WARNING: I'm not as up on transculture/transpolitics as I'd like to be; this may be politically incorrect.
Back in high school.....way back....we studied archetypes, and we had to come up with a song or work of art or story that was an example of each archetype. The one assigned to my group was "transformation" (others included "the golden age," "loss of innocence," and....I don't remember the rest...T_T).
I think I came up with the song "Our Mother the Mountain" by Townes van Zandt, where this pretty lady turns into a creepy witch creature and curses the narrator's children. Uh, it's a good song. Someone else brought in a copy of The Little Mermaid (the Disney film).
Lately I've been thinking about transgender allegories, so I'm glad I remembered this assignment. I guess I'm just going to list a few stories I think are appropriate and let there be discussion, if discussion is desired.
THE LITTLE MERMAID: Mermaids, first of all, are women from the waist up, fish from the waist down. The transwoman's condition, perhaps, is similar: a woman in the mind (above the waist), a man in the body (riiiiight below the waist, essentially). Or however you want to interpret that. Anyway, Ariel loses a part of herself (her voice) but gains a vagina (her legs) and enters a new and sometimes scary world that she nevertheless has yearned for since forever (the land of the humans! above the surface!)--for transwomen, I suppose that would be the world of femininity/womanhood.
Here's a longer analysis. PINOCCHIO: He wants to be "a real boy." That's all I got. There's the thing with the lying, and his nose (which seems weirdly phallic, now), but I don't know how to interpret those as anything but the obvious: don't lie or bad things will happen, children! Maybe....something to do with living a double life? The more honest you are with yourself and others about your identity, the closer you'll get to being truly yourself?
Butterflies, Moths: Clearly. Not going to explain. An essay by Annie Dillard, "Transfiguration"--I feel like this could tie in somehow. And that poem by archie the cockroach,
"the lesson of the moth." Perhaps. I've done no mental work on these; I just sense potential.
I'd link to the essay, but I can't easily find it online, so perhaps I'll type it up sometime and post it on Google Docs or something.
Werewolves!
Basically I think transfolk need more stories out there that they can point to and say "Hey, that's about me!"
Edited to add:
Also I have recommendations that are less indirect. :D
"Luna" by Julie Ann Peters. A book about a girl who's brother (well, sister) is trans. YA fiction.
"Middlesex" by Jeffrey Eugenides. A book about an intersex person who grows up as a girl and then lives through adulthood as a man.
"Transamerica," a movie about a transwoman and the son she didn't know she had fathered.
"Princess Knight" by Osamu Tezuka (my hero!). A comic about a prince/princess who is born with two souls: one male and one female. Not really about a transperson, but still cool.
I'm not going to list a certain movie that I love because it would be a spoiler, just like I won't tell you the title of my favorite werewolf book. SPOILERS!
There are more but I can't remember them right now.............