Creepy First Times
Not everybody wants to share the story of their first time, but given Kendra Wilkinson's infamous sex tape, it shouldn't be surprising that she wrote all about losing her virginity at 13 in her memoir, Sliding Into Home. "We had no idea what we were doing," she described of her first time, but that was not the case when she went to sleep with Playboy's head honcho Hugh Hefner. "One of the girls asked me if I wanted to go upstairs to Hef's room… It seemed like every other girl was going, and if I didn't it would be weird," the reality-TV star and new mom recalls in her autobiography. "One by one, each girl hopped on Hef and had sex with him… for about a minute. I studied their every move. Then it was my turn… it was very weird. I wasn't thinking about how much older Hef was—all the body parts worked the same. I wanted to be there." Sure, it wasn't her first, but it was her first time with a man in his eighties who's done it many times—and that counts for something.