http://www.amazon.com/Self-Made-Man-Womans-Journey-Manhood/d...
There are also a lot of interesting works by transgender people, but the perspective there is different, since they usually report that they never felt comfortable in their birth gender.
Ben Barres (formerly Barbara Barres) wrote a great piece in Nature ("Does Gender Matter?") after the Larry Summers debacle. There's an interview with him here: http://www.nytimes.com/2006/07/18/science/18conv.html?pagewa...
Pretty convincing stuff on the role gender plays in our interactions with each other. To me, what's so fascinating about the experience of transsexuals is that they literally have controlled experiments going on-- they're the only people who can experience life in two different bodies. What a useful perspective to have-- I'll never know what life is like as someone of another gender/race/ethnicity, but I imagine it would be incredibly mind-expanding if I could.
There's Robert Rosenthal's study that showed that others' belief that you are "gifted" actually results in an IQ increase. There's the famous "McKay" study, in which test subjects evaluated identical academic papers by "John" and "Joan" McKay. And on and on.
What's really interesting is the experience of post-op transsexuals, like biologist Ben Barres (who was Barbara Barres until he was in his 40s). These folks are the true secret shoppers of gender-- and the ultimate control group in terms of understanding how gender affects one's experience of the world. It would be really interesting to find a comparable race test case (an updated "Black Like Me").
A few years ago I wrote about this phenomenon in Slate-- I looked at women and ambition in general. Check out the piece if you're interested in a more generalized analysis: http://www.slate.com/articles/news_and_politics/the_gist/200...