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6 Two-Second S*x

Holly Madison was once Hugh Hefner’s number-one girlfriend. She moved in at the Playboy Mansion in the early 2000s at the age of 21, while Hef was 74 years old.

In her tell-all memoir released in 2015, Madison claimed she couldn’t even recall what s*x with Hef felt like beyond having a heavy body on top of her.

Hefner’s final wife, Crystal Harris, even said that she only had one instance of s*x with her late husband; she claimed it lasted for just about two seconds.

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5 Orgy Bedtime Ritual

In another part of Madison’s story, “girlfriends” needed to take part in Hefner’s bedtime ritual, involving a “group orgy” in which King Hugh would be the focus of their pleasure-inducing activities. He multitasked in the ceremony as he also smoked pot and watched p*rn somewhere along the way.

 Every girl would get her turn, albeit very briefly before Hef moved to his actual girlfriends and finished himself off. In fact, according to Madison, he always finished himself off.


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