While studying creative writing I came across Billy Tipton. I love jazz and his work has is light enough to really enjoy, without the melancholy of the blues. A good example on Youtube http://www.youtube.com/watch?v=f3JAAxFYEws .

But what struck me more than anything s that Billy Tipton was born Dorothy Lucille Tipton in 1914.
As a woman, it is unlikely that he would have been allowed success in his chosen field, as a man he enjoyed a successful career.

He even adopted three sons with his partner Kitty Oakes and they did not realise he was born female until his death.

He explained his anatomy as being because of an accident that damaged his genitals and broke some ribs requiring the binding of his chest.

I cannot answer the reasoning behind his apparent transition as that is information known only to him. There are questions:
• Was it to improve his career position? – although, during his early career, he only appeared as male to perform, and was seen as lesbian.
• Was it to enable a more publicly acceptable 'lesbian' relationship, by appearing as a man with a woman?

Is there really more to it than that, or did he transition just for economic advantage and/or for his relationship with women to be more acceptable.

Of course, that then raises questions about why, as woman, she could not have the career that he could have as a man. It also raises questions about why a lesbian relationship may have been unacceptable.