Ex-Playboy bunny opens up about dating Hugh Hefner & life in the iconic mansion

Ex-Playboy bunny opens up about dating Hugh Hefner & life in the iconic mansion

December 18, 2020

AN EX-PLAYBOY model has lifted the lid on what really went on inside the Playboy mansion and what it was like dating Hugh Hefner. 

Jenna Bentley, 31, used to live at Hefner’s famous LA estate and attended sex parties so exclusive she had to sign confidentiality contracts.

Jenna, who was discovered at a Phoenix Suns basketball game at the age of 18, spoke to Gina Stewart in her Get Naked With Gina series about her experience in the party house. 

The model moved into the mansion a few years into her modelling career and later appeared on the front cover of the magazine.

Jenna said: “I had to sign a non-disclosure agreement for many reasons. You can assume I met many famous musicians, politicians, celebrities.

“All I can say is there were lots of fun sex parties, but the rest… oh if only the walls could talk!”

After moving into the mansion, Jenna “dated” Hugh for a few months, and said people made wild assumptions about their sexual relationship. 

She said: “Hollywood has a way of portraying things a certain way, but really, do you think an 87-year-old man is sleeping with nine hot blonde 20-year-olds?!

“It was an incredible opportunity and I’m so happy I got to experience that lifestyle.”

Jenna now says she earns more from OnlyFans than she ever did with her runway modelling, magazine work and print work.

Hefner sold the Playboy mansion before he died, but was allowed to continue living there until his death aged 91 in 2017. 

Hefner bought the mansion for $1million in 1971 and it was sold for $100million in 2016 under the condition that the Playboy founder could continue to rent it for life.

Over the years, the home became famous for lavish, wild parties and Playboy Bunnies.

A-list celebrities such as Jack Nicholson, Warren Beatty, Leonardo DiCaprio and Eminem all visited Hefner's home.

Hefner's Playboy bunnies were also known to live in the mansion and were subject to mandatory 9pm curfews and film nights three times a week where Hefner's favorite 1950s flicks would be played.

The property is said to include a wine cellar, three zoo buildings, a game house, tennis and basketball courts, a waterfall, pool and the famous grotto where Hefner would entertain.

It was also home to the editorial offices of Playboy Magazine, launched by Hefner in 1953.

The womaniser-in-chief lived in private quarters on the second and third floors of the mansion up to his death.

In interviews and memoirs Playmates have complained about the state of the mansion.

In her memoir Bunny Tales, Izabella St. James wrote: "Everything in the mansion felt old and stale."


In 1953, a time when states could legally ban contraceptives and the word "pregnant" was not allowed on "I Love Lucy," Hefner published the first issue of Playboy, featuring naked photos of Marilyn Monroe and an editorial promise of "humor, sophistication and spice."

The Great Depression and World War II were over and Playboy soon became forbidden fruit for teens and a bible for men with time and money, primed for the magazine's prescribed evenings of dimmed lights, hard drinks, soft jazz, deep thoughts and deeper desires. Within a year, circulation neared 200,000.

Within five years, it had topped 1 million.

Hefner and Playboy were brand names worldwide. Asked by The New York Times in 1992 of what he was proudest, Hefner responded: "That I changed attitudes toward sex. That nice people can live together now.

"That I decontaminated the notion of premarital sex. That gives me great satisfaction."

Censorship of the magazine was inevitable. Playboy has been banned in China, India, Saudi Arabia and Ireland.

In the 1950s, Hefner successfully sued to prevent the U.S. Postal Service from denying him second-class mailing status.

7-Eleven stores for years did not sell the magazine. Stores that did offer Playboy made sure to stock it on a higher shelf.

Women were warned from the first issue: "If you're somebody's sister, wife, or mother-in-law," the magazine declared, "and picked us up by mistake, please pass us along to the man in your life and get back to Ladies Home Companion."

We shared how the Playboy mansion is now a ROTTING cesspit after looters raid it following Hugh Hefner’s death

And the last bunny at Hugh Hefner’s Playboy Mansion likened it to ‘a care home’.

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