It Looked Glamorous from the Outside — Holly Madison Shares the Truth

The former Playboy model was with Hefner for seven years.

Holly Madison used to say how “disgusting” it was to do anything with Hugh Hefner in his California estate that she “hated.”

Madison, who is now 45, started dating Hefner, the man behind Playboy, when she was 22. Hefner died in 2017.

The two were together from 2001 to 2008, but the father of four was also dating other women at the same time, such Kendra Wilkinson and Bridget Marquardt. They were 53 years apart in age.

Madison, who used to be a Playboy model and a reality TV star, has talked about a lot of things that have happened in the house over the years. These had strict regulations that residents had to follow, including not wearing lipstick.

On Owen Thiele’s podcast In Your Dreams, Madison has discussed about the law about group sex parties. Hefner’s women have to follow it too.

The mother of two said that sex was “very different” when she and Hefner were alone, but it was “disgusting” when other people were there.

“I hated it.” “I made it very clear that I didn’t like it,” she stated.

Madison said that her time alone with Hefner was a lot more “normal.” Then she remarked, “It was a lot more normal than you might think if it was just him and me.”

The Girls Next Door star stated she didn’t mind dating someone younger than her, but she knew that other people would condemn her for it.

She told Thiele, “There was a time when I couldn’t post anything without someone in the comments saying something like, ‘Oh, old balls.'”

“Some people’s balls might get old and gross, but I’ve never seen that happen.”

Madison also talked about how she and Hefner would have sex with the lights off on the podcast. She went on to say, “All cats are gray in the dark.”

The former model said that the many sex parties usually happened on the same two days of the week.

“After the club, it was always Wednesdays and Fridays.” In 2015, she told Buzzfeed that it was always the same since that’s how he wanted to live.

Madison added that all of Hugh’s girlfriends had to do it because they “understood it as a necessary and expected part of living there.”

“And it felt like work to me,” I said.

Madison said in 2022 that her ex-boyfriend was likewise quite controlling about how she looked.


“I reached a point not too long after I got there where I kind of broke under that pressure and felt like I had to look exactly like everyone else,” she revealed on A&E’s Secrets of Playboy.

“I thought, ‘I’m going to cut my hair so I can look different,’ because it was naturally very long.”

Madison said that when she cut her hair, Hefner “flipped out” and told her in a severe way that the cut made her “look old, hard, and cheap.”

“I remember times, probably in the first couple of years I lived there, when I felt like I was stuck in a cycle of gross things and didn’t know what to do,” she said.

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