Justin Timberlake cheated on Cameron Diaz with a Playboy bunny during the early stages of the celebrity couple’s relationship, according to the model.
Zoe Gregory, who moved into Hugh Hefner’s famous Los Angeles mansion in 2001, says she “connected” with the Sexy Back singer in the property’s infamous grotto after meeting him at a party.
In an exclusive interview with DailyMail.com, the British model, now 49, said Timberlake initially rejected her advances by telling her he was dating the Charlie’s Angels star.
But when Gregory joked that his girlfriend “wasn’t with you right now,” he agreed to take off his shorts and jump into Hugh Hefner’s indoor pool, she claims.
Former Playboy model Zoe Gregory (in blue cap) revealed she “hooked up” and “played” with Justin Timberlake (front right) when he visited the Playboy Mansion while dating Cameron Diaz.
Timberlake, who was 25 at the time, began dating Cameron Diaz, then 34, in 2003. Gregory claims she became involved with the singer during the early stages of his relationship with the actress.
British-born Gregory moved into Hugh Hefner’s famous Los Angeles mansion in 2001 as one of his seven girlfriends.
“I didn’t want to look like a coward. We both went into the grotto and took off our gear (down to our shorts) and ended up fooling around,” he told DailyMail.com.
“I didn’t have sexual relations with him, but they caressed us and we kissed.”
Gregory’s revelations could prove embarrassing for the singer, nicknamed “the trouser snake” by fans.
Timberlake, 43, was known for being a womanizer on the road before settling down with actress Jessica Biel, 41, in 2012 and having two children.
Last year, the former NSYNC frontman became the subject of explosive allegations when ex Britney Spears wrote in her memoir that he had encouraged her to have an abortion during their ill-fated relationship.
Timberlake’s new album, Everything I Thought It Was, is due out next month and his team will be eager to get some positive publicity ahead of the release.
But while promoting his new book, From Britain to Bunny – released last month – Gregory says the pop star couldn’t resist his advances after she saw him at one of Playboy boss Hefner’s star-studded parties in the early 2000s.
The former Playboy model recalled how Timberlake stripped down to his shorts and jumped into the mansion’s infamous grotto (pictured).
Gregory recalled meeting several celebrities, including wrestler Stone Cold Steve Austin, during star-studded parties at the mansion.
The former Playboy model was photographed with Donald Trump and sex therapist Dr. Ruth Westheimer at an event.
She was one of several bunnies sharing a bed with Hef in the mansion at the time, even though he was already in his 70s and reliant on Viagra to perform.
Timberlake reportedly only started seeing Diaz after he reportedly met her at the Kids Choice Awards in 2003.
The actress was 34 years old at the time, while Timberlake was just 25. They dated for four years before announcing their separation in January 2007.
Meanwhile, Gregory broke up with Hefner in 2004 and admits that she cheated on him more than once during their three-year relationship.
Speaking from his home in Miami, he said: ‘They rented out the back of the mansion for events about three times a month.
‘It was great because so many superstars attended, Nicolas Cage and Eminem, that I met them all.
‘We weren’t allowed to go to these parties, but two of the girls and I would sneak in there once Hef was past his bedtime.
‘We would have to be careful with the security guards patrolling because some of them would let you know.
Zoe was part of a harem of bunnies that lived on the property and shared a bedroom with Hugh.
Timberlake reportedly began dating Diaz after he reportedly met her at the Kids Choice Awards in 2003. The couple broke up in 2007.
Timberlake, 43, was known for being a womanizer on the road before settling down with actress Jessica Biel, 41, in 2012. The couple (pictured in 2022) have two children.
It would be a reprimand if he found out. And if you struck out more than three times he would throw you out of the house, so you had to be careful.
‘I met a lot of famous people during those nights out. But I only dated one couple and one of them was Justin.
“He was in the grotto one night and he had a big head and said something about Cameron Diaz, because that’s who he was dating at the time.
“I was like, ‘Well, she’s not with you right now, so what’s wrong?’ You’re at the Playboy Mansion, so what do you think she’s going to happen here? “‘
‘He said, ‘Oh, okay!’ He was being arrogant because he was drunk.
To be honest, I just wanted to cross it off my list. It was literally a five minute thing and from what I can remember, it was decent.
“But I was so afraid of being caught that I couldn’t continue for long. Before I could continue, we both put our clothes back on and said goodbye.
Among the stories Gregory tells in his new book is Hefner’s unique way of remembering the women he had slept with.
Instead of notches on the bedpost, Hef had an array of underwear dating back decades hanging from the bedroom ceiling. Some had been there so long that they were covered in cobwebs.
“I had never seen anything like it and I loved it,” he said.
As Hefner aged, his mind deteriorated, Gregory said. ‘The last time I saw him in person was when I went to the mansion for a party. I greeted him and he looked very old and I thought: I don’t want to remember him like that.
Gregory left the Playboy mansion in 2004 when he fell out with his number one girl, Holly Madison.
‘It was a centerpiece of her room and I thought, if only the walls could talk. I would love to meet the women who threw their thongs there and hear their stories.
‘The big gold chandelier to the right of his bed was covered with thongs from all the girls who had been there over the years. I’d say there were a few hundred up there.
‘You could see decades of different styles of panties, from full panties to tiny thongs. I gave him a pair before I left, one red and one tiny black.
‘I decided that before I leave this house, I’m going to make sure some of my thongs are there because I was legendary.
Gregory was one of the Playboy boss’ girlfriends since 2001, but left the Playboy mansion in 2004 when he fell out with his number one girl, Holly Madison.
She said she regularly contracted sexually transmitted diseases from Hefner, who died in 2017 at age 91.
But as he got older, his sexual appetite diminished and he liked watching pornography more than having sex.
‘After having a few drinks and smoking some weed, you could tell he was in his own bubble. He would lie there and let everyone get on and off him, but he concentrated more on the girls performing and the porn on TV.’
But when it came to his orgies, Gregory said, “One night I counted 17 girls in bed, that was the most.”
“We couldn’t fit everyone on the bed, so some of the girls were sitting on the floor waiting their turn.”
Gregory said he has fond memories of the old man. ‘I wanted to make him happy because he was making my dreams come true.
“I love that guy, he’s my hero, because he prepared me for life and gave me every opportunity I ever dreamed of. I have nothing bad to say about that man, it’s all love.
“I didn’t find him physically attractive. There were certain gestures of his that I loved because they were very gentlemanly and old-fashioned.
‘Men don’t act like that anymore and I loved that, but did I find it physically sexy? No.’
She said she kept in touch with him by phone after leaving the mansion, but his mind began to deteriorate around 2019.
‘The last time I saw him in person was when I went to the mansion for a party. I greeted him and he looked very old and I thought: I don’t want to remember him like that.
From Britain to Bunny is now available to purchase at Britaintobunny.com.