Hugh Hefner had a plethora of bizarre rules his girlfriends were under strict instructions to follow – including what colour their hair had to be, what time they should be inside the Playboy Mansion by, and prohibiting the women from speaking to his employees.

American publisher Hefner, who died in September 2017, founded men’s lifestyle and entertainment magazine Playboy in December 1953.

The Illinois native, who was worth an estimated $43million when he died, fuelled media interest by sharing a luxury mansion and embarking on relationships with multiple women, one of which was 45-year-old Holly Madison – a woman who was once described as his ‘number one girlfriend’.

The star, who previously lived at the Californian property with the star,, has recently opened up about what was expected of herself and other models at the mansion.

Speaking about sleeping with Hef, Madison told the In Your Dreams podcast host Owen Thiele that he expected his girlfriends to perform ‘disgusting’ sex acts.

“Well, it’s a very different story between when we were just by ourselves than with everybody else in the room,” she told the 28-year-old Theatre Camp actor.

“Everybody else in the room, no. That was disgusting. I hated it. I made it very known I hated it.

“If it was just me and him, it was a lot more normal than you would think.”

Interestingly, staging group sex sessions wasn’t the only rule that Hefner would impose on his girlfriends.

The golden rule was monogamy… at least for Hefner’s girlfriends

It’s widely understood that Hefner would often have multiple girlfriends on the go at once.

However, while the pensioner was allowed to embark on various relationships, he allegedly expected his lovers to remain exclusively faithful to him and him alone.

In her 2015 memoir, Down the Rabbit Hole: Curious Adventures and Cautionary Tales of a Former Playboy Bunny, Madison wrote: “While Hef could date an entire sorority house full of girls, we were to remain totally loyal.”

Another of the editor’s former girlfriends, Izabelle St. James, 49, previously explained how ‘weird’ it was to be part of a group dating the same guy.

“He created his own world, his own fantasy where he set his own rules. And I wanted to learn more,” she revealed.

One colour lipstick was banned from the mansion

Henfer was reportedly extremely strict and often controlled what his girlfriends could and could not wear, including banning a particular colour of lipstick from the mansion.

“Among the many unspoken rules at the mansion, the red lipstick rule was one of the more notorious,” Madison wrote in her memoir. “I’m not over-exaggerating here.

“Hef absolutely despised red lipstick and wouldn’t allow his girlfriends to wear the colour.”

The Oregon-native explained that the business mogul believed wearing red lipstick was a choice made by ‘older mature woman’ and that he wanted his playmates to remain ‘very young and fresh-faced’.

Hugh Hefner’s former girlfriend Holly Madison has lifted the lid on some of the media tycoon’s practices (Denise Truscello/WireImage)

Platinum blonde hair was paramount

It wasn’t just lipstick shades that Hefner allegedly took issue with; it was hair color too.

Madison claimed during an interview on the 2021 Power: Hugh Hefner podcast that if you were cast as one of the father-of-four’s girlfriends, then you were required to have blonde hair.

“You were expected to look a certain way,” she confirmed.

Some of the most famous blonde playmates include Bridget Marquardt, Hefner’s third wife Crystal, and even Blondie’s Debbie Harry.

Speaking about dying her hair, Crystal told People last year that she’d routinely have ‘blisters’ on her scalp from the practice.

Abide by the curfew

According to St. James, Hefner had a strict 9pm curfew in place for all of his girlfriends due to fears of them cheating on him if they were out late.

“We had to be home by 9pm,” she once told Fox News Digital, “Hef didn’t want girls to go out and party without him. I suppose he didn’t want us to have the opportunity to be unfaithful.”

Former Playboy model Jenna Bentley once told the Daily Mail that if you missed the strict curfew, you’d be made to sleep on the lawn.

Sign on the dotted line

Bentley once told the Daily Mail that she’d signed an ‘iron-clad’ NDA so she wouldn’t be able to reveal what she saw going on behind closed doors at the Playboy mansion.

However, Crystal has previously claimed that she was not subjected to signing any legislation during her relationship and subsequent marriage with Hugh.

Christmas was to be spent in the mansion

Girlfriends residing at the California mansion were allegedly unable to return home for Christmas, according to Madison’s memoir.

“Girlfriends were given ‘off’ days before or after the holiday to visit family and friends, but there were no exceptions for the actual day itself,” she wrote

She added: “That was the one house rule that no one seemed to mind, because Christmas was when Hef was most generous with his girlfriends.”

Hefner reportedly wouldn’t let his girlfriends go home for Christmas (Charley Gallay/Getty Images for Playboy)

Residents must relinquish their former homes

Not only were Playboy models banned from spending Christmas outside of the mansion walls, but they were also reportedly expected to give up their previous homes.

“You weren’t allowed to have an apartment of your own, which, while I lived there, there were some women who did; they just kept that a secret from him,” Madison said on the Power: Hugh Hefner podcast.

Some of the girls famously lived in the house rent-free, while others paid for their rooms.

Payday often came with some repercussions

In her 2006 memoir, Bunny Tales: Behind Closed Doors at the Playboy Mansion, St. James claimed that collecting weekly wages and allowances from Hefner was somewhat difficult.

“We had to go to Hef’s room, wait while he picked up all the dog poo off the carpet – and then ask for our allowance.

“We all hated this process.”

The Ninja Cheerleaders actress also claimed the businessman would use the intimate opportunity to air any grievances with his girlfriends, including complaining about ‘the lack of harmony’ among them.

St. James also claimed: “If we’d been out of town for any reason and missed one of the official ‘going out’ nights he wouldn’t want to give us the allowance. He used it as a weapon.”

Izabelle St. James was one of the Playboy editor’s former girlfriends (Amy Graves/Getty Images)

There was a ban on drugs

Hefner’s dislike of illicit substances has been well documented.

He even went as far as to state in his will that any of his heirs would be blocked from receiving their inheritance if they became ‘physically or psychologically dependent on drugs or alcohol’.

It’s said that alongside his family, the media tycoon banned his girlfriends from taking drugs or becoming dependent on alcohol too.

No ‘mingling’ with the staff was allowed

The Playboy Mansion, which consisted of 29 rooms, reportedly needed around 80 full-time staff members to remain fully operational.

These included landscapers, butlers, cleaners, and more who Hefner’s girlfriends were allegedly forbidden from canoodling with.

“You weren’t supposed to be hanging out with the butlers,” said St. James.

Meanwhile, Madison wrote in her memoir: “The girls were not allowed to ‘fraternise’ with the staff unless absolutely necessary.

Hugh Hefner’s ex-girlfriend Holly Madison has opened up about the less-than-enjoyable side of dating the Playboy founder.

Madison, now 45, had the ‘privilege’ of being Hefner’s ‘number one girlfriend’ back when she was staying at the Playboy mansion in the 2000s.

While the infamous LA residence was filled with people coming and going, a few women were very clearly mainstays as they were the girlfriends of the late mogul – who passed away aged 91 in 2017.

One of those women was Madison and following her time on the reality TV show The Girls Next Door, she has opened up about what things were really like, including their sex life.

Holly Madison has opened up about her sex life with Hugh Hefner (Chad Buchanan/Getty Images)

Speaking on the In Your Dreams Podcast with Owen Thiele, Madison explained what it was like sharing Hefner with his other girlfriends at the time, Bridget Marquardt and Kendra Wilkinson, as well as the overall experience.

Speaking about the sex, she insisted it was ‘normal’ despite the 50-year age difference between her and Hef but admitted there was one act she hated doing with him.

She said: “Well, it’s a very different story between when we were just by ourselves than with everybody else in the room.

“Everybody else in the room, no. That was disgusting. I hated it. I made it very known I hated it.

“If it was just me and him, it was a lot more normal than you would think.”

Madison also stated that she was previously ridiculed on social media if she ever spoke about her sex life, because of the age gap.

She added: “I think everybody has this real horror story of how gross an old man’s body must be.

She said she had normal sex with Hefner despite the significant age difference (Laurence Cottrell/FilmMagic)

“I feel like there was a time when I couldn’t post anything without some dumba** in the comments like, ‘Oh, old balls’, or something like that and look, maybe some people’s balls do get old and nasty, but I’ve never seen such a thing.”

Despite having a relatively normal sex life when it was just the two of them, Madison has also opened up about the difficulties of living in the ‘fast lane’ and the struggles being Hefner’s girlfriend brought her.

Holly Madison has opened up about the ‘fishbowl’ life of living in Hugh Hefner’s Playboy Mansion and how her mindset ended up ‘warped’.

Madison dated Hefner from 2001 to 2008, and was even named as his ‘number one girlfriend’ on reality TV show The Girls Next Door.

However, since the Playboy publisher passed away in 2017 at the age of 91, Madison – among other Playmates – have come forward to reveal certain realities of what he was like alongside what it was like living in the infamous Playboy Mansion.

Madison has previously reflected on the difficulties of living life in the ‘fast lane’ alongside why the mansion felt like a ‘cult’ and lifted the lid on her and Hefner’s sexual relationships, including certain ‘disgusting’ elements but also one stereotype she often found discussed online which was far from the truth.

However, she’s since opened up about not just the physical aspects of her relationship with Hefner, but mental too, realizing with hindsight she ‘thought’ she was ‘connecting’ with him but actually ‘didn’t know him well’.

The 45-year-old told the New York Post: “I had this mindset of being in love, and it was kind of tinged with a little bit of Stockholm syndrome.

“I thought I was connecting with [Hefner], when really I was just somebody who had trouble connecting with people my whole life. And I’d met somebody who was like a master manipulator.”

Looking back, Madison sees herself as ‘somebody who was young and impressionable and just kind of in a fog almost’.

And even further than being in a ‘fog’, Madison notes she now thinks her mindset at the time of her relationship with Hefner was actually ‘warped’ and she was exhibiting ‘cognitive dissonance’.

Holly Madison said she needed perspective (Mark Sullivan/WireImage)

Madison explained she may’ve initially thought she was ‘in love’ but did soon realize she ‘made a bad decision’ but ultimately was so ‘in over [her] head’ she just had to try and ‘justify’ it.

She also reflected on how being at the Playboy Mansion affected not only ‘part’ of her life but also her ‘reputation’ which meant she then had to figure out how to ‘make it okay’ once on the outside of it all.

Though Madison noted that she was ‘lucky’ to be able to ‘turn lemons into lemonade, with things like the reality show, and other side hustles’.

Holly Madison has revealed why one element of her relationship with Hugh Hefner wasn’t the ‘horror story’ many expect.

Hefner and Madison dated from 2001 to 2008, with Madison starring as his ‘number one girlfriend’ on reality TV show The Girls Next Door.

Since the Playboy publisher passed away at the age of 91 in 2017, many Playmates have since come forward to share stories from inside the infamous mansion.

Madison has been open about the difficulties of living life in the ‘fast lane’ alongside why the mansion felt like a ‘cult’.

However, alongside talking about how ‘disgusting’ certain elements of her relationship with Hefner were, including a sex act she ‘hated’ doing with him, she’s also since combated a certain negative stereotype to do with Hefner and, in particular, his age.

Speaking on the In Your Dreams Podcast with Owen Thiele, Madison opened up about her sex life with Hefner.

Despite the 50-year age gap between the pair, she noted how ‘normal’ the sex was.

She also addressed certain negative stereotypes which she’s faced as a result of having sex with an older man.

Madison continued: “I think everybody has this real horror story of how gross an old man’s body must be.

“I feel like there was a time when I couldn’t post anything without some dumba** in the comments like, ‘Oh, old balls’, or something like that and look, maybe some people’s balls do get old and nasty, but I’ve never seen such a thing.”

Ultimately, if it was just Madison and Hefner in a room together, she said their sex life ‘was a lot more normal than you would think’ however, there was one act she found ‘disgusting’.