Holly Madison was Playboy Editor Hugh Hefner’s No. 1 girlfriend for seven years. She regrets her time in the Playboy mansion. (Photo: Playboy)

Holly Madison, one of Playboy owner Hugh Hefner’s gaggle of girlfriends from 2001 to 2008, said competition among his harem of busty blondes at the Playboy Mansion fueled a suicidal depression and took a toll on the women who competed for his attention.

Hefner died at 92 on Sept. 27 and has been widely venerated for his ground-breaking views on sexuality, free speech and civil rights.

But the life of a Playboy bunny was often far from glamorous, even if you were Hef’s No. 1 girlfriend.

In her telling expose, “Down the Rabbit Hole,” she detailed her life, which was so shallow and unfulfilling she once considered killing herself in the bathtub.

“It was a constant struggle,” said Madison in the book. “There was so much competition among the other women. There was a lot of fear.”

Madison, who was Hefner’s “No. 1 girlfriend” from 2001 to 2008.

“If I just put my head under water and take a deep breath in, it would all be over,” Holly wrote in Down the Rabbit Hole. “I don’t think he cared if we enjoyed sex. I don’t think he cared about my happiness at all.”

While most people think living inside the Playboy Mansion is glamorous and fun, Holly said it was a gilded cage fraught with loneliness, insecurities and vicious in-fighting.

Holly desperately wanted to marry and have children with Hefner. But she said Hef often pitted the girls against each other to create petty rivalries so he could keep his girlfriends under his thumb.

Not surprisingly, Madison said being part of Hef’s harem made her extremely insecure and unhappy.

holly madison plastic surgery before after

Holly Madison got numerous plastic surgeries for free as one of Hef’s girlfriends.

“He cared about his own happiness, nothing more,” said Holly. “He believed that all a pretty young girl could possibly want from life was a little bit of money and a little bit of fame.”

Holly said she learned a lot from her seven years as Hef’s girlfriend, but has no happy memories of the Playboy Mansion.

Madison starred on the hit Playboy reality TV show the “Girls Next Door” and appeared in Playboy magazine while dating Hef.

When Madison first met Hef, the fabled editor had seven girlfriends. Madison said she joined in thrice-weekly group sex orgies with all of them. The orgies were often not sexy at all.

The girls were all required to take a bath before the sex session, while Hefner took a Viagra pill. During the boring orgy, Hefner lied inert on his back as several TV screens played porn in the background.

In assembly-line fashion, the girls each took a turn mounting Hef for a few seconds/minutes. Holly’s role as the No. 1 girlfriend was to have anal sex with him, while the other girls merely had brief vaginal intercourse, as Celebrity Health Fitness has reported.


Holly Madison was required to have group sex orgies with Hugh Hefner and his other girlfriends 3 times a week while living at the Playboy Mansion.

All of the girls felt sorry for the one who had to have anal sex with Hef. No condoms were ever used.

Holly said all the girls hated the thrice-weekly orgies “and tried to get it over with as quickly as possible.”

Madison was advised early on to “fake” everything. “My turn was over just as quickly as it had started,” said Holly.

holly-madison-nude-playboy kendra bridget

As Hugh Hefner’s No. 1 girlfriend, Holly Madison’s job was to have anal sex with Hef after he had vaginal sex with his other girlfriends.

Even though Madison wanted to marry and have children with Hef, she claimed she has no fond memories of their relationship.

“After some years have passed, I don’t really find him to be a very genuine person,” said Holly. “I don’t even care what his reaction is to this [book]. I’m doing this for me and I’m doing this so people can learn from my mistakes.”

Hugh Hefner’s son, Cooper Hefner, has slammed Madison as an opportunistic gold digger who used Hef to get famous.

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