Demystifying Femininity and Unlearning Masculinity
The idea that crossdressing can be a continual process of demystification very much resonates with my personal experiences. I consciously recognized my own desire to be female when I was eleven. As much as I wanted to be female, I was taught to believe that this was not a realistic possibility for me. For this reason, I began to channel my female inclinations into fantasies or role-playing, in which I’d imagine I’d turned into a girl somehow. The fact that these fantasies always began with me being a boy (rather than simply imagining myself as a girl from the start) is indicative of how illegitimate I felt my own desires to be female were. I was convinced that I could never attain actual femaleness; in my mind, the best that I could hope for was merely pretending to be female or being “turned into” a girl.
After a year or two of imagining myself becoming a girl (typically a rather tomboyish one who went off on adventures and such), I started experimenting with conventional femininity. This was due both to me wanting to explore my own feminine inclinations and to the fact that (like most people) I was taught to believe that femininity was an intrinsic part of being female. My growing fascination with femininity was also very much intertwined with my growing attraction to women. As a teenager who was dealing with sexual attraction for the first time, I found it hard not to conflate my desire to be female with my sexual attraction for women. And in this respect, feminine accoutrements—whether clothing, cosmetics, or other accessories—became highly symbolic of both.
In chapter 14, “Trans-Sexualization,” I explained that trans people who have not transitioned, and who therefore are unable to take their own physical sex for granted, often experience sexual arousal in association with their own cross-gendered thoughts and expressions. While this is true for virtually all trans people, there are a couple of factors specific to crossdressers that intensify this phenomenon. First, testosterone, which significantly boosts one’s sex drive across the board, undoubtedly plays some role in amplifying cross-gendered sexual arousal for those who are hormonally male. Second, we live in a culture in which women are frequently viewed as sexual objects, and much of women’s clothing emphasizes and exaggerates women’s sexuality. For crossdressers, there is no way of getting around the cultural eroticism that surrounds “women’s” clothing. Many crossdressers, particularly early in their crossdressing, become particularly interested in the most highly sexual articles of feminine clothing precisely because of the symbolism associated with them. Unfortunately, I have heard women criticize, even ridicule, this tendency among crossdressers, sometimes even suggesting that a crossdresser who covers their own body in hyperfeminine or hypersexual articles of clothing somehow sexualizes womanhood as a whole. Such criticism seems to purposefully ignore the fact that many teenage girls similarly tend to dress in sexually provocative or revealing ways when they hit puberty and begin to explore the cultural meanings associated with adult female sexuality. Both teenage girls and crossdressers are exposed to many of the same cultural messages about femininity and female sexuality (albeit from rather different vantage points) and thus both are drawn to experiment with hyperfeminine and hypersexual clothing as a way of literally “trying on” the symbolic meanings associated with adult female sexuality. And most crossdressers, like most cissexual women, eventually move beyond their “teenage girl phase” (as some crossdressers refer to it) and come to recognize sexually provocative clothing as but one of the many options available to them, but not necessarily one that they wish to indulge in every day.
I know that it’s common for outsiders to focus on the more sexual aspects of MTF crossdressing (just as they focus on the more sexual aspects of femaleness in general). However, I personally found that, if anything, the social, emotional, and psychological effects of being crossdressed were far more profound than the sexual ones. The truth is that gendered clothing is extraordinarily symbolic of the sex of the body that presumably lies underneath; this is why wearing the clothing associated with the other sex is an almost invariant feature of cross-gender expression and identity across cultures and throughout history. Prior to my transition, dressing up in “women’s” clothing was the closest I ever got to actually being a woman, to having my body be aligned with how I imagined it. For me, the fact that “women’s” clothing was symbolic of being female far outweighed any sexuality-related symbolism it may have had.
As with many MTF spectrum folks, my crossdressing passed through a series of stages. Each was a demystification process that I began by experimenting with some aspect of femaleness/femininity that seemed unknowable and fascinating to me. Over time, my exploration and experimentation of that aspect of femaleness/femininity led to it becoming demystified; what had previously seemed out of my reach eventually became something that I was capable of, that was within my realm of possibility. The main motivating force behind my exploration of crossdressing was to make sense of my ever-present desire to be female. While this may distinguish me from other crossdressers (e.g., those who are motivated by feminine rather than female inclinations), I believe that the stages I passed through (which are described below) are shared by many crossdressers.
The first stage of crossdressing I passed through was the “clothing phase.” It began with trying on individual articles of clothing one at a time (this was after a several-year period where I made due with blankets, curtains, shoelaces, and such while “pretending” to be a girl). Sometimes I would put on a pair of heels, stockings, or a dress, or dabble with cosmetics or shave my legs. Each was its own mini-transformation, where a part of my body would begin to resemble that of a woman in certain ways. After a while, I began to put it all together, to dress completely as a woman from head to toe. I looked rather ridiculous when I first began to do this, but over the course of many years, I slowly figured out what worked for me and what did not. Eventually, I reached the point where I could fairly consistently appear female to myself when I looked in mirror. This “mirror moment” was always the highlight of any crossdressing session for me, as I found it strangely comforting to be able to see my female reflection staring back at me.
As the name suggests, my clothing phase was primarily about becoming familiar with, and eventually demystifying, “women’s” clothing. I eventually even stopped thinking about them as “women’s” clothes; after all, they were all my clothes, as I was the one who purchased and wore them. Similarly, I also stopped thinking of myself as being “crossdressed,” and instead began referring to myself as simply being “dressed.” Toward the end of this stage, I was no longer very excited by the idea of wearing “women’s” clothes just for the sake of it. However, while they had lost their mystified properties, I still understood them as having the transformative property of facilitating my appearance as female. It is this latter role that “women’s” clothing played in the next stage of my crossdressing, when I began to venture out in public.
The “public phase” began with my earliest attempts to go out into the world as a woman. My very first experience involved walking around a shopping mall for about fifteen minutes, followed by purchasing a milkshake at a fast-food drive-through window. The fact that nobody seemed to give me a second glance, and that the cashier said, “Thank you, ma’am,” as she handed me my change, completely blew me away. Like the mirror moments, these experiences of having my femaleness acknowledged in some small way were profound and moving. Over time, I continued to go out dressed in public more and more, typically doing rather mundane things such as going to museums or shopping. I always made sure that there were lots of people around and that I could easily “get away” in the event that something bad happened. Admittedly, the early sense of excitement associated with being dressed as female in public was enhanced by the inherent sense of danger that unfortunately plagues any public crossdressing experience. The fear, of course, was not merely that I would be noticed or “read” as a crossdresser (which happened on countless occasions during the many years that I publicly crossdressed), but that I might be targeted for violence if I was ever “found out” by the wrong person.
It was during my public phase that I first began going to crossdresser support and social group meetings (this was in Kansas in 1994, before the word “transgender” came into vogue). They were my first opportunity to speak openly about my crossdressing and to meet others who shared that experience. It also provided me with the chance to learn some of the techniques that other crossdressers used to make their female appearance more convincing. I was fortunate enough to have an amazing crossdresser named Deborah take me under her wing. Among other things, she showed me how to use cosmetics to effectively cover my beard shadow, an invaluable skill for any crossdresser who wishes to be gendered by others as female. It’s common for people to dismiss crossdressers for what is perceived to be their exaggerated use of makeup. However, the truth of the matter is that crossdressers (unlike cissexual women) typically have beard shadows, which are perhaps the dominant visual cue we rely on when gendering people as male. While I would have preferred to have the privilege of forgoing makeup if I wished, my beard shadow made it virtually impossible for me to be regularly gendered as female without it.
Complaints about how crossdressers overuse cosmetics are often related to more general critiques that claim that crossdressers exaggerate stereotypically feminine dress and behaviors, thus turning themselves into caricatures of women. Often, these sentiments are rooted in the oppositional sexist assumption that cissexual women are entitled to express and explore femininity while those assigned male are not. Even those critiques that are not downright oppositional sexist are still cissexual-woman-centric, in that they view MTF crossdressing solely in terms of how it portrays cissexual women, rather than viewing it from an MTF spectrum perspective. Back when I crossdressed, I very much enjoyed dressing and acting in a highly feminine manner, but not because I thought that women really were or should be that way. If I indulged in an exaggerated form of femininity, it was only because I never really had the chance to explore that side of myself growing up as a boy. I spent virtually every day of my life wearing T-shirts, jeans, sneakers, and no makeup. So for me, crossdressing represented a rare opportunity to fully indulge my femininity.
The other factor at the time that motivated me to try to achieve stereotypical femininity was that I wanted others to gender me as female. Back when I was crossdressing—when I was still physically male—that never would have been possible had I gone out sans makeup or wearing unisex clothing. To a large extent, I purposely chose the clothing and cosmetics I wore when I crossdressed based on their ability to hide or play down my male physique and facial features. In fact, the public stage of my crossdressing was really the one time in my life when I did go out of my way to emulate how some women looked, walked, talked, moved, and so on. I found that this increased the likelihood that I would be gendered female, which was my overall goal, and which also ensured my safety.
One question that many queer-identified friends asked me back when I was crossdressing was why it was so important for me to “pass” as a woman. Their concern seemed to stem from the common use of the term “pass” in lesbian and gay communities as a synonym for “hide” (i.e., a gay male who “passes” for straight is typically assumed to be hiding or playing down his queerness). This use of the word “pass” is completely different from its use in the transgender community, where it typically refers to whether one is appropriately gendered as the sex one identifies or presents oneself as. From my perspective as a crossdresser, what gay people call “passing” (i.e., hiding) was what I did every day when I lived as male. In contrast, when I dressed and “passed” (in the transgender sense) as a woman, it was a rare moment of being “out” for me, of having others see and acknowledge a part of me that I normally kept hidden.
Eventually, having other people gender me as female became demystified. While I still enjoyed it (as I did with the mirror moments), it was no longer enough in and of itself to ease the gender dissonance that I felt. It was at this point that I moved into the “interactive stage,” when I began to go out with other people while I was crossdressed. While I had come out to a number of friends as a crossdresser during my public stage, I now began cultivating relationships with people who primarily or solely knew me when I was in girl-mode. More often than not, these were people who I met via personal ads and who were aware that I was a crossdresser from the start. Over an extremely intense two-year period of my life, I sort of lived a dual life, where I was in boy-mode most of the time, but about one or two times per week I would go out and interact with others (often on dates) as a woman.
Some of the people I saw during this period were men who might be described as admirers of MTF spectrum people. With them, I primarily engaged in role-playing relationships in which we would create sexually charged scenarios based on exaggerations of gender stereotypes. While many people assume that male “tranny-chasers” are closeted homosexuals who are turned on by the “guy” (or the “penis”) under the dress, all of the men who I role-played with were primarily attracted to women and, in particular, to femininity. In conversations I had with them, each said that what attracted them to MTF spectrum people was the extreme femininity that many of us (including myself at the time) sometimes displayed. For me, these role-playing experiences were important in helping me demystify the connection between femininity and sexuality. As with previous phases of my crossdressing, acting out my submissive feminine fantasies felt exciting and empowering early on. But over time, once they had become demystified, I found that they began to lose both their erotic and experiential potential.
What played an even greater role in demystifying femaleness and femininity for me were the relationships I cultivated with women around this same time. Most of these women were bisexual or bi-curious, and our relationships involved me being in girl-mode some or most of the times we got together. While I was quite feminine when I was with them and crossdressed, I did not engage in the exaggerated femininity that I had during my role-playing experiences with men. In retrospect, what was most important for me about these experiences with women was that they allowed me to begin to integrate my personality (i.e., the person I was when in boy-mode) with my femme self. In a sense, this represented a merging of boy-mode and girl-mode for me, a sort of mending of the fracture in my psyche that had developed in response to the effemimania and enforced ignorance I’d experienced as a child.
After about two years of being in the interactive phase, of being in relationships with other people while I was in girl-mode, something unexpected happened: I lost interest in crossdressing. This was extraordinarily disconcerting to me at first, as being a crossdresser was such a huge part of my identity at the time. I remember lying in bed one morning and thinking, I wonder where I should take my crossdressing next? as if I simply needed to find some new aspect of femaleness or femininity to experiment with, some new crossdressing stage to pioneer, in order to regain interest in it. However, by this point, I had explored femininity and female gender roles as much as possible within the context of being a crossdresser. Fortunately for me, this was when Dani (who was my girlfriend at the time) introduced me to Kate Bornstein’s and Leslie Feinberg’s writings. Their books allowed me to start viewing myself as bigendered rather than as a crossdresser. I began to see my expressions of femaleness and femininity not merely as something that existed outside of myself that I could emulate or imagine but never truly experience, but rather as an intrinsic and legitimate part of my person, as something that came from within me.
Thinking of myself as bigendered also helped me make sense of another new development in my life: that people were beginning to pick up on my femininity even when I was in boy-mode. Strangers began to assume that I was gay, and on rare occasions even gendered me as female. These changes, which occurred despite the fact that I was dressing the same and had not consciously altered my behavior, took me by surprise. I eventually realized that over those many years of crossdressing I must have unlearned many of the rote masculine mannerisms that I’d acquired during my adolescence and early adulthood—behaviors that had served as a selfdefense mechanism that allowed me to escape effemimanic derision. In other words, during the years that I crossdressed, it wasn’t so much that I learned how to be female (as I was no longer employing any of the contrived and stereotyped feminine mannerisms I practiced back when I was crossdressing), but that I had in effect unlearned maleness.
If it were not for my years as a crossdresser, I doubt that I would have been able to demystify femaleness and unlearn maleness to the point that I could live for several years as a feminine bigendered boy—an identity that preceded my decision to transition. While I certainly do not believe that crossdressing is merely a phase that eventually leads to becoming a transsexual woman, I do believe that many crossdressers experience similar phases of demystifying femaleness/femininity and unlearning maleness/masculinity over the course of their lives. While crossdressing may seem highly contrived to many outsiders, from an MTF perspective, it is an invaluable way to reconcile our female/feminine inclinations with our male/masculine bodies and socialization. It provides a way to allow parts of ourselves that we have been made to feel shame about, that we have learned to hide or repress, to show through and become integrated with the rest of our personalities.