A 25 Year Old Gay Man Loses His Virginity to a Woman (1990)

"This tape is an exploration of my latent heterosexuality with porn star / performance artist Annie Sprinkle as instructor and sage. After assuaging my fears that I can have sex with a woman & still maintain my gay identity, Annie warms me up with some playful, sensual wrestling. She then instructs in the use of a tampon while relating men's need to make war with their inability to menstruate. For the rest of the tape, she guides me through the specifics of sexual exploration, positions of coital congress as well as post- coital ritual."

Documentary