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Answer (don't look 'till you vote):

22!!! Bet you didn't expect that one, did you? And he didn't start masturbating 'till 18!

 

In other news, he's recently married a 24 year old with whom he wants to spend "the rest of his life" (he's 84).

Source: http://www.ontheredcarpet.com/Hugh-Hefner-reveals-age-he-lost-his-virginity-and-says-wives-cheated-on-him/7947289



"I don't understand how someone could like Tolstoy and Dostoyevsky, but not like Twilight!!!"

"Last book I read was Brokeback Mountain, I just don't have the patience for them unless it's softcore porn."

                                                                               (The Voice of a Generation and Seece)

"If you cant stand the sound of your own voice than dont become a singer !!!!!"

                                                                               (pizzahut451)