Found two documentaries on youtube that I'd like to share with you.
The first one is 'old'. It's from 2002. Since then, a lot of things in UK (and European) trans* legislation have changed.
It's not great quality, which is a pity because I think it's a pretty neat documentary. If you find a better quality video somewhere, be sure to let me know. :)
The two-part film (10 parts on youtube) called 'Make me a man' and follows four trans*men who are at different stages of their transition. I'll link you to the first part.
http://www.youtube.com/watch?v=WycFCltxNvI The second documentary is called 'the boy who was born a girl' and follows 16-year-old Jonathan who just started his hormone therapy and has the most amazing mother ever.
http://www.youtube.com/watch?v=qWQPvzCZ64U