I don't know if these two were mentioned here or not but I thought I would point out 2 good documentaries that deal with trans issues.

The first is called "Creature"
IMDb link: http://www.imdb.com/title/tt0198385/

The other is "Prodigal Sons"
IMDb: http://www.imdb.com/title/tt1295068/

You can read about them both.

I liked them both for different reasons.

Prodigal Sons was more interesting and powerful. The trans issues are more background to the family struggles.

Creature on the other hand is more about Stacy as she goes from female impersonator who struggles also as a hooker. She begins her transition on camera and we watch as she blossoms into a beautiful woman. She has her own family to struggle with.

I saw them both on Netflix instant view. Creature is no longer available that way but Prodigal Sons still is.

I have seen "Prodigal Sons" and enjoyed it very much.  Just tagged "Creature" for the DVD.