Now 45, Madison was privileged to be Hefner’s ‘number one girlfriend’ during her stay at the Playboy home almost two decades ago.

Although the residence had a revolving door of guests, numerous women moved in permanently at the famous Los Angeles estate before Hefner died in 2017 at the age of 91. Madison has lately been extremely open about her experiences in the mansion, revealing specifics of a “disgusting” s**ual act she found uncomfortable with Hefner and talking about her general s** life with the late star.

She also discussed on the “Girls Next Level” podcast how Hefner allegedly neglected to get ladies to sign NDAs prior to their sleeping together.

Madison had this to say about him: “He wanted to be the best host possible and wanted his guests to have the best time of their lives.” People are typically perplexed as to why we were not asked to sign non-disclosure agreements (NDAs), and he did not have any folks signing NDAs. This does not come as a surprise to me because ‘Hef’ wanted nothing to get in the way of him having fallen asleep, and I feel that a lady would stop and ask, “Wait, what am I doing?” if he were going to have someone stop to sign a paper before they entered the bedroom.

Madison earlier discussed her s** life with Hefner on the In Your Dreams Podcast with Owen Thiele.

Madison pointed out how ‘natural’ the s** was with the Playboy founder, despite their 50-year age difference.

She also seized the chance to challenge some unfavorable preconceptions she has come across because of her relationship with an older man. “I think everyone tends to have this exaggerated horror story about how ugly an older man’s body might be,” Madison said.

Madison explained that their personal life was startlingly more normal when it was just She and Hefner together than many would have first assumed. She created a picture of a basic daily life with times of real closeness that defied public opinion of their relationship.

The more subtle and intricate aspects of her connection were revealed in her memoir, which she published in 2015, as well as in various podcast appearances, where she stated that she frequently believed Hefner was rather dominant in their relationship.

This dynamic highlighted the conflict between the glitzy façade and the reality of their intimate encounters, therefore contributing to her general discontent during that period. Madison’s observations expose the difficulties hiding beneath their apparently perfect lives, therefore offering a more complex view of their time together.

May 14, 2025