Dillon, assigned female at birth, was raised in the town of Folkestone in Kent, England. He received his undergraduate education at St Anne's College, Oxford, where he was president of the Oxford University Women's Boat Club and won a University Sporting Blue award for rowing, competing in the Women's Boat Race in 1935 and 1936. After graduating he took a job at a research laboratory in Bristol.
Dillon had long been more comfortable in men's clothing and knew that he was not a woman. In 1939, he sought treatment from Dr. George Foss, who had been experimenting with testosterone to treat excessive menstrual bleeding; at the time, the hormone's masculinizing effects were poorly understood. Foss provided Dillon with testosterone pills but insisted Dillon consult a psychiatrist first, who gossiped about Dillon's desire to become a man, and soon the story was all over town. Dillon fled to Bristol and took a job at a garage. The hormones soon made it possible for him to pass as male, and eventually the garage manager insisted that other employees refer to Dillon as "he" in order to avoid confusing customers. Dillon was promoted to tow truck driver and doubled as a fire watcher during the Blitz.
Dillon suffered from hypoglycemia, and twice injured his head in falls when he passed out from low blood sugar. While he was in the Royal Infirmary recovering from the second of these attacks, he happened to come to the attention of one of the world's few practitioners of plastic surgery. The surgeon performed a double mastectomy, provided Dillon with a doctor's note that enabled him to change his birth certificate, and put him in contact with the pioneering plastic surgeon Harold Gillies.
Gillies had previously reconstructed penises for injured soldiers and performed surgery on intersex people with ambiguous genitalia. He was willing to perform a phalloplasty, but not immediately; the constant influx of wounded soldiers from World War II already kept him in the operating room around the clock. In the meantime Dillon enrolled in medical school at Trinity College, Dublin under his new legal name, Laurence Michael Dillon. A former tutor of Dillon's persuaded the Oxford registrar to alter records to show that he had graduated from all-male Brasenose rather than the women's college St Anne's, so that his academic transcript would not raise questions. Again he became a distinguished rower — this time for the men's team.
Gillies performed at least 13 surgeries on Dillon between 1946 and 1949. He officially diagnosed Dillon with acute hypospadias in order to conceal the fact that he was performing sex-reassignment surgery. Dillon, still a medical student at Trinity, blamed war injuries when infections caused a temporary limp. In what little free time he had he enjoyed dancing, but he avoided forming close relationships with women, for fear of exposure and in the belief that "One must not lead a girl on if one could not give her children." He deliberately cultivated a misogynist reputation to prevent any such problematic attachments.
In 1946 Dillon published Self: A Study in Ethics and Endocrinology, a book about what would now be called transgender, though that term had not been coined yet. He described "masculine inverts" as being born with "the mental outlook and temperament of the other sex," using Stephen Gordon in the novel The Well of Loneliness as an example. Since this form of inversion was innate — a hidden physical condition similar to intersex — it could not be affected by psychoanalysis and should instead be treated medically. "Where the mind cannot be made to fit the body," he wrote, "the body should be made to fit, approximately at any rate, to the mind."
Self brought him to the attention of Roberta Cowell, who would become the first British trans woman to receive male-to-female sex reassignment surgery. Though Dillon was not yet a licensed physician, he himself performed an orchidectomy on Cowell, since British law made the operation illegal. Cowell's vaginoplasty was later performed by Gillies.
Dillon qualified as a doctor in 1951 and initially worked in a Dublin hospital. He then spent the 6 years at sea as a naval doctor for P&O and the China Navigation Company.
Dillon had not revealed his own history in Self, but it came to light in 1958 as an indirect result of his aristocratic background. Debrett's Peerage, a genealogical guide, listed him as heir to his brother's baronetcy, while its competitor Burke's Peerage mentioned only a sister, Laura Maude [sic]. When the discrepancy was noticed, he told the press he was a male born with a severe form of hypospadias and had undergone a series of operations to correct the condition. The editor of Debrett's told Time Magazine that Dillon was unquestionably next in line for the baronetcy: "I have always been of the opinion that a person has all rights and privileges of the sex that is, at a given moment, recognized."
The unwanted press attention led Dillon to flee to India, where he spent time with Sangharakshita (Dennis Lingwood) in Kalimpong, and with the Buddhist community in Sarnath. While at Sarnath, Dillon decided to pursue ordination and became Sramanera Jivaka (after the Buddha's physician). Because Sangharakshita refused to allow Jivaka full ordination, and other frustrations with Sangharakshita's management of Triyana Vardhana Vihara, Jivaka turned to the Tibetan branch of Buddhism. He went to the Rizong Monastery in Ladakh. He was reordained a novice monk of the Gelukpa order, taking the name Lobzang Jivaka, and spent his time studying Buddhism and writing. Despite the language barrier he felt at home there, but was forced to leave when his visa expired. His health failed, and he died in a hospital at Dalhousie, India, on May 15, 1962, at age 47.
Writing under both of his Buddhist names, Jivaka published Growing Up into Buddhism, a primer on Buddhist practice for British children and teens, and A Critical Study of the Vinaya, which looks at the Buddhist rules for ordination and defeat. Both books were published in 1960. Additionally two books by him were published in London in 1962: The Life of Milarepa, about a famous 11th century Tibetan yogi, and Imji Getsul, an account of life in a Buddhist monastery.
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