There's Something About Miriam (2004) Episode 4

There's Something About Miriam was a British reality television show filmed in 2003. It featured six men wooing 21-year-old Mexican model Miriam Rivera without revealing that she was transgender until the final episode.

https://en.wikipedia.org/wiki/There%27s_Something_About_Miriam

for a fascinating collection of Transgender documentaries go here
https://concen.org/torrents?title_op=allwords&title=transgender%20collection&title_1_op=not&title_1=&seeds=1&order=title&sort=asc