14. Russell Brand

In his autobiography My Booky Wooky By Russell Brand, the comedian and actor detailed his first sexual experience. In true Brand fashion, his story recounted a night filled with debauchery in Hong Kong, which resulted in the loss of his virginity to a prostitute. From his memoir, Brand describes how he visited a sleazy dive bar in Hong Kong with his dad. The father and son then took three prostitutes back with them to their hotel room. Brand recalled how “back in the hotel [his] dad set about unwrapping his two prostitutes. [He] sat on the edge of the other twin bed. She must have known [he] was a virgin as soon as the bungling encounter commenced.” Unsurprisingly, that wasn’t Brand’s last encounter with Hong Kong prostitutes. His book goes on to tell that he “had sex with loads more prostitutes, never wore a condom and never fell in love.” Charming.