Roberta Cowell was a Spitfire pilot in World War 2, spent a couple of years as a prisoner of war, and after the war became a racing driver. After a divorce to her estranged wife, she began to see a therapist about her feminine side and then finally turned to doctors for the answer after a tennis match with a friend ended in the joke that she should wear a brassiere (bra). Its unclear if Roberta may have indeed been intersex on some level. A brilliant woman doctor, a gland specialist, examined Roberta as well as two gynaecologists, two GPs, a professor of anatomy and an endocrinologist. Their conclusion: they were amazed not that “Robert” was so feminine, but that such a female person could seem outwardly so masculine. They discovered an abnormal flow of female hormones in his body.
Deciding that this was she wanted, Roberta became the first known British male to female transsexual to have had sex reassignment surgery; peformed on the 15 May 1951 by Dr Harold Gillies, who coincidentally also performed the female to male SRS of Michael Laurence Dillon. Its mentioned in 1951 that Michael asked Roberta to marry him. Unfortunately she did not return his affections and declined his offer. In 1954, she published an autobiography of her journey to womanhood: the Roberta Cowell story. Apparently the sensational book nearly outed Michael, who left the country around the same time of its publication. Roberta reportedly slipped back into the crowds and lived out her days.