Madonna has always been known for her colorful love life, with two marriages and a string of flings with younger men. However, a recent bombshell revealed in the Disney+ documentary, In Vogue: The 90s, sheds light on a steamy fling the Queen of Pop had with Jenny Shimizu, an openly gay model. Jenny Shimizu, now 57, disclosed that her encounters with Madonna made her feel like a “high-class hooker.”
The former mechanic, known for her appearance in Calvin Klein’s iconic CK One fragrance advert, shared details of her late-night hookups with Madonna in the 90s. Jenny expressed how she would fly across Europe for rendezvous with Madonna, who is currently dating Jamaican footballer Akeem Morris, 28. She described the experience as feeling like a high-class hooker, recalling scenarios where she would receive calls from Madonna asking her to meet at her show in Paris, prompting Jenny to catch a plane over after finishing her work in Milan.
Jenny candidly shared, “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.” She described the thrill of being at Madonna’s beck and call for late-night encounters, emphasizing the physical nature of their relationship. Despite being married to Michelle Harper since 2014, Jenny reminisced about the excitement of being summoned to Madonna’s hotel room at the Ritz in the early hours of the morning for intimate moments, only to fly back to Milan afterward.
In her memoir released last year, Jenny first disclosed her relationship with Madonna, highlighting the intense physical connection between them. She emphasized that their interactions were primarily focused on the heights of sexual ecstasy rather than emotional bonding. Jenny reveled in the power dynamic of being at Madonna’s disposal for sexual encounters, finding arousal in the spontaneity and passion of their liaisons.
Interestingly, Jenny was concurrently dating actress Angelina Jolie during the same period, with their relationship beginning when they starred together in the film “Foxfire.” Angelina publicly acknowledged her affection for Jenny in 1997, despite being married to Jonny Lee Miller at the time. She admitted, “I fell in love with her the first second I saw her,” expressing a deep connection with Jenny that transcended traditional boundaries. Angelina’s openness about her feelings for Jenny showcased the complexity and fluidity of relationships during that era.
In a surprising turn of events, Madonna seemingly came out as gay in 2022 on TikTok, adding another layer to her already enigmatic persona. Holding up a pair of neon pink knickers, she playfully declared, “If I miss, I’m gay,” before tossing the underwear across the room. This casual revelation hinted at Madonna’s fluid sexuality and willingness to embrace her authentic self, regardless of public perception.
The documentary, In Vogue: The 90s, provides a glimpse into the era’s most significant fashion and showbiz moments, featuring interviews with Vogue editor-in-chief Anna Wintour and various A-list celebrities. The second volume, set for release soon, promises more insights from personalities like Victoria Beckham, Sarah Jessica Parker, and Stella McCartney, offering a comprehensive look at the cultural landscape of the 90s.
Subheadings:
**Madonna’s Steamy Fling with Jenny Shimizu**
**The Complex Dynamics of Madonna’s Relationships**
**Exploring Madonna’s Sexual Identity and Self-Expression**