One of the main characters in The Drowning Girl by Caitlin R. Kiernan, the viewpoint character's girlfriend, is a male-to-female transsexual. This is a minor spoiler, as the reader doesn't find out she's TS until several pages after she's introduced (but still fairly early in the book). The story as a whole is fantastical, or seems so (it's published as fantasy/horror, under the Roc imprint, but the narrator is so unreliable that some or all of the fantastic occurrences may or may not have happened as she remembers them). But Abalyn's being transgendered is treated very realistically. It's a very dark book, but with a fairly upbeat ending; I recommend it highly.

The narrator, Imp, has various mental problems and readily admits this to the reader. She's writing to try to make sense of the strange things that have happened to her, or that she remembers happening. But she seems to have two different sets of memories of how events played out, and she isn't sure which, if either, is correct. She begins by telling us, fairly coherently, about her childhood, about an old painting of a girl about to drown herself which has influenced her art, about possibly seeing a girl drown herself in the quarry near her home when she was a girl, about how she met her girlfriend Abalyn, and about their life together. Then, as she gets to the inexplicable events that intersected with her breakup with Abalyn, she gets more confused, and the prose gets more stream-of-consciousness and harder to read -- but remains very rewarding, through that point to the more readable narrative that concludes the book.

Kiernan herself is trans. I haven't read anything else by her except this and The Red Tree (which doesn't have any trans characters in it, but which I recommend strongly; it's about as good as The Drowning Girl, though a little darker), but I plan to read more eventually.

A few quotes:

I haven't said anything about Abalyn being a transsexual..... She wouldn't have wanted me to make a big deal out of it, and it never mattered to me. That's why I haven't really brought it up until now.

 

...it was difficult for me to imagine that this beautiful woman had ever been a boy. I mean, that she'd ever been caught inside the body of a boy, of a man.

 

"...I think it's kind of neat. I mean, how many people ever experience physical transformation on the level you have?" ... ...."I've always been a woman, Imp. The hormones and the surgery, they didn't change me from one thing to another. That's why I hate the phrase 'sex change.' It's misleading. No one ever changed my sex. They just brought my flesh more in line with my mind. ...."

...I didn't understand, but I would. In the weeks and months to come... I'd learn a lot more -- too much -- about being one sort of being on the inside and another on the outside.

Links:

• An interview with Kiernan from 2008
• Gary K. Wolfe's review of The Drowning Girl
• Episode 109 of the Coode Street Podcast where Kiernan was a guest and spoke about The Drowning Girl

When Wasps Make Honey, the sequel to Wine Can't be Pressed into Grapes, is now available from Smashwords in EPUB format and Amazon in Kindle format. See here for more information.