trying to remember the name of a book i read 20 years ago.

i know this is a long shot, but i read a book back in 2008 about a guy who was really just a complete playboy. i remember it had a black cover and was very crude. there was an entire chapter about how the guy had sex with over 200 women and how he suspected a couple of them were actually men. i don’t have much else to go off but it’s been floating around my mind lately and would love to know if anyone remembers it