Cassie Ventura Details 4-Day Freak Offs, Hiring Escorts for Ex Sean "Diddy" Combs in Testimony

Cassie Ventura testified about the alleged “freak offs” she says Sean “Diddy” Combs had her participate in, including how hiring for the encounters became her responsibility. 

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Watch : Sean “Diddy” Combs Made Escort Perform Shocking Act on Ex Cassie Ventura, Prosecutor Alleges

As Sean “Diddy” Combs’ trial unfolds, details are emerging about his alleged “freak offs.”

During her testimony May 13, pregnant Cassie Ventura, who dated Combs on and off for a decade until 2018, recounted her experience with the sexual encounters.

“In the first year of our relationship he proposed a sexual encounter he called voyeurism, a sexual encounter with a third party,” Ventura said in her testimony, per NBC News. “It entails hiring an escort and setting up so I can perform for Sean…it involved Sean watching me with another person, and he would direct us in what we were doing.”

When asked who oversaw hiring those escorts, Ventura alleged, “Eventually it became a job for me, I had the contacts to set it up in the hotel room and all of that. At the beginning Sean set it up.”

Soon, she said the sexual encounters became a job. “There was no space to do anything else. Staying out for days on end, taking drugs and drinking, having sex with a stranger, they would be 36, 48, 72, hours,” she said. “The longest one was four days, even more on and off including recovering, recovering from the drugs, dehydration.”

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Sean "Diddy" Combs Sex Trafficking Trial: All the Revelations (Live Updates)

The singer—who is expecting her third baby with husband Alex Fine—also recalled her emotional state at the time.

“I was 22 at the time,” she noted. “My stomach churned. I didn’t have a concept of how that would that be a turn on, but I accepted the responsibility. I was confused, nervous, but also loved him very much and wanted to make him happy.”

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She continued, “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. I didn’t know what ‘no’ could turn into.”

The Perfect Match actress explained the control Combs—17 years her senior—allegedly held over her.

“Whether it was career, sex, everything—I didn't have much of a say,” she noted. “I was super young, I didn't know if he would be upset enough to be violent or not want to be with me at all, over time if I didn't do it.”

In her testimony, Ventura also alleged Combs blackmailed her to participate in the freak offs using “actual videos and photos of the sexual encounters with the escort.”

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“It was always in the back of my mind that I would somehow be hurt by him,” she added. “Sean is a really polarizing person. He was very charming, it was hard to decide in that moment when he was telling you what he wanted. I just didn't know what would happen.”

Combs is on trial for charges of racketeering, sex trafficking by force, fraud or coercion and transportation to engage in prostitution—all of which he’s denied.

For more on the case against the music mogul, keep reading.

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Cassie Ventura Said Hiring For “Freak Offs” Became “a Job” For Her

Cassie Ventura told prosecutors May 13 that during the first year of her decade-long relationship with Sean "Diddy" Combs, he “proposed” the introduction of voyeurism into their sexual relationship. It first began with her “hiring an escort and setting up” so that she could “perform” for Combs, who would watch her with another person.

Eventually, she said, orchestrating these sex performances “became a job” for her. 

“I had the contacts to set it up in the hotel room and all of that,” she recalled, “at the beginning Sean set it up.”

Ventura said that her “stomach churned” when he first proposed the experience.

“I didn’t have a concept of how that would be a turn on, but I accepted the responsibility,” she said. “I was confused, nervous, but also loved him very much and wanted to make him happy. 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.”

She admitted, “At some point, I felt I didn't have much of a choice.”

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Cassie Ventura Alleges “Violent Arguments” With Sean “Diddy” Combs Led to “Physical Abuse and Dragging”

Ventura, who dated Combs on and off from 2007 to 2018, said that he was “frequently” violent towards her during their relationship.

"Yes, they were violent arguments, usually resulted in physical abuse and dragging, different things," she testified to jurors. "He would mash my head, knock me over, drag me, kick me."

She said that her injuries were often visible, adding, “I would get knots on my forehead, black eyes, red eyes, bruises all over my body.”

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Defense Wanted Pregnant Cassie Ventura Seated Before Jury to Avoid "Sympathy"

With Ventura ready to take the stand after male escort Daniel Phillip May 13, Combs’ defense requested that she be seated in the witness box before the jury enters, since she is eight months pregnant.

“Because I think there is a prejudicial quality,” defense attorney Marc Agnifilo told the judge. "Pregnancy is beautiful and wonderful. It is also a source of potential sympathy."

Ventura was ultimately brought in after the jury was seated, indicating that his defense team lost the motion.

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Male Escort Says He Could Hear Sean "Diddy" Combs Assaulting Cassie

When Ventura didn’t join Combs right when he called for her on one occasion, Phillip testified May 12 that Combs threw a liquor bottle in her direction, then grabbed her by her hair and dragged her into the bedroom. “She was screaming,” Phillip said, and, from the next room, ”what I heard sounded like him slapping her.” Phillip said he heard Combs say, “’I tell you to come here, you come here now, not later.’”

Phillip said he was “terrified” and did not intervene.

He further testified that he overheard what sounded like Combs assaulting Ventura on a separate occasion at the Essex House hotel in New York. “I heard her yelling, 'I’m sorry, I’m sorry,' someone was being slapped around and slammed around the room," Phillip said. "And I looked around the corner and I saw Mr. Combs walk out of the hotel altogether without clothes, he might have had a towel on.”

Ventura came out of the room and jumped into Phillip’s lap, he testified. “She basically tried to convince me that 'it's OK' and 'I’ll be OK,’” Phillip continued. “And I said, 'It is not OK and you need to get help.'”

“I tried to explain to her that she was in real danger if she stayed with him,” Phillip said.

Asked by prosecutor Maureen Comey why he didn’t call the police, Phillip testified that he thought of Combs as “someone with unlimited power, and chances are, even if I did go to the police, that I might still end up losing my life.”

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Escort Says Cassie Ventura Paid for Sex While Sean "Diddy" Combs Watched and Masturbated

Daniel Phillip, who said he was running a male stripper revue during the time in question, testified that he was paid “a few thousand dollars” to have sex with Ventura while Combs watched at Manhattan’s Gramercy Hotel in 2012. Phillip said that Combs wore a robe, a baseball cap and a bandanna covering his face, but he recognized him by his voice.

Ventura paid him and said she “would tip me when I leave," Phillip told the court. "We ended up having sex, rubbed baby oil on each other for a couple minutes. [Combs] was sitting in a corner masturbating.”

Afterward, the witness continued, Ventura gave him “a couple of thousand more.”

Phillip said that he was contacted multiple times over the next year to have similar encounters with Ventura and Combs at other hotels and at their respective homes in New York. He said that Combs recorded him and Ventura having sex once or twice, and that sometimes Combs would intervene and have sex with Ventura while Phillip was there.

In her 2023 lawsuit accusing her ex of sexual assault and physical abuse, Ventura alleged Combs forced her to have sex with male prostitutes.

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Cassie Ventura Had “Purple Eye” After Being Attacked by Sean "Diddy" Combs, According to Witness

Ventura “was scared," Florez said on the stand. "She was in the corner, hood on, covered up. I couldn't see her face, she was pretty much in the corner. On the floor was a destroyed flower vase."

When Ventura left the hotel she had a “purple eye,” Florez said. Once she was gone, Florez said, he and the desk manager went upstairs to remind Combs of “hotel rules.” Combs thought the manager was recording him on his phone and grabbed it, Florez continued, and when Combs tried to grab his phone, Florez said he pinned Combs against a wall. "We said we are not recording you,” Florez testified, “and de-escalated the situation.”

Prosecutors showed the surveillance footage of the attack—in which Combs appears to be hitting, kicking and dragging Ventura—that was slowed down from what was published by CNN in May 2024. (The defense had previously alleged that the clip was sped up, making the altercation look more violent than it was.) The jury was also shown video that Florez recorded on his cell phone when he responded to a call of a woman in distress on the sixth floor.

Florez testified that he did not call police at the time because Ventura wouldn’t answer questions about what happened and told him she just wanted to leave.

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Former Hotel Security Guard Says Sean "Diddy" Combs Offered Him Cash to Stay Quiet About Cassie Attack

Los Angeles Police Officer Israel Florez was a security guard at the InterContinental Hotel when Combs attacked Ventura on March 5, 2016. (In her opening statement, Geragos called surveillance footage of the attack, which was first published by CNN in May 2024, “overwhelming evidence of domestic violence,” but over infidelity discovered on a cell phone and “not over sex trafficking.”)

Florez testified May 12 that he saw evidence of an altercation on the morning in question, and Combs offered him “a stack of money” to look the other way.

Under cross-examination, Florez said he “100 percent” interpreted the gesture to be Combs trying to bribe him.

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Defense Says Sean "Diddy" Combs Is "Complicated," the Case Is Not

In her opening statement, defense attorney Teny Geragos said prosecutors were trying to turn consensual sex into sex trafficking, but “it will not work.”

“Sean Combs is a complicated man,” she said, “but this is not a complicated case.”

“This case is about Sean Combs’ private, personal sex life,” Geragos continued, “which has nothing to do with his lawful businesses.”

Her client was violent, took drugs and had anger issues, she told the court, and there will be times during this trial when “you think he is a jerk, he is mean. But he is not charged with being mean. He is not charged with being a jerk.”

Geragos said, “The evidence is going to show you a very flawed individual, but it will not show you a racketeer, a sex trafficker or somebody transporting for prostitution.”

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Prosecution Accuses Sean "Diddy" Combs of Being a Kingpin During His Trial

Prosecutor Emily Johnson accused Combs of using a sprawling network of employees to carry out illegal acts, like dayslong “freak offs,” which were detailed in the federal indictment, according to NBC News reporters in the courtroom.

“He sometimes called himself the king and expected to be treated like one to cater to all his desires,” she told the jury. “He 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."

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Opening Statements From the Prosecution at Sean "Diddy" Combs’ Sex Trafficking Trial Begins

 Johnson began her argument before the jury by describing Combs as a “larger than life" person who ran a criminal enterprise.

Highlighting an example of his alleged criminality, Johnson told the jury that the Bad Boys Record founder was “on the hunt" for Ventura one night after he learned that she had begun a romantic relationship with someone else. Johnson accused Combs of beating “her brutally, kicking her in the back and flinging her around like a rag doll” after he found her.

“He threatened her and said if she defies her again he will release video of her having sex with male escorts," she continued. "Souvenirs of the most humiliating nights of her life."

The prosecutor alleged that Combs’ inner circle covered up “crime after crime.”

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When Will Sean "Diddy" Combs’ Sex Trafficking Trial End?

Presiding Judge Arun Subramanian told jurors that he believes the trial will possibly conclude by July 4. He said that he hopes the trial will be done by then, although it “could go longer, but I don't expect that it will."

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Sean "Diddy" Combs’ Kids Show Their Support At His Trial

As the rap mogul arrived for the first day of his sex trafficking trial May 12, his mom Janice Combs was present along with six of his eldest kids.

His and late ex Kim Porter’s kids Quincy Brown, Christian “King” Combs, Jessie Combs and D’Lila Combs, his and ex Misa Hylton's son Justin Combs, as well as his and ex Sarah Chapman's daughter Chance Combs had the chance to greet their dad with a hug before he sat down with his attorneys.

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Who is on the 12-Person Jury For Sean "Diddy" Combs’ Trial?

The prosecution and Combs’ defense team agreed to a jury of eight men and four women, as well as four men and two women as alternates for the trial.

Combs’ attorney Marc Agnifilo argued that the prosecution was intentionally removing potential Black jurors, telling the judge that it “leads to a pattern and they need to give reason for strikes.”

However, prosecutor Maurene Ryan Comey denied the accusations, responding, “We have conducted ourselves without any bias. The jury is diverse with a number of nonwhite (panelists).”

The 12 jurors live in New York City or Westchester include a 69-year-old male actor and massage; a 31-year-old male investment analyst; a 51-year-old male scientist; a 30-year-old female deli clerk; a 42-year-old female nursing home aide; a 41-year-old male communications clerk at a correctional facility; a 68-year-old male retired banker; a 68-year-old retired telecommunications company; a 43-year-old female physician assistant; a 39-year-old male social worker; a 67-year-old male logistics analystand a 74-year-old female treatment coordinator.

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