Numerous former Playboy bunnies have opened up about their experiences of life at the Playboy Mansions – including their most intimate moments with founder Hugh Hefner.
Eight years ago, in 2017, the Chicago-born magazine publisher passed away at the age of 91, and since then, more and more of his former girlfriends have spoken out about living in the Playboy Mansion – his Los Angeles estate that he purchased back in 1971.
Hefner was married three times and had numerous girlfriends, with three of those, Kendra Wilkinson, Holly Madison and Bridget Marquardt, all shooting to fame with their reality TV show, Girls Next Door.
As well as a 2022 documentary, Secrets of Playboy, other girlfriends have given their insight into their lives as one of Hefner’s girlfriends.
Upon his death, his third and final wife Crystal Hefner, is believed to have inherited $7 million in cash as well as a $5 million home in Hollywood.
After marrying an 86-year-old Hefner at the age of 26 herself in 2012, Crystal stayed with him until the end.
In her biography she released last year, titled Only Say Good Things: Surviving Playboy and Finding Myself, Crystal described sex with him alone as being ‘blue little pill nights’ due to the medication he needed to perform in the sheets.
She also shared that she’d played the same Madonna song each time so that ‘no other music [would] be contaminated by this place’ for her.
‘Odd and robotic’
In the book, she also described their sex life as ‘odd and robotic’, as she wrote: “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 the experience as if Hefner ‘was just going through the motions of something that had once been fun and sexy. Or maybe it was never fun and sexy’.
‘Disgusting’ sex act and ‘normal’ manhood
Hugh Hefner with third wife Crystal back in 2014 (Charley Gallay/Getty Images for Playboy)
Speaking on the In Your Dreams Podcast with Owen Thiele, Holly Madison explained what it was like having sex Hefner along with his other girlfriends at the time, compared to when they were alone together, which she described as ‘a lot more normal’ than what was expected.
Madison explained: “Well, 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. If it was just me and him, it was a lot more normal than you would think.”
She added: “I think everybody has this real horror story of how gross an old man’s body must be. I feel like there was a time when I couldn’t post anything without some dumb*** in the comments like, ‘Oh, old balls’, or something like that and look, maybe some people’s balls do get old and nasty, but I’ve never seen such a thing.”
‘How embarrassing’
Holly Madison and Hefner were together from 2001 to 2007 (Michael Bezjian/WireImage)
While speaking on her own podcast Girls Next Level with her co-host Marquardt, Madison described how Hefner acted during the orgies she was involved in.
“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.
“Especially as we got later down the road when there would be, like, a lot of conflict with the other girls.
“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.”
Having to be ‘intoxicated’ to get through it
Kendra Wilkinson and Hefner (Denise Truscello/WireImage)
Kendra Wilkinson, who starred alongside Madison and Marquardt as one of Hefner’s three girlfriends that featured on The Girls Next Door, also released a memoir about her time in the Playboy Mansion.
The book, titled Sliding into Home, was released back in 2011 and it detailed how Wilkinson ‘survived’ the orgies she was involved in.
“I had to be very drunk or smoke lots of weed to survive those nights – there was no way around it,” she wrote.
‘Two giant TV screens’ in bedroom ‘playing porn’
Speaking on their podcast, Madison and Marquardt even painted the picture of what his bedroom looked like.
“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,” Marquardt shared.
Madison added: “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.”
Bridget Marquardt (far right) described what Hefner’s bedroom looked like (Jason LaVeris/FilmMagic)
‘Black book’
While Marquardt touched on the fact that Hefner had a journal which detailed who had been having sex with him and when.
“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.”
While both Madison and Marquardt also spoke of how they heard tales from other ‘bunnies’ that he’d called them out if they refused sex with him on personal grounds.
They shared: “He’d be like, ‘Oh, you’ve been on your period for three weeks.’ “
‘Almost comical’
Like Crystal, Madison also published a book on her time in the Playboy Mansion, titled Down the Rabbit Hole: Curious Adventures and Cautionary Tales of a Former Playboy Bunny.
Reflecting on how she was ordered to put on pajamas when she was first asked to live in Hefner’s estate, 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.”
‘Nobody knew the hell’
Sondra Theodore and Hefner (Images Press/IMAGES/Getty Images)
Another of Hefner’s girlfriends, Sondra Theodore – who dated then socialite for five years between 1976 and 1981, reflected on their time together while being interviewed for A&E’s Secret’s of Playboy.
“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.”
Like having ‘sex with your grandpa’
Meanwhile, twins Karina and Karissa Shannon also spoke about how their 19th birthday was ruined after they were invited to Hefner’s bedroom.
Speaking on the A&E docuseries, Karissa claimed that they were both offered a pill that made them ‘the most inebriated we’ve ever been’, before engaging in sex with the then 86-year-old.
“We had never done a threesome together before, we would never want to,” Karina said, to which Karissa added: “And that was our 19th birthday. You’re never going to forget that. He didn’t even finish. Just imagine this, just his old hand kind of shakes [as he’s] touching your boob.
Karina Shannon, pictured to the immediate left of Hefner, and her twin sister Karissa – pictured to the immediate right of the millionaire, back in 2009 (Michael Bezjian/WireImage)
“It’s like you’re having sex with your grandpa. And he laid there, looking up, and he was like, ‘My babies, my babies. You love me.'”
Karissa continued: “We ran down the hall to the spare bedroom we were staying in. We hit the shower, steaming hot. Our skin was red from just trying to, like, sterilize.”
Hefner wouldn’t use ‘protection’
Karissa also claimed how there was a time when a number of Hefner’s girlfriends caught chlamydia at the same time due to the millionaire being unwilling to put a condom on.
“The problem is Hef doesn’t like to use protection. 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,” she 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.”
Cleaning ‘dildos’ from the floor
Hefner’s former valet described picking ‘dildos’ from the floor (RICH SCHMITT/AFP via Getty Images)
In the same docuseries, Hefner’s former valet, Stefan Tetenbaum, explained how he used to have to collect dildos from his bedroom floor after his sex sessions before readying the room for another round.
“I had to put on rubber gloves and pick up the dildos from the floor and put them in a special bucket,” he explained.
“The maids would take them downstairs, spray them with a steam cleaner to sterilize them and then put them in plastic bags. I would carry them back upstairs and put them back in the headboard.”
‘Hefner taped everything in his bedroom’
Tetenbaum went on to explain how his former boss captured surveillance footage of everything that went on in his bedroom – even when he invited guests to ‘use’ the room.
“Hefner taped everything in his bedroom and many men and stars and athletes came into the bedroom and had sex with these girls. Most of the time Hefner never participated. He just watched, he was a voyeur,” Tetenbaum said.
Madison also claimed in the documentary that he kept videos and photos of women to blackmail them. In 2022, Crystal took to Twitter to share that she had discovered ‘thousands’ of prints from disposable cameras.
“I found thousands of those disposable camera photos you are talking about @hollymadison,” she typed.
“I immediately ripped them up and destroyed every single one of them for you and the countless other women in them. They’re gone.”
Girls Next Door star Holly Madison has explained why Playboy founder Hugh Hefner had an ardent hatred of lipstick.
Hefner, who died in 2017 from sepsis brought on by an E. coli infection, is best known for creating his larger-than-life Playboy empire.
Founded in 1953, the business initially began as a lifestyle and entertainment magazine, but has since branched out into sexual wellness, gaming, and beauty spaces.
Famous for its photo spreads, the magazine has had famous faces such as Pamela Anderson, Jenny McCarthy, and Raquel Pomplun grace its front cover and becoming Playboy Playmates – a model who appeared in the centerfold of the monthly publication.
Despite never being a Playboy Playmate herself, Madison, 44, appeared in four pictorials beside her Girls Next Door co-stars.
Her first was in the November 2005 issue, four years after she moved into the Playboy mansion and became one of Hefner’s girlfriends.
Madison and Henfer dated for seven years (Denise Truscello/WireImage)
It’s understood Madison was facing credit card debt when she began living at the infamous Californian abode, and that she became the founder’s ‘#1 Girl’ in 2002.
The former flames dated for seven years before calling it quits on their romance in 2008.
Speaking on an episode of the Ahead of the Curve with Coco Mocoe podcast, the mum-of-two recalled Hefner’s strict rules when it came to the women living in the mansion.
Talking about Hef’s ‘control tactic’ surrounding his aversion to a bit of red lippy, Madison explained: “I think it was a control tactic, but also, when I was brand-new, I wore red lipstick out a couple of times, and he didn’t say anything about it, because when you were the new girl in the group, you were always treated well.”
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Madison recently opened up about her experience in the Playboy mansion (Mark Sullivan/WireImage)
Madison went on to share a particular phrase she had previously heard: “Somebody said, like, the higher up you are in a cult, the worse you’re treated, because they want the new people to bond and feel into it.”
But after half a year of Madison living at the Playboy residence, everything began to change.
“It wasn’t a big deal until, like, six months into it, when I was living in his bedroom and I was the main girlfriend,” she continued.
The model said her ex-flame didn’t like her wearing red lipstick (Denise Truscello/WireImage)
“That he felt like he had the leeway to yell at me over it.”
Madison then opened up on her theories as to why Hefner was so controlling over his girlfriends’ makeup choices.
“I think he didn’t love it,” she claimed.
“Because when he invented the concept of a Playmate in the ’50s, he wanted the women to look very young and fresh-faced because he felt like the look in the ‘50s at the time was very – he described it as ‘somebody’s older sister’.”
Explaining a little more behind the businessman’s reasoning, Madison went on: “It was more sophisticated, fashion model, red lipstick.
“It was a lot of fabric and big skirts and everything, and he hated that.”
Instead, she claimed: “He wanted skimpy and fresh-faced and very young-looking.”
And if you thought that was a bit odd – wait for this.
A former Playboy Bunny who once lived with Hugh Hefner now spends her days living in a tent.
Louise Glover was once one of the many models who resided in Hefner‘s infamous Playboy Mansion in Los Angeles.
At the peak of her modelling career in the 2000s, Louise was crowned 2006’s Model of the Year – making her the first Brit to get this title.
But in 2010, Louise suffered some health complications that made her change her lifestyle.
The model once lived with Playboy founder Hugh Hefner (@louiseglover/Instagram)
At the age of 27, she developed septicemia after having breast implant surgery and later went into cardiac arrest.
Ultimately, the model, who had worked with brands like Nike and Reebok over the course of her career, hailed the ordeal as a ‘wake-up call’.
“I nearly died because I was so ill from the infection. That was a wake-up call for me,” she told The Sun.
“I started to train and moved into fitness and lifestyle modelling. I had deals with most of the major brands.”
As to how she found herself living in a tent, while living in Windsor, London, and paying £750 ($983) in rent a month, Louise found that her business dwindled and that she was struggling to make ends meet.
Now, she lives in Reading in a field where she pays just £60 ($78).
Louise Glover pictured in London in 2012 (Alex Moss/FilmMagic)
But Louise is trying to stay positive.
“I am trying to stay upbeat and make the most of my situation, but it is difficult,” she admitted. “I need to get myself out of this pickle soon. Things have to change before winter hits.”
Her current situation is a far cry from her days at the Playboy Mansion.
“It was the best time, like another world,” she said of her time partying with celebrities while working for Hugh Hefner.
“I didn’t even think about it that much at the time, but I was hanging out with the biggest names in the world.”
Louise went on: “I loved all the other Playboy models, we were like a family. I really liked Hugh, he was a total gentleman.”
She further described the mansion as ‘incredible’ and said they had ‘wild parties’ there.
The 41-year-old is now a personal trainer (@louiseglover/Instagram)
In light of her current financial situation, people have urged Louise to start an OnlyFans page, but she said she won’t ‘lower [herself] to that – despite the impressive amount of cash many women make on the platform.
Louise said: “I have too much self-respect for myself to go stripping as some have suggested. People ask me, ‘Why don’t you do OnlyFans?’.
“But I would rather get my life together and live here, in this field. I don’t need to lower myself to that. I have morals and self-respect.”
A former Playboy model who is now homeless has lifted the lid on what it was like living at Hugh Hefner’s mansion back in the 2000s.
At one point, Louise Glover was living the high life: Living in Los Angeles in the Playboy Mansion and rubbing shoulders with some of the biggest celebrities in the world.
But that life likely seems a lifetime away as her living conditions now are considerably different.
The British model almost died at the age of 27 after developing septicemia following breast implant surgery, and later went into cardiac arrest.
She insisted that this was a ‘wake up call’ for the model and she decided to shift away from Playboy and move towards fitness and lifestyle modelling.
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Louise Glover has spoken positively about her time in the mansion (@louiseglover/Instagram)
“I nearly died because I was so ill from the infection. That was a wake-up call for me,” she recently told The Sun. “I started to train and moved into fitness and lifestyle modelling. I had deals with most of the major brands.”
However, despite having some success following the career shift, while living in London and paying £750 ($983) in rent a month, her business began to struggle.
Now, she lives in Reading, UK, in a field where she paid just £60 ($78) to set up her temporary home.
Glover still reminisces positively about living at the mansion, however, and has insisted it was a wonderful experience for her.
“It was the best time, like another world,” she said of her time partying with celebrities while working for Hugh Hefner. “I didn’t even think about it that much at the time, but I was hanging out with the biggest names in the world.”
Louise went on: “I loved all the other Playboy models, we were like a family. I really liked Hugh, he was a total gentleman.”
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The 41-year-old is now a personal trainer (@louiseglover/Instagram)
Due to her new financial difficulties, many people on social media have suggested the model simply start an OnlyFans page.
However, the model is vehemently opposed to going down this route, despite the financial success the platform has allowed for some women.
Louise said: “I have too much self-respect for myself to go stripping as some have suggested. People ask me, ‘Why don’t you do OnlyFans?’.
“But I would rather get my life together and live here, in this field. I don’t need to lower myself to that. I have morals and self-respect.”
Hugh Hefner’s ex-girlfriend Kendra Wilkinson has detailed a ‘nasty’ poo habit that she couldn’t escape in the Playboy Mansion.
Wilkinson was just 18 years old when she entered the infamous mansion, ultimately moving in with Hefner, who was 60 years her senior.
She moved out in 2009 after five years in the Mansion as she met her now ex-husband Hank Baskett.
And since she left the well-known house after five years of residence, Wilkinson hasn’t been afraid to speak about her experiences.
Speaking on The Kyle and Jackie O Show on KIIS FM, Wilkinson opened up on of Hefner’s habits she was not a fan of.
Hugh Hefner and Kendra Wilkinson (Denise Truscello/WireImage)
“[The Playboy Mansion] was pretty nasty. You know, there was dog poop everywhere. And Hef would wobble by and just pick it up with his bare hands,” Wilkinson said.
Elsewhere in the podcast, Wilkinson was asked about ‘going to P Diddy’s parties back in the day’.
Diddy, whose real name is Sean Combs, was charged with racketeering and sex trafficking by force, fraud or coercion – all of which he has denied.
Wilkinson has since spoken out about going to ‘one or two’ parties with Combs present.
She said on KISS FM: “I remember just going to like one or two, but again, like I had a great time in my youth.
“Like, I didn’t really see anything. Like I never saw anything really bad happening around me. Sex is sex, in my opinion.”
When asked if she saw anything abnormal to that of a typical ‘Hollywood party,’ Wilkinson responded: “Look, you’re going to the Playboy Mansion. You know, there’s girls topless in the grotto. Don’t we already know that.”
