Sean Combs, aka P. Diddy told Playboy Magazine that he had been trying to lose his V-Card since age 7. He even tried to do it by climbing on top of a girl who was nine or ten, but his mother and babysitter stopped him. So it wasn't until he was 13 that he managed to lose it at a cheap hotel in the Bronx, and he's not ashamed for having his first experience there either.