Hugh Hefner’s former girlfriend has provided insight into their intimate life together.
The founder of Playboy, Hefner, reportedly claimed to have been with over 1,000 women before his passing at age 91 in September 2017. He was well-known for dating multiple women simultaneously.
According to Business Insider, after parting ways with his second wife, Kimberly Conrad, Hefner began dating several Playmates, including Baywatch actress Brande Roderick. Around that time, he also became involved with twins Sandy and Mandy Bentley, eventually dating all three women for two years.
In a 2011 interview with the Daily Beast, Hefner stated: “When the relationship with Brande broke up, I added more girls. At one point, it was up to seven. Izabella [St. James] was one of those seven.”
He later reduced his number of live-in companions to three women: Holly Madison, Bridget Marquardt, and Kendra Wilkinson.
These three women have publicly shared their experiences of living with Hefner, and Madison has previously provided details about their sexual relationship.
The Holly’s World star once described their intimate moments as ‘normal’ when it was ‘just me and him’.
In a conversation with Alex Cooper on the Call Her Daddy podcast in 2021, Cooper inquired if the intimate encounters were ‘always in missionary’.
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“It wasn’t this way the first time I was there,” Madison answered. “He was on top the first time, but he was always laying down every other time that I remember.”
When asked about Hefner’s size, Madison described it as ‘normal’ and confirmed that he relied on Viagra.
Cooper also asked: “Did you ever have an orgasm with him?”
The former Playboy model responded with a no, explaining that she was ‘too messed up’ to climax. She clarified that she was often ‘drunk or high’.
During the podcast, the 45-year-old mentioned Hefner’s specific preferences.
“He always had a fixation on everyone always being fully shaved,” she explained, adding: “He would get mad if somebody wasn’t shaved.”
Madison also mentioned his preference for ‘nothing sticking out’.
“His obsession with young women was semi gross,” she concluded.