MADONNA has had a famously colourful love life, having been married twice – and enjoyed a string of flings with younger men. However, one of the many bombshells revealed in Disney+ documentary, In Vogue: The 90s is that the Queen of Pop, 66, had a steamy fling with Jenny Shimizu, 57, which left the openly gay model feeling like a “high-class hooker.” The former mechanic – who was in Calvin Klein’s famous advert for its first unisex fragrance CK One – confesses she would fly across Europe for late-night hookups with Madonna, who’s currently dating Jamaican footballer Akeem Morris, 28. She says: “I mean, you are not going to say no to Madonna in the 90s. It was 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.” Jenny, who has been married to Michelle Harper since 2014, adds with a laugh: “My wife is going to kill me.” Jenny first revealed she’d had a relationship with Madonna in her memoir last year. 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.”
Late-night lesbian romps with Madonna made me feel like a high-class hooker…I was also dating another A-list star
MADONNA has had a famously colourful love life, having been married twice – and enjoyed a string of flings with younger men.
However, one of the many bombshells revealed in Disney+ documentary, In Vogue: The 90s is that the Queen of Pop, 66, had a steamy fling with Jenny Shimizu, 57, which left the openly gay model feeling like a “high-class hooker”.
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Jenny Shimizu has revealed she “felt like a high-class hooker” with MadonnaCredit: Getty
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The pair enjoyed late-night hookups in the 90sCredit: Rex
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Madonna seemingly came out as gay in 2022 on TiktokCredit: Getty
The former mechanic – who was in Calvin Klein’s famous advert for its first unisex fragrance CK One – confesses she would fly across Europe for late-night hookups with Madonna, who’s currently dating Jamaican footballer Akeem Morris, 28.
She says: “I mean, you are not going to say no to Madonna in the 90s.
“It was 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’.
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“And I would go to her hotel room at the Ritz at four in the morning and have sex and fly back to Milan.”
Jenny, who has been married to Michelle Harper since 2014, adds with a laugh: “My wife is going to kill me.”
Jenny first revealed she’d had a relationship with Madonna in her memoir last year.
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.”
Another A-list lover
Shockingly, actress Jenny was also dating Angelina Jolie at the same time, having met when they starred in Foxfire together.
All the ways Madonna is turning into Gemma Collins, from dodgy fashion to raunchy lingerie shoots and cavorting with animals
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Jenny was also dating Angelina Jolie at the timeCredit: Alamy
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Angelina said she “fell in love with her the second she saw her”.Credit: Film Comany
Angelina confirmed their romance herself in 1997, while she was married to Jonny 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.”
Madonna seemingly came out as gay 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”.
She tossed the underwear across the room and showed they had, indeed, missed the bin she was aiming at.
She then gave a shrug to camera and turned to walk away.
In Vogue: The 90s features interviews with Vogue editor-in-chief Anna Wintour, along with a host of A-list celebrities, revealing some of the juiciest showbiz and fashion moments from the decade.
The second volume, released tomorrow, includes snippets from Victoria Beckham, Sarah Jessica Parker and Stella McCartney on her and Liv Tyler’s infamous ‘Rock Royalty’ vests that they wore to their first Met Gala in 1999.
Rock Royalty
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Stella McCartney and Liv Tyler turned up to the Met Gala in Rock Royalty vestsCredit: Getty
“I went with Liv because she was one of my best friends, and we really didn’t know what to expect,” Stella recalls. “I was like, ‘What are we going to wear?’ and I bought these vests and went down to a place called Filth Mart and asked them to stamp these vests for me.
“They were like, ‘When do you need them?’ ‘I need them in about three hours.’”
Stella went to Liv’s apartment with the vests – which refer to the fact they are both daughters of rock stars – and was stunned when she discovered a hair and makeup artist there.
She was also shocked by the number of paparazzi at the Met, taking their picture.
She continues: “We didn’t know what the hell we were letting ourselves in for.
Inside Madonna’s love life
Madonna has had a rollercoaster of a love life…
Sean Penn: Married the actor in 1985; the couple divorced in 1989.Warren Beatty: Had a high-profile relationship with the actor in the early 1990s.Vanilla Ice: Brief relationship in the early 1990s; he claimed she proposed to him, but he declined as he was “too young”.Carlos Leon: Dated the personal trainer in the mid-1990s and they were rumoured to be engaged; they share a daughter, Lourdes.Guy Ritchie: Married the British film director in 2000; the couple divorced in 2008. They have a son, Rocco, and adopted a son, David, together.Jesus Luz: Dated the Brazilian model from 2008 to 2010.Brahim Zaibat: Was in a relationship with the French dancer from 2010 to 2013.Timor Steffens: Had a brief relationship with the Dutch dancer in 2014.Ahlamalik Williams: Dated the American dancer, who is 36 years her junior, from 2019 to 2022.Josh Popper: Dated for a year from 2022 to 2023; he is 35 years her junior.Akeem Morris: Been dating since July 2024; he is 38 years her junior.
“We went up the stairs and were like, ‘What the hell was that?’
“We couldn’t believe what was going on. We were literally fish out of water.
“And the next day we were on the front cover of Women’s Wear Daily, which was apparently a big deal. We didn’t know.”
Afterwards, many people started recreating the Rock Royalty vests – and Stella even brought out her own versions in 2022, selling them for £525.
“I remember I had a fitting and, I swear to God, Giselle came in one of those rip-offs. To my fitting,” she adds with a laugh.
Victoria Beckham’s ‘Gucci’ school bag
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Victoria Beckham reveals she used to carry a Gucci carrier bag to schoolCredit: Disney +
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She was always obsessed with fashionCredit: Rex
Elsewhere in the documentary, Victoria Beckham opens up on her obsession with designer gear from a very young age.
She says: “I loved the idea of luxury.
“My mum’s friend used to wear a lot of Coco Chanel fragrance. When she finished them, she’d give them to me. I mean, she would drain the bottles, there was nothing left for me, but I used to put them all out on my window sill because I loved how they looked.
“I remember one time she gave me the empty bottles in a Gucci plastic carrier bag.
“Oh my gosh, I would carry my school books to school every day in this Gucci plastic carrier bag until the bottom fell out. I felt so special.
“I felt like I was owning a part of that luxury brand.”
She can definitely afford more than a carrier bag from Gucci now!
THAT Lil Kim outfit
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Lil Kim wore a breast-exposing outfit to the 1999 VMAsCredit: Getty
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The pasty stayed on with eyelash glue, even when Diana Ross gave it a jiggleCredit: Image Direct
One of the most iconic outfits from the 90s was Lil Kim’s 1999 VMAs look – a purple jumpsuit with one boob completely out aside from a matching pasty covering the nipple.
And her stylist Misa Hylton reveals it was actually Missy Elliot who inspired the daring number.
She says: “Missy was like, ‘Lil Kim is such a bad b***h. If I was Lil Kim, I’d just f**k it and have my t*tty out, and I was like, ‘Hmm, interesting.’
“I knew that it was risque but I just wanted to create this look, so I found this beautiful Indian bridal fabric.
“It was lavender, and sequins and a little bit of white lace. It was absolutely gorgeous and I knew I wanted it to be feminine, because she was going to have one boob out.
“Kim loved the outfit and you can see in all the photos. She’s glowing, she’s feeling happy. She loved it, she’s feeling like Queen Bee.”
She hilariously adds: “That pasty was stuck on with eyelash glue but it stayed on all night, even after Diana Ross gave it a little jiggle!”
And Missy adds: “Can you imagine Kim doing that in this period of social media? They would’ve been like Instagram down, Facebook down, Twitch down, everything down!”
Stream In Vogue: The 90s exclusively on Disney+ – Volume I (eps 1-3) is out now, and Volume II (4-6) from 20th September
Read the full story on www.thesun.co.uk
https://www.thesun.co.uk/tvandshowbiz/30511405/madonna-jenny-shimizu-lesbian-sex/