In 1933, a young woman tramped across a quad at Oxford University, the lilac shadow of an elm sliding over her face, a cache of philosophy books tucked under one arm. She should have been happy. One of a few hundred female students admitted to Oxford University at that time, Laura Dillon enjoyed the rare privilege of a top-notch education. And with blond hair and an athletic figure, she attracted the attention of Oxford men. She might have married well. The trouble was, she didn’t want these well-born men to open the door for her, didn’t want their solicitations and love notes. She wanted to be one of them.
As a young girl, she had played with bows and arrows; she’d beat up neighborhood boys; she’d retreated to a shed and built bookshelves. Everyone figured she’d grow out of her tomboy phase, but she didn’t. At 15, she began binding her breasts. At 17, she realized she wasn’t female at all. And now, at Oxford, she ached to be allowed into boxing matches where women were forbidden to go; she dreamed of wearing a suit jacket and drinking whiskey in a gentleman’s club. But when she tried to befriend the men around her, they thought she was flirting; they couldn’t see her as anything but a silly girl. “For me, naturally, the social world was closed. I had long been finding it more and more difficult to…go to a party where young men were politely condescending,” Dillon would later write.
Then one day she wandered down to the Oxford University boathouse and discovered she could be happy so long as she stayed on the water. She was an enormously competent rower. On the river, she became a set of arms, a coil of muscles, a strong back. Her wiry body was made for the oar, for curling up and then the heaving backwards thrust. By her second year at Oxford, she’d won a Blue—a most-valuable player award—and been elected president of the Oxford University Women’s Boat Club. “Work and rowing: this was my life at Oxford,” Dillon wrote.
The Oxford men’s team was famous around the country; when Oxford raced against Cambridge, newspaper men would stand along the banks snapping photographs, and mobs of fans would run alongside the boats, screaming encouragement. But the women’s team was a joke. Wearing flowered skirts and bloomers, the women rowed downstream rather than up. College authorities forbade them to race in a pack, for fear they might jostle one another and injure their wombs. Laura convinced the coaches to let women compete like men: all in a pack, upstream, wearing uniforms. And uniforms, to Laura, meant blazers, shorts, and flannel trousers: men’s clothing.
It was the uniforms about which she became most passionate. She convinced a local sporting-goods store to donate outfits to her team, and she argued to anyone who would listen that “the psychology of dress [was] all-important.” She would know. As a little girl, Laura had hungered to wear a sailor’s jacket just like her brother’s, with brass buttons and braid anchors; she’d pleaded so relentlessly that she finally got one, and she wore it with a pillbox cap that read “H.M.S. Renown.” That suit had stood for the very essence of what she wanted—some fluttering vision of her future self. Now, she’d invented a grown-up version of that sailor’s suit, and wore it everywhere. She cut her hair short, too.
One day, when she was launching a boat, a newspaper photographer happened to be hanging around, snapping pictures to promote the upcoming match between the Oxford and Cambridge men’s teams. Laura was stepping into the boat—her schoolboy haircut hidden under the cap, her blazer turning her figure boxy—when the photographer aimed his camera at her. She hardly noticed. The next day, the Daily Mirror tabloid depicted “L.M. Dillon” as a bizarre, androgynous person caught in the glare of a flashbulb. Underneath the picture, a caption demanded to know what the creature was: “Man or Woman?” She was not even sure how to answer that question herself, and now people all over England would flip through the newspaper and ask themselves, “Who is this ‘L.M. Dillon?’”
But much as she may have wanted to, Laura simply could not stop wearing blazers and trousers; when she put on a dress to please her family, she found the experience as painful as having her teeth drilled by a dentist. “It may be asked why I needed to dress in a ‘mannish’ way or have an Eton crop [hairstyle], thus calling attention to myself. It is impossible to explain to anyone who has not had the same experience,” Dillon wrote later. “I could not do other than I did.”
Dillon wasn’t the only woman in post-WWI England who chose to wear men’s clothing. In November 1928, the author Radclyffe Hall swept into a London courthouse decked out in a leather driving coat and a cowboy hat. Independently wealthy, she behaved exactly as she pleased, and what pleased her was to call herself “John,” strut around in the finest men’s suits, and write a candid, semi-autobiographical novel called The Well of Loneliness that shocked the British nation. The novel tells the story of a girl born to landed gentry—only she isn’t exactly a girl. Her father understands that his infant daughter was meant to be a boy, and so he names her Stephen; as she grows up, he encourages her to fence and argue and ride astride a horse like a man.
Though the novel offered nothing more explicitly homosexual than a kiss, its author was immediately hauled into court on obscenity charges. Hall’s novel had acknowledged that women could desire each other sexually—and that was enough to make the book dangerous. In the 1920s, many British people simply had no idea that lesbians existed at all. Paradoxically, the highly publicized obscenity trial would put lesbianism on the front pages and help nurture a new gay subculture. The magistrate in the 1928 trial ruled that every copy of the novel would have to be destroyed; the book remained under a ban until 1949. But bootlegged copies circulated among a fast-growing underground; women hid copies in paper bags and passed them around to one another. With almost no other such books available, The Well of Loneliness became the final word on female homosexuality.
At Oxford, lesbians dressed like Stephen in lovely wool trousers and blazingly white button-down shirts; Radclyffe Hall’s haircut—the so-called Eton crop—became a fad. The hair would be clipped close to the skull all over, except for a curtain of bangs that covered the forehead and threatened to fall into the nearest eye; the bangs could be tossed aside with a haughty rearing of the head. The haircut, named after the most exclusive boys’ school in England, connoted not just maleness but also privilege—the freedom of women who’d inherited their wealth and would never have to marry.
The Well of Loneliness inspired a mannish style that would endure for decades—and that confused many gay women who had no urge to cross-dress. One lesbian, who encountered the book in 1949, felt that it was more harmful than helpful as she tried to sort out her own identity: “It…sold me the idea that all lesbians were masculine and tall and handsome and Stephenish.” A number of modern-day scholars have echoed this point: The first and most famous “lesbian novel” might actually describe a woman who identified as a male—in today’s lingo, Stephen would be called a transgender man. One thing is clear: No literature at all existed to guide those female-bodied people who wished to become men. The Well of Loneliness offered no solutions. The book taught that the Stephens of the world would just have to bear up and endure their isolation. Meanwhile, medical literature would have offered Laura Dillon just as little hope.
The word “transsexual” had yet to be coined in English. The idea that a person with a female body might identify as male (and vice versa) simply did not exist in most of Europe and America. Only in Germany had doctors quietly begun to attempt the first sex changes; these daring surgeries had spawned at least one book about gender swapping, a novel based on the true-life transformation of a male artist into a female ingénue named Lili. But these medical and literary experiments were virtually unknown in England.
Things might have gone differently if Michael Dillon—formerly Laura—had lived long enough to publish his own story.
Laura Dillon had no way to explain her compulsion to be seen as a man. So one day, she screwed up her courage and asked a friend at Oxford for a diagnosis. The friend told Laura that she was a “homosexual.” Laura had never heard the word before, but decided to wear the label with dignity, like an ugly but serviceable suit. When she went home to Folkestone—the small town where her family lived—after the Oxford term ended, she thought she should tell someone. She chose her Aunt Edie—a boyish woman who’d once been a tennis star—as her confidant. Laura biked over to Aunt Edie’s house one afternoon and, after they’d sat down to tea, announced that she was a homosexual.
Aunt Edie burst out laughing. “What have you been reading to put this nonsense into your head? You must get married right away to cure this silliness,” the woman declared. Laura biked away, pedaling in slow motion, shattered. She would get no help from her family. No one seemed to understand her—not even homosexuals. At Oxford, Laura ran into a friend from high school who’d grown into a confident lesbian. This friend urged Laura to stop being so repressed and “take a woman”—a piece of advice meant kindly but as unhelpful, in its way, as Aunt Edie’s. “This advice was to be given to me again and again, even by well-known doctors, yet never did I take it. Somehow it seemed wrong,” Dillon wrote.
Laura did have eyes for women—but they always seemed to be straight women on the verge of marriage. She fell torridly in love with a Shirley Temple look-alike on her rowing team. When Laura confessed her passion, the girl rebuffed her as kindly as possible: If Laura had been a man, the girl said, she would no doubt have fallen in love. And then the adorable blond went off and engaged herself to some suitor. Laura could not seem to develop an enthusiasm for lesbian sex; she would have had to strip off her blazer and the bindings on her chest until she was naked and female; her lover would have desired exactly what Laura hated about her body. Nor did she belong in Oxford’s lesbian subculture, striding arm-in-arm across campus with the bluestockings, discussing women’s right to work.
After many months of trying, Laura began to realize that she wasn’t a homosexual after all. She appeared to be something else, and she still knew no name for it. One day, she sidled into a smoke shop and bought herself a pipe. It fit perfectly in her hand. She brought it back to her room, packed it with a wad of tobacco, lit it up, and took an experimental puff. She gagged and coughed. Her lungs burned. In secret, Laura taught herself to suck on a pipe as if she were an Oxford don, to puff thoughtfully and then to exhale the pungent smell of maleness. She was beginning to guess what she’d need to survive. She didn’t have a word for it yet, but in the shape of the pipe, that question mark of polished wood in her hand, she saw her future.
And indeed, she did become a man. Laura Dillon began taking testosterone pills in 1938, just after they became available on the market. Testosterone worked like magic; within a few years, Laura was living as a tow-truck driver named Michael, a fellow with broad shoulders, a husky voice, and the beginnings of facial hair. He underwent a mastectomy and changed his legal identity in the mid-1940s, and then endured a series of grueling surgeries to obtain a penis. Soon afterwards, a handful of other people began secretly using medicine to change their sex.
In 1952, Christine Jorgensen became the first to go public. After she told her story to journalists, her glam-shot photo appeared on front pages across America. Rather than hiding or fleeing the country, Jorgensen decided to use her fame to become a role model and spokesperson for the sex-change operation. With her ice-blond hair, designer gowns, and charming manners, she outclassed all those who tried to ridicule her. In 1967, she published Christine Jorgensen: A Personal Autobiography, which immediately jumped to the bestseller list and kicked off a new literary genre.
A number of sex-change narratives followed, from Jan Morris’s gorgeously written Conundrum to Renee Richards’s tell-all bio Second Serve. Through the early 1990s, these personal stories were almost exclusively written by people who’d transformed into women. Transgender men remained invisible. Things might have gone differently if Michael Dillon—formerly Laura—had lived long enough to publish his own story. He died of a sudden illness in 1962 while wandering the Himalayas, just days after he sent a manuscript to his literary agent in London. In that autobiography, he told the story of his groundbreaking medical transformation from woman to man. Dillon’s brother threatened to burn the manuscript and made it clear that he would block its publication. And so the book never did go into print.
Had Dillon survived, however, he surely would have been able to override the objections of his family. He would have gone public with his story in the early 1960s. His book (which was to be titled Out of the Ordinary) would have announced that female-to-male sex changes did exist; and he himself, a well-spoken man who was training to become a Buddhist monk, would have offered a compelling role model for people who wanted to make the same gender leap. He might have become the male Christine Jorgensen, but he died at just the wrong time. And so transgender men remained nearly invisible until slightly more than a decade ago, when the murder of Brandon Teena gave us a different—and far more tragic—hero.