I like the theme and the title.

Hmm... Pink Floyd's "Arnold Layne" is about a transvestite, Bowie's "Rebel Rebel" very well might be, the Traveling Wilburys' "Tweeter and the Monkey Man" (sung by Bob Dylan) apparently features a transexual title character as well.... Oh, then there's Monty Python's possibly immortal "Lumberjack Song", though maybe it's not so immortal after all (for all sensitive heroes of the future) if it's hard to handle how the lumberjack's compatriots are downright puzzled by how he dresses in Women's Clothing.... I don't know if I can add to your Musical Theater plate, sadly. I wonder: How would a mix be categorized if it contained nothing but musical theater songs?