[@Owen_G_Richards](https://writing.exchange/@Owen_G_Richards )
The only thing I could think of off the top of my head that might help you was the late 14th century trial of Eleanor Rykener, who was most likely a transgender person. A search for them brought me to this article: https://publicmedievalist.com/transgender-middle-ages/
The article also talks about the Roman de Silence and several transvestite saints, who may or may not have been transgender. You might also want to look at this article:
https://scholarworks.wmich.edu/cgi/viewcontent.cgi?article=1814&context=mff
And the works she cites, some of which look interesting.
I can't think of anything specifically having to do with Henry VIII's time.