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Diddy escort shares alleged shocking details of Cassie 'freak off' parties after being named in trial

Home> News> US News

Updated 09:02 4 Jun 2025 GMT+1Published 08:35 4 Jun 2025 GMT+1

Diddy escort shares alleged shocking details of Cassie 'freak off' parties after being named in trial

Shawn Dearing has opened up after his escort alias was made public

Jess Battison

Jess Battison

Featured Image Credit: ANGELA WEISS/AFP via Getty Images

Topics: Diddy, Cassie Ventura, Celebrity News, Celebrity

Jess Battison
Jess Battison

Jess is a Senior Journalist with a love of all things pop culture. Her main interests include asking everyone in the office what they're having for tea, waiting for a new series of The Traitors and losing her voice at a Beyoncé concert. She graduated with a first in Journalism from City, University of London in 2021.

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@jessbattison_

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Warning: This article contains discussion of sexual harassment and domestic violence which some readers may find distressing

One of Sean ‘Diddy’ Combs’ former escorts has opened up with shocking claims about the infamous ‘freak off’ parties.

Shawn Dearing was named during the ongoing high-profile trial as the hip-hop mogul faces charges of racketeering, sex trafficking and transportation to engage in prostitution. Diddy denies all charges.

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The ex-escort was one of more than 10 men hired for the rapper’s parties, as alleged during Cassie Ventura’s testimony.

And now that this has been made public, Dearing (who is known professionally as Skyler) has decided to speak out about his experience, claiming to have been hired for ‘more than a dozen’ of these controversial sessions.

During her testimony, Ventura spoke about the drug-fuelled ‘freak offs’ Diddy allegedly orchestrated that could ‘last up to four days’.

An image of Shawn Dearing was shown during the trial (SDNY)
An image of Shawn Dearing was shown during the trial (SDNY)

Dearing says he wants to give ‘some credence’ to the singer’s story as he ‘never wanted to open my mouth’ about it.

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But speaking of Ventura, he told PEOPLE in an exclusive interview: “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.”

Having allegedly been hired online for Comb’s ‘freak offs’, the former escort says he first met him and Ventura around late 2014 or early 2015.

“It was only me, him, and her,” he added. “He never touched me. We did everything under his direction.”

Dearing claimed that he didn’t witness any physical abuse, but that he did ‘notice forms’ of what he thought to be ‘psychological abuse’.

Diddy has denied all charges. (Johnny Nunez/WireImage)
Diddy has denied all charges. (Johnny Nunez/WireImage)

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He recalled one ‘freak off’ when he claimed Ventura became like ‘a drone’ when Diddy ‘left the room for a moment’ as she often wouldn’t speak ‘because she knew she couldn’t’.

“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,’” he claimed.

And when the ‘freak off’s turned ‘dark’, Ventura would allegedly change.

“You could see that it was kind of like the spirit was leaving the body,” Dearing said.

If you are experiencing domestic violence, please know that you are not alone. You can talk in confidence to the national domestic violence helpline Refuge on 0808 2000 247, available 24/7, or via live chat, available 10am-10pm, Monday to Friday.

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Alternatively, if you have been affected by any of the issues in this article and wish to speak to someone in confidence, contact The Survivors Trust for free on 08088 010 818, available 10am-12.30pm, 1.30pm-3pm and 6pm-8pm Monday to Thursday, 10am-12.30pm and 1.30pm-3pm on Fridays, 10am-12.30pm on Saturdays and 6pm-8pm on Sundays.

  • Dawn Richard speaks out on alleged horrific things she saw Diddy do towards Cassie
  • Male escort ‘The Punisher’ describes graphic 'details' of ‘freak off’ party at Trump Tower with Diddy and Cassie
  • Cassie testifies about Diddy moment that left her 'shocked' as jurors are shown 'freak off' party videos in court
  • New details emerge over ‘harrowing’ alleged ‘love contract’ Diddy had ex-partner sign

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