Last night, I put in some anime to pass the time before I went to sleep and discovered a very sweet yet interesting story. The anime is called "Kasimasi: Girl Meets Girl" and it's about a boy (who other people call feminine) who gets transformed into a girl following an encounter with an alien spacecraft. The girl, called Hazumu, has to deal with her new role in society, but despite being inept about a lot of things at first, she is perfectly fine with her new gender. This is the closest thing I've seen to a show that deals with transsexualism. However, this show focuses more on the protagonist's life after the transition.
Here is the first episode, for those of you who are interested:
Kashimashi Girl Meets Girl Ep1