Hugh Hefner's Sex Life: Playboy Founder Says He's Slept With More Than A Thousand Women

Hugh Hefner Reveals How Many Women He's Slept With

Hugh Hefner is the original Playboy, and the magazine's founder reveals he's made a lot of notches in his bedpost over the years. Somehow, we're not surprised.

In a new interview with Esquire, the 86-year-old confesses to sleeping with thousands of women over the years.

"How could I possibly know? Over a thousand, I'm sure," Hefner replied when asked how many women he's taken to bed in his lifetime. "There were chunks of my life when I was married, and when I was married I never cheated. But I made up for it when I wasn't married. You have to keep your hand in."

Hefner was first married in 1949 to a Northwestern University student named Mildred Williams, with whom he has two children -- Christie and David -- before divorcing in 1959.

It would be another 40 years before Hefner would marry again -- giving him ample time to bed the thousands of women he claims to have wooed, without cheating.

During his 12 year separation from Conrad, Hefner had relationships with many of the young models featured in his magazine, including twin sisters Sandy and Mandy Bently, and even dated seven women at once. His relationship with Playboy Playmates Holly Madison, Bridget Marquardt and Kendra Wilkinson was made public with the reality series "The Girls Next Door."

In 2008, all three women decided to leave both Hefner and the Playboy mansion, prompting Hefner to start dating Crystal Harris, who was 60 years his junior, along with 20-year-old twins Kristina and Karissa Shannon. Hefner broke things off with the twins and proposed to Harris in 2010.

The couple planned to marry in June 2011, but Harris decided to call off their nuptials just five days before they were scheduled to exchange their vows. Hefner and Harris reconciled and Hef tied the knot for the third time this past New Year's Eve. And while Hef knows there are those who doubt their marriage, they don't concern him in the least.

"All our friends think it's made in heaven," Hefner told Esquire of his new bride. "It's only people who don't know us, who simply see us as stereotypes in terms of age and beauty… I just feel very, very fortunate to have found her at this stage in my life. I saved the best till last."

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Drew Barrymore

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