A Pocket Full of Change: Trannies, Transformation, and the Gender Gap

Essay by Brien Michael

I.

Shakespeare fancied cross dressers. So did Virginia Woolf. As did Oscar Wilde. So when Norah Vincent, author of Self-Made Man: One Woman’s Year Disguised As A Man, takes on her project, she enters an esteemed literary club whose members have dallied with the imperatives and artifices of sex and gender. The one difference is that Vincent not only writes about this passage, she’s also its subject. Her mission is simply to live the life of a man.

On and off for a year-and-a-half, Vincent dons the physical trappings of maleness, adopts the characteristics of typical masculine behavior, and insinuates herself into situations that test the limits of both of these. She wants to collect data that might both challenge and/or confirm her own convictions about maleness—its prerogatives, its frustrations, its essential nature, and its environmental constructs—but she also just wants to be one of the guys. The result is an experiment that pushes her identity’s very boundaries, threatening to dissolve her sanity in the pursuit.

Vincent’s introduction, “Getting Started,” lays out the book’s objective: she wants to understand her experience of invisibility as a “man” (versus her conspicuousness as a woman) and probe “the deeper sociological implications of passing as the opposite sex.” What evolves is a bookish, sensitive, bespectacled guy, breasts pressed flat by a spandex sports bra, face stubbled by an intricate process, shoulders squared by weight lifting, and pants packed with a silicone cock. Hello, Ned, a nickname that Vincent earned during a childhood as a self-proclaimed tomboy who, even from birth, made “you think there was a gay gene.” Ned was the incarnation of all the gender ambiguity that Norah had suffered through and survived.

In Vincent’s upbringing lies one of the book’s significant questions and dilemmas: Is gender as pre-determined as biological sex? Vincent seems to believe that it is, that her “instinctive loathing for dresses, dolls and frills,” her “weird attachments and fetishes that came so young and against all social programming”—for all things typically male—suggest that “gender identity . . . is in the genes as surely as sex and sexuality are.” Vincent’s reliance on a genetic trinity—sex, orientation, gender—so early in her project is problematic. First, it asserts that girls who like anything but dolls and makeup are suspect, somehow not quite girls (or not girly enough), the result of a “crossed wire somewhere, or the hormonal equivalent.” And in turn, it posits the same conclusion for the opposite sex. Boys who don’t like or do boy things will grow up to be less-than-men, disenfranchised sissies.

This would seem to contradict another of Vincent’s claims and a premise of her project: that men are empowered in certain ways simply because they are men, because they have balls and a beard, simply because they’re not women, no matter whether they’re flaming gay or attend NASCAR rallies. Vincent’s insistence that she “was the happily twisted result of some gland or helix gone awry” is a gay-positive, gender-neutral salute. But it does little to sort out the messiness that gender and sex and sexual attraction make in the real world.

Yet it is exactly gender’s messiness that makes Vincent’s book so wonderful. It is her observations, full of “prejudices and preconceptions,” that contribute the most to her story, that construct Ned’s story, that make his-story, a compendium of personal transformation and gender reassignment.

Vincent’s take on sexuality is both dependent on and independent of gender. Though a lesbian, she posits that there’s still a sexual dimension to her relationships with men; men behave certain way with men, women with women, and men with women. Desire triangulates behaviors and relationships—where some men want to fuck, other men rather kill—but desire can just as likely result in men, gay and straight, collectively resorting to misogyny in order to dominate women.

Vincent’s sexual politics are an intriguing hybrid of Michel Foucault, Camille Paglia, and Andrew Dice Clay—equal parts power dynamics, queer theory, postmodern feminism, and raunchy, lip-smacking innuendo. And because Vincent’s not afraid to say fuck, cock, and pussy, the reader is treated to a perspective that’s as unabashed as it is astute. It’s intellectually rigorous without being stuffy, and should anyone dare to suggest that the exercise is just an exaggerated pissing contest (even if only with her alter ego) just you try making a plastic penis pee. (This was the one thing, prurient though it may be, that I wished she had disclosed; what did she do if there were only a urinal available?)

Vincent’s prose is spry and wry, at times campy and at others painfully serious. It is always sensitive, attentive to Ned’s external surroundings and his internal terrain, and therefore provocative and insightful. And because Vincent reveals the impacts of Ned in her personal life—the revelations, the disappointments, as well as the strain of a year-and-a-half intermission—we mourn Ned’s passing as much as we applaud and occasionally denounce Vincent.

*

In the first chapter, “Friendship,” Ned joins a bowling team in an all-men’s league. Understandably fearful of exposure, but perhaps more nervous of ridicule for the inevitable, numerous gutter balls, Ned ventures into a men’s club redolent of “cigarette smoke, varnish, machine oil, leaky toilets, old candy wrappers and accumulated public muck” where the unspoken signs all say “NO GIRLS ALLOWED.” It’s here that we get the first look at Ned beyond the mirror of the make-up table. She describes seeing her fellow bowlers and her self-consciousness:

I was dressed as down and dirty as Ned got in a plaid shirt, jeans and a baseball cap pulled low over the most proletarian glasses I could find. But despite my best efforts, I was still far too scrubbed and tweedy amid these genuine articles to pass for one of them. Even at my burliest, next to them I felt like a petunia strapped to a Popsicle stick.

I was surrounded by men who had cement dust in their hair and sawdust under their fingernails. They had nicotine-sallowed faces that looked like ritual masks, and their hands were as tough and scarred as falcon gloves. These were men who, as one of them told me later, had been shoveling shit their whole lives.

What Ned comes to understand through his time in the league is the underlying affinity that men can demonstrate with each other simply by virtue of being men. Even a simple introduction, a handshake, was a bonding experience, so different than “women who’ve known each other for a long time . . . [who when hugging are] like two backward magnets being pushed together by convention. . . . On some level men didn’t need to learn or remind themselves that brotherhood was powerful. It was just something they seemed to know.”

But the brotherhood is not always easy to navigate. In the chapter “Life,” Ned shacks up at a monastery, not just observing “men living together in close quarters without women” but cloistering himself with them, participating in their prayers, their religious rituals, and in the daily tasks that occupied their time away from—and with—each other. Once a week the monks participated in social night, a kind of verbal circle jerk to foster “greater closeness and openness.” What resulted was painful, filled with “long silences, and then little pathetic attempts to fill the silences with talk that sputtered and rarely flew.”

Vincent suggests that the men were without the skills or the experience to do anything else, that, in fact, most men are socialized to be strong but silent, that words, which so often reveal feelings, are the purview of women. “Women are still often the communicators, the interlocutors between men and themselves, men and their children and even men and each other. Observing the monks, [I] couldn’t help thinking that without the connective tissue, without the feminizing influence, these guys were like bumper cars trying to merge.”

Vincent’s picture of maleness at the monastery is stark and rightly so. The brothers seem unable to live together without abusing one another, even if only by subtly impugning each other’s ability to belong and get along, ironically fostering further dissension.

It’s in these situations that Ned seems most suspect. Not that his disguise became transparent, but that Ned did and said things that indicated his fluency with the language of emotions, like calling an old, sweet, senile monk cute. Make no mistake, the monks never thought Ned was a woman, though they did think he was feminized, most probably gay. More importantly, though, they thought he was soft, ignorant of “masculine boundaries”; he was a “threat to their fragile ecosystem of terse masculine rapport.” Ned’s punishment was to be severed from anything resembling an unhealthy attachment—relationships with brothers that might provide support and guidance, that might increase Ned’s chances for successful integration into the community, were promptly dismantled, even if there were no sexual connotations.

But of course, there were plenty of those. Though Vincent doesn’t reject the possibility that she developed crushes on some of the men, she doesn’t believe her feelings were primarily sexual or romantic, “though the twisted mentality of that place, always on the lookout for forbidden desires, had made me wonder.” Vincent’s experience allows her to see first hand the “damage done to [men] in those rites of passage we all condone and inflict to make them into men.” However “successful” the brothers had been at internalizing these rites, sublimating their sexuality whether gay or straight and subjugating their feelings, Vincent left the abbey with a sense of relief at escaping its psychic distress. Perhaps, too, with a sense of guilt, not all of it attributable to the Catholicism she was once again severing.

Of course, Vincent’s quick to point out that her time at the monastery and forays into sex clubs are extreme and represent neither a universal experience in men’s lives nor a gauge for typical behavior. Nonetheless, they do reveal something (unpopular, or even unsavory) about how men act around other men and how they perceive women. Vincent is exploring the exceptional to discover the ordinary: what happens in a place without the normalizing influences of dominant culture.

As perceptive as Vincent is in wading through the sexual complexities and ambiguities at the abbey, one moment that she describes at the bowling alley struck me as particularly not-so-nuanced. Ned is visited by the attentions of an older man from another team, a “kind of guy who was far too decent to be creepy, the avuncular type who had turned his sexual response to you into deep affection . . . old enough to have gained some kind of relief from his urges.” Vincent seems to believe that the man knew, on some level, at least, that Ned was Norah. The way he treated her made her feel like a woman, “a girl actually, very young and cared for.”

It’s striking that Vincent doesn’t consider the possibility that the man never thought Ned to be anything other than what he appeared: a young, attractive, awkward guy, flattered and embarrassed by special attention. Vincent’s sensitivity, acuity, and candor were transparent to the monks, and they were distressed by them. It seems likely that at least one man in the bowling league would be disarmed by Ned’s charms, if not titillated by Ned himself. Vincent claims that she has spent her “life as a woman either flirting or butting heads or maneuvering somewhere on the sexual spectrum with every man” she’d ever met. But Vincent’s sexual egalitarianism, ironically, doesn’t seem to extend to her life as a man.

*

One of the most curious, and telling, aspects of Vincent’s experience was how people continued to perceive their world in light of their established expectations. When her bowling team and the monks met Ned, they may have though him a bit of Nancy, but they never thought he wasn’t a guy. As Ned’s time with each group wound down, Vincent often deliberately let bits of Ned slide: she wouldn’t stubble her face; she would even loosen her bindings. “To me it should have seemed obvious that something wasn’t quite right . . . [but] people saw in [Ned] what I had conditioned them to see. When I removed the beard, they saw nothing but a shaved boy.” In the book’s conclusion, “Journey’s End,” Vincent points out that “even in the thick of the project when I went out into the world as myself, during the off periods when I was writing or taking a break from full-time Ned, people almost invariably mistook me for a man even when I was wearing a tight white T-shirt without a bra.”

Vincent continues, “Knowing as I do now that my gendered state of mind could have such a powerful effect on other people’s perceptions of me, it is no wonder that that state of mind warped my own perceptions as strongly as it did.” Vincent’s sexual sleight-of-hand, as temporary as it might have seemed, was not just a transformation; it was in her own eyes a transgression. The explicit duplicity was always at the fore of her mind, and she expended considerable energy how to remedy it. It becomes ever clearer that, as playful as it might have been at the beginning, the experiment was not a game, that her guilt, if not her fear of retribution, was real. She often ends a chapter with a confession, and while at the monastery she actually delivers a true confession to a monk.

Each revelation was embarrassing and fearful, a “coming out,” of sorts, and with it, you sense that Vincent revisited the same shame and catharsis of her first, original coming out. She notes in the introduction, “I can say with relative surety that in the end I paid a higher emotional price for my circumstantial deceptions than any of subjects did. And that is, I think, penalty enough for meddling.”

“Easy for you to say,” one might argue, but Vincent seems sincere about the extent of her guilt. Her breakdown, the psychological melding of Norah and Ned that came about from her meddling, is also difficult to call to question. Though Vincent took great pains to disclose her true identity to the bowling team, to a few monks, even to many of the women she dated, she clearly wrestled with the moral ambiguity in the deception. Moreover, a certain amount of dishonesty was unavoidable; inherent in the sociological pursuit, it’s a common fate for anthropologists who exchange their journal for a roasted leg-of-man. Participating is far more complicated than observing.

II.

Vincent’s objective was to go undercover in an attempt to uncover some of the cultural, even biological, imperatives that drive men. Her means were disguises, and though after she washed off the stubble she was still coated with a sticky psychological residue, her physical transformation was temporary. “Am I a transsexual or a transvestite, and did I write this book as a means of coming out as such? The answer to both parts of that question is no.” Confessional as Vincent’s story may be, it was not a means of expressing desire for permanent change. In fact, Vincent attests that “being Ned was often an uncomfortable, alienating experience, and far from finding myself in him, I usually felt kept from myself if some elemental way.”

What if, however, a need for change went beyond the generic objectives of observing, recording, and understanding the “other” to the specific, personal objectives of becoming the “other”? Pagan Kennedy’s The First Man-Made Man chronicles that desire. Her book is a type of strange, beautiful love story, where a woman longs for the man of her dreams, a man that lies trapped inside her own body. It is a quest story, as the woman searches for ways to remake her body into the man’s, to reshape the world to conform to her desires. Kennedy deftly handles a complex subject in which language is deconstructed, bodies molded, and identities shifted. It is a postmodern fairy tale in which the magic wand becomes the surgeon’s scalpel and the prick from an enchanted spinning wheel awakens the dreamer from his dreamless sleep.

*

Michael Dillon was born Laura Dillon in 1915; ten days later her mother died. Unable to care for her or her brother, Bobby, her father left Dillon in the care of two spinster aunts in Folkstone, a seaside town on the English Channel. She was raised in the residue of Victorian values and the tyranny of her Aunt Toto’s delicate constitution, neurotic and narcissistic. Like Vincent’s experiences of childhood, Dillon preferred all thing typically male:

She shot at targets with her bow and arrow; built bookcases, a nail between her pursed lips; and beat up the occasional neighbor boy who deserved it. She read Tarzan books, dreamed of Africa, hopped along the rocks at the seashore, stared out at the distant, invisible lands where she would make her future.

But unlike Vincent, once puberty hit, Dillon found herself deeply ashamed of her body, unable to resolve the physiological transformation occurring with her previously stable sense of self. Her budding breasts “developed pernicious plans of their own, womanly plans that humiliated her.” It was when she was in her late teens that she experienced an event that would lead her to acknowledge the discrepancy between inside and outside and search for a way to transform herself into the man that she knew herself to be.

Dillon and a friend were hiking up a seaside cliff when the boy opened a gate, waiting for her to proceed first. Kennedy recounts:

It was the first time a boy had ever opened a door for her. “Suddenly, I was struck with an awful thought . . . : ‘He thinks I’m a woman.’ It was a horrible moment and I felt stunned,” Dillon wrote later. “I had never thought of myself as [female] despite being technically a girl. I finished the walk in silence, the silence of despair, and he never knew what he had done to upset me. But life would never be the same again. People thought I was a woman. But I wasn’t. I was just me.”

Around the same time, Dillon was “gripped by a spiritual hunger.” As her body transformed, she sought truth, the meaning of life, some solid and stable universal law that she could rely on as her body betrayed her. These two quests—for truth and for gender—consumed the rest of her life, and as Kennedy subtly suggests throughout the book, they were deeply, inextricably entwined.

Kennedy also deftly entwines Dillon’s personal story of transformation with the concurrent medical and psychological advances that made such dramatic physiological changes possible. She is quick with intellectual analysis—smart, stylish, engaging—but is sometimes shy about offering cultural commentary, which is in sharp contract to Vincent. Her narration is fast-paced (you can tell she writes fiction and is good at it), though sober, her treatment is never maudlin, and the book’s 200-some pages could not be more engaging and edifying were they doubled.

As Dillon moves from Oxford undergraduate to intrepid petrol mechanic fighting fires during German air raids to tweedy medical student in Dublin, we encounter Magnus Hirschfeld, whom in 1919 founded the Institute for Sexual Science in Berlin, “the world’s first center devoted to research of sexuality and gender.” Twentieth-century progress and the permissiveness of Berlin between the wars allowed Hirschfeld to assemble sexual curiosities—plaits and buns collected by a hair fetishist, a masturbatory apparatus, and women’s thigh-high boots, for example—as well as stories and first-person accounts of sexual experiences that helped normalize what was previously thought deviant. Primary among them were accounts from Nazis seeking witness to, and relief from, their afflictions, and by the time Hitler came to power in 1933, Hirschfeld had fled Germany and the Institute was razed, its studies lost to oppression.

A growing understanding of human physiology, namely the differences between testes and ovaries and the ability to isolate the chemicals that were produced by them, led to bizarre, sometimes questionable medical procedures. Dr. Eugen Steinach, Director of the Biological Institute of Vienna, performed “nothing more than glorified vasectomies,” cutting the conduits that release sperm and thereby raising levels of the testosterone, or “vital juices” into the body. In the 1920s testosterone had yet to be named, so men “got Steinached,” and famous recipients of the dubious procedure included W.B. Yeats and Sigmund Freud. Though the operation was intended to spur youth and vigor, it was entirely ineffectual. It did, however, serve to act as a “powerful placebo. Men madly pursued the cure . . . and it became the fad operation of its era.”

A whole field of quack medicine called organology developed in the 1920s to promote the regenerative effects of sex hormones. In 1923, Serge Voronoff grafted a sliver of a chimp’s testicle onto a man’s. Dr. John Brinkley, an American with a mail order degree, used goats instead because they were cheaper and more plentiful. The differences between monkey and goat made no difference to the patients; the only result was “a nasty infection.” Kennedy is quick to draw the reader’s attention to the fact that, though questionable in their result, these procedures were also an attempt at transformation, from old to young, decrepit to vital.

The testosterone that was eventually produced synthetically in 1935 was the catalyst for another type of transformation: Laura’s attempt to become Michael, to effect a physical change far beyond an Eton cut and trousers. “She became the first woman on record to take the drug with the intention of changing her sex.” This was not vanity; it was survival. But the biggest physical changes were yet to come.

Kennedy shows how through good luck Dillon encountered a plastic surgeon at the Royal Infirmary in Bristol who offered to give her a double mastectomy and introduce him to Sir Harold Gillies. In the 1940s plastic surgeons “were a small, maligned cadre of physicians, still regarded as quacks, [who] scandalized their colleagues with their willingness to cater to their patient’s desires.” In the 1920s, Gillies was the first plastic surgeon to set up private practice in Britain; he learned his trade treating soldiers blown apart in World War I.

He would let the flap of skin curl on itself and then sew it into a tube, sealing off the inner side from the air. These tubes of skin, or “suitcase handles,” could grow on the patient’s body for weeks at a time; they could be moved about, end over end, across the body until they reached their final destination; or they could stretch like stalks to wherever you needed the flesh. The “tube pedicle” . . . revolutionized surgery. . . . A U-shaped handle of flesh could be grown on the chest and moved to the face to form a nose; an extra roll hanging off the stomach could become a penis.

Gillies’s intent was not just to reconstruct a physical nose but to rebuild a sense of self, to reshape what was miswrought, either by accident or nature, into what was or what should have been. “Gillies made happiness a reason for surgery—which in turn upended the traditional relationship between doctor and patient.” He believed that Dillon “was trapped in the wrong body. And so he needed to change that body. It was that simple.”

*

Of course, it wasn’t that simple, neither the physical requirements (13 or 17 operations to construct and maintain the penis) nor the psychological consequences. Though Dillon would assert in his 1946 book Self: A Study in Ethics and Endocrinology “that there’s only one way to determine whether a person is male or female: ask the person. True sex may have nothing to do with the appearance of the body,” Dillon spent many painful years in-between genders, the object of taunts and humiliation. Even if people bothered to ask him the question, they would have already decided on the answer. Moreover, even after the transformation was nearly complete, when Dillon easily “passed” on the street without comment, he suffered. He was a man literally coming into his own, but without the birthright of ordinary pleasures that manhood might convey.

Dillon finds support in the form of an aspiring male-to-female transsexual. Roberta Cowell had discovered Dillon’s book and eventually met up with the author in a crowded restaurant in London in 1950. As Kennedy suggests, it must have been like looking in the mirror. Cowell, hair cropped short, blushing in the heat of the room and of Dillon’s gaze, must have resembled “Laura Dillon, an awkward girl, still stuck in between, aristocratic yet ostracized, a refugee from her former life.”

For Dillon, the sexy platinum blond that Roberta was becoming was a woman he could pin his hopes of happiness to. For among all women available, she would be the one whom he could trust to keep his secret, who wouldn’t clamor for children (because it was physiologically impossible), who could ultimately understand the tremendous pain and sacrifice required to consummate desire. Not sex, the act, but sex the body.

But the affair was not to be. In a surprising twist to their courtship, Dillon became the one to perform Cowell’s castration—a document drawn up between the two even indemnified Dillon from any malfeasance should Roberta have died during surgery. Once performed, Roberta “could change her birth certificate. Then she’d be a legal woman; he was a legal man, and they could get on with their lives.” Not long after Roberta had healed, she visited a gynecologist and obtained a note that she was an intersexual, “a person born with anomalous genitals.” And not long after that, she stopped returning Dillon’s phone calls. Cowell consented to meet Dillon one more time to break the news in person, and though the exact record of what transpired has been lost, years later she explained her objections, indicating that he was not man enough for her. “[It] would have been like two females getting married, and I was certainly not interested in him in that kind of way.”

Dillon’s heartbreak only further underlines what a unique case he represented. Kennedy suggests that Dillon’s logic was that he was the only one that Roberta could marry; they were fated to be together, the only transsexuals in Britain. But though Roberta came to embody these hopes, they resided in Michael alone. After Roberta broke their engagement, Dillon sensed the unlikelihood of creating this kind of life with a biologically-born female, a “real” woman who wanted children and who could give them to a “real” man. Spurned by Cowell, without a medical position after graduation, Dillon finally relinquished his hopes in the ordinary. They just drifted away.

At this point, Dillon’s life drifts too. The second half of the book explores Dillon’s spiritual pursuits, something that compelled Dillon as a teenager. Kennedy describes Dillon’s Buddhist study as a novice and his desire to become a monk, and through her telling, we see him invest the same passion in Buddhism, the same frustrated desire, as he did in conventional marriage. But the tradition “forbade anyone who belonged to the ‘third sex’ from higher ordination.” Unclear as to what that meant for him, Dillon asked a monk if men injured in war would be barred. When they told him not any more, Dillon confessed his third sex status. They told him that he would never be a monk.

III.

On the surface, Vincent and Kennedy write about different things—gender roles and transsexualism, respectively—and it is only through Vincent’s playacting that there would seem to be merit in discussing these works contiguously. Progressives have been trained to understand gender, and the roles that each of us adopts, as culturally constructed. Our identities, including our sexual ones, are always open to interpretation. Or interpolation.

Yet Vincent and Kennedy both assert that gender and orientation are innate. Their protestations are ironic given that they attempt to persuade us that physiology can be changed to conform to desire. Yet, ultimately, both these books illuminate that biology is far from superficial, even when it is molded from plastic.

To discuss sex—in a literal as well as a literary context—is to realize that the body can seem as fixed or as flexible as the identity that inhabits it. Whether you believe that men and women “are that different in agenda, in expression, in outlook, in nature” as Vincent claims or that gender is a “song you make up as you go along,” as asserts Kennedy, you stand in good company.

You may also stand to change your mind. Though neither Vincent nor Kennedy dawdle over the nature/nurture dilemma, it is a question they wrestle with. Vincent notes in an interview at the back of her book “gender roles are born at least in part—perhaps in large part—of natural inclination. . . . Maybe instinct conditions us far more than we know or may want to believe,” but neither believes that gender—even biological sex—is essentially determined. As Vincent goes on to say, “This doesn’t mean, however, that either sex should be mindlessly shackled to a prescribed or straitjacketed role, even if the vast majority of each sex tends to make a traditional choice. The key here is choice.” I believe Kennedy’s sympathies lie with this assertion as well. Dillon and Cowell, as well as tens of thousands of other transsexuals, make a choice to overcome the biggest discrepancy in their lives, “the nightmarish sense of not fitting together, of your insides not matching your outsides.”

Fashioning identity is a tenet of postmodern life, and ultimately identity is a matter of perception. Though it’s common to talk about protean nature of identity, its shape-shifting proclivities, there’s something in the genes that’s difficult to contend with, which might explain my childhood adoration of watered silk gowns despite wearing only corduroy jeans. As Vincent says in her introduction, “I have always been and remain fascinated, puzzled and even disturbed at times by gender, both as a cultural and a psychological phenomenon whose boundaries are both mysteriously fluid and rigid.” It’s this conspicuous paradox that is apparent in both Vincent and Kennedy’s books and in the very nature of gender itself.

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