Lili Elbe

Like Roberta Cowell, Lili Elbe was also born a male and later transitioned to female but unlike Roberta, she didn't realise she wanted to be a girl until later in life.
Elbe's journey began when her wife Gerda Gottleib needed a model for some of her work which included illustrations for fashion magazines and books. When Lili tried on the feminine attire, it was like a fire was lit in her soul. She loved wearing women's clothes and the couple would later move to Paris, France where Lili began to build her preferred identity. The couple separated 1930 and Lili went to Germany where, under the supervision of Magnus Hirshfeld, Lili had her biological male organs swapped surgically for female organs. The last operation which would've allowed her to have children with a womb backfired as her body rejected it and Lili died of surgical complications. While it is sad that she didn't live a long life and have kids with her new lover, it should be noted that if she had lived, she would've been rounded up by the Nazis and put into a concentration camp before being killed like many LGBT people during the Second World War.
Lili's grave is in Dresden, Germany and in 2015, Focus Features who had made a biopic about her called The Danish Girl financed a new headstone for her after her original headstone was destroyed in the 1960s.