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Cassie Told Diddy She Was ‘Always Ready’ for Freak-Offs, Messages Show

May 15, 2025
in News, U.S.
Cassie Told Diddy She Was ‘Always Ready’ for Freak-Offs, Messages Show
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Cassie Ventura told her former partner Sean “Diddy” Combs that she was “always ready” to participate in freak-offs in a 2009 message shown in court on Thursday.

“I’m always ready to freakoff,” Ventura said in a message to Combs, adding, “It can be whenever.”

She testified that at the time, she “wanted to make him happy.”

The prosecution has alleged that “freak-offs” are days-long, drug-fueled parties organized by Combs where participants were coerced into performing sexual acts.

The Context

Defense attorney Anna Estevao led the cross-examination of Ventura, a key prosecution witness, on Thursday. Combs and Ventura began dating in 2007, and their relationship lasted over a decade.

Combs is facing federal charges of sex trafficking, racketeering and transportation to engage in prostitution. He has pleaded not guilty to all charges.

The defense has argued that the sexual activities between Combs and Ventura were consensual.

What To Know

In 2007, Ventura messaged Combs that she had “never felt so loved, safe and empowered.”

In another message, Cassie wrote she “couldn’t wait” to have a child with Combs.

In 2009, she wrote that she was “a very lucky woman” and she would “fly wherever you need me.”

She also acknowledged that she had an “aggressive sexual side” in another 2009 message.

Ventura did not show much visible reaction to the messages being read in court beyond some sighing.

Ventura is eight and a half months pregnant. U.S. District Judge Arun Subramanian asked the defense to finish cross-examination by Friday so she will not have to return for another week of testimony. He said the defense should “streamline” their questioning.

“In what universe did you not understand that this was important?” he said, referring to the sensitive timing.

During opening statements, defense attorney Teny Geragos said the case is about “voluntary adult choices made by capable adults in consensual relationships.”

The prosecution, however, said victims were threatened by Combs in order to force them to perform sexual acts.

“He used lies, drugs, threats and violence to force and coerce first Cassie and later Jane [another former girlfriend and prosecution witness whose identity is being withheld] to have sex with him in front of male escorts,” Assistant U.S. Attorney Emily Johnson said.

Ventura testified on Tuesday that she felt “disgusted” as she participated in the freak-offs.

“I felt pretty horrible about myself,” Ventura said.

She said the encounters were often filmed and became what she described as “blackmail materials” that she feared could be leaked.

“I was scared, I felt trapped, how do you get out of this situation?” Ventura said during her testimony on Wednesday.

What People Are Saying

Cassie Ventura, during her testimony on Wednesday: “[Combs] was abusive and controlling, he was physically abusive, he put me down a lot as much as I would be built up, the sheer embarrassment, how he treated me in front of other people.”

Assistant U.S. Attorney Emily Johnson, during opening statements: “[Combs] used his companies to manipulate women, forcing them with male escorts to have sex while he watched. He and his inner circle made sure he got everything he wanted.”

Defense attorney Teny Geragos, during opening statements: “This case is about Sean Combs’ private personal sex life. The government has no place in his private bedrooms. They say it is not about his private sex life, but the evidence will show that it is.”

What Happens Next

Combs’ trial is expected to last eight to ten weeks. If convicted, he faces a maximum sentence of life in prison.

Do you have a story that Newsweek should be covering? Do you have any questions about this story? Contact [email protected].

The post Cassie Told Diddy She Was ‘Always Ready’ for Freak-Offs, Messages Show appeared first on Newsweek.

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