[Image: Wikimedia Commons]
Another chapter in the increasingly grotesque saga of Sean “Diddy” Combs has emerged, this time courtesy of a former male escort who claims he witnessed the mogul’s so-called “freak offs” spiral from kinky to downright sinister.
Shawn Dearing, who took part in “more than a dozen” of these sessions with Diddy and Cassie, told People in a June 9 interview that the parties weren’t just sleazy, they were straight-up sinister.
“I just would say overall, the tone was a little darker towards the last times I’d seen them, I got to see the dark side of things.”
And by “dark side,” he’s not talking about mood lighting and incense. According to Dearing, Cassie seemed less like a willing participant and more like a woman trapped in the world’s most twisted male fantasy.
“It was more of a ‘doing this to please him’ type of spirit overall. I can tell when the energy was different.”
“It was evil … and she was under that.”
Evil. He didn’t say awkward or uncomfortable, he said evil.
Jane Doe in Diddy Trial Says She Fainted When She Read Cassie Lawsuit: ‘I Was in Shock’
Full details here: https://t.co/zhrOjaM7Kr pic.twitter.com/ilA5W3nbhI
— Complex (@Complex) June 9, 2025
And yet, Diddy kept it moving like it was just another night in VIP. For Cassie, it sounded like an emotional hostage situation wrapped in velvet ropes.
“In my opinion, in that situation, she didn’t know if this was a beast she could control or not anymore,” Dearing 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.”
A beast she couldn’t tame, what an image. But hey, when your empire is built on excess and ego, maybe losing the plot is just the next stop on the tour.
Diddy was arrested in September 2024, slapped with charges including sex trafficking, transportation to engage in prostitution, and racketeering conspiracy. He’s pleaded not guilty to all of them and denies everything, but the pile of accusations isn’t exactly shrinking.
Sean ‘Diddy’ Combs bribed hotel security guard $100K to hand over Cassie beating video, then called him on Easter: ‘God put you in my life for a reason’ https://t.co/MXQke27nNf pic.twitter.com/AuBce0EntU
— New York Post (@nypost) June 3, 2025
Cassie, who dated Diddy from 2007 to 2018, delivered gut-wrenching testimony last month that echoed Dearing’s account. She told the court she felt trapped, degraded, and physically wrecked by the “freak offs.”
“Sometimes [the freak offs] were back to back,” she testified. “And I was doing the freak off with an infection. … It just was a mess, really painful for a long time.”
Let that sink in: repeated sex parties while battling infections, because saying no apparently wasn’t an option. For someone who once branded himself the “Bad Boy for Life,” Diddy’s alleged behaviour reads less like rebellion and more like systemic abuse.
Dearing said he first met Diddy around 2014 or 2015, before he even knew who the guy was. After leaving the escort scene in 2017, he claimed Diddy tried to rope him back in, but by then, he’d seen enough.
“I stepped away from that, realizing it was darker,” Dearing said. “Because honestly, I do care about these ladies. So I had to step away.”
He hasn’t taken the stand, but the jury saw his photo as part of the evidence, and Cassie specifically identified him, then known as “Skyler”, from the Cowboys4Angels site. If you’re keeping track, yes, Diddy was allegedly recruiting escorts like it was Uber Eats.
Meanwhile, Diddy’s defence team is flailing like it’s closing night on a bad Broadway run. Over the weekend, they requested yet another mistrial, this time because the prosecution presented “demonstrably false” evidence related to claims that Diddy once dangled Cassie’s friend Bryana “Bana” Bongolan over a balcony. (Because apparently that was the unbelievable part.)
Previously, they’d asked for a mistrial when someone mentioned Diddy allegedly had Kid Cudi’s car firebombed. Judge Arun Subramanian denied that one, too, likely because you don’t get a do-over every time someone brings up your greatest hits in domestic terrorism.
The trial continues, with closing arguments expected in early July.
[Source: US Weekly]
