I recently rented Almost Myself: Reflections on Mending and Transcending Gender, a documentary about transsexual women, including one who wants to de transition back to male after 20 years living as female. Some very interesting stories and perspectives.
Zythyra
I saw this too -- it definitely seemed targetted to a cisgendered audience IMO. I got this "OMG, check out what I found!!!" vibe from some of the commentary from the director. But I thought the story of Josef Kirchner was really fascinating -- awful and amazing, one of the most turbulent experiences with gender I can imagine. Be sure to see the extra part added after the film was released. It makes his life make a lot more sense.
Also, Kate Bornstein is awesome.