Cassie Questioned About Diddy's Alleged “Swingers” Lifestyle During Trial

BY Caroline Fisher
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Cassie and Sean "Diddy" Combs during 2006 MTV European Music Awards Copenhagen - Red Carpet Arrivals at Bella Centre in Copenhagen, Denmark. (Photo by KMazur/WireImage)
Recently, Cassie recalled going to sex clubs with Diddy, and watching him sleep with other women during their relationship.

Cassie has taken the stand yet again today amid her ex-boyfriend Diddy's long-awaited sex trafficking trial. The songstress is being cross-examined by his defense, who seem to be trying to prove that his "freak offs" were consensual. They read various text messages the former couple exchanged in court. In some of them, Cassie showed interest in sleeping with Diddy. Once, she told him "I'm always ready to freak off, it can be whenever."

Cassie was also questioned by Diddy's defense attorney Anna Estevao. She asked her if she had conversation with him about a "swingers lifestyle" during their relationship. She said she had, and recalled going to sex clubs with the Bad Boy founder and watching have sex with other women multiple times.

Estevao also asked Cassie if the freak offs were related to their swingers lifestyle, per TMZ. "Related in a sexual way, yeah. But they're very different," she responded.

Diddy Trial Day 4

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Cassie Ventura and Sean "Diddy" Combs attend the Heavenly Bodies: Fashion & The Catholic Imagination Costume Institute Gala at The Metropolitan Museum of Art on May 7, 2018 in New York City. (Photo by John Shearer/Getty Images for The Hollywood Reporter)

Cassie has said plenty more about her relationship with Diddy during the trial so far. At one point, for example, she recalled him allegedly rushing through one of their freak offs after learning that Suge Knight was at a nearby diner.

“I was crying, I was screaming, like ‘Please don’t do anything stupid,’” she explained. “I was really nervous for them, I didn’t know what they were going to do.”

She also accused Diddy of physically assaulting her after being told she was attending Drake's OVO fest in Toronto. "Sean came to my home & tried to attack me. I was thrown into the bed frame," she alleged. Cassie also seemingly confirmed that she sustained an eye injury during the alleged assault, and that D-Roc took her to a doctor for it.

About The Author
Caroline Fisher is currently a News Editor at HotNewHipHop. Her time at HotNewHipHop began in 2023 when she began writing about music and pop culture full-time. Since then, she has helped cover major stories including the YSL RICO trial, Drake and Kendrick Lamar’s explosive feud, Diddy’s ongoing legal battle, and awards shows such as the BET Awards. Being from Chicago, she also got the opportunity to attend Summer Smash 2024 and review Chief Keef’s historic homecoming show. She additionally covered sets by Flo Milli, Playboi Carti, Bktherula, and more.

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