Madonna's ex Jenny Shimizu jokes she felt like a 'high class hooker' during their late-night liaisons as she gives rare insight into their 'crazy' romance in Vogue documentary

Madonna's ex-girlfriend Jenny Shimizu joked that she felt like 'a high class hooker' during the height of their steamy romance.

The model, 57, has offered rare insight into her relationship with the singer, 66, in the Disney+ documentary In Vogue: The 90s, which takes a look-back at the stars that defined an iconic decade in the magazine's history. 

In the sixth and final episode of the series, Jenny shared that she enjoyed a romance with Madonna at the same time that she was dating Angelina Jolie, admitting that she would fly across Europe for late-night liasons with the star.

The actress, who married her wife Michelle Harper in 2014, added that on one occasion she flew from Milan to Paris to spend the night with Madonna, before jetting back to Italy for her next show.

She said: 'I mean you are not going to say no to Madonna in the 90s. 

'Not only was it great feeling like a high-class hooker, because it was, 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 the Ritz at four in the morning and have sex and fly back to Milan.'

Jenny, who married her wife Michelle Harper in 2014, previously detailed her romance with Madonna in her 2023 memoir, writing that their relationship was driven by a deeper physical connection than physical.

She said at the time: '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 fashion star rose to prominence after being approached to model for Calvin Klein, and as well as being the first Asian model to walk for Prada, she was also the first minority model to open the show.

At the same time she and Madonna were dating, Jenny was also involved in a romance with her Foxfire co-star Angelina Jolie.

Angelina confirmed their romance herself in a 1997 interview, saying: '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 (Jonny Lee Miller).'

In the documentary, Jenny also reflected on her own rise to prominence as a fashion star, saying: 'My wife is going to kill me, but that time was so crazy and fun and there was something heartfelt about certain moments. 

'I remember my friends brought me to Times Square and they were like, ''look!'' and I had just done a Banana Republic campaign and underneath it said American Beauty.

'Never in my life had I been described as American and as a beauty. Being Japanese and being gay and walking down the street and being harassed, but for one second seeing that campaign, it was such a big statement and I'm grateful to Calvin Klein because he did something that was so positive.'

The documentary In Vogue: The 90s is a star-studded look at the fashion industry during the decade.

It speaks to former Vogue editors including Edward Enninful and celebrities such as supermodel Naomi Campbell, actress Gwyneth Paltrow and Sex And The City star Sarah Jessica Parker. 

The documentary also showcases rare, never-before-seen archives from key figures in the industry and reveal the untold story of the decade's most celebrated pop cultural moments and movements.

Other contributors will include designers Tom Ford, Marc Jacobs and Jean Paul Gaultier, actress Claire Danes, models Amber Valetta and Tyson Beckford, director Baz Luhrmann and politician Hillary Clinton.

Meanwhile, adding to her lengthy list of romances, Madonna is currently dating Jamaican footballer Akeem Morris, 28.

The pair appeared to have first met in 2022 after appeared on her August 2022 cover issue of Paper Magazine.

The final three episodes of In Vogue: The 90s will be available to stream on Disney+ from Friday, September 20.