9. Nick Cannon
Nick Cannon’s marriage to Mariah Carrey wasn’t his first experience with an older woman. On an episode of Lopez Tonight, Cannon revealed that he was only in middle school when he had sex for the first time. Cannon recalled how he lost his V-card in a sleeping bag with a high school girl. But when Cannon suggested they try a different position, the older girl shouted “just get off of me!” A poor, deflowered Cannon remember how “she ran into the bathroom with all of her friends and they were in there laughing.” Completely embarrassed by the experience, Cannon left in tears.