Several women who previously dated Hugh Hefner have spoken in frank terms about what intimacy with the Playboy founder was like, following renewed attention after Holly Madison discussed her own experiences.
Madison, one of Hefner’s most publicly recognizable former partners, was in a relationship with him from 2001 to 2008. During that time, she became his “number one” girlfriend and moved into the Playboy Mansion, where the relationship structure meant sharing him with other women.
Now 46, Madison has also addressed the public scrutiny around their 53-year age gap, including years of online commentary about Hefner’s body. Speaking on the In Your Dreams podcast, she said she had “never seen such a thing” and explained that they would typically have sex with the lights off.
What she has been most vocal about, however, is her aversion to sex involving multiple people, which she has described as upsetting and humiliating compared to being alone with him.
“If it was just me and him, it was a lot more normal than you would think,” she said.
“It’s a very different story between when we were just by ourselves than with everybody else in the room. Everybody else in the room, no. That was disgusting.
“I hated it. I made it very known I hated it.”
Since Hefner died in 2017 at 91, more former girlfriends and women associated with Playboy have shared critical accounts of what they say happened behind closed doors. Some of the most serious allegations and concerns were later explored in A&E’s docuseries Secrets of Playboy.
‘Less sex-savvy than teenage boys’
Crystal Hefner, who was married to Hefner at the time of his death, described her experiences in her memoir, Only Say Good Things: Surviving Playboy and Finding Myself. In it, she claims Hefner was ‘less sex-savvy than some of the teenage boys I’d been with years ago’.
Madison has also revisited details from her time at the mansion on Girls Next Level, the podcast she co-hosts with fellow Girls Next Door alum Bridget Marquardt. On the show, Madison compared Hefner’s behavior in bed to a lack of participation, saying: “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. Especially as we got later down the road when there would be, like, a lot of conflict with the other girls.”
She said, per the New York Post: “You’re literally sitting there naked having sex in front of a group of people who hate you and talk s*** about you while you’re having sex, and you can hear it. It was just, like, hell.”
Marquardt has also described the environment around Hefner’s private space as unpleasant. She alleged that his bedroom was chaotic and cluttered, describing a scene that felt more like a storage room than a glamorous retreat.
“We walked in and it was just a disaster in there. The lights were out, but there were two giant TV screens in there that were playing porn … There’s just so much junk,” she said.
Madison added her own description of the same room, saying: “It was just hoarder-style. Imagine thinking you’re this big player and you’re bringing all these girls home, and your room looks like s***. It’s like the weird eccentric millionaire version of the guy with the mattress on the floor and a Pulp Fiction poster.”
Other accounts in Secrets of Playboy included claims from Karissa and Kristina Shannon, who alleged that sexually transmitted infections were an issue because Hefner didn’t like to use condoms.
“From the butlers, we’d just order a big bowl and we’d put hot water in it, then we’d put rags in it,” Karissa said. “So whoever was having intercourse with him, when they were finished, they can wipe him off. And then the other girl could do it.”
‘There was no way around it’
Kendra Wilkinson, who was part of the well-known group dynamic with Hefner alongside Madison and Marquardt, also addressed the experience in her book Sliding into Home. She wrote that she relied on substances to cope with those nights, stating: “I had to be very drunk or smoke lots of weed to survive those nights – there was no way around it.”
Hefner was married three times and had multiple girlfriends over the years, but Madison, Wilkinson, and Marquardt became especially famous due to the reality series Girls Next Door. In the years since, a number of women connected to Playboy have continued to share their perspectives on intimacy, consent, and power dynamics within the mansion.
In her 2024 memoir, Crystal Hefner also described parts of their sex life in clinical terms, alleging it often revolved around what she called ‘blue little pill nights’ due to medication she says he needed.
She further claimed she would play the same Madonna song each time so that ‘no other music [would] be contaminated by this place’ for her.
Crystal also characterized the routine as repetitive, writing: “This was a well-oiled and well-practiced sequence of events. One that went the same exact way every time.
“Picking some girls from the party and bringing them up. Changing into the uniform for the job: silk pajamas. The dimming of the lights. The music. The porn. Passing the pot. And then the sex.”
She described it as though Hefner ‘was just going through the motions of something that had once been fun and sexy’.
Crystal added: “Or maybe it was never fun and sexy.”
On Girls Next Level, Marquardt also alleged the existence of a detailed ledger tracking financial and sexual arrangements.
“The black book kept track of a few different things,” she explained. “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.”
Madison has documented her own version of life at the mansion in her book Down the Rabbit Hole: Curious Adventures and Cautionary Tales of a Former Playboy Bunny.
Describing how she was instructed to dress when she was first invited to live on the property, she wrote: “When I think about it now, it’s almost comical. Every red-blooded American male has no doubt fantasized about what went on in Hugh Hefner’s bedroom with his harem of blond bombshells. The answer? Not a whole lot.”
She added: “My turn was over just as quickly as it had started.”
Sondra Theodore, who dated Hefner between 1976 and 1981, also shared her recollections in A&E’s Secrets of Playboy, describing the relationship as increasingly unsettling toward the end.
“He scared me a lot at the end because you couldn’t satisfy him — he had to have more and more and more,” Theodore recalled.
“I might as well have been a vibrator, I might as well have been a sex toy — because that’s what it was. And nobody knew the hell I was in.”
Kristina and Karissa Shannon, who were featured in the same docuseries, said they were invited to Hefner’s bedroom on their 19th birthday and later associated the night with distressing memories.
During an interview for the series, Karissa claimed they were offered a pill that made them feel ‘the most inebriated we’ve ever been’, before having sex with the then 86-year-old.
“We had never done a threesome together before, we would never want to,” Kristina said.