Last year, one of the episodes of the BBC series "Moving On" told the story of a young crossdresser. The episode was called "Dress to Impress." It was a very sympathetic portrait of the young man.
The whole episode was formerly available on youtube and the bbc website, but now all you can get (for free) are clips. You can buy the episode for 1.99 at Amazon.
Here are two clips that are up on youtube.
Dress to Impress - short clip
Dress to Impress - longer clip