Hugh Hefner with Holly Madison
Julie Hambleton
Julie Hambleton
January 27, 2024 ·  6 min read

Holly Madison Recalled The “Gross” Experience Of Sleeping With Hugh Hefner And Being “Afraid To Leave” The Mansion.

Everyone knows the Playboy brand as well as its famous (or should we say infamous) founder, the late Hugh Hefner. Though he died in 2017 at the age of 91, former Playboy Bunnies and other women have continued to speak out about the atrocious things that went on both in the Playboy clubs and the Playboy Mansion. A warning: Some of the topics in this article could be triggering for survivors of sexual abuse and harassment.

The Truth Behind Hugh Hefner and Playboy

Playboy rose to fame on the back of the toxic masculinity that most of society is now beginning to take a stand against. Since founder Hugh Hefner’s death in 2017, many of the women that used to be involved with him are speaking out about what went on in his clubs and particularly in the Playboy Mansion. A recent docu-series on A&E called Secrets of Playboy is just one piece that is revealing so many of the horrible things that Hefner and Playboy allowed, and encouraged. (1)

Sondra Theodore, a former “girlfriend” of Hefner’s who is now 65, says that he hosted group sex at the mansion at least five nights per week. He also hosted what he called “pig nights” where he brought in dozens of “ugly” prostitutes to have sex with his friends. He regularly dosed girls in the mansion and in his clubs up on alcohol and Quaaludes which Hefner referred to as “thigh openers”. When he got the girls on those, they would essentially do anything that he or his friends wanted. (2)

“The group sex was at least five nights a week” she said in the documentary. “They had a protocol. He liked to direct and you didn’t segue away from it because you could tell it irritated him.”

Hugh Hefner

No Consequences In The Clubs

In the Playboy clubs, there were essentially no rules. The members could basically do as they pleased without fear of any consequences. In one incident, Soul Train host Don Cornelius allegedly held two Playboy bunnies hostage in his home and raped one of them. Everyone at the club knew about it, but nothing was done, nothing was reported, and he continued to go to the club afterward with no consequences whatsoever. Unfortunately, this kind of mistreatment of the bunnies was completely normalized.

“It was cult-like. The women had been groomed and led to believe they were part of this family,” Miki Garcia, former director of Playmate promotions said. (3)

Read: Man Used Internet Registry to Track down and Beat up Pedophiles

The Mansion Was No Better

Holly Madison who used to live in the mansion was Hefner’s “main girlfriend” for a time. She described her relationship with the mogul as a version of Stockholm syndrome. Madison says that he refused to wear protection during sex and that living in the house nearly drove her to suicide. She has since written a book about her experience, and also why it took her so long to leave.

“I remember there were times probably within the first couple years I lived there when I felt like I was just in this cycle of gross things and I didn’t know what to do” she explained.

She had a 9 pm curfew and Hefner discouraged her from leaving the mansion unless it was for a family holiday. He forbade her to wear red lipstick and freaked out on her once when she cut her hair. He made sure to pit all of his girlfriends against one another so that they hated each other rather than supporting one another. Despite all of this, leaving wasn’t necessarily an easy option. This is what led Madison to nearly commit suicide.

“I was afraid to leave. Something always lingering at the back of my mind since the very beginning. If I left there there was this mountain of revenge porn waiting to come out,” she explained, though she said in the beginning he completely “love bombed” her. “When you’d go out with Hef he was taking all kinds of naked pictures of these women when we’re wasted out of minds and he would print off eight copies, for him and all the women and pass them around. It was just gross.”

Hugh Hefner, Holly Madison (left), Bridget Marquardt (center), and Kendra Wilkinson (right) at the Los Angeles premiere of 'House Bunny' held at the Mann Village Theatre in Westwood, USA on August 20, 2008
Hugh Hefner, Holly Madison (left), Bridget Marquardt (center), and Kendra Wilkinson (right) at the Los Angeles premiere of ‘House Bunny’ held at the Mann Village Theatre in Westwood, USA on August 20, 2008. Shutterstock

Despicable Acts

Hefner’s personal doctor also lived in the mansion with her father and witnessed some pretty atrocious things. As she got older, around the age of 17, Hefner began trying to get her to also participate. One time, she walked in on him giving fellatio to their dog. This wasn’t the only time a dog was involved either. Former Playboy Bunny Mother PJ Masten described what happened once when a bunch of Hefner’s friends showed up to the mansion with a woman who was so drunk and drugged she could barely stand.

“All the guys were laughing when she got out of the limousine. She was drunk and drugged,” she described. “All of a sudden out of nowhere a German Shepherd shows up. They got her so messed up they made her give the German shepherd oral sex. You want to talk about depravity? This is despicable!”

The Secrets Are Out

Between this new documentary series and the various books and confessionals that have now been written about Playboy, Hefner and his brand are finally being shown for what they really were. Playboy, which is no longer owned or affiliated with Hefner or his associates, has written a statement about the documentary and applauded all the women for coming forward.

“Today’s Playboy is not Hugh Hefner’s Playboy. We trust and validate these women and their stories and we strongly support those individuals who have come forward to share their experiences,” the statement said. “As a brand with sex positivity at its core, we believe safety, security and accountability are paramount. The most important thing we can do right now is actively listen and learn from their experiences. We will never be afraid to confront the parts of our legacy as a company that do not reflect our values today. As an organisation with a more than 80% female workforce, we are committed to our ongoing evolution as a company and to driving positive change for our communities.”

We can only hope that the women involved can find peace and that this series helps other women who have experienced sexual abuse and trauma find peace as well.

Keep Reading: Owen Wilson Volunteered to Take DNA Test for His Third Child Whom He Was Never Going to Meet

Sources

  1. EXCLUSIVE: ‘He really believed he owned these women.’ How Hugh Hefner demanded orgies five nights a week, drugged women with ‘leg spreader’ Quaaludes and hosted weekly ‘Pig Nights’ with ‘ugly’ prostitutes, new doc reveals.” Daily Mail. Daniel Bates. January 17, 2022.
  2. Former Playmates say life with Hugh Hefner at Playboy Mansion was ‘cult-like’.” Cosmopolitan. Jade Biggs. January 19, 2022
  3. He really believed he owned these women.’ How Hugh Hefner demanded orgies five nights a week, drugged women with ‘leg spreader’ Quaaludes and hosted weekly ‘Pig Nights’ with ‘ugly’ prostitutes, new doc reveals.” YC. Your Content Staff. January 18, 2022.