Madonna Makes Shock Confession About Her Best Sex Ever

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The 67-year-old stunned her celebrity audience with the confession.

Madonna attends the Saint Laurent Womenswear Spring/Summer 2026 show at Paris Fashion Week on September 29, 2025, in Paris, France.
Stephane Cardinale - Corbis/Corbis via Getty Images

The Queen of Pop did not hold back when she was asked in a new promotional video who her “best d--- down” was.

Pop star madonna performs in Rio's Maracana Stadium before some 115,000 spectators Nov. 6
The playwright Jeremy O. Harris, Bob the Drag Queen, dancer Ivy Mugler, ID’s Marcello Gutierrez, and Lopez ask away in a sneak peek first obtained by Page Six on Thursday. STR New/REUTERS

“I’m only going to name dead people,” Madonna said, before dropping the bombshell. “John Kennedy Jr.,” she whispered, prompting her audience of fellow celebrities to shriek, “Shut upppppppp!”

Madonna, 67, is promoting her latest album, “Confessions II,” in an unconventional way—planning to release a tell-all video in collaboration with Grindr, featuring various cultural icons who pepper her with questions.

In a sneak peek, first obtained by Page Six on Thursday, she singled out the late JFK Jr. from a crowd of her star-studded previous romances, which include rapper Tupac Shakur and artist Jean-Michel Basquiat.

Tupac Shakur, Sting, Madonna, and Ingrid Casares
Tupac apparently did not compare to JFK Jr. WWD/Penske Media via Getty Images

The shocking revelation apparently wasn’t news to designer Raul Lopez, who said Madonna is the third person he has heard talking about the Kennedy scion’s skill in bed.

“Everyone says his d--- was crazy and he was a good f---,” Lopez said, to which Madonna responded with a sly, “Mmm hmm.”

JFK Jr., who died aged 38 when the plane he was piloting crashed, is no longer alive to tell his side of the story, but their tryst in the late 1980s has been widely documented by the many people fascinated by the Kennedy clan.

American attorney John F Kennedy Jr (1960 - 1999) (dark jacket, back to camera) and Pop singer Madonna (born Madonna Ciccone) talk together at the MGM Grand Garden Arena, Paradise, Nevada, June 28, 1997.
John F. Kennedy Jr. and Madonna talk at the MGM Grand Garden Arena, Paradise, Nevada, June 28, 1997. Michael Brennan/Getty Images

“She came on to him, and it was flattery. She was at the top of her game,” an unidentified friend said in 2024’s JFK Jr.: An Intimate Oral Biography. “He loved her body. It was all about physical attraction; it wasn’t going to be anything beyond that.”

But the source claims they may not have gone all the way during their tryst, which they referred to as “barely a fling.”

“They didn’t have the protection measures and she was very on top of HIV prevention,” they said, sharing that they had “fun in other ways.”

galleries/2009/07/14/remembering-jfk-jr/jfk-jr-23_ebl08x
JFK Jr. was later married to Carolyn Bessette Kennedy. They both died in 1999 when the plane that JFK Jr. was piloting crashed. Newscom

Others say he was captivated by the singer.

“The dashing, dark, muscular Kennedy gave her a set of keys to his apartment,” J. Randy Taraborrelli wrote in 2012’s After Camelot.

Meanwhile, JFK Jr.’s mother and former first lady Jackie Onassis was befuddled by the singer’s behavior.

“Jackie had spent her entire celebrity life avoiding paparazzi, whereas Madonna would court paparazzi. And Jackie just couldn’t understand any of that,” Taraborrelli told People in a 2023 interview.

It also didn’t help, in the eyes of Onassis, that Madonna was still married at the time to Sean Penn, whom she wouldn’t divorce until January 1989 after years of marital turbulence.

Madonna and Sean Penn in 1986.
Madonna and Sean Penn in 1986. Vinnie Zuffante/Getty Images

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