Everything Holly Madison Has Said About Her ‘Gross’ and ‘Boring’ Sex Life With Hugh Hefner

Their First Meeting

While appearing on Bridget’s podcast, Holly recalled “drinking so many vodka cranberries all night” to calm her nerves while she partied with Hugh and a group of women, including one she referred to as a “recruiter,” at former Hollywood hotspot Las Palmas.

“The first thing that happens is the recruiter says, ‘Daddy …’ I’m gagging as I’m saying this but everybody used to call him ‘Daddy’ in the bedroom, which is so gross,” Holly said. “So, she’d be like, ‘Daddy, do you wanna get the new girl?’ And I s—t you not, next thing I know he’s on top of me.”

Holly admitted that she wasn’t “getting up” because of her intoxicated state, though she noted that Hugh making the first move wasn’t a common occurrence.

“Later on, things would get so routine, like he wouldn’t move. He would be like a bump on the log in the middle of the bed,” she said of the former editor-in-chief. “So, I guess he thought if I was the first one he was gonna have sex with he had to get up, because I was so f—king wasted … And I’m like, ‘OK, so that happened.’”

‘Mortified and Embarrassed’

Holly also opened up about their first date during a December 2021 episode of the “Power: Hugh Hefner” podcast.

Noting that she didn’t expect the date to be “traditional,” she admitted that she wasn’t prepared for “what would eventually happen.”

“[Hugh] was literally pushed on top of me,” she said at the time. “After it happened, I was just mortified and embarrassed and it had way more of an emotional impact on me than I thought it would.”

After stating she “wasn’t expecting to have sex that night,” Holly worried how the decision would impact her reputation. “All of a sudden, it felt like everybody was going to know about me, and I was horrified by it,” she said.

‘Manipulative’

Holly reflected on her time living in the Playboy Mansion in the A&E documentary series titled Secrets of Playboy, which premiered in January 2022.

“At the mansion, the indoctrination, I feel, starts almost immediately when you’re there, and you start hearing about how wonderful Hef is from his circle of friends,” the Dancing With the Stars alum said in the first episode. “So, in the beginning, Hef is what you would now call a love bomber. He’s somebody who tells you ‘I love you’ almost immediately.”

She then stated that Hugh was inaccurately portrayed on television. “I feel like on The Girls Next Door, Hef was portrayed as, like, a kindly grandpa, but that’s not how he is,” Holly explained. “It would make me so angry how manipulative he was. Hef controlled every aspect of our life.”

‘Gaslit’

Holly continued to make scathing claims against Hugh in Secrets of Playboy.

She admitted to feeling “gaslit” into believing Hugh was a “really good guy,” adding that he created a “cult-like” environment in the Playboy Mansion.

“You had a 9 o’clock curfew, you were encouraged to not have friends over, you weren’t really allowed to leave unless it was like a family holiday,” the Holly’s World star claimed.

“The sex always happened kind of like the same time, the same night,” she added about their regimented late-night rendezvous. “We would go out to a club every Wednesday and Friday, and that would be expected when we got home.”

Securing the Invite

During an April 2021 episode of the “Call Her Daddy” podcast, Holly said she “had to sleep” with Hugh before she was allowed to move into the famous mansion.

“I’m not trying to slut-shame anybody or anything, but nobody ever got asked to move in unless they had slept with him,” she claimed.

‘Boring Basic Sex’

Also during the “Call Her Daddy” podcast, Holly told host, Alexandra Cooper, that her sex life with Hugh was “boring” and “basic.”

“I knew it was because of him. I was healthy. He was just too old,” she explained at the time. “When I had first gotten into that situation and something happened in my mind that first night I had sex, where I felt like, ‘Ok I did that. I like breached my own boundaries and I wasn’t comfortable with it. Now I have to make this situation into something.’ I almost locked myself into this box.”

Crocodile Tears

Holly claimed that Hefner used to “fake cry” if he was refused sex.

“If we were emotional about something or asking for something, he would start fake crying,” she said on the August 29 episode of the “Girls Next Level” podcast. “It was such bad acting and so obvious.”

TMI?

Holly revealed that Hugh continued to use baby oil as lubrication during sex even though she repeatedly asked him to stop.

“I do not recommend this. It is an infection waiting to happen,” she said on the September 19 episode of the “Girls Next Level” podcast with cohost Bridget Marquardt. “It’s disgusting. I don’t know what his hang-up was with it.”

“It got to the point where I was constantly irritated by this baby oil because it throws off your pH, so you’re constantly gonna [have] yeast infections,” she continued.  She said that after her gynecologist advised her to stop using it as a lubricant, and whens he told Hugh, he allegedly responded, “Well, people use baby oil on babies.”

“And I’m like, ‘Yeah, on their skin. Not internally. You’re not supposed to put it there,’” Holly said. “It got to the point where I refused to use it, but then other people would tell me that he would — in the bedroom — put it on his hand and then put it on me when my back was turned and I didn’t know he was doing it.

She added, “Which is so foul and so nonconsensual and so gross. I had forgotten about that for the longest time, but I was reminded of it for some reason and it made me angry all over again.”