Another dark and disturbing chapter has surfaced in the legal saga surrounding music mogul Sean “Diddy” Combs, as former male escort Shawn Dearing has come forward with explosive allegations about the now-infamous “freak offs” involving Diddy and singer Cassie.
In a June 9 interview with People, Dearing claimed he participated in more than a dozen of these private sex parties between 2014 and 2017 — events he said evolved from risqué to deeply disturbing.
“The tone was a little darker towards the last times I’d seen them,” he said. “I got to see the dark side of things.”
That “dark side,” Dearing emphasized, wasn’t just about wild nights. According to him, Cassie — who dated Diddy from 2007 to 2018 — appeared emotionally broken and mentally cornered.
“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.”
Dearing painted a chilling picture of Cassie as someone emotionally trapped in what he described as an uncontrollable, possibly dangerous situation.
“In my opinion… she didn’t know if this was a beast she could control or not anymore. So she was along for the ride, because who knows where this beast is going, and there’s no way to tame it.”
Cassie’s Testimony Echoes His Words
Dearing’s account aligns closely with Cassie’s own heartbreaking courtroom testimony delivered last month. She spoke of enduring back-to-back “freak offs,” even while suffering infections, claiming she felt physically and psychologically destroyed.
“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.”
From Glamour to Allegations
Diddy, once hailed as hip-hop’s king of excess, is now battling serious federal charges including sex trafficking, transportation to engage in prostitution, and racketeering conspiracy. He has pleaded not guilty and denied all accusations.
But the list of allegations continues to grow.
Dearing, who was once listed under the alias “Skyler” on escort site Cowboys4Angels, claimed Diddy attempted to lure him back into the scene in 2017 after he had stepped away.
“I stepped away from that, realizing it was darker. Because honestly, I do care about these ladies. So I had to step away.”
Though he has not taken the witness stand, his photo has been entered into evidence, and Cassie herself identified him in court.
Diddy’s Legal Team: Desperate Defense
In what’s becoming a courtroom circus, Diddy’s defense team recently requested another mistrial— this time over claims that he allegedly dangled Cassie’s friend Bryana “Bana” Bongolan over a balcony, calling the testimony “demonstrably false.”
This follows a previous mistrial request tied to accusations that Diddy had Kid Cudi’s car firebombed— a claim the judge dismissed as insufficient grounds to halt the trial.
With closing arguments expected in early July, the trial has now evolved into a moment of reckoning not only for Diddy, but for an industry still grappling with the blurred lines between power, consent, and exploitation.
As the testimony stacks up, the spotlight isn’t just on a superstar’s fall from grace — it’s on the system of silence and complicity that allowed alleged abuse to continue unchecked for years.
