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Sean “Diddy” Combs’ defense tried to suggest Thursday during their cross-examination of his ex-girlfriend Cassie Ventura that his depraved “freak-offs” were simply part of a “swingers lifestyle.”

Ventura pushed back against the idea amid an hours-long grilling by Combs’ lawyer Anna Estevao, even as she acknowledged having conversations with the mogul about the lifestyle.


  Cassie testifies about bruises she says she suffered after Diddy beat her, as he looks on from the defense table, in thsi court sketch from Wednesday. REUTERS Cassie testifies about bruises she says she suffered after Diddy beat her, as he looks on from the defense table, in thsi court sketch from Wednesday. REUTERS

The R&B singer testified she occasionally watched Sean “Diddy” Combs have sex with other women and that it had happened between two and four times.

“It happened, but not often,” Ventura said, noting that Combs had brought up her watching him with other women “frequently enough.”

When Estevao floated that Diddy’s “freak-offs” were simply part of being a swinger, Ventura offered a nuanced take.

“Related in a sexual way, yeah,” she said, before drawing a distinction, “They’re very different.”


  Musicians Sean “Diddy” Combs and Cassie Ventura attend the GQ Men of the Year Party at Chateau Marmont on November 13, 2012 in Los Angeles, California. Jeff Vespa Musicians Sean “Diddy” Combs and Cassie Ventura attend the GQ Men of the Year Party at Chateau Marmont on November 13, 2012 in Los Angeles, California. Jeff Vespa

Defense attorneys revealed before the trial that they’d make the case that Combs was a free-loving swinger, rather than a predatory sex-trafficking rapist.

“There’s a lifestyle, call it swingers or whatever you will, that he thought was appropriate because it was common,” said Marc Agnifilo, one of Combs’ defense attorneys, during an April hearing.

The cross-examination often delved into the nature of Combs’ and Ventura’ relationship, which she testified that she believed was monogamous.

Ventura contended that Combs carried on relationships with other women.


  Lawyer Anna Estevao cross-examines Casandra “Cassie” Ventura during Sean “Diddy” Combs’ sex trafficking trial in New York City, New York, U.S., May 15, 2025, in this courtroom sketch. REUTERS Lawyer Anna Estevao cross-examines Casandra “Cassie” Ventura during Sean “Diddy” Combs’ sex trafficking trial in New York City, New York, U.S., May 15, 2025, in this courtroom sketch. REUTERS

“You’re making me look like a side piece and that’s not what I thought I was,” she texted him at one point.

The singer acknowledged she had a brief fling with rapper Kid Cudi in part to retaliate against Combs’ own infidelities.

Combs would become insanely jealous if he suspected Ventura was seeing other men, in particular Kid Cudi, she testified.

She said used a burner phone during her relationship with Kid Cudi, even though she was on a “break” from Combs.

“I did not want him to find out,” she testified. “I thought it would be way too dangerous.”


  Singer Britney Spears, Rapper P. Diddy and Singer Cassie pose for photos at Cassie’s 21st Birthday at Jet Nightclub at The Mirage Hotel and Casino on September 08, 2007 in Las Vegas, Nevada. WireImage Singer Britney Spears, Rapper P. Diddy and Singer Cassie pose for photos at Cassie’s 21st Birthday at Jet Nightclub at The Mirage Hotel and Casino on September 08, 2007 in Las Vegas, Nevada. WireImage

Combs allegedly threatened to blow up Kid Cudi’s car before it subsequently exploded, Ventura previously testified.

Ventura also said Wednesday from the witness stand that the Bad Boy Records founder convinced her it would be “fun” to go to sex clubs.

She also faced pushback from Combs’ defense for her accusation that he controlled her appearance.

“Would you send [Combs] photos of your clothes and your hair and ask him what he thought?” Estevao asked.


  Sean “Diddy” Combs watches as his former girlfriend Casandra “Cassie” Ventura testifies at his sex trafficking trial in New York City, New York, U.S., May 13, 2025 in this courtroom sketch. REUTERS Sean “Diddy” Combs watches as his former girlfriend Casandra “Cassie” Ventura testifies at his sex trafficking trial in New York City, New York, U.S., May 13, 2025 in this courtroom sketch. REUTERS

“Yeah,” Ventura said, later acknowledging that Combs ran a fashion brand called Sean John and “had a big impact on fashion over many decades.”

Estevao’s questions seemed to be in response to Ventura’s testimony over the last two days claiming the Bad Boy Records producer controlled every aspect of the way she looked, down to the color she painted her nails.

Before a “freak-off,” Combs asked her if she got her nails done, if she was tan and if she had been waxed, she testified.

Ventura maintained a composed, cordial demeanor even as she was peppered with questions — and lengthy readings of X-rated texts — centered on intimate details of her sex life with Combs.


  Cassie (L) and Sean “Diddy” Combs pose backstage during the Puff Daddy and The Family Bad Boy Reunion Tour presented by Ciroc Vodka and Live Nation at Barclays Center on May 21, 2016 in New York City. Kevin Mazur Cassie (L) and Sean “Diddy” Combs pose backstage during the Puff Daddy and The Family Bad Boy Reunion Tour presented by Ciroc Vodka and Live Nation at Barclays Center on May 21, 2016 in New York City. Kevin Mazur

The R&B singer’s tenor with Estevao even verged into lighthearted at times, as the pair shared laughs.

At one point, Estevao called Cassie “very beautiful and charming,” drawing a laugh and smile out of her.

As a lunch break approached, Combs’ lawyers also quizzed Ventura about the fallen music producer’s alleged addictions.


  Sean “Diddy” Combs listens as his former girlfriend Casandra “Cassie” Ventura testifies at his sex trafficking trial in New York City, New York, U.S., May 14, 2025 in this courtroom sketch. REUTERS Sean “Diddy” Combs listens as his former girlfriend Casandra “Cassie” Ventura testifies at his sex trafficking trial in New York City, New York, U.S., May 14, 2025 in this courtroom sketch. REUTERS

“What was he addicted to?” Estevao asked.

“Success,” Ventura said.

“What substances?” Estevao continued.

Ventura said it varied but that Combs at one point was addicted to opiates, and that she had witnessed him going through withdrawal from those drugs “more than once.”


  Cassie Ventura was seen looking stoic as she made her way to court, as she is set to come face to face with her abusive ex, Sean “Diddy” Combs. BACKGRID Cassie Ventura was seen looking stoic as she made her way to court, as she is set to come face to face with her abusive ex, Sean “Diddy” Combs. BACKGRID

Combs, 55, has pleaded not guilty to charges of racketeering, sex trafficking and transportation to engage in prostitution.

He could face life in prison, if convicted.

Ventura, 38, a pregnant mother of two, has testified for three days — and counting — about her decade-long relationship with Combs.

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