How Awful Was Sex With Hugh Hefner? It Was Even Worse Than You Think

It's not exactly Sonny Koufax describing Vanessa's sex with Sid as "...that big, white, wrinkly body on you with his loose skin and old balls," but it's close. Holly Madison, former girlfriend of Playboy founder Hugh Hefner, described doing the dirty with Hef as "traumatic," and left her feeling horrified.

Ya don't say?

Note to the ladies out there: If you're looking to snag a ride to pound town from a local silver fox: you might want to reconsider. "After it happened, I was just mortified and embarrassed," Madison told the Power: Hugh Hefner podcast of her first time partaking in senior citizen sex.


As part of her media tour to promote January's A&E docuseries: “Secrets of Playboy,” Madison described the first night her and Hefner played a little game renowned divorce mediator Jeremy Grey refers to as "just the tip."

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

At the time Hefner was 75 years-old and Madison was 21. She's previously admitted that she moved to the Playboy Mansion and dated Hefner as way to get out of debt.

After their first date and corresponding (presumed) Viagra-fueled nightcap, Madison, with Hefner's blessing, moved into the Playboy Mansion. “I felt like, ‘There’s no taking that back, so I might as well get what I came for,'” said Madison. “I felt like by moving myself in and getting what I wanted from the situation, that was demanding respect in a way.”

Madison, who dated (along with a handful of other women) Hefner for seven years, added: “I felt like if I didn’t do that, I was just going to be haunted by this experience."

That makes sense, because the only way to avoid being haunted by the recollection of having sex with someone more than 50 years your senior, is to move in with them and continue sleeping with them.

Despite their sizable age gap, it's easy to see why Madison was initially so willing to knock boots with Hefner. Like Sid before him, Hefner had already achieved so much, was still goal-oriented, focused and had a five-year plan. Old balls and all.


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Anthony is a former high school basketball intramural champion who played a leading role in creating two offspring. He spends his weekends hoping for an MTV Rock N' Jock revival. Follow him on X (@OhioAF).