Madonna’s Steamy Lesbian Love Triangle Affair Revealed: Queen of Pop, 66, Romped With Lesbian Model Jenni Shimizu, 57 — Who Dated Angelina Jolie
Madonna's lesbian fling with Jenny Shimizu occurred while the model was dating Angelina Jolie.
Sept. 20 2024, Published 1:15 p.m. ET
Pop superstar Madonna once had a steamy fling with openly gay model Jenny Shimizu.
RadarOnline.com can reveal the romance made the former mechanic feel like a "high-class hooker" as Madonna, now 66, would fly her across Europe for late-night hook-ups – despite the fact she was dating Angelina Jolie at the time.
Madonna has been visiting the Kabbalah center to cope with recently losing her brother and stepmom.
Shimizu, 57, said: "I mean, you are not going to say no to Madonna in the 90s.
"It was a great feeling like a high-class hooker, because it really did feel like that.
"I would get a phone call saying, 'Can you meet me at my show in Paris you're in Europe, right?' and I would be like, 'Yeah I'm just finishing Prada, I'll catch a plane over.'
"And I would go to her hotel room at the Ritz at four in the morning and have sex and fly back to Milan."
Jenni Shimiazu said Madonna made her feel like a "high-class hooker”.
Shimizu, who has been married to Michelle Harper since 2014, then joked: "My wife is going to kill me."
The model, famous for starring in Calvin Klein's first ad for its first unisex fragrance CK One, spoke in depth about the romance in new Disney Plus documentary In Vogue: The 90s.
Shimizu first revealed she’d had a relationship with Madonna in her memoir last year.
Shimiazu appeared in a Calvin Klein advert for unisex scent CK One.
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She said: "It wasn't about an emotional bond, it was about taking each other to the heights of sexual ecstasy.
"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 sex."
The model began dating Jolie when they featured in 1996 movie Firefox and the Tomb Raider star admitted to the romance when she was married to ex-husband Johnny Lee Miller.
She said: "I fell in love with her the first second I saw her.
"I would probably have married Jenny if I hadn't married my husband."
Angelina Jolie began dating Shimiazu when they co-starred in movie Firefox.
Madonna sparked rumors concerning her sexually in 2022 on TikTok.
She held up a pair of neon pink knickers, scrunched up in her hands, and said: "If I miss, I’m gay".
The singer tossed the underwear across the room and showed they had missed the bin she was aiming at, before shrugging to the camera and walking away.
Speaking to gay magazine Advocate in 1991, Madonna admitted she had female "crushes".
She said: "I've had lots of crushes. I think I've only been in love with men, because ultimately the approval I seek is my father's."
Madonna is currently dating Jamaican footballer Akeem Morris, 28, and has previously been married to actor Sean Penn, 65, and movie director Guy Ritchie, 56.
Madonna is currently dating Jamaican footballer Akeem Morris - nearly 40 years her junior.
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