Former Playmate lifts the lid on Hugh Hefner’s infamous Halloween parties

A former Playmate has revealed what it was like behind the scenes at Hugh Hefner’s epic Playboy Mansion Halloween parties, recalling how she spent four hours getting coated in latex body paint and watched famous people have sex.  

Jenna Bentley, 32, from Montana, first cut her teeth as a Playboy Bunny at one of the celebrations, which were some of the wildest, lavish, and most incredible events that took place at the famous house.

The model, who shares sexy content on her Instagram page, had been invited to the party with a guy she was dating. When she met the Playboy founder, she was asked if she would like to get her naked body painted as a butterfly to join in the festivities.

Looking back: Former Playboy Jenna Bentley, 32, opened up about attending one of Hugh Hefner’s famous Halloween celebrations at the Playboy Mansion when she was 18 

Famous face: Jenna, who was invited to the party with a guy she was dating, said she met the late Playboy founder (pictured in 2008) that night

Famous face: Jenna, who was invited to the party with a guy she was dating, said she met the late Playboy founder (pictured in 2008) that night 

Memories: The model said Hefner asked her if she wanted to get naked and have her body painted as a butterfly to join in the festivities (pictured)

Memories: The model said Hefner asked her if she wanted to get naked and have her body painted as a butterfly to join in the festivities (pictured) 

‘I was blown away by everything, every detail was perfect and no expense was spared,’ Jenna told Jam Press. 

‘I met Hef before the party began and he asked if I’d like to get involved by being body painted. I obviously said yes. It felt surreal.’

Jenna, who was 18 at the time, had to spend four hours having the latex paint applied to her body in preparation for the event. 

‘Everyone was so professional, but I really had to stand there completely naked while the color was painted on,’ she recalled.  

Tedious: Jenna readily agreed and spent four hours having latex paint applied to her body

Tedious: Jenna readily agreed and spent four hours having latex paint applied to her body

Process: Jenna recalled having to stand completely naked while the latex paint was applied to her body, which was 'plucked bare'

Process: Jenna recalled having to stand completely naked while the latex paint was applied to her body, which was ‘plucked bare’ 

Concern: Jenna admitted that she was worried she would start sweating and the paint would run off of her body

Concern: Jenna admitted that she was worried she would start sweating and the paint would run off of her body

Concern: Jenna admitted that she was worried she would start sweating and the paint would run off of her body 

Goal: The experience made her realize that she wanted to become a Playboy Bunny

Goal: The experience made her realize that she wanted to become a Playboy Bunny 

‘I was completely plucked bare. There wasn’t a hair on my body, and the costume was so intricate and detailed with tiny jewels everywhere. 

‘I was so worried about getting sweaty and the paint coming off or spilling something down it, but it was perfect.

‘Everyone had different costumes and the house was completely transformed. We didn’t party inside the mansion, but there was a huge marquee put up outside on the grounds. 

‘It was like something out of Vegas. It had a massive production value.’

Once painted, Jenna mingled with the many famous faces in attendance and witnessed plenty of X-rated shenanigans.

Where the magic happened: The Playboy Mansion was where Hefner hosted his debaucherous celebrations of excess with exclusive celebrity guest lists

Where the magic happened: The Playboy Mansion was where Hefner hosted his debaucherous celebrations of excess with exclusive celebrity guest lists

Wild times: Jenna, pictured at another Playboy Mansion party, said 'people were having sex everywhere' on the property, including the grottos, pool, and the pumpkin patch

Wild times: Jenna, pictured at another Playboy Mansion party, said ‘people were having sex everywhere’ on the property, including the grottos, pool, and the pumpkin patch

Secrets: Jenna declined to name any names, but added that 'you can assume there were famous musicians, politicians, and celebrities there'

Secrets: Jenna declined to name any names, but added that ‘you can assume there were famous musicians, politicians, and celebrities there’

What an opportunity: Jenna said the party had 'massive production value,' explaining that 'it was like something out of Vegas'

What an opportunity: Jenna said the party had ‘massive production value,’ explaining that ‘it was like something out of Vegas’

‘People were having sex everywhere,’ she recalled. ‘In the grottos, in the pool, I even saw one couple doing it in the pumpkin patch.

‘I couldn’t reveal any names of who was getting down and dirty. You can assume there were famous musicians, politicians, and celebrities there.

‘It was so much fun. If only the walls could talk.’

What started out as a private party for Hef and his friends over the years turned into debaucherous celebrations of excess with an exclusive celebrity guest list.

Jenna, who is now a multimillionaire thanks to her successful OnlyFans page, spent the evening getting acquainted with the other Playboy Bunnies and knew she wanted to be one, too. 

Strike a pose: Jenna appeared on the cover of Playboy in 2018

Strike a pose: Jenna appeared on the cover of Playboy in 2018 

Success: Jenna is now a multimillionaire thanks to her successful OnlyFans page

Success: Jenna is now a multimillionaire thanks to her successful OnlyFans page

Life-changing: Jenna's first Playboy Mansion party was particularly memorable for her because it made her realize that she was pansexual

Life-changing: Jenna's first Playboy Mansion party was particularly memorable for her because it made her realize that she was pansexual

Life-changing: Jenna’s first Playboy Mansion party was particularly memorable for her because it made her realize that she was pansexual

Candid: 'It was such an intense experience,' she said. 'It was the first time I really knew that I was attracted to women. I'd always thought I was straight until that night'

Candid: ‘It was such an intense experience,’ she said. ‘It was the first time I really knew that I was attracted to women. I’d always thought I was straight until that night’

‘The other girls were so lovely and I had so much fun,’ she said. 

The night was also particularly memorable for Jenna because it made her realize that she was pansexual. 

‘It was such an intense experience,’ she said. ‘It was the first time I really knew that I was attracted to women. I’d always thought I was straight until that night.’

‘I’d had feelings of attraction to women from a young age, but I mistook it as thinking they were pretty and that I wanted to look like them.

‘The older I got, the clearer it got in my mind, but I never told my mom or my family because I was confused.

‘The best analogy I can give to how I feel about my sexuality and being pansexual is: I like the wine but not the label.’



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