According to the model, Justin Timberlake cheated on Cameron Diaz with a Playboy bunny during the early stages of the famous couple’s relationship.
Zoe Gregory, who moved into Hugh Hefner’s famous LA mansion in 2001, says she “hook up” with the Sexy Back singer in the property’s infamous cave after meeting him at a party.
In an exclusive interview with DailyMail.com, the British model, now 49, said Timberlake initially refused her advances by telling her he was dating the Charlie’s Angels star.
But when Gregory teased that his girlfriend “wasn’t with you right now,” he agreed to strip down to 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 “fooled around” with Justin Timberlake (front right) when he visited the Playboy Mansion while dating Cameron Diaz
Timberlake, who was 25 at the time, started dating Cameron Diaz, then 34, in 2003. Gregory claims she hooked up with the singer during the early stages of his relationship with the actress.
British-born Gregory moved into Hugh Hefner’s famous LA mansion in 2001 as one of his seven girlfriends
‘He didn’t want to look like a wimp. We both went into the cave and both took off our gear – down to his shorts – and we ended up messing around,” she told DailyMail.com.
“I didn’t have sex with him, but we loved and kissed.”
Gregory’s revelations could be embarrassing for the singer who fans call “trouser snake.”
Timberlake, 43, was known for his womanizing 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 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 keen to generate positive publicity ahead of the launch.
But while promoting her new book, From Great Britain to Bunny – released last month – Gregory says the pop star couldn’t resist her advances after seeing 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 cave (pictured)
Gregory recalled meeting several celebrities, including wrestler Stone Cold Steve Austin, during star-studded parties at the mansion
The former Playboy model was pictured at an event with Donald Trump and sex therapist Dr. Ruth Westheimer
She was one of several bunnies who shared a bed with Hef at the mansion at the time, despite the fact that he was already in his seventies and relied on Viagra to perform.
Timberlake reportedly just started seeing Diaz after reportedly meeting her at the Kids Choice Awards in 2003.
The actress was 34 at the time, while Timberlake was only 25. They dated for four years before announcing their divorce in January 2007.
Gregory, meanwhile, split from Hefner in 2004 and admits she cheated on him more than once during their three-year relationship.
Speaking from her home in Miami, she said: “They rented out the back of the mansion for events about three times a month.
‘It was great because there were so many superstars there – Nicolas Cage and Eminem – I met them all.
“We weren’t allowed to go to these parties, but me and two of the girls would sneak over there when it was past Hef’s bedtime.
“We’d just have to watch out for the guards on patrol because some of them would let him know.”
Zoë belonged to a harem of bunnies who lived on the property and shared a bedroom with Hugh
Timberlake reportedly just started seeing Diaz after reportedly meeting her at the Kids Choice Awards in 2003. The couple called it quits in 2007.
Timberlake, 43, was known for his womanizing 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 shame if he found out. And if you struck out more than three times, he would kick you out of the house, so you had to be careful.
‘I met so many famous people on those nights out. But I’ve only been in touch with a few and one of them was Justin.
“He was in the cave one night and had a big head and said something about Cameron Diaz because he was dating him at the time.
“I thought, ‘Well, she’s not with you right now, so what’s going on? You’re at the Playboy Mansion, so what do you think is going to happen here?’
“He said, ‘Oh okay!’ He was cocky because he was drunk.
“Honestly, I just wanted to cross it off my list. It literally lasted five minutes and as far as I can remember, it was decent.
‘But I was so afraid of getting caught that I couldn’t continue for much longer. Before it could go any further, we both put our clothes back on and said our goodbyes.’
One of the stories Gregory tells in her new book is Hefner’s unique way of remembering the women he had slept with.
Instead of notches on the bedpost, Hef had a huge amount of decades-old underwear dangling from the bedroom ceiling. Some had been there so long that they were covered in cobwebs.
“I had never seen anything like it before and I loved it,” she said.
As Hefner grew older, his mind deteriorated, Gregory said. “The last time I saw him in person was when I went to the mansion for a party. I said hello and he looked really old and I thought, I don’t want to remember him like that.
Gregory left the Playboy mansion in 2004 when she fell out with his number one girl Holly Madison
‘It was such a focal point of his room and I thought, if only walls could talk. I’d love to meet the women who threw their thongs out there and hear their stories.
“The big, gold chandelier to the right of his bed was covered in thongs from all the girls who had been there over the years. I’d say there were a few hundred up there.
‘For decades you saw different types of panties, ranging from full-fledged underwear to small thongs. I threw a few on before I left, a red one and a small black one.
“I decided before I leave this house, I’d make sure some of my thongs were up there because it was legendary.
Gregory was one of the Playboy boss’ live-in girlfriends from 2001, but left the Playboy mansion in 2004 when she fell out with his number one girl Holly Madison.
She said she frequently contracted sexually transmitted diseases from Hefner, who died in 2017 at age 91.
But as he got older, his sexual desire waned and he enjoyed watching porn more than actually having sex.
‘After he had a few drinks and smoked a bit of weed, you could tell he was in his own bubble. He lay there and let everyone get on and off, but he was most focused on the girls’ performances and the porn on TV.”
But as for his orgies, Gregory said: “I counted seventeen girls on the bed one night – that was the most.
“You couldn’t get us all on the bed, so a few girls sat on the floor waiting for their turn.”
Gregory said she has fond memories of the old man. ‘I wanted to make him happy because he made my dreams come true.
‘I love that man, he is my hero, because he set me up for life and gave me all the opportunities I ever dreamed of. I don’t have a bad word to say about that man, it’s all love.
‘I didn’t find him physically attractive. There were certain ways of his that I loved because they were so gentle and old-fashioned.
‘Men don’t behave like that anymore and I thought that was great, but did I find him 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 said hello and he looked really old and I thought, I don’t want to remember him like that.
From Britain to Bunny is available to purchase now at Britaintobunny.com.