My Gender Workbook: How to Become a Real Man, a Real Woman, the Real You, or Something Else Entirely
by Kate Bornstein, Diane DiMasa
Read in college, for leisure. A lot of other books and blogs I was reading referenced My Gender Workbook, so I was excited to finally get my hands on a copy. Sadly, it's not really what it says on the tin. Rather than presenting different options and asking difficult interesting questions, My Gender Workbook has a strong agenda, all the exercises push you towards that agenda, and there's not a lot of other interesting stuff, especially if you're already familiar with the (101-level) arguments. I ended up skimming it.
tl;dr: Good for people who haven't ever thought about it before; less good for people who already have significant trangst.