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Madonna Has Surprising Take on Receiving 'Hole Pics' During Steamy Chat About Intimacy

Photo of Madonna
Source: Grindr/YouTube

Madonna exposed cheeky sexual preferences during a chat about her new album.

May 29 2026, Updated 4:06 p.m. ET

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Madonna got candid about her sexual preferences.

In a chat with Bob the Drag Queen, Jeremy O. Harris, Raul Lopez, Ivy Mugler and Marcello Gutierrez, she considered what it would be like to receive a “hole pic.”

The pop princess was inspired to open up about intimacy while dishing on her new album, Confessions II.

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Source: Grindr/YouTube

Madonna said 'hole pics' can be 'beautiful.'

"How do you feel about a hole pic?" she asked the group.

While she acknowledged “they could be beautiful,” some of the other stars weren’t as convinced.

"If you don’t like the way they look? Pass. Until you get a nice brown star!" the singer joked.

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Madonna Was Intimate With JFK Jr.

Image of Madonna discussed intimacy in a candid chat about her new album.
Source: Grindr/YouTube

Madonna discussed intimacy in a candid chat about her new album.

In the same conversation, Madonna unexpectedly revealed her best-ever s-- was with the late John F. Kennedy Jr.

Lopez asked, “Who was your best d--- down?” to which the musician insisted she was “only going to name dead people.” Madonna then placed a hand over her mouth and whispered, “John Kennedy Jr.”

“Everyone says his d--- was crazy and he was a good f---…you’re the third person I’ve heard say that,” Lopez confessed.

The “Vogue” singer agreed, “Mmm hmm.”

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When Did JFK Jr. and Madonna Date?

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Image of Madonna gushed over her s-- life with JFK Jr.
Source: MEGA

Madonna gushed over her s-- life with JFK Jr.

Kennedy and Madonna had a fling in the late 1980s after she separated from then-husband Sean Penn.

In July 2016, a friend of JFK Jr. elaborated on their special bond.

“It was a flirtation, and when other people referred to her as M around that time, just by her first initial, he would say, ‘I started that,’” the source revealed. “He called her M when he wrote or faxed her. There were no cell phones then and he was always very territorial that he started that moniker for her.”

The insider added, “I think she gave it right back to him and she teased him and she was irreverent and he liked it.”

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What Wrong Between the Stars?

Image of John F. Kennedy Jr. and Madonna had a fling in the late 1980s.
Source: MEGA

John F. Kennedy Jr. and Madonna had a fling in the late 1980s.

The pair’s bond reportedly faded due to their contradictory lifestyles.

“The flirtation kind of continued and they would try to get together but it was hard because she was on tour and he was working,” the friend detailed. “They saw each other a few times and they had a flirty and friendly banter but it wasn’t a ‘relationship.’ They would fax notes back and forth – they might have gone out twice but from what he said, it was, ‘We could never get together’ and then it kind of faded but they stayed friendly.”

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Image of Madonna did not want to pose on the cover of JFK Jr.'s magazine.
Source: MEGA

Madonna did not want to pose on the cover of JFK Jr.'s magazine.

Indeed, Madonna reportedly turned down Kennedy’s request for her to pose on the cover of his magazine, George, by sending him a fax.

She allegedly wrote, “Dear Johnny boy, Thanks for asking me to be your mother, but I’m afraid, I could never do her justice. My eyebrows aren’t thick enough for one. When you want me to portray Eva Braun [Adolf Hitler’s wife] or Pamela Harriman I might say yes! Hope you’re well. Love, Madonna.”

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