Born in wartime England 1915, Dillon was assigned female at birth, however at the age of 24 he began his transition to a male by starting hormone treatment with testosterone – the effects and risks of which were poorly understood. He went on to receive one of the first recorded double mastectomies for gender reassignment. He then came to meet the pioneering Harold Gillies who performed up to 13 procedures on Dillon between 1946 and 1949, to complete the first ever female-to-male phalloplasty. His professional career took him from the motor garages of Bristol to the medical school at Trinity College Dublin. Published author, naval surgeon, and finally, a Buddhist monk – a rich, complex, and inspiring tale.