Hugh Hefner, founder of Playboy and someone known for hosting wild parties and bedding many women, passed away in 2017 when he was 91 years old.
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Now, nearly a decade later, a few of the people who he spent his time with have come forward with stories of their time with a man who embraced his larger-than-life reputation.
Hefner’s last wife, Crystal Harris, met him when she was 21 years old and he was 60 years her senior in 2008. The two got married five years later and while not much was known about their relationship at the time, her book Only Say Good Things: Surviving Playboy and Finding Myself delves deeper into her time in the Playboy Mansion.
Highlights
- A handful of the "girlfriends" who were present in Hugh Hefner's Playboy Mansion have opened up about "hating" intimacy with the publisher.
- Crystal Harris, Holly Madison, and Bridget Marquardt were among the women who spoke up.
- Kendra Wilkinson confessed she needed alcohol or weed to endure the distressing group s--x nights at the Playboy Mansion.
The women who were in the Playboy Mansion with Hugh Hefner have opened up about their experiences with the founder
Image credits: Charley Gallay/Getty Images
Regarding their more intimate moments, Crystal described Hefner as someone who required her to have “odd and robotic” s–x with him, as well as the other women who were around at the time, as reported by PEOPLE.
“This was a well-oiled and well-practiced sequence of events. One that went the same exact way every time,” she wrote. “Picking some girls from the party and bringing them up. Changing into the uniform for the job: silk pajamas.”
Image credits: Charley Gallay/Getty Images
Image credits: Prime Video
She later went on to describe that Hefner was merely “going through the motions of something that had once been fun and s–xy. Or maybe it was never fun and s–xy.”
Their marriage lasted until Hefner’s passing in 2017.
Hefner had multiple "girlfriends" within his mansion
Image credits: Alan Light
Holly Madison was another woman who spent a significant amount of years with the Playboy founder. She moved into the mansion in 2001 when she began facing credit card debt and potential homelessness, soon becoming Hefner’s “lead” girlfriend.
She spoke in detail to SiriusXM’s In Your Dreams in May 2025 about how she “hated” the “disgusting” group s–x nights that took place, but on the other hand, the private intimate moments they shared were “more normal than you’d think.”
When co-host Owen Thiele called her bluff, Madison defended, “Nobody does… There was a time when I couldn’t post anything [on social media] without some dumba– in the comments like, ‘Oh, old balls.’”
Image credits: Netflix
Their relationship ended in 2008 when Madison wanted to marry Hefner and have his children — only to be met with a blatant refusal.
The now 45-year-old and her co-star on Girls Next Door, Bridget Marquardt, decided to make their own podcast titled Girls Next Level, with their earlier episodes reflecting on their time in the bedroom with Hefner.
Intimate moments were never quite as intimate as some of the girls would have hoped
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Image credits: Prime Video
Madison explained that the voyeuristic aspect of having the other “girlfriends” watch was a particularly uncomfortable moment for her.
“He wouldn’t move. He would be like a bump on the log in the middle of the bed. I can’t explain to you guys how embarrassing that whole routine was,” she said, according to the New York Post.
“Especially as we got later down the road when there would be, like, a lot of conflict with the other girls,” adding that it was never a pleasant experience to be intimate with someone while a “group of people who hate you and talk sh–t about you” watch on.
“It was just, like, hell,” she described.
Holly Madison gave a detailed explanation in a SiriusXM interview of her time in the mansion
Image credits: Prime Video
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Marquardt also chimed in to discuss how Hefner had a tendency to keep tabs on all the girls.
She said, “The black book kept track of a few different things. It kept track of when somebody collected their allowance. He would mark it off so you couldn’t ask for it twice. It also kept track of who slept with him and when.”
Hefner and Marquardt’s relationship was documented on the reality show from 2005 to 2009. Her encounters with the publisher were “definitely no more than a minute.” After the two lost touch, she revealed that she was no longer welcome in the Playboy Mansion.
Image credits: Glenn Francis
Kendra Wilkinson, the last “girlfriend” who was featured in The Girls Next Door joined the conversation with her 2011 memoir Sliding into Home. She echoed what many others had said about the unpleasant experience of group s–x.
“I had to be very drunk or smoke lots of weed to survive those nights — there was no way around it,” she wrote.
Safe to say, the E! reality show left out a lot of what was hiding behind the four walls of Hefner’s infamous mansion. From the drama unfolding amongst the various women to the toll it took on a handful of them, these now-public stories have finally allowed viewers to dissect what really happened in those secret, un-aired moments.
Many netizens did not show much sympathy for the women involved, citing his wealth and the money they received
