Playboy star Holly Madison opens up about ‘mortifying’ sex with Hugh Hefner

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A Playboy housemate asked to move in with Hugh Hefner the morning after they first slept together.

Holly Madison has previously spoken at length about her time inside the Playboy Mansion, which she has referred to as a “cult-like environment”.

Now, interviewed about her involvement with Playboy on the Power: Hugh Hefner podcast, Holly has revealed that she was invited to sleep with Hefner for the first time after a rare night out for the tycoon.

Holly remembered returning home from her first night out with Hefner, saying: “That night we all went upstairs. I wasn’t necessarily expecting to have sex that night, I thought it would be more of a first date.

“I thought it would be more the type of thing where I kind of, saw what happened and saw what was going on, if I wasn’t comfortable with it I wouldn’t have to do anything, and I could make my decision on whether I wanted to come back for date number two or not.

“I was wasted, he was literally pushed on top of me, and after it happened, I was just mortified and embarrassed. It had way more of an emotional impact on me than I thought it would.”

Holly went on to live with Hefner for several years, and she described how her feelings were left confused after the incident, having admired him for so long.

“I had always kind of admired Hef from the limited interactions I had with him. I thought he was really smart, I really looked up to him, so I liked him," she admitted.

“So it wasn’t that the idea of possibly having sex with him repelled me so much… it was more the group aspect that was really out of my comfort zone.”

And, the model acknowledged that it might seem counterintuitive that she decided to press on in her engagements with Hefner despite struggling with the first night.

But, she explained that once she had taken her first steps, she decided that she might as well continue, all with the objective of getting a centrefold in the Playboy magazine.

“The next morning I found Hef where he was, and I was like, ‘hey, I know you have a spot open, what do you think about me moving in and we’ll see how it works out’," she continued.

“I don’t know how anybody else sealed the deal as far as moving in, or if they ever did it that quickly. He seemed a little taken off guard, and he was like, ‘oh yeah we’ll see how it goes’.

“I felt like by moving myself in and getting what I wanted out of the situation, that was like demanding respect in a way.

“Because I felt like if I didn’t do that, then I was just going to be haunted by this experience and going back to all the problems I had in the real world.”

Holly eventually split up with Hefner, and left the Playboy mansion in 2008. She has since written a memoir, ‘Down the Rabbit Hole’, where she detailed her life with the Playboy boss.

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