Madonna Opens up on Who Was the “Best Sex of Her Life”

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Madonna has identified the well-known celebrity who had the “best sex of her life.” In a new video advertising her upcoming album, Confessions II, the 67-year-old Vogue singer collaborated with the LGBTQ+ dating app Grindr.

Fashion designer Raul Lopez asked the Queen of Pop to describe the “best d*** down” she has ever had in a preview that Page Six was able to secure. Madonna retorted, “I’m only going to name dead people.”

Then she covered her mouth and said in a whisper, “John Kennedy Jr.”

“Everyone says his d*** was crazy and he was a good f***,” Raul continued. “Mmmhmm,” said Madonna.

“You’re the third person I’ve heard say that,” Raul went on. In the late 1980s, as her notoriously tumultuous marriage to Sean Penn was ending, Madonna started seeing Kennedy. Among Kennedy’s rival late loves are Tupac Shakur, Luke Perry, and Jean-Michel Basquiat.

The romance was brief and never became serious, according to RoseMarie Terenzio and Liz McNeil’s 2024 book JFK Jr.: An Intimate Oral Biography.

Sumit Rajan

Sumit is a Sr. Editor at Black Sports Online. When not dissecting NBA and NFL storylines, you’ll find him cheering for Manchester United, testing out new fountain pens, or scaling a mountain.

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