JFK Jr.'s Mistress Reveals Shocking Affair Details, Including Steamy Paint and Sex Sessions

Sybil Hill, who claims to have been a long-time mistress of John F. Kennedy Jr., has shared new details about their passionate relationship. Hill described how their romance, which began in 1991, continued before and during JFK Jr.'s marriage to Carolyn Bessette, and included both emotional and physical intimacy.
According to Radar Online, Hill said she first met JFK Jr. at a Manhattan diner, where sparks flew immediately. Hill went up and introduced herself to JFK Jr., and the chemistry led to wild bedroom sessions in the years to come as she recalled.
The former political scion's love of painting reportedly became a pretext for intimate encounters. "John liked to paint, and our painting sessions often turned into s-- sessions," Hill said, describing how the hobby led to romance and deeper emotional connection.
She also revealed that JFK Jr. kept her love letters by his bedside, including one she wrote when he asked her to pick up maps from his apartment: "I just poured my heart out," she said.
Their relationship was complicated by JFK Jr.'s romance with Bessette. Hill recalled a final encounter before his engagement announcement: "We made love, but I could see he was conflicted. Finally, I put my hand over John's heart and said, 'You have to follow your heart.' He dropped his head and said simply, 'I'm sorry.' I knew he was leaving me for Carolyn." Heartbroken, Hill moved to Aspen, Colorado, but said he later reached out during his troubled marriage.
Hill described a passionate night together in February 1998, during which JFK Jr. confided about his marital struggles.
"I lit a fire in the fireplace. We started out on the couch, then moved down to an Oriental rug on the floor, and ended up upstairs in the bedroom," she said. She recalled his words of commitment: "John gazed into my eyes and said, 'No, Sybil, you're the only one.'"
Their affair effectively ended with JFK Jr.'s tragic death in a 1999 plane crash alongside Bessette. Reflecting on their relationship, Hill said, "I'll never know if John would have come back to me, but I treasure the thought that he would have."
In separate news, Before meeting Carolyn Bessette, John F. Kennedy Jr. had a high-profile romance with actress Daryl Hannah, which began in 1988 and lasted several years, Vanity Fair reports.
Their relationship, marked by tabloids and public attention, included playful moments like rooftop dancing in New York City and shared outdoor interests such as skiing and camping.
Tensions arose due to Kennedy's growing attraction to Bessette, leading to the eventual end of his relationship with Hannah in 1994. Kennedy married Bessette in 1996, while Hannah later wed musician Neil Young in 2018.
Friends and biographers note that Kennedy's connection to Bessette quickly overshadowed his romance with Hannah.
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