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(NewsNation) — A former escort who allegedly participated in sexual encounters with Sean “Diddy” Combs and Casandra “Cassie” Ventura said he witnessed a shift in her demeanor over time, describing how what initially seemed like consensual adult play became increasingly “performative.”
Shawn Dearing, who worked under the name Skyler and said he participated in more than a dozen encounters with the couple, told NewsNation that Ventura’s behavior evolved from “jovial” to forced compliance as the relationship progressed.
“Initially, when I had in the early days of seeing them, it seemed it was very jovial, like, you know, two adults who wanted to explore further, but as the encounters grew, there was an energy about these situations that devolved,” Dearing said Tuesday on NewsNation’s “Banfield.”
Ex-escort says Cassie silenced him when he tried to talk about Diddy encounter
“I can definitely say there’s a spirit that had changed through time. I don’t know what happened behind closed doors with them, but there were signs,” Dearing said.
Dearing described witnessing Combs leave the room during one of their encounters. When Dearing attempted to speak with Ventura, she quickly silenced him.
“There was a moment where I kind of had a realization of the depths of the situation,” Dearing said. “You could tell there was something that had come over her in a sense that she knew it may cause jealousy or something of the nature if her and I interacted in some way with him not there.”
Former escort believes Cassie was going through the motions
Dearing characterized Ventura’s later behavior as going through the motions rather than genuine participation, describing how “she would put on the smile and then continue in her role, put on the smile, put the head down, and then just continue in the role.”
When pressed about whether Ventura appeared frightened, Dearing was careful in his language, saying he wouldn’t characterize her demeanor as fearful but rather as understanding “her role” in the situation.
“I wouldn’t say frightened. I say she just understood the situation to the extent that she needed to,” Dearing said, calling Ventura “a badass lady” who maintained her composure despite the circumstances.
The prosecution in Combs’ trial has claimed Ventura was coerced into participating in sexual encounters, which Combs called “Freak Offs.” Defense attorneys argue the encounters were consensual and between adults.
“I’ve received guidance from individuals,” Dearing said. “I’m here speaking with you, attempting to just have my side heard, and ultimately, I just want Cassie respected.”
Diddy, Cassie hotel video central to prosecution’s case
Combs is facing federal charges of sex trafficking, racketeering and other crimes. His trial began with testimony from Ventura, in which she talked about the “Freak-Offs,” text messages between her and Diddy and a hotel surveillance video.
That video, obtained by CNN, was first released in 2024 and showed Combs running in a towel after Ventura, who can be seen standing by the hotel elevators. In the video, Combs appears to aggressively grab and drag Ventura down, kicking her before picking up her luggage.
Ventura testified about the incident, and jurors were shown the complete video as evidence. Ventura said she reached a $10 million settlement with the Intercontinental Hotel in Los Angeles.
Several others have taken the stand during Combs’ trial, including the former CFO of Bad Boy Entertainment, multiple former assistants and rapper Kid Cudi.
Combs has pleaded not guilty to all charges and remains in federal custody.