The corresponding list of British trans men would of course be a lot longer and go back to the 17th century if not earlier. It was of course a lot more difficult for trans women to pass until external hormones became available in the 1940s. Transitions could be only social until the 1950s when male-to-female surgery became available for a few, for those with luck, pluck or the right connections. Yes, some gender surgeries had been done in Germany and the Soviet Union in the 1920s and 1930s, but very very few.
The following list is of trans women who transitioned and would have stayed so if death or arrest by police had not happened. This list does not include stage performers unless living as female full-time offstage, and does not include oscillators. So no Fanny and Stella, nor Gladys Shufflewick, nor Ron Storme.
This is of course a list of those that we know about. There is probably at least as many again who were not reported in the press. John Randell discussed 61 cases in his 1960 MD thesis summarising his first 10 years working with trans persons. Many of these must have socially transitioned even though they realised that Randell's obduracy would prevent them from being approved for surgery. We know that he did approve Ina, Terri and Gloria - and there must be others. Likewise Dr Burou in Casablanca performed over 3,000 operation on trans women from 1956 onwards, but we can name barely 30 of them.
Lavinia Edwards: social transition 1825.
Mary Mudge: social transition 1850s.
Norma Jackson: social transition 1931.
November1945: an unnamed serving Sergeant (a full-time soldier and not a conscript) assigned to Hamburg was allowed to travel to Denmark for male-to-female surgery, after extensive medical evaluation by the Medical Officer and a psychologist.
Dorothy Medway: social transition 1945, surgery late 1953.
Betty Cowell: social transition 1950, surgery 1951.
X, unnamed Scots woman, having undergone surgery petitioned in 1957 to have her sex corrected on birth certificate etc as Ewan Forbes had done two years earlier, but was refused.
Georgina Turtle: surgery 1957, social transition 1957.
April Ashley: social transition 1956, surgery May 1960.
Ina Barton: social transition 1960, surgeries completed 1962.
Terri Rogers: surgery 1962.
Gloria Greaves: surgery 1964.