one to his job as a window dresser at the Gap, although his co-workers know fully about his life and occasionally come to his Saturday night parties. "It's like, whether I have lipstick or no lipstick, it's me," he says.

    After the Gay Pride Parade in 2001, Ina was in the neighborhood of the Silver Swan and stopped by to get a drink and visit with its owner, Renata, a straight woman who is accepting of transgendered people and invites them to eat at her restaurant en femme. Renata told Ina that he should start hosting a weekly party and invite his friends. There are other bars in New York where transgendered people go but Ina says his party is "a little bit purer." He has asked patrons to leave the premises. "It's more like a social club for people who want to dress up to express their feelings instead of being isolated in the four walls of their room," he says. "At least they are now out and they can be accepted. I think that's why most of my girls are so thankful to me, they have a place where they can express their feelings after five days of work. Some of these girls are married, you know.

    "They go to their twin sister," he says. "I call it their twin sister after their transformation," by which he means dressing in women's clothing. Ina estimates that 95% of his girls are cross dressers, or CD, as he says, and then there are "one or two" who have had gender reassignment surgery. But not many gay men show up, although Ina stresses that they are welcome. I asked Ina whether he identified himself as a gay man. "No, I don't think so," he said sternly. "The gays hate me because I look so feminine. And I am not a pre-op, so I don't know where I belong. I'm just pure Ina." The happy-family GLBT moniker doesn't really fit Ina snugly. "It's supposed to be like one happy family," Ina says, "but it's like going to a supermarket. If you want meat, just go the meat section; if you want vegetable, you just go to that one aisle, but everything is in one house."

    At Ina's party that night, the tables had been pushed back, and Fran and Brianna had formed an impromptu dance circle. I didn't join in because I wanted to adhere to my role as "observer and analyst," but that was more difficult than I had anticipated. I had hoped to watch Fran interact with transsexuals who had already completed their surgical procedures, but a pesky older man kept making abstracted circles around me, like a shark pondering his strategy before lunging. When he did, the attack was swift and precise. After the briefest of introductions, he asked me if I wanted to go to his car for 15 minutes. I tried to be diplomatic. "Thanks, but I don't think so," I said. And then he began again. I was a full head taller than him and when I looked down at him again after trying to avoid eye contact, I said, "I really should just stay here with my friends." Then I explained to him that I was a guy underneath the clothing.

    Now, that may seem like a strange thing to say. Clearly, I was doing such a fine job of being a woman that I needed to remind him I was a man. Clearly. I blurted out my anatomical status because of my awkward incomprehension of his desire, but when he looked at me with extreme exasperation and said "I know that!," my inept comment actually clarified the befuddling spectacle of a man attracted to the outer trappings of femininity but cognizant that there is nothing feminine underneath the clothing. The fantasy is what matters, and I deflated his by being so blunt. "Some of them admire the transformation," Ina says, "just the hardship of the transformation -- the time and effort the girls put into it. Nowadays not all girls dress nicely. The ladies in my bar are more feminine than women on the street."

    Tri-Ess, the largest support and advocacy group for heterosexual crossdressers, touts the idea that crossdressing is a gift, not a punishment ("Crossdressers are blessed with an additional facet to our personalities," one of their pamphlets states). If, as Ina believes, the men at her party are allured by the hardship of the transformation, a case could be made that they also have an admirably esoteric and civilized proclivity -- a gift. But my suitor, if he had a gift, had not yet learned how to handle it. I may have shot down his fantasy, but he was like a maimed animal not wanting to die. It was better to put him down than let him suffer. Out of kindness, you understand. His inability to take "no" for an answer -- as if those two little letters put together was the one word he had failed to learn as a child -- would have been comical if I didn't feel so repulsed by him. I was beginning to understand what women talk about when they say that men don't understand the word "no." After approximately five more minutes of this, during which Fran would look over occasionally, I said, "I'm a journalist," almost whispering, "and I'm writing about some people at this bar, so would you please just leave me alone?"

    In journalism school, we've talked extensively about the techniques notable undercover journalists have used: the skin-darkening pills John Howard Griffin took so that he could write Black Like Me; the melodramatic protestations of insanity Nellie Bly put over on the residents of a Manhattan boarding house so they'd lock her up in the loony bin, which led to Ten Days in a Madhouse. What we haven't talked about is the distinctly modern presumption undergirding all undercover work: that it is possible to become someone you are not, not just in a play, but on the stage of life.

    For Fran, the issue is more complex: he's trying to become someone he says he always has been, but who no one can see since they see Frank instead. As this article went to press, however, Frank decided that becoming a woman wasn't really worth the pain it would cause him and his family. Frank and his wife made a compromise of sorts. Frank decided not to become a woman, but he still plans on dressing as Fran a considerable amount of time -- to work, to parties, maybe even to church. A few weeks after I met Fran, I asked him if it bothered him when strangers noticed that he was a man dressed like a woman. "Yeah, I guess it bothers me," he said. "But things like that, like voice and appearance, can be worked on. I'm not going to be a pretty girl -- some little vivacious glamour girl -- but I think I could get decent and my voice, for example, I went to that workshop, so I know that things are possible, that there are people out there that can help you." Fran's wife told him she is going to learn how to handle it.

    I don't know what it's like to feel like you're a woman trapped inside a man's body. But when I went home after the Silver Swan and took off the clothes Fran had loaned me and the makeup she had applied, I did know what a relief it was to be myself again, something Fran, who left Frank in New Rochelle, had been feeling all night.