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Doomed love of the ace who changed his sex

Roberta Cowell and Michael Dillon had an intense, but ultimately tragic, relationship
Roberta Cowell and Michael Dillon had an intense, but ultimately tragic, relationship

She was the aristocratic medical student, while he was a dashing Spitfire pilot and a father of two.

The extraordinary intense, but ultimately tragic, relationship between Britain’s first man and woman to undergo gender reassignment surgery is revealed in a new documentary.

Laura Dillon, the sister of the eighth baronet of Lismullen, was the first woman in the world to become a man through surgery.

She then became besotted with Robert Cowell and carried out the castration which paved the way for him to become the first British man to undergo sophisticated surgical gender assignment.

Cowell, who changed her name to Roberta, became a celebrity when the surgery was revealed, but her daughter tells the documentary of the torment of the family left behind who she resolutely refused meet.

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The son of Major-General Sir Ernest Cowell had been a celebrated racing driver before the war and served in the RAF as a Spitfire pilot.

He was shot down over Germany in 1944 and after being freed from a prisoner of war camp returned to the race track.

In her unpublished memoirs, Cowell wrote: “Outwardly I made frantic efforts to show the world at large how masculine and assertive I could be, but I discovered my conscious mind was predominantly female.”

In 1948 Cowell, aged 33, walked out on his wife and their two young children. Cowell changed his name, started wearing dresses and began taking hormones. Desperate for more advice he had read, Self: A Study in Ethics and Endocrinology, by a young medical student called Michael Dillon and arranged to meet the author.

During the meeting Dillon revealed he had once been Laura, the sister of Sir Robert Dillon.

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In 1945 Dillon won a place at Trinity College Dublin to read medicine but wanted to go further with the gender transformation and asked Sir Harold Gillies, a pioneering plastic surgeon, to operate on her genitals. He agreed.

After their first meeting Dillon fell passionately in love with Cowell. Dillon introduced Cowell to Sir Harold to ask if he would complete a second gender reassignment operation.

It was unlawful to remove testes unless medically necessary. Dillon agreed to risk his medical licence to carry out the castration in 1951, allowing Sir Harold to secretly construct a vagina for Cowell.

Cowell, desperate for fame and money, sold her story to a magazine. Dillon, fearing his own exposure, fled and became a ship’s surgeon. In 1958 Cowell was made bankrupt. At about the same time Dillon was tracked down by a reporter and, devastated by public expose and subsequent family rejection, became a Buddhist monk in the Himalayas. He died in 1962, aged 47.

Cowell continued to revel in her fame but faded into obscurity. She died aged 93 in 2011.

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The Sex Change Spitfire Ace — Secret History will be broadcast on Channel 4 at 8pm on October 24.