‘We had a fondle’: Playboy bunny Zoe Gregory claims Justin Timberlake cheated on ex Cameron Diaz in Hugh Hefner's grotto

The Playboy bunny, who lived with the late Hugh Hefner in his infamous mansion, claimed to have made out with the Justin Timberlake
PUBLISHED FEB 19, 2024
Playboy bunny Zoe Gregory reportedly says Justin Timberlake made out with him while dating Cameron Diaz (Getty Images and Denise Truscello/WireImage)
Playboy bunny Zoe Gregory reportedly says Justin Timberlake made out with him while dating Cameron Diaz (Getty Images and Denise Truscello/WireImage)

MIAMI, FLORIDA: Zoe Gregory has some bombshell disclosures that also include Justin Timberlake.

The Playboy bunny, who lived with the late Hugh Hefner in his infamous mansion, claimed to have made out with the singer despite him being in a relationship with Cameron Diaz at the time, Daily Mail reported.

Playboy bunny Zoe Gregory and Justin Timberlake had steamy encounter

The two reportedly met at a party before things got sexual between them at Hefner’s grotto.

Gregory told the publication, “He didn't want to look like a wimp. We both got in the grotto and we both got our kit off – down to his shorts – and we ended up fooling around.”

“I didn't have sex with him, but we had a fondle and we made out,” she revealed.

George Maloof, Zoe Gregory, Hugh Hefner, Holly Madison, Izabella St. James, Sheila Levell (Photo by Denise Truscello/WireImage)
George Maloof, Zoe Gregory, Hugh Hefner, Holly Madison, Izabella St. James, Sheila Levell (Photo by Denise Truscello/WireImage)

Zoe Gregory met Nicolas Cage and Eminem at Playboy mansion

The 50-year-old also asserted that she was not loyal to the editor-in-chief of Playboy magazine.

Bridget Amarquardt, Holly Madison, Hugh Hefner, Zoe Gregory, Sheila LeVell, (front row) Cristal Camden and Izabella St. James (Photo by Denise Truscello/WireImage)
Bridget Amarquardt, Holly Madison, Hugh Hefner, Zoe Gregory, Sheila LeVell, (front row) Cristal Camden and Izabella St. James (Photo by Denise Truscello/WireImage)

She shared, “They would rent the back of the mansion out for events about three times a month. It was great because so many superstars attended – 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 down there once it was past Hef's bedtime,” she mentioned.

Gregory further disclosed, “We would just have to watch out for the security guards on patrol because some of them would let him know. It would be a telling-off 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 during those nights out. But I only hooked up with a couple and one of them was Justin.”

LOS ANGELES, CA - SEPTEMBER 17: Justin Timberlake attends the 70th Emmy Awards at Microsoft Theater
Justin Timberlake attends the 70th Emmy Awards (Getty Images)

Playboy bunny Zoe Gregory wanted Justin Timberlake ‘off my list’

She noted, “He was in the grotto one night and 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 now, so what's up? You're in the Playboy Mansion so what do you think is going to go down here?’”

“He said, 'Oh Ok!' He was being cocky because he was drunk. I just wanted to tick him off my list, to be honest,” Gregory told Daily Mail.

She also added, “It was literally a five-minute thing and from what I can remember, he was decent. But I was so scared of getting caught that I couldn't continue for too long. Before it could go any further, we both put our clothes back on and said goodbye.”

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