Cassandra "Cassie" Ventura; Shawn Dearing.Credit : Dimitrios Kambouris/Getty for Paramount+; Courtesy of Shawn Dearing
A former male escort hired to perform at Sean “Diddy” Combs’“Freak Off” parties has broken his silence after prosecutors showed his photo during the music mogul’s federal sex trafficking and racketeering trial. In an exclusive interview with PEOPLE, he shared an emotional message for Casandra “Cassie” Ventura.
Shawn Dearing was one of more than 10 men Combs, 55, allegedly forced his ex-girlfriend to have sex with during their nearly 11-year relationship, according to prosecutors. The escorts’ identities were revealed in court testimony and evidence submitted by the government.
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“She was so uplifting — the kindest and most respectful person," Dearing, 37, says of Ventura, 38. “She was genuine throughout the whole experience."
Prosecutors submitted a photo of Shawn Dearing as evidence during Diddy's trial. SDNY
Dearing said that he is only speaking out now to give "some credence" to Ventura's story and because his photo and alias were already made public during Combs' trial.
“I never wanted to open my mouth,” he says. “I don't seek attention. I don’t want to go out there and make it seem like I’m trying to get my name known off of this experience."
When discussing Ventura, he says, “You got me tearing up! I want what’s best for her, honestly, because she … she's a badass lady, man. She's awesome. So I want her respect first and foremost.”
Ventura testified on Wednesday, May 14, that she knew Dearing as “Skyler” and met him through the website Cowboys4Angels. She said he was one of many escorts Combs hired via the site for his “Freak Offs,” what federal prosecutors have called “elaborate and produced sex performances” that the Bad Boy Records founder allegedly orchestrated and coerced Ventura and others into joining.
Dearing stated that the identities of Ventura and Combs were not disclosed to him until he met them for the first time, around late 2014 or early 2015. He claimed Cowboy4Angels founder Garren James told him only that the clients were “A-List.”
Shawn Dearing and his dog Ezzy at home in Hawaii on May 28, 2025. Courtesy of Shawn Dearing
Dearing says he was hired for “more than a dozen” sessions, which typically took place at either a bungalow at The Beverly Hills Hotel or a condo off of Sunset Blvd. in Los Angeles, which he believes belonged to Ventura.
“It was only me, him, and her," Dearing says, referring to himself, Combs, and Ventura. "He never touched me. We did everything under his direction."
While Dearing says he did not witness Combs physically abuse Ventura, the model stated that he did “notice forms” of what he believed was “psychological” abuse.
Ventura's “kindness” was “being abused in [an] improper manner,” Dearing claims.
“She was there under his control, and there was that knowing and understanding that if she didn't do what he said — I don't know what the consequences could have been, but I could tell there was that constant energy of knowing that we must perform for him or else," he felt.
Sean "Diddy" Combs watches as Casandra "Cassie" Ventura leaves for a break in her testimony during Combs' sex trafficking trial in New York City on May 15. REUTERS/Jane Rosenberg
Ventura broke down in tears when asked about the “Freak Offs” during the fifth day of testimony on Friday, May 16, claiming that Combs pressured her to participate in his sex parties with physical violence and threats of blackmail.
“I had to do 'Freak Offs’,” she said during redirect, after giving testimony on Wednesday, May 14, that she did not want to do “Freak Offs.”
Dearing claims, "There were times where she wouldn't speak if he wasn't in the room, because she knew she couldn't.” He adds, “It was a power complex thing with him.”
He remembers one “Freak Off” when he says Ventura allegedly became like “a drone” after Combs “left the room for a moment.”
“She just sits there staring at the ground, and I ask her a question. She's like, ‘No, no, no. Not until he gets back.’ So it’s like, ‘Oh, okay,’ “ Dearing claims.
When the “Freak Offs” would turn “dark,” Ventura's demeanor would change, Dearing says. “You could see that it was kind of like the spirit was leaving the body,” he adds.
A self-described “man of faith,” Dearing is no longer an escort and is “on a different path these days.”
After some “soul searching,” he left L.A. in 2017 and returned to Hawaii, where he was born and raised. The move was “more of a back to my roots situation [rather] than getting out of LA type of deal,” he explains.
Combs’ trial is in its third week. He was arrested in September 2024 and charged with sex trafficking, racketeering, and transportation to engage in prostitution. He has pleaded not guilty on all charges.
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