The best books to make you think about gender (and sex)

Although I endorse Rothblatt's ideal of a sex-irrelevant society, I think he fails to fully comprehend the subordination by sex that females currently experience. And if he hadn't been so rich (like Jenner), he might not have voluntarily become a member of that sexed underclass. (I suspect his money has largely insulated him from the negative effects of being perceived as a woman.) That said, this 1995 book is a pioneering classic. (Though I think the subtitle should have been "A Manifesto on the Freedom from Gender" — not " A Manifesto on the Freedom of Gender".)

Another classic, written in 1984 by the author of Against Our Will: Men, Women, and Rape, Brownmiller covers a lot: body, hair, clothes, voice, skin, movement, emotion, ambition. She says in her prologue, "I offer this book ... in the hope that the feminine ideal will no longer be used to perpetuate inequality between the sexes, and that exaggeration will not be required to rest secure in biological gender." 

For those of us who grew up thinking we were the weaker sex/gender, this is a must-read book. When the deck is not stacked in favour of upper-body strength and short bursts of speed, and when factors such as height and weight are controlled (as the latter is, for example, in wrestling competition), women may actually be the stronger sex. I was particularly intrigued—no, annoyed—to read about sports that became segregated by sex only after women proved their superiority (for example, skeet shooting and rifle shooting).

I have always thought that we desperately need to hear from transmen and transwomen to help distinguish the effects of biological sex from those of cultural gender conditioning—more specifically, to illuminate both the influence of our respective high levels of estrogen or testosterone) and, in a word, sexism. Using interviews with transmen, Schilt very much does the latter. Consider this book a thorough precursor (2010) to the much-publicized experiences of Martin and Nicole (Google it); Martin concludes, about his experience being treated as Nicole, "It sucked." Indeed. (And the surprise experienced by so many transmen at their post-trans experiences supports the view that most women have no idea how easy men have it.)

Reading much like a novel, Vincent's book is a first-person account of a woman going undercover as a man (cross-dressing drag rather than trans, per se) to discover what men are like: "I found masculinity distilled, unmitigated by feminine influences, and therefore observable in a concentrated state" (p181).  An intriguing contrast to Schilt's book, Vincent says "It was hard being a guy" (p275); "Someone is always evaluating your manhood" (p276); "I saw how degraded and awful a relentless, humiliating sex drive could make you" (p277).