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Madonna's Ex Jenny Shimizu 'Felt Like a High Class Hooker' When Flying Across Europe to Have S-- With Singer in the '90s

Photo of Madonna and picture of Jenny Shimizu.
Source: MEGA

Jenny Shimizu is giving all the dirty detail about her and Madonna's '90s fling!

Sept. 24 2024, Published 5:19 p.m. ET

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Madonna's ex Jenny Shimizu is taking a sensual walk down memory lane.

In Hulu's new docuseries In Vogue: The 90s, the famed model reflected on her former relationship with the Queen of Pop roughly three decades after her intimate romance with the "Material Girl" singer turned heads at the height of Madonna's fame.

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madonna jenny shimizu high class hooker dating s
Source: MEGA

Jenny Shimizu talked about what it was like dating Madonna in a new Hulu docuseries 'In Vogue: The 90s.'

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"I mean, you’re not gonna say no to Madonna in the '90s," Shimizu, 57, recalled toward the end of the six-episode series. "Not only was it great feeling like a high class hooker — because really it was. 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. I’d go over to her hotel, to the Ritz, at like 4 in the morning, have s--, and then fly back to Milan," the Fox Fire actress confessed of her erotic history with the "Like a Virgin" hitmaker, 66.

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madonna jenny shimizu high class hooker dating s
Source: MEGA

Madonna had Jenny Shimizu at her beck and call.

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Shimizu then joked, "My wife is going to kill me," in reference to her longtime lover Michelle Harper, who she tied the knot with in 2014.

Looking back on the moments she spent dating Madonna, Shimizu admitted, "That time was so crazy and fun."

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madonna jenny shimizu high class hooker dating s
Source: MEGA

Jenny Shimizu said she felt like a 'hooker' while dating Madonna roughly 30 years ago.

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While there was a great deal of hot bedroom behavior in the '90s, Shimizu noted there was also "really something heartfelt about certain moments."

One specific memory Shimizu holds near and dear to her heart is the very first time she saw herself on a billboard in New York City.

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"I remember my friends bought me to Times Square and said 'Look!' And I had just done a Banana Republic campaign. And underneath it said, 'American Beauty,' and never in my life had I been described as American or as a beauty," she explained.

"Being Japanese and having my parents going through internment camps, and being gay, and — to walk down the street and always get harassed in some way, for one second, seeing that campaign… it was such a, you know, it was a big statement. And I really am grateful to Calvin because he actually did something that was so positive globally," Shimizu added.

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madonna jenny shimizu high class hooker dating s
Source: MEGA

Jenny Shimizu also dated Angelina Jolie in the 1990s.

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The renowned model previously opened up about her and Madonna's fling in her memoir, which released last year.

"It wasn't about an emotional bond, it was about taking each other to the heights of sexual ecstasy," Shimizu penned in the book. "I loved the fact that I was at this woman's beck and call. It turned me on, being ordered to her room whenever she felt like s--."

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Source: OK!

In the midst of Shimizu and Madonna's romance, the model also had a brief fling with Angelina Jolie, who reportedly admitted to Girlfriends magazine in 1997 that the relationship "could have been a deep love."

"I probably would have married Jenny Shimizu if I hadn't married my husband," Jolie declared at the time, referencing her ex Jonny Lee Miller. "I fell in love with her the first second I saw her."

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