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Those curious about whether Kendra Wilkinson, 29, actually had a physical relationship with Hugh Hefner , 88, during her time as one of his girlfriends living in the Playboy Mansion starting in need not wonder anymore. Kendra, who says she was 18 when she first moved in to the Playboy Mansion while Hefner was 78, rose to fame on E! The series focused on the lives of Hefner's girlfriends who lived with him at the Playboy Mansion, including Holly Madison and Bridget Marquardt. It was so much fun.
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Hugh Hefner’s Wives and Girlfriends Through the Years (Photos)

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The 14 Worst Things About Hugh Hefner, as Revealed in Holly Madison's New Book

In honor of their recent nuptials, let's take a look at the other ladies in Hef's past. Playboy founder Hugh Hefner has had countless lovers over the years — some more notable than others. Here's a chronological history of the wives, girlfriends, and Bunnies who found themselves in his bed. Because Hef has never been a one-woman man, there's a lot of overlap. Hef married his first wife in Mildred cheated on Hugh while he was in the Army, but she later gave him a free pass for sleeping with other women.
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The Many Loves Of Hugh Hefner

Most of the general public is fascinated by Hugh Hefner; most men envy him and see him as some sort of hero. His ideals on sexual curiosities and interests were not well thought of in his earlier years, as he was at times a topic of controversy. Luckily times have changed. Pictures of her are non-existent! Born: April 24, Dated Hefner: Some time in the early s Occupation: At first, she worked as a secretary at the main office in Chicago, but worked her way up to assistant cartoon editor of Playboy magazine.
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By Dailymail. Former Playboy bunny Holly Madison has lifted the lid on what really goes on in the Playboy mansion and the depression she suffered while being married to Hugh Hefner. The year-old details how, as a year-old college dropout and struggling Hooters waitress, she first met Hefner in and, after a night out clubbing with his 'girlfriends', realized that she was expected to sleep with him.
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