Folks~~
As a librarian, I have this sort of sacred belief that reading the right books can prepare a person for anything. Never was this proven more true to me than when my wife came out to me as being a woman trapped in a man's body. I didn't know it, but I had already read a number of books and watched a couple of movies that helped me chew on this idea of gender being out of sync with the body. I thought I'd post my annotated bibliography here for others in case it might help anyone. Feel free to add your own.

Luna by Julie Anne Peters. This is a teen book about a sister whose older brother is coming out as a girl. It's a VERY compelling read.
I Will Fear No Evil by Robert Heinlein. The premise is of an old man whose brain is transplanted into the body of a nubile female. This book is VERY sexist in a lot of ways, but it does make for some interesting brain food.
Commitment Hour by James Alan Gardner. This book is a sci-fi read about a society that has children swap genders every year on their birthdays until they are 18 when they must choose: male, female, or neuter. I enjoyed this one quite a lot!!!
The Man Who Folded Himself by David Gerrold. This sci-fi is about a man who is able to time travel by means of a belt. The time-travel model used involves parallel universes, and he winds up meeting himself born female. Not so much a trans-gender book as it is this idea of how gender fits into one's personality.
Movies:
Normal. The story of a couple in mid-west America and what happens when the husband reveals his desire to become a woman. Note: the trans-woman in this story tends to be very out and even somewhat in-your-face about her transitioning, which may not be typical for all who transition. Supremely well-acted, and a very moving script.
Mrs. Doubtfire. I know this isn't technically a trans-gender situation, but I did find it interesting that when Robin Williams' character dressed as a woman, he was much more nurturing.
Boys Don't Cry. I'm not sure I'll ever be able to watch this one again because it's so painful. It was the first trans-themed movie I watched, and it really got me to understand the emotional side of things.
TV:
Star Trek: The Next Generation, episode The Outcast. This episode deals with a race of aliens who claim to be genderless and their reactions when one of their own starts to display "female" behaviors and emotions. Very compelling storytelling here.
Quantum Leap. In many episodes, Sam leaps into a female character and has to try to act and speak as the host body normally would. Some episodes are better than others, but on the whole, the show does a pretty good job.
Babylon 5: This one gets an honorary nod. In the pilot, The Gathering, the character of Delenn was supposed to be male and transition into being female at a point later in the show. Her makeup and lines from The Gathering are all supposed to reflect a more masculine role. In the end, the producer was dissatisfied with the results of the voice manipulation, so Delenn was altered to reflect a different kind of transition.
After Dana came out to me, I read a lot more books (mostly non-fiction) and started to seek out any movies/TV I could find to help me better understand my wife. If you folks want my expanded list of reading and viewing, I'd be happy to share.

~~E