Featured Image Credit: Laurence Cottrell/FilmMagic
Topics: Sex and Relationships, Hugh Hefner, Celebrity
Britt Jones
Topics: Sex and Relationships, Hugh Hefner, Celebrity
An ex-Playboy Bunny girlfriend of Hugh Hefner has revealed what was inside of the little ‘black book’ the editor-in-chief used to keep on his playmates.
Holly Madison, who dated Hefner between 2001 and 2008, has been open about her experiences with the magazine boss.
Madison was Hef’s ‘number one’ in the Playboy Mansion, which means that while she was his favorite girlfriend, that doesn’t mean she was the only one.
The 46-year-old has explained all the things that people might be itching to know about.
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From their mandatory orgies, to the rules he gave his girlfriend, the condition of his home, and even Hefner's 'black book'.
This book was something that she alleges made her uncomfortable, explaining that when she left the mansion, she wanted to destroy it and all it contained.
Since Hefner's death in 2017 at age 91, there has been much on the topic of the book, including in the A&E docuseries Secrets of Playboy.
Then there’s Madison’s Girls Next Level podcast, which she hosts alongside another one of Hefner’s ex’s, Bridget Marquardt.
In one of their episodes, Marquardt claimed Hefner had a journal, and this little book detailed more than just thoughts and dreams.
It told Hefner 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.”
They went on to alleged that they had even heard from other women in the mansion that Hefner would use the book to ‘report' on their performance as girlfriends.
"He’d be like, 'Oh, you’ve been on your period for three weeks,'" the pair recalled.
According to Madison, the book was something she wanted to go.
She recalled: "When I was moving out of the house - I wanted [to] so badly, but I had no access - if I could have gotten to the drawer and burned that book, I would have.”
She explained: "Because I’m just so disgusted with how he keeps a record of who he has sex with each night and takes all these nudes of all the girls when they’re in the limo and drunk and flashing, and then prints them out, hands them to every girl in the limo, puts them in a scrapbook."
Madison went on to claim: "So, that was another thing that made me feel weird and afraid to leave, I feel like there was this mountain of revenge porn that everybody is going to see at some point, so I might as well hide here - it was just gross."
But they weren’t the only ones who hated the book and his allowance process.
In her 2006 memoir Bunny Tales: Behind Closed Doors at the Playboy Mansion, Hef’s ex, Izabella St. James said it also involved dog poop: "We had to go to Hef's room, wait while he picked up all the dog poo off the carpet - and then ask for our allowance.
"We all hated this process."
"Hef would always use the occasion to bring up anything he wasn't happy about in the relationship," she wrote. "Most of the complaints were about the lack of harmony among the girlfriends - or your lack of sexual participation in the 'parties' he held in his bedroom."
St. James also claimed: "If we'd been out of town for any reason and missed one of the official 'going out' nights he wouldn't want to give us the allowance. He used it as a weapon."
Hefner was married three times and had several girlfriends, with three of those, Kendra Wilkinson, Madison and Marquardt, all rising to fame with their reality TV show, Girls Next Door.
However, a number of former Playboy Bunnies have opened up about intimacy with the late businessman.
Madison spoke on the In Your Dreams podcast, where she revealed: “If it was just me and him, it was a lot more normal than you would think.
“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.”
In her 2024 biography, titled Only Say Good Things: Surviving Playboy and Finding Myself, Hefner’s third and final wife, Crystal, described sex with him alone as being 'blue little pill nights' due to the medication he needed to get jiggy between the sheets.
She also claimed that she'd played the same Madonna track every time so that 'no other music [would] be contaminated by this place' for her.
Elsewhere in the book, Crystal called their sex life 'odd and robotic', as she penned: “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’.
Crystal added: “Or maybe it was never fun and sexy.”
Madison recalled how she was told to put on pajamas when she was first asked to live in Hefner's estate, writing in her book: “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.”
Another of Hefner's girlfriends, Sondra Theodore - who dated the magazine publisher for five years between 1976 and 1981, opened up about their time together during an appearance on A&E's Secrets 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.”
Twins Karina and Karissa Shannon also spoke about how their 19th birthday was ruined after they were invited to Hefner's bedroom.
While being interviewed for the A&E docuseries, Karissa claimed that they were both offered a pill that made them '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,” Karina said.
Meanwhile, 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.
“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.”