I've finished two books this year!
She's Not There: A Life in Two Genders, by Jennifer Finney Boylan
This was an entertaining read. Tells the story of Jenny (Jim), a professor at Colby who is a transsexual. She successfully made the complete switch to female, with the support of her wife and her closest friend. There were lots of general life stories from Jenny, about family and growing up, friends, travels, and her two sons.
This was also a difficult read, because it's a subject I can never fully understand. I identified much more with Grace, Jenny's wife; there are some heartbreaking passages as Jenny gears up for the operation, and I can almost feel Grace's sorrow at unwillingly, but necessarily, losing the life she's built for herself. Jenny also includes some email from her friend Richard Russo, that offer some of the conflicting emotions he himself is feeling, and I could also identify with that. What I would have loved to seen, though I don't think it would have really been possible for Jenny to properly explain, is more of the psychology behind the transformation. I had a lot of trouble truly understanding where she was coming from; I imagine I would still have had that trouble even if the book were nothing but psychology, because I don't have that sense of mis-assigned gender. But it seems like the most that that feeling is really explained is "I should be female. I feel female. I will eventually go crazy if I do not make this transition", which is all well and good for Jenny, but still makes it difficult for me to identify with.
I would recommend it, with the caveat of reading it as an autobiography (which, realistically, is how I think the author intended it), and not necessarily as a treatise on being a transsexual.
(side note: I like how one of the amazon keywords is "monkey orphanage". Yes, there really is a monkey orphanage mentioned in the book.)