MYRA BRECKINRIDGE by Gore Vidal

 This is one of my ancient paperbacks that I've never read and I finished on Tu 11/16/23- "Thought provoking and hilarious".

For the first section of the book you believe the narrator is a woman, but actually it is a man waiting for 'sexual reassignment surgery'- Myron changes to Myra.

From the book's page at Wikipedia:

"An attractive young woman, Myra Breckinridge is a film buff with a special interest in the Golden Age of Hollywood—in particular the 1940s—and the writings of film critic Parker Tyler. She comes to the Academy for Aspiring Young Actors and Actresses, owned by her deceased husband Myron's uncle, Buck Loner. Here, she gets a job teaching, not just her regular classes (Posture and Empathy), but also, as part of the hidden curriculum, female dominance.

The spirit of the times is reflected in Myra's attendance at an orgy arranged by a student. She intends only to observe but suffers a "rude intrusion" by a member of the band The Four Skins, from which she derives a perverse, masochistic enjoyment. At an earlier regular party, after "mixing gin and marijuana", she eventually gets "stoned out of her head" and has a fit, before passing out in a bathroom.

As part of her quest to revolutionize Hollywood and American society, Myra preys upon a student named Rusty Godowski, and eventually anally violates him with a strap on. The rape leaves Rusty, previously a gentle lover, violent and brutish in regard to sex, causing his relationship with Mary-Ann, his girlfriend and fellow student, to deteriorate. The two break up, and Myra recommends Rusty to Leticia Van Allen, a casting agent who has sex with the young men she represents.

Still in the process of transitioning from male to female and unable to obtain hormones, Myra transforms into Myron, and, as a result of the injuries she has sustained in a car accident, is forced to have her breast implants removed. Now a eunuch, Myron decides to settle down with Mary-Ann.

I have read a few of Gore Vidal's novels and this one was totally different. For the late sixties this was probably outrageous, but these days it was pretty tame. Myron goes back to a man and today this wouldn't be allowed.