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Madonna's ex-wife Jenny Shimizu says she felt like 'a high-class prostitute' during their 'crazy' relationship

Madonna's ex-boyfriend is speaking out.

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

“I mean, you wouldn't be able to say no to Madonna in the '90s,” Shimizu, 57, said in the final episode of the six-part series.

Madonna (left) and Shimizu in 1993. MediaPunch/Shutterstock
Shimizu at the Richard Tyler Spring 1994 Ready-to-Wear Runway Show. Penske Media via Getty Images

“It was not only like feeling like a high-class prostitute — because that’s really what 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 say, ‘Yeah, I’m just finishing Prada. I’ll be on a plane right after Prada.'”

“And I would do that,” Shimizu said. “I would go to her hotel, the Ritz, at four in the morning, have sex and then fly back to Milan.”

Madonna (second from left) and Shimizu (right). Corbis/VCG via Getty Images

After detailing his past romance with the now 66-year-old Madonna, Shimizu joked, “My wife will kill me.”

Shimizu has been married to Michelle Harper since 2014.

Recalling her life as a model in the 90s, Shimizu said, “That time was really crazy and fun. There were some heartwarming moments.”

Shimizu at Refinery29’s F–k the Fashion Rules panel in August 2015 in NYC. Getty Images

Madonna has never publicly confirmed her relationship with Shimizu.

The “Hung Up” singer, who has a huge gay following, came out about her sexuality in 1991.

“I think everybody has a bisexual nature. That's my theory,” he said in an interview Advocate Those days.

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

He has six children: Lourdes Leon27, Rocco Ritchie, 24, David Banda, 19, Mercy James18, and twins Stella and Estere12.

Madonna at Milan Fashion Week on September 21, 2024. ipa/instarimage

Shimizu had a romantic relationship with the “4 Minutes” singer around the same time as his brief relationship with Angelina Jolie.

In 1997, Jolie told Girlfriends magazine“If I hadn't married my husband (Jonny Lee Miller) I probably would have married Jenny Shimizu. I fell in love with her the first time I saw her.”

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

In an interview in 2001 Rolling StoneJolie reportedly called her relationship with Shimizu “a discovery.”

“I realized I was looking at her the same way I looked at men,” “and it was awesome, and it was a discovery.

“It never crossed my mind that I would one day experiment with a woman or kiss her, it wasn't something I was looking for,” he said. “I just fell in love with a girl.”

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