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Madonna’s ex Jenny Shimizu says she felt ‘like a high class hooker’ during their ‘crazy’ relationship

Madonna’s ex is talking.

Model Jenny Shimizu shared secrets about her relationship with the legendary singer in the 1990s in the new Hulu docuseries “In Vogue: The 90s.”

“I mean, you’re not gonna say no to Madonna in the ’90s,” Shimizu, 57, said in the final episode of the six-part series.

Madonna, Jenny Shimizu in 1993. Mediapunch/Shutterstock
Jenny Shimizu at the Richard Tyler Spring 1994 Ready to Wear runway show. Penske Media via Getty Images

“Not only was it great feeling like a high class hooker — because really it was,” she recalled. “You’d get a phone call like, ‘Hey can you meet me at my Paris show. You’re in Europe right?’ So I’d be like, ‘Yeah, I’m just finishing Prada. Right after Prada I’ll catch a plane over.’”

“And I would,” Shimizu added. “I’d go over to her hotel, to the Ritz, at like four in the morning, have sex, and then fly back to Milan.”

Madonna, Jenny Shimizu. Corbis/VCG via Getty Images

After detailing her past romance with Madonna, now 66, Shimizu joked, “My wife is gonna kill me.”

Shimizu has been married to Michelle Harper since 2014.

Looking back on her life as a model in the ’90s, Shimizu said, “That time was so crazy and fun. There’s something heartfelt about certain moments.”

Jenny Shimizu at Refinery29’s F*ck The Fashion Rules panel in NYC in Aug. 2015. Getty Images

Madonna has never publicly confirmed her relationship with Shimizu.

The “Hung Up” singer, who has a huge gay following, addressed her sexuality back in 1991.

“I think everybody has a bisexual nature. That’s my theory,” she said in an interview with Advocate at the time.

Madonna was married to actor Sean Penn from 1985 to 1989 and to film director Guy Ritchie from 2000 to 2008.

She has six children: Lourdes Leon, 27, Rocco Ritchie, 24, David Banda, 19, Mercy James, 18, and twins Stella and Estere, 12.

Madonna at Milan Fashion Week on Sept. 21, 2024. IPA/INSTARimages

Shimizu was entangled with the “4 Minutes” singer around the same time that she had a brief relationship with Angelina Jolie.

In 1997, Jolie told Girlfriends magazine, “I probably would have married Jenny Shimizu if I hadn’t married my husband [Jonny Lee Miller]. I fell in love with her the first second I saw her.”

Angelina Jolie at the Toronto Film Festival on Sept. 8, 2024. AFF-USA/Shutterstock

In a 2001 interview with Rolling Stone, Jolie reportedly called her relationship with Shimizu “a discovery.”

“I realized that I was looking at her in a way that I had looked at men,” the “Maleficent” star said. “And it was great, and it was a discovery.”

“It had never crossed my mind that I was going to one day experiment with or kiss a woman, it was never something I was looking for,” added Jolie. “I just happened to fall for a girl.” 

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