Holly Madison opens up about her disturbing experiences with Hugh Hefner inside the Playboy Mansion, revealing degrading group sex rituals, emotional manipulation, and the dark reality behind the glamorized lifestyle she once lived.

More than a decade after leaving the lavish walls of the Playboy Mansion, Holly Madison has once again shattered the fantasy that once surrounded her life with Hugh Hefner.

In a recent episode of the “In Your Dreams” podcast, Madison offered a disturbing and deeply personal account of what she described as “disgusting” group sexual encounters during her years as one of Hefner’s girlfriends—a period often glamorized by pop culture but now increasingly seen through a darker, more troubling lens.

Madison, who rose to fame in the early 2000s as one of the central figures in the reality show The Girls Next Door, lived at the mansion from 2001 to 2008 and was widely regarded as Hefner’s “main girlfriend.”

But behind the curated image of glamour and carefree parties, she reveals there was a far more complex, and often emotionally draining, reality.

According to Madison, she never enjoyed the group sex that was an unspoken part of life at the mansion. “I hated it,” she confessed, saying it made her feel used and disconnected, like she was expected to participate in something that diminished her sense of identity and control.

While one-on-one encounters with Hefner were described as comparatively more “normal,” Madison notes that even those came with their own surreal elements.

The lights were always kept off during sex, an environment she says added to the eerie atmosphere of their intimate moments. She jokingly compared it to the saying “all cats are gray in the dark,” a metaphor that barely masks the discomfort and detachment she felt at the time.

Madison also recounted the bizarre physical setting of the mansion, detailing the presence of strange trays filled with items like Vaseline, Pepto Bismol, and baby oil.

These trays, she says, were placed in nearly every room—from bathrooms to tennis courts—and seemed like a silent testament to the transactional and almost mechanical nature of sex within the mansion’s walls.

The entire environment, according to Madison, was charged with unspoken expectations, isolation, and subtle forms of control.

This isn’t the first time Madison has spoken about her time with Hefner. In her bestselling 2015 memoir Down the Rabbit Hole, she described the mansion as a psychologically manipulative space, comparing it to a cult-like environment where women were pitted against one another and subjected to emotional gaslighting.

She has recalled how young women arrived at the mansion often seeking fame or security, only to find themselves trapped in a world where their personal agency was slowly eroded.

In the same memoir, Madison revealed that Hefner once left his will lying around where she could see it—highlighting a section that offered her $3 million should he die while they were still together.

For her, this gesture didn’t feel like generosity, but rather a veiled attempt to buy loyalty and discourage her from leaving. This manipulation, she said, created a confusing mix of guilt, obligation, and dependence that kept her tethered to a relationship she had long wanted to escape.

Publicly, Hefner was known as a champion of sexual freedom and the architect of an empire that fused adult entertainment with mainstream celebrity culture.

But Madison’s accounts—and those of other former Playmates and Mansion residents—have chipped away at that image, revealing a system where emotional coercion and exploitation were common, even as the women involved were smiling for cameras.

Since leaving the mansion, Madison has made it her mission to reclaim her story. She’s now the host of Lethally Blonde, a true-crime series that focuses on violence and victimization within the adult entertainment industry.

Her work seeks not only to shed light on crimes that often go ignored but also to humanize the women behind the headlines—many of whom, like herself, were caught in environments that encouraged silence and submission.

Madison’s story is particularly significant in a post-#MeToo cultural landscape, where discussions about consent, power, and manipulation have taken center stage.

Her revelations force a reexamination of institutions and individuals once seen as progressive or liberating, highlighting the subtle and often invisible mechanisms that keep women in positions of vulnerability.

She remains one of the most outspoken former Playboy models, using her platform not just to reflect on the past, but to challenge the ongoing romanticization of Hefner and the culture he built.

For many who admired the Playboy brand from a distance, Madison’s words are a stark reminder that glossy surfaces can hide uncomfortable truths.

The reaction to her interview has been mixed—while many applaud her honesty and bravery, others continue to defend Hefner and the legacy of Playboy.

But Madison seems unfazed by the backlash. Her purpose, she says, isn’t to tear down a brand or a person, but to give voice to the silent complexities that once defined her world.

In sharing her experience, Holly Madison isn’t just revisiting the past—she’s demanding that it be seen in full. Not as fantasy. Not as fame. But as a cautionary tale of what happens when youth, ambition, and power collide behind closed doors.