Goldsmith lost his virginity in high school to a prostitute, arranged by his friend Anthony Hatzenberg, a Jewish kid who went by the name Tony Mambo.
The Puerto Rican woman invited Goldsmith up to her apartment and complained about her bladder and internal problems and told him she needed an operation.
She took his $5 and sat on the bed which was covered in damp T-shirts.
Goldsmith delivered lines that his friend Tony had given him: ‘Edie honey, I’m new at this game. You’ve got to show me the ropes’.
She did and he writes that he ‘felt powerful’ and that Edie had ‘made me a man’.
While at Boston University Goldsmith became obsessed with a woman who lived opposite his dorm and used to undress naked in the window.
After running into her at a laundromat, they ended up in bed at her place.
Goldsmith knew he was on his way to becoming a legend among his friends as he made sure they could all see what we were doing from their dorm window.
He writes that he pulled the woman’s underwear off and as they had sex he was ‘exhilarated to learn I could make a grown woman moan’.
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