Cassie Ventura Says Sean 'Diddy' Combs Watched 'Freak Off' Videos Of Her While On A Commercial Flight

By Jacquez Printup on May 14, 2025 at 3:30 PM EDT

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During Cassie Ventura's second day of testimony in Sean "Diddy" Combs' federal trial, in which he faces charges of racketeering and sex trafficking, the vocalist recounted a disturbing incident where she said her ex-boyfriend allegedly watched "freak off" videos on a commercial flight in front of other passengers.

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Cassie Ventura Felt 'Trapped' While She Was With Diddy

Diddy and Cassie are seen at the Neon Carnival in Coachella
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On May 14, Cassie took the stand to begin her second day of testimony in Diddy's federal trial. If convicted of all charges, he could spend life in prison.

During her first day of testimony, the 38-year-old detailed the alleged "freak offs" Diddy pressured her to participate in. Through tears, the "Me & U" singer recalled being urinated on, which almost caused her to choke, and being pushed to have sexual intercourse while on her menstrual cycle.

On day two, Ventura further testified about the "freak offs" and said that Diddy used to blackmail her with videos of her having sex with other men.

"It is horrible and disgusting. No one should do that to anyone," she said of the alleged blackmail, according to NBC News. "It could ruin everything I worked for, make me look like a sl-t."

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"I wasn't supposed to be on those videos," she added. "I didn't want to be in them."

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Cassie Was Worried A Video Of Her Having S-x May Have Been Leaked Online

Diddy looks on top of the world as he parties with ex-girlfriend Cassie in Jamaica back in 2013.
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Later, Cassie described her terror upon learning a video of her at one of Diddy's alleged freak offs may have been leaked online.

She testified that someone shared the news with her while working at an Atlantic City event. She reached out to Diddy, expressing her concern over the leaked footage, adding that it "would put my career in jeopardy" and bring shame to "my mother [and] my family."

That unsettling feeling about the alleged "freak offs" being on video only intensified when Cassie reportedly saw Diddy watching them during a commercial flight.

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Cassie Told Diddy He Was 'Embarrassing' Her On A Commercial Flight

Cassie Ventura seen incognito after baby birth
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As her testimony continued, the mother of two recounted an argument she had with Diddy during a 2013 trip to France, when, during their flight home, he allegedly "pulled up 'freak off' videos on his laptop that I thought were deleted."

Cassie continued, "He was showing them with other people around. I said, 'You are embarrassing me.' I was scared. I felt trapped. How do you get out of this situation? I felt trapped."

The "Step Up" actor later testified that despite feeling like she had nowhere to turn, she arranged another freak off within hours of their landing, claiming Diddy threatened to release the videos if she didn't.

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The 'Perfect Match' Actress Opens Up About Freak Offs At Age 22

Diddy and Cassie at the 2017 Met Gala
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During her first day on the stand, Cassie reflected on the first time Diddy allegedly asked her to have sex with another man while he watched.

Cassie stated she was "22" and felt thoroughly "confused" by Diddy's request. However, she admitted to going along with his alleged demands because she "loved him very much and wanted to make him happy."

She added, "It wasn't something that I wanted to be doing, especially as regularly as it became. But again, I was in love and wanted to make him happy. At some point, I felt I didn't have much of a choice."

Later, Cassie explained that planning the alleged "freak offs" became her full-time job, adding that she had no time for anything else.

"Staying out for days on end, taking drugs and drinking, having sex with a stranger," she said in court. "They would be 36, 48, 72 hours, the longest one was four days."

"I felt disgusting. I felt humiliated," she said. "I didn’t have the words to show how horrible I felt. I couldn’t talk to anyone about it."

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The Rapper Allegedly Had A Voyeurism Fantasy

Diddy and Cassie arrive at McGregor Vs Mayweather holding a bottle of champagne
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Cassie also testified that early in her decade-long relationship with Diddy, the rapper allegedly discussed his voyeurism fantasy with her.

"He described it as a fantasy he had where he would want to see me having sexual interactions with another male so he could watch," Cassie said in court.

"I loved him, I didn't want him to think I thought anything bad of him," she added.

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