Roberta Cowell was the first known British trans woman to undergo sex reassignment surgery. Born Robert Marshall Cowell in 1918, she was a British racing driver and Second World War fighter pilot who was captured by the Germans and imprisoned for five months in Stalag Luft I until the prison was liberated by the Red Army in April 1945. After separating from her wife of seven years in 1948, suffering from depression and flashbacks to the war, consultation sessions with a second Freudian psychiatrist revealed that her unconscious mind was predominantly female. Between 1950 and 1951, Roberta underwent a inguinal orchiectomy and vaginoplasty and in May 1951, was able to have a new birth certificate issued showing her change of name and change of recorded sex. At this time, transsexuality had become closely associated in the public mind with male homosexuality and effeminacy amongst men, both highly taboo subjects. Cowell's story broke ground, disrupting this narrative. Although she remained active in flying and British motor racing up until the 1970s, she found it very difficult to gain employment. Roberta died in October 2011 - only six people attended her funeral and in accordance with her instructions, her death was not publicly reported until two years later. Illustrated with black and white photographs.