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Sean "Diddy" Combs ex-girlfriend and R&B singer Cassandra "Cassie" Ventura, during the rapper’s sex trafficking trial, took to the witness stand for four days and described the alleged “freak-offs.”
Cassie Ventura, according to the BBC, is one of the central witnesses in the Diddy trial. Now, 38 and pregnant with her third child, she had an 11-year, on-and-off relationship with the rapper. The two met when she was an aspiring singer at the age of 19.
During her testimony on Tuesday, Ventura spoke about the “freak-offs” she was allegedly forced to take part in with Combs and how the rapper also directed her to sleep with different male escorts. According to the BBC, the singer said:
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“Control was everything, from the way that I looked... to what I was working on."
Ventura said in court that Combs would watch and direct the s*xual activities she would have with male escorts, strippers or dancers.
She also alleged that the rapper would pay the men anywhere from $1,500 to $6,000 in cash.
"If Sean wanted something to happen, that was what was going to happen… I couldn't say no."
After Cassie Ventura spoke about the details of the alleged “freak-offs” with Diddy and male escorts, American blogger and columnist Perez Hilton took to X and shared his opinion on the rapper’s sexuality.
On May 22, 2025, the media personality wrote:
“Diddy would have been way happier if he wasn't such a repressed homosexual.”
Cassie Ventura reveals how Diddy was “controlling” the alleged freak-offs
During her testimony, Ventura disclosed that sometimes she would hire male escorts as the rapper would be busy. However, she would only follow his directions as the freak-offs allegedly had a specific "pattern" of sexual acts. She alleged:
"He was controlling the whole situation… He was directing it."
Perez Hilton, further quoted Cassie Ventura admitting that:
“Sometimes Sean and the escort would have intercourse with me … It was just like a lot happening at once.”
The 38-year-old, as per Perez Hilton, also revealed the details on how Diddy used the semen of the male escorts that were hired during the freakoffs. When the prosecutor questioned her, “At what point would escorts ejaculate?” Cassie alleged:
“Usually when it was OK for them, per Sean. But usually when they did, usually they did it on me… And then Sean and I would go in the next room, and he would want me to put the semen on his body.”
Notably, the male exotic dancer Sharay Hayes, who was known as “The Punisher,” also testified about his “freak offs” with Sean “Diddy” Combs and Cassie Ventura on day 7 of the rapper’s trial.
He alleged meeting the two for the first time at Trump International Hotel and Tower in New York City. However, he didn’t recognize them at first and met them again eight to 12 times.
Meanwhile, while testifying against Combs, Cassie admitted to the jury that she was high on drugs and often took ecstasy or MDMA.
She also revealed that although she felt sick and nauseous “almost every time” and even though she puked, the rapper would ask her, "get up and continue" with the freak offs.
