Seriously grim reason Hugh Hefner didn't want Playboy models wearing lipstick

Hugh Hefner reportedly inflicted a number of restrictions onto the lives of his much-loved Playboy 'Bunnies' - one of which affected their use of a particular make-up bag staple.

According to one of his former girlfriends, 45-year-old Holly Madison, the late magazine boss had a specific grudge against lipstick.

So much so, that he banned it from the infamous California mansion.

Ever since Hefner passed away in 2017, aged 91, a slew of his ex-lovers have come forward, lifting the lid on the often-unnerving realities of living with the controversial media mogul.

Crystal Harris - Hefner's third wife - revealed recently the pair endured 'odd and robotic' sex with no kissing, romance or intimacy in that bedroom.

Kendra Wilkinson, meanwhile - another of the publisher's ex-girlfriends - claimed this week that their physical relationship left her unable to feel true intimacy with any other partners.

In 2022, Hefner's other former flame Holly Madison told A&E’s Secrets of Playboy that he was incredibly controlling about the way she looked.

"I kind of broke under that pressure and being made to feel like I needed to look exactly like everybody else," she previously explained, revealing that Hefner had 'flipped out' when she one day decided to 'chop' all 'my hair off so I can at least look a little different'.

Madison claimed lipstick was banned by Hefner (Denise Truscello/WireImage)

It wasn't just his girlfriends' hair that supposedly saw Hefner exert his control. According to Madison, lipstick - red, specifically - was forbidden in the Playboy Mansion.

"I think it was a control tactic," she admitted during an episode of Coco Mocoe podcast's Ahead of the Curve podcast last year.

Madison also noted that 'new girls' were often allowed at the start before he had full control over them.

"When I was brand new, I wore red lipstick out a couple of times, and he didn't say anything about it, because when you were the new girl in the group, you were always treated well."

The TV star continued: "Somebody said, like, the higher up you are in a cult the worse you're treated because they want the new people to bond and feel into it."

Madison explained why she thought the lipstick rule existed, saying: "I think he didn't love it because when he invented the concept of a playmate in the '50s, he wanted the women to look very young and fresh-faced.

Hefner had a number of girlfriends at one time (Denise Truscello / Contributor / Getty)

"He felt like the look in the ‘50s at the time was very - he described it as somebody's older sister, explaining what he didn't like. He wanted skimpy and fresh-faced and very young looking."

Madison went on to explain that to Hefner, red lipstick was a choice made by 'older mature women', which put him off as it wasn't 'the barely legal thing anymore'.

Detailing the moment everything changed, she said: "It wasn't a big deal until, like, six months into it, when I was living in his bedroom and I was the main girlfriend, that he felt like he had the leeway to yell at me over it."

Elsewhere during the podcast, the mother-of-two opened up about how the Playboy lifestyle led to her contemplating suicide.

If you’ve been affected by any of these issues and want to speak to someone in confidence, please don’t suffer alone. Call Samaritans for free on their anonymous 24-hour phone line on 116 123.

• Playboy model Crystal Harris reveals real reason she abruptly called off wedding to Hugh Hefner
• Former Playboy model Holly Madison made very sad admission about ‘gross’ reality of her relationship with Hugh Hefner
• Playboy star Hugh Hefner’s widow Crystal made shock confession about their sex life
• List of Hugh Hefner’s strict and bizarre rules for Playboy Bunnies living in mansion