A former male escort who participated in Sean “Diddy” Combs’ alleged “freak offs” with Cassie claimed the “energy” of the sex parties changed over time.
“I just would say overall, the tone was a little darker towards the last times I’d seen them,” Shawn Dearing alleged to People in an interview published Monday, June 9. “I got to see the dark side of things.”
Dearing claimed that he participated in “more than a dozen” freak offs with Diddy, 55, and Cassie, 38, who dated off and on from 2007 to 2018. According to the model, Cassie (full name Casandra Ventura) seemed like she was participating in the parties only to appease her then-boyfriend.
“It was more of a ‘doing this to please him’ type of spirit overall. I can tell when the energy was different,” he told the outlet, adding, “It was evil … and she was under that.”
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Dearing went on to say that he felt like Cassie was “playing a role” rather than doing something she enjoyed. “In my opinion, in that situation, she didn’t know if this was a beast she could control or not anymore,” he continued. “So she was along for the ride, because she had to, because who knows? Who knows where this beast is going, and there’s no way to tame it.”
Diddy was arrested in September 2024 and charged with sex trafficking, transportation to engage in prostitution and racketeering conspiracy. He pleaded not guilty to all charges and has denied all the allegations against him.
Cassie testified about the alleged freak offs last month, telling the court that she felt she couldn’t say no despite feeling “dirty” afterward. She also claimed that she developed persistent urinary tract infections because of the freak offs, noting that she would still participate even while ill. “Sometimes [the freak offs] were back to back,” she alleged. “And I was doing the freak off with an infection. … It just was a mess, really painful for a long time.”
Dearing claimed Diddy first hired him in late 2014 or 2015 but noted he didn’t know the rapper’s identity before taking the job. After he quit escorting in 2017, Diddy allegedly tried to hire him one more time, but he declined.
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“I stepped away from that, realizing it was darker,” Dearing told People. “Because honestly, I do care about these ladies. So I had to step away.”
Dearing has not testified in the trial, but his photo was shown to the jury as evidence. Cassie mentioned him during her testimony, saying she knew him as “Skyler” when she hired him through the website Cowboys4Angels.
Diddy’s trial is still ongoing and is expected to wrap up by early July. Over the weekend, his legal team again asked for a mistrial, claiming that the prosecution presented “demonstrably false” evidence related to the allegation that Diddy dangled Cassie’s friend Bryana “Bana” Bongolan over a balcony in 2016.
The defense previously asked for a mistrial over testimony related to the firebombing of Kid Cudi’s car, but Judge Arun Subramanian denied the request.
If you or someone you know has been sexually assaulted, contact the National Sexual Assault Hotline at 1-800-656-HOPE (4673). If you or someone you know is experiencing domestic violence, please call the National Domestic Violence Hotline at 1-800-799-7233 for confidential support. If you or someone you know is a human trafficking victim, contact the National Human Trafficking Hotline at 1-888-373-7888.
