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Yet we continue to wonder how much of gender performance is cultural and how much is biological. That’s the heart of the riddle, the part that really baffles us. And it’s that part of the riddle that gender-variant people may ultimately help resolve. My conversations with transgendered, transsexual, and intersexual people over the past few years have helped me understand a number of facts that I had not recognized previously. First, despite the social changes initiated by the second wave of feminism, we as a society still maintain some fairly inflexible strategies for policing the boundaries between the sexes. Each time you relieve yourself in a public place, for example, you implicitly accept the idea that Door Number 1 (women) and Door Number 2 (men) are the only options, and that each person will know precisely to which category he or she belongs, and use the “appropriate” toilet. To most of us, the choice may not seem quite as oppressive as that between the “White” and “Colored” bathrooms that were contested by the civil rights movement, but the significance is the same. A ritual boundary is being enforced, as the opponents of the Equal Rights Amendment recognized when they claimed that the ERA would result in a promiscuous mingling of the sexes in bathrooms.

Similarly, many people pay lip service to the idea that males and females have both a “feminine” and a “masculine” side, and as I finish the final draft of this book, a great deal of attention is being devoted to the rise of the “metrosexual,” an urban feminized man. Yet a male-bodied person who expresses his femininity by wearing dresses quickly discovers the limits of social tolerance. Women have more freedom to dress as they please, as I discovered on a rainy night in Washington, D.C., when I attended a support group meeting for cross-dressers. As I sat in the meeting in my sweatshirt and jeans—the only female-bodied person in the room and the only person wearing pants—I realized that little more than a century ago, I would have been just as freakishly attired as the male-bodied people around me in their dresses, high heels, and makeup. According to the social standards of 1902, I, too, was “cross-dressed.” Even in 1932 my garb would have been considered suspicious. But because our culture now permits women to wear clothing once thought of as “masculine,” my outfit was unremarkable. Not so for the outfits on the people around me. They are defined (and define themselves) as “transgendered” partially because they yearn to express aspects of femininity denied to male-bodied persons by cultural norms. While most male-bodied persons don’t seem to feel a desire to wear dresses and use cosmetics, the ones who do so encounter extraordinary social ostracism and violence. The great majority of transgendered people who are the victims of hate crimes are male-bodied persons dressing and living as females.

That doesn’t mean that women are free of gender-based limitations and bias. Western women may wear pants, and some may have claimed the right to work, play, and have sex like men, but as any woman of a certain age will be happy to tell you, female cultural power is still largely a function of youth and beauty. Women of all ages spend an inordinate amount of their time and resources maintaining an attractive appearance. Young women are indoctrinated into this feminine cult at a young age, with girls typically beginning to shave, pluck, paint, and perfume at around eleven or twelve years old. Throughout adolescence, girls learn that their perceived value as people is tied to their appearance; they must be fit, fresh-smelling, and fashionably attired in order to lead happy, successful lives. The pressure to maintain a pleasing appearance increases as we age. Few straight men spend as much time on the scale, in the salon, or at the gym as their female counterparts. Why spend so much time, energy, and money to look young, fit, and fertile if being a middle-aged woman is not somehow related to a loss of prestige and power? Middle-aged men seem immune to this pressure. One of my sources—a surgeon transitioning from male to female at age fifty—told me that her spouse simply cannot understand why a successful middle-aged man would surrender his cultural power to assume the lower-caste status of a middle-aged woman. “Who will want you?” she asked, a poignant expression of the creeping sense of invisibility and insignificance many aging women feel.

Male privilege remains a very real phenomenon in our supposedly postfeminist society. Many of the transmen (female-to-male, or FTM, transsexual people) I interviewed noted that, as men, they are treated far more respectfully and deferentially than they were as women. “I get a lot of white male privilege. Oh, my god! I can’t even believe that. When I would go into stores before, they had security guards following me around, because I was this sort of big motorcycle leather dyke. Now, they’re like, ‘Can I help you, sir? Is there anything we can do for you?’” says Tom Kennard, a burly, middle-aged transman. “They will give men power, and you just have to take it. I have to figure out how I can use that power responsibly.”

Those who travel in the other direction, from male to female, are conversely aware of the loss of privilege that is an unavoidable consequence of their decision to transition. In giving up their maleness, transwomen often give up high incomes, social status, and, very often, the ability to support themselves in their chosen profession. Trans-women tend to be more visible, and thus less employable, than trans-men. They are more often the victims of violence and discrimination, simply because they are seen or “read” in a way that transmen are not. But they also have surrendered the social protections of maleness. Though men can be sexually violated, they are not usually victims of rape except in all-male environments such as prisons. Transwomen seem to be at high risk for rape, however, both before and after their surgical transition. This may be because, as one source told me, transwomen aren’t raised with the “don’ts” that most natal women absorb from their mothers and other women. These spoken and unspoken prohibitions (don’t go home with strange men, don’t walk down dark streets by yourself, don’t open the door to strangers) circumscribe our lives, but they may also provide some measure of protection. Transwomen learn late the painful lesson most natal women absorb in adolescence: that being a woman automatically confers vulnerability to sexual assault. This is true even if one retains the (hidden) insignia of masculinity, a penis. As a woman, I know intimately the sense of physical vulnerability that transwomen encounter when they assume the social role of women. That sense of shared vulnerability is one of the strongest bonds I have felt with the transwomen I interviewed for this book.

Fear and mistrust of men and masculinity still permeate discussions of gender. Neither women nor individual men appear to trust or think kindly of males as a group, a prejudice that seems justified when one considers the disproportionate propensity of males for committing acts of physical violence and aggression. As I have researched this book, I have learned from transmen just how painful and shocking it is suddenly to be perceived as a threatening figure, purely by virtue of one’s maleness. Women may cross to the other side of the street to avoid sharing the sidewalk with you; they stop looking you in the eye. A wall goes up, and those transmen who have lived as lesbians for years before their transitions find that wall particularly disturbing. “It’s really upsetting to me that men are perceived as bad,” says Tom Kennard. “And I wonder how boys, men who grow up as men, deal with that. How do they internalize that? What does it do to them? Because when I talk to them, they know about this. But they’re just like, ‘Well, what can you do?’”