Holy cow was this series great... had so much incredible potential. It only ever had a pilot aired, but there was SO much in that pilot alone, thinking back I can't believe it was only one episode. So amazing.
Starred Joseph Fiennes (lead from Shakespeare in Love and Flash Forward) as a closeted middle aged MTF who was slowly beginning to unravel her gender dysphoric feelings. Carrie-Anne Moss played the wife!
Written / created by the same team who created Glee and Nip / Tuck.
I highly recommend finding a copy if you can. I think it was never officially released so is only available via torrent.
Seriously heart wrenching to watch. Never seen anything on film come close to portraying the confusion and frustration of those first few moments of really getting in touch with one's gender dysphoria and realizing you can do something about it, and all the conflicts that come along with finally being unafraid to be yourself.
Here's the wiki on it though it's out of date :
http://en.wikipedia.org/wiki/Pretty/Handsome