MICHAEL DILLON, A BEARDED MEDICAL STUDENT, fiddled with his pipe and then lit it nervously. The year was 1950; the city, London; the restaurant, discreet. Dillon shared his table with a person so odd-looking that the other diners in the restaurant ogled and whispered to one another. He—or was it a she?—wore a blazer and trousers, cropped hair, and tie, but seemed to be hiding breasts under the suit jacket. In fact, Roberta Cowell had been born male, but she could not live as a man anymore. She had begun dosing herself on massive amounts of estrogen—enough to melt away her muscles and put a blush in her cheeks. With no idea how to push her transformation further, Cowell was stuck in a no-man's-land between the sexes—a terrible place to find yourself in 1950.
The word transsexual had yet to enter common usage. Almost no medical literature acknowledged that thousands of people felt trapped in the wrong body and would do anything—including risk death—to change their sex. Michael Dillon, the medical student, had authored what was then one of the few books in the world to delve into the subject. In an eccentric little volume called Self: A Study in Ethics and Endocrinology, he had argued on behalf of people like Roberta Cowell. Dillon proposed an idea that seemed wildly radical at that time: why not give patients the body they wanted? Thanks to recent technological breakthroughs, doctors could transform a man into a woman and vice versa. But because of the stigma against these sex changes—as well as laws that prohibited castration—only a few people in the world had ever crossed the line.
Roberta Cowell had discovered Michael Dillon's book and decided she had to meet the open-minded scholar. She'd written to him care of his publisher and they'd exchanged a flurry of letters. Now, finally, they sat across from one another.
Dillon turned out to be handsome, Cowell reported in her autobiography. "He was a good deal younger than I had expected and wore a full beard. Not bad-looking, he was a very masculine type."
Maybe too masculine. Despite his progressive attitude about sex-change treatments, Dillon "appeared to have a very low opinion of women." It was an attitude that Cowell couldn't abide.1 After they'd eaten, she lingered at the table to debate the issue of women's intelligence. They ordered coffee. Dillon gestured with his pipe as he lectured her about the differences between the male and female brain. He clearly liked to throw his opinions around, especially with a lady present.
Cowell played along. After all, if she was ever to emerge from the awful limbo of her body, she would need his help. Dillon seemed to relish his role as her protector, fingering his droll little beard, dropping Latin words and medical terms. He assured her that sex changes did exist. It was now possible for surgeons to entirely reshape the human body, he claimed. In fact, he possessed startling proof of exactly what medical science could do.
Then, Michael Dillon fell silent. He puffed smoke and fidgeted with his coffee cup but did not drink. He glanced up at Roberta, then, finally, spoke. "I don't really see why I shouldn't tell you. Five years ago I was a woman."2
More than a decade earlier, an athletic blonde named Laura Dillon roared through the streets of Bristol on her motorbike. She wore her hair short, and a sports jacket hid her breasts; a skirt, her only concession to femininity, flapped around her calves. With her broad shoulders, patrician accent, and Eton haircut, she could easily pass for a pampered young man. In fact, Laura had grown up thinking of herself as above the common lot. Her brother, the eighth baronet of Lismullen, presided over a threadbare estate in Ireland, and her family still retained a residue of an ancient fortune.
At first glance, Laura seemed to be a fellow just out of Oxford, dismounting his motorbike with a dashing leap. But blink again and Laura was nothing but a cross-dressed girl. People who passed her on the street couldn't help staring, confused by the double image she presented. The children and old ladies were the cruelest, shouting insults or demanding Laura explain herself. When they came toward her, Laura froze her face into a mask. She refused to let them see how they got to her.
Still, she preferred their taunts to the alternative: female clothing. Evening gowns terrified her—they invited young men to slide their arms around her waist. Ordinary dresses filled her with the sickening sense that she had been obliterated. She knew herself to be a man, a man who was disappearing inside a ridiculous body, underneath breasts and hips. She didn't think she could go on this way anymore.
Pills saved her. Laura Dillon had managed to get hold of testosterone pills in 1938, soon after she'd graduated from college. She became the first woman on record to take the drug with the intention of changing her sex. Over several years, the hormone therapy transformed her into a muscular, deep-voiced man with fuzz on his cheeks. As soon as Dillon could look entirely male, he became invisible. Pumping petrol at the garage where he worked, greasy in his coveralls, Dillon easily passed as just another workingman. More than passed. He became bland-looking, unremarkable, ordinary—which was what he'd always wanted. He could stroll down the street now, could step into a hardware store or a men's bathroom, without attracting the least bit of attention. By the early 1940s, Dillon had mustered the courage to leave the garage for medical school—under his male name.
But hormones could only take Dillon so far. If other men caught a glimpse of him in the locker room or public baths, they would immediately know he had been born female. So in the early 1940s, Dillon sought out Sir Harold Gillies, Britain's top plastic surgeon. Gillies had reconstructed the genitals of soldiers who'd been bombed or burned, but he had never built a penis from scratch on a woman's body. It would be grueling, and Gillies could not guarantee the results.
At least the operation would be legal. While an arcane law protected male genitals from "mutilation," no such bans applied to female genitals and reproductive organs.
Dillon would eventually undergo a series of thirteen operations to construct a penis.* He began the treatments in 1946, while he was a student at Trinity College medical school in Dublin, and he finished his surgeries in 1949, a year before he met Roberta Cowell. Gillies had to harvest skin for the new organ from Dillon's legs and stomach; Dillon suffered from oozing infections where the skin had been flayed; at times, he was so debilitated he had to walk with a cane.
And why did Dillon want the penis so badly? Not necessarily for sex. Rather, a penis would serve as a membership card into the world of men, their bathrooms, their rowing teams, and their gentlemen's clubs in London. The lack of a penis had held him back, "for without some form of external organ he could hardly undress for the shower with the rest of the crew,"3 as Gillies noted. Furthermore, if Dillon fell ill, a penis would allow him to check into a hospital without having to explain why his genitals did not match the rest of his body. A penis, along with the beard and the pipe, would hide his history, keep his secret that much safer. Dillon feared, above all, the tabloids. If the rumor got out that Michael Dillon, brother to a baronet, had once been a girl, the gossip would surely be trumpeted in every low-class newspaper in Britain. As Dillon saw it, a penis would help to safeguard his privacy and his family's honor.
Sir Harold Gillies greets patients at Rooksdown in 1941. They were mangled by war, factory accidents, and cancer, but in the hospital they formed a close-knit community. British Association of Plastic Surgeons
So during the mid-i940S, Dillon lived a curious double life: he was both a medical student in Dublin and a patient in England. During the university term, he shadowed doctors on their hospital rounds, assisted in the surgical theater, and even performed an appendectomy. When the term ended, Dillon would ride a train through the English countryside to a small town called Basingstoke, home to Rooksdown House, the hospital overseen by Sir Harold Gillies. Here, men in military uniforms—their heads swaddled in bandages—lolled on park benches, putting cigarettes to the holes where their mouths should have been. Burn victims, a platoon of shot-up soldiers, children with cleft palates and survivors of factory accidents—Dillon joined this small society of the mutilated and maimed.
Sir Harold, as the patients called him, understood that recovery had as much to do with the mind as the body. Some of the patients at Rooksdown were so disfigured that, even with the best care, they would remain outcasts for the rest of their lives. Such patients had to be encouraged to relearn the art of happiness, which is why Sir Harold banished many of the rules that make hospitals such grim places and coaxed his charges into dancing the fox-trot, growing zinnias in the garden, or venturing out into the town surrounding the hospital for a beer. As a result, Rooksdown became the kind of place where, even in the middle of the night, you might come across a one-eyed man teaching himself to ride a bicycle down the hall. Or a burn victim wearing blue toenail polish. Or a surgeon pouring a pint of human blood into the tomato patch. "This was no ordinary place," Sir Harold wrote, with typical understatement.4
Dillon thrived at Rooksdown. He befriended a man with plastic ears, the girl who'd been scalped by a factory machine, and the navy officer who'd had his genitals ripped off by the gears of a machine. Stunted by years of ridicule, Dillon flowered in the tolerant atmosphere of Rooksdown: he turned witty, expansive, even popular. Dillon regarded the hospital as a year-round summer camp for misfits, and eagerly looked forward to seeing old friends every time he returned. One Christmas Eve, he made a grand entrance to a Rooksdown party in his wheelchair, and held court from its low-slung seat.
In the town surrounding the hospital, local people had grown used to seeing patients without noses or jaws walking around town. At the post office or on the street, Dillon and his friends could expect smiles and hallos from the villagers. But the patients knew that once they boarded the train, they would become pariahs at the very next town—passengers would flinch, stare, scuttle away from them.
Dillon had one advantage over most of the other patients: in that world beyond Basingstoke, he could pass as an ordinary man as long as he kept his clothes on. Still, this passing came at an emotional cost; a rigidly moral man, he had to lie constantly. When he returned to Dublin and ran into his fellow medical students, he had to invent stories to explain why he limped and sometimes had to walk with a cane. He blamed his troubles on the war—insinuating he'd been maimed in the Blitz, which he had not.
To keep the other students from asking questions, he cultivated a reputation as a stodgy bachelor, an older student who sequestered himself in the little house he owned. Now and then he asked young women out to dances and swooped around the floor in his white tie and tails. But Dillon didn't go on second dates. "One must not lead a girl on if one could not give her children. That was the basis of my ethics," he wrote later.5
Ethics weren't the half of it. How many women would be willing to risk the scandal of marrying the first artificial male? None, probably. At any rate, he didn't care to risk finding out. To marry a young woman, he would have to confess too much to her: the thirteen operations, the testosterone pills, the years of living as Laura. He was terrified, too, of what would happen if he ever did work up the nerve to tell a girlfriend about himself; he imagined how the smile would freeze on her face and her eyes would dart away, and how, when she looked back at him, she would no longer see him as a real man. He couldn't bear that. And so he avoided women. He brooded over the unfairness of his fate—it seemed he'd been given manhood, only to be denied a wife and children.
Still, he loved the way he looked in his tie and tails; he enjoyed a night of dancing, and an evening of playful flirting eased his loneliness a bit. So he took out a nurse or female student now and then, but he never let her closer than the arm's length of a waltz. He kept his distance by treating women in a "rough brotherly fashion," developing a reputation as a bit of a woman-hater. He liked to lecture his dates about how the female brain was more suited to housework than intellectual pursuits—a strategy guaranteed to stifle any romance.
Dillon claims that his misogyny was all an act, one of the tools he used to keep women from falling in love with him. But, in fact, he did believe the female mind to be a strange and rather frightening organ. Women had hurt him, over and over, even before the sex change. In Laura Dillon's teenage and university years, she had fallen in love with at least two straight women. Both of them had pushed Laura away. The worst part was that these would-be sweethearts had regarded her as a lesbian rather than as the man she wanted to be. Dillon had enjoyed only a few close friendships, and these had almost always been with men—backslapping boys who accepted Dillon as a brother.
So, women could not be trusted. Dillon had learned this early on. By age thirty-five, he had vowed never to fall in love.
And then Roberta Cowell slid into the seat across from him at that London restaurant, and he dared to hope again. Her wrists—slim and delicate from the estrogen treatments—peeped out of the cuffs of her sleeves. Her cheeks flamed pink, so soft below the short man's haircut. In the blur of Roberta Cowell's face, he could see the lovely ingenue she would become. Somewhere in there lived the one woman who could understand him, the one woman who could recognize him as a real man.
He had decided, from the logic of his profound isolation, that Cowell must be his soul mate. Dillon was lonely in the way we can all recognize, and he also suffered from a brand-new, twentieth-century solitude, too, one that had never existed before—the loneliness of a medical miracle, of the person who has experienced unique states of mind and body. He'd dared to confide in so few friends, and even the kindest of them had never really understood.
But now, he shared a table with the first person he'd ever met who'd entered that blur of hormones, who planned to transform her body just as he had. She relied on him, he liked to believe, not just as a doctor but also a man with a superior mind, who could guide her through difficulties. Dillon, too, had endured the torment of the in-between period when the hormones began pushing his body toward androgyny; he knew what it was like to stumble through a city street where passersby stared at him.
She was three years younger than he was, but seemed younger than that. She implored him for help; she needed him utterly. Dillon had waited his whole life for a woman to fasten her eyes on him the way she did, to ask for his protection.
And so he trusted Roberta immediately. By the end of lunch, he'd poured out his story to her—surprising even himself with his openness.
Then they parted. He returned to Dublin, where he was finishing up the last year of medical school, but Roberta continued to haunt him, to tug at his heart. He mailed her letters brimming with advice and tender confessions. "The chief feeling you arouse in me, Bobbie, is a desire to protect you and to treat you gently and steer you along," he wrote.6 Whenever Dillon traveled to London, he made sure to call on her.
At one of these early meetings, "he . . . whipped out the penis, which he was very proud of," wrote Cowell. "It wasn't any kind of seduction scene. He just wanted me to see what medical science had achieved. I had never seen anything like it. It was huge, and in a constant state of semi-erection." She made a joke about the thing being rough-hewn. He didn't laugh. "Dillon did not exactly have the most perfectly developed sense of humor," according to Cowell.7 Though, really, how could he have laughed? He'd unzipped for her; he'd showed her the evidence of his excruciating pain, all those operations and infections. He'd wanted her to see how he'd turned that suffering into a handsome piece of flesh. And all she could do was snigger.
Still, he refused to be discouraged. In his terrible loneliness, Roberta Cowell began to haunt his thoughts. For the first time in his life, Dillon allowed himself to believe that one person might be able to understand him. He sent her long confessional letters about his girlhood and his years at Oxford. He wanted her to know everything. She wrote back to him, when she could find the time. They talked on the phone, when she was in.
It was 1951 now; Cowell had turned herself into a va-va-voom peroxide blonde; she'd begun venturing out onto the streets of London in a wig, skirt, makeup. She had yet to go through the vaginal-construction surgery and the face-lift, but already she scorched the eyes of sailors as she flitted past them on the sidewalk.
Dillon was a virgin. He locked himself in his flat, stared at her photograph, and trembled with passion. And for the first time, he submitted to the feeling entirely. "I need to have two whiskies in me before I could start off 'my beloved Bobbie,' " he wrote her. "I have never called anyone that before and you know what my inhibitions are like."8 In an effusion of letters, written on scraps of paper in between his rounds at the hospital where he worked as a student doctor, he poured out his feelings. She replied with brief notes, signed with nothing more than a scrawny "B." Dillon chalked that up to her female modesty. Sometimes he sent two letters a day. "Oh Bobbie, Oh Bobb-bee, come to me soon, I am wanting you all the time," he wrote to her. And: "You probably have had experience in the 'zones of eroticism' and I have had none. Still, you could teach me."9 He wrote and wrote and wrote.
Roberta Cowell's side of the correspondence has not survived. Michael Dillon might have been a man given to impulsive leaps and grand gestures, but he was not delusional. He took it for granted that they would marry, and so she must have given him some reason for hope, some endearments on which to hook his passion.
Besides, as Dillon saw it, he was the only man she could marry. Once she had gone through her final surgery, they would be the only postoperative transsexuals in all of Britain. Surely they were fated to be together. Separately, they were two people who each guarded a secret, each of whom could be destroyed by a rumor or a tenacious reporter. Together, married, they would be much safer, much less likely to be exposed by the press; they would become blessedly invisible; just another frowsy heterosexual couple. That was Michael Dillon's ambition: to be ordinary. To melt into the crowd.
He wrote to tell her that as soon as he passed his examinations and became a doctor, they could go ahead and marry. He suggested a wedding at sea to avoid embarrassing their families. They might adopt children. They would certainly buy a proper set of china. If Dillon was aware that Cowell had already been married—to a woman—and fathered two daughters, he did not allow this to spoil his plans. Nor did he dwell too much on the other peculiarities of Cowell's past: as a man, Cowell had raced sports cars professionally and designed engines; she still liked to jump behind the wheel of a dragster and tear around the track. Surely, as a full-fledged woman, she'd give all that up to be a housewife?
Of course, she had reason to be demure about his offer; she was gathering the legal documents she would need to change from male to female; she was learning how to sway across the room and dangle her fork in a ladylike fashion. She would need time to adjust, he understood that.
His most pressing worry was his medical exams, which he thought he might fail. He felt he should have a job as a doctor—or the promise of one—before he asked Bobbie to marry him. He wrapped up a ring and nestled it inside an empty Players' cigarette package and sent it off to her, instructing her to tuck this gift away in a drawer. She was not to open it, not even to peek, until he'd passed his exams.
It was now the summer of 1951. Robert Cowell had become Roberta Cowell in the eyes of the British government. She had become a legal woman; Dillon was a legal man; they could marry, if they chose to. Dillon was cramming for his medical school finals. He thought he would probably fail the first time he took them—after all, he'd missed a lot of school for his trips to Rooksdown. He wore his lucky Oxford tie on the day of the final examination. The tie did its work: Dillon passed. He had become, to his own astonishment, a licensed doctor.
He fired off a letter to Bobbie. You can open the package now, he told her. Surely, she would take him seriously when she saw the diamond winking up at her from the palm of her hand. Didn't every woman want a diamond? He was a doctor now. Didn't every woman want that, too? He desperately needed a yes from her.
He had mailed the letter, and now he began the long, awful vigil, waiting for her reply. Dillon believed that if he and Bobbie threw their lot in together, they could live as other people from good families did: a housekeeper, a little garden, some handsome furniture. Roberta Cowell would make an excellent match. Like Dillon, she came from the upper classes; her father, Sir Ernest Cowell, had been the honorary surgeon to King George VI. If Dillon married and raised some adopted children, if he managed to shake off his reputation as a loner, he could do more than just pass as a born male. He would feel like one, too.
Like so many other people in the 1950s, Dillon had enormous hopes for the institution of marriage. It would be the badge of his citizenship, a passport into the land of the ordinary.
But would she have him? Would she agree to recognize the penis Gillies had made—that organ that had once inspired her hoots of laughter—as a penis indeed?
Several years before, in his book Self Dillon had argued that transsexuals were ordinary people who just happened to be trapped in the wrong body. With the right surgeries and pills, he insisted, these people could become model citizens. It was a blazingly original idea in a time when most of the top medical minds still had no idea that transsexuals existed.
In Self, Dillon became one of the first scholars in the world to work out a classification system for gender identity and sexual desire. He insisted that homosexuals who cross-dressed (for instance, butch lesbians) belonged in a completely different category from transsexuals.* A butch lesbian might be able to hide out in a dress when she had to, to masquerade as a feminine woman in order to survive. But for a woman who knew herself to be a man, no such option existed; she had to stride down the street with a male swagger, had to wear a blazer. Transsexuals, he wrote, "have the most difficult life of all, for the cannot conceal their forms from curious eyes . . . Their peculiarities are forever being forced upon them by the thoughtless persons who gaze after them and loudly voice the question, 'Is that a man or a girl?' "10 Homosexuals, at least, had the closet. Transsexuals did not. They were always on display.
Therefore, Dillon argued, the transsexual patient needed "his body [to| be made to fit his mind"; this was the only therapeutic model that would work for him. Transsexuals could not be talked out of their urges; psychiatry would not help. It was their bodies that didn't fit, and so the only cure was to give the patient a new body.11
Two decades later, Dr. Harry Benjamin would say much the same thing—only he would say it in much clearer language to a far broader audience. Benjamin, lifted to prominence by his famous friend Christine Jorgensen, became known as the expert on transsexuality in the 1950s—indeed, he is often credited with coining the term transsexual even though others had used the word before him. When Benjamin died at the age of 101, the New York Times described him as the "first student of transsexualism to discern that it was different from homosexuality or transvestism—phenomena with which it was often confused. He also saw that transsexuals required medical assistance."12
In fact, the credit for these insights should properly go to Michael Dillon, who stumbled toward the same revelations during the early 1940s. Though Dillon was the first, he was never recognized as such. His obscure book, Self, reached only a small readership. At the time Dillon wrote, no surgeon in England or the United States would admit to performing a sex-change operation. Both countries had laws (the so-called mayhem statute) that forbid anyone from mutilating a man who could be drafted as a soldier—so physicians refused to amputate healthy testicles lest they be hauled into court. Laws aside, doctors were leery of operating on bodies to fix what they viewed to be a psychological condition, a mere neurosis. They'd sworn, under the Hippocratic oath, to do no harm. Harm, back then, included sex-change operations.
Dillon argued for a new kind of medical morality, one that took into account the patient's deepest urges. He'd met men at Rooksdown who'd had their faces burned into a red mask during war. These men would never have sweethearts or jobs unless their faces could be fixed. Transsexuals confronted the same situation; they felt stuck in deformed bodies that humiliated them. He insisted that the sex-change operation was not a violation of the Hippocratic oath—instead, it was a necessary treatment for people who needed to have their misshapen body restored to wholeness. Dillon had argued that if transsexuals were given the right body their troubles would end; he set out to prove this point with his own life. In 1950, he—and his surgeon, Gillies—believed he would settle down, sober up, marry, and muddle on as an ordinary man.
Of course, it's a hard job for anyone to act ordinary for years on end. The trouble for Dillon was he couldn't seem to stop editing his identity. When the sex change was behind him and his body sculpted to his satisfaction, Dillon decided to modify his mind. He pored over the books written by mystics in an attempt to calm his whirling thoughts and refurbish his personality. When books didn't save him, he pursued extreme treatments. Dillon wanted to reshape his psyche as spectacularly as Sir Harold Gillies had once overhauled his body. His longing pulled him to India, years before hippies began beating a path there, in search of some final transformation. "The conquest of the body proved relatively easy," he observed at the end of his life. "But the conquest of the mind is a never-ending struggle."13
Dillon's tale proves just how far a human being can bend, how protean we are, how raw with possibility. He inhabited a dizzying array of roles: schoolgirl, doctor, besotted suitor, sailor, mystic. And yet, no matter how much he managed to mold his body and mind, Dillon could never manage to blot out a certain stubborn nub of himself, an essential quirk of his personality. Dillon could never change his desire for change.
*According to DiHon, the number of operations w as thirteen and treatment ended in 1949Gillies's medical notes contradict this recollection. According to Ciillies, Dillon underwent seventeen operations, from 1946 through 1955, all of them presumably related to the creation and maintenance of the penis. I have chosen to hew to Dillon's recollection of events.
*Dillon did not use the term transsexual in Self—the term had vet to enter common usage. Instead, he tended to use vague phrases (such as "these people") to indicate those who wished to change their sex.