Myra Breckinridge

I guess it's satire (fans of Gore Vidal will know what I mean) but as a genre-defying and ingenious way of examining gender and the newly-assertive femininity of the 1960's this takes some beating, although, for my tastes, the follow-up "Myron" asks more questions about transitioning and gender-relations. Not seminal but quite foundational, and often funny (so maybe it is a satire)