At Diddy Trial, Ex-Girlfriend Cassie Details “Disgusting,” “Humiliating” “Freak-Off” Sex

Sean “Diddy” Combs’ so-called “freak-offs” were described at length during his sex trafficking and racketeering trial in New York on Tuesday by Cassie Ventura, his ex-girlfriend and the woman whose civil complaint launched a federal investigation into the rap mogul that led to his arrest on a five-count indictment where she is names as “Victim-1.”

Ventura also revealed from the witness stand on Tuesday that the video of Combs attacking her in 2016 in a hallway at the InterContinental Hotel in Los Angeles shows her fleeing a “freak-off” that suddenly turned violent. She told the court that back in March of 2016, she had her first big movie premiere coming up and beforehand had told Combs that she was eager to do a freak-off but was worried about “wrecking” her body before the event. At the hotel, she recalled to the court, she was suddenly punched in the eye by Combs, bruising her face; at this point, she fled the room while he was “in the bathroom or on the phone.” Jurors viewed for a fifth time in two days the video footage of the horrible beating that followed. 

Ventura’s arrival at Combs’ trial was touted on Monday during the opening statement by the defense as a six-year reunion for the former on-and-off couple, whose tumultuous relationship went on for a decade after the R&B singer signed to his label, Bad Boy Records. On the first day of her testimony, a heavily pregnant Ventura described in detail the frequent outbursts of violence and drug-fueled hotel room sexual trysts she says she was forced into participating in, and often initiated, by Combs as a victim of his abuse and coercive control.

Combs is accused by federal prosecutors of two decades of abuse of women, trafficking of sex workers and turning his music and fashion empire into a criminal enterprise. He was arrested in Manhattan in September and has been held since at a Brooklyn jail. In a five-count indictment, Combs is accused of sex trafficking, racketeering and transportation to engage in prostitution. He has denied all charges against him and said that he is innocent of all crimes of which he has been accused. 

Prosecutor Emily Johnson asked Ventura hundreds of questions over the 7 hours that she testified about her relationship with Combs on Tuesday. As she began her career with Bad Boy, she said her manager then had to work “with one arm tied behind his back” as all decisions had to go through Combs. Ventura also testified that over the initial three years of her relationship with the mogul, she was helped with her finances by his assistants and spoke to them every day, often about Combs’ mood. The conversations the couple had were frequently about her body and looks. 

“Appearance was very important to him — my appearance,” Ventura said. “We had tons of conversations about my body at that time…keeping my shape a certain way,”

At times, Ventura testified, she would be punished by Combs if he disapproved of her behavior by having his staff take away her possessions. This included her jewelry and her car, she said, and at times she was kicked out of her apartment. The involvement of Combs’ staff with Ventura and the crimes of which he stands accused is crucial to the feds proving the racketeering element of their indictment and that a criminal enterprise existed.

Johnson moved the testimony to the “freak-offs” in the afternoon, having Ventura answer question after question about the male sex workers and how they were hired, by Combs and at times by Ventura, via Craig’s Live and a company called Cowboys for Angels; the drugs taken at the events, which she testified included ecstasy and MDMA, ketamine, GHB and psychadelic muchrooms, and how they made her feel; the progression of the sexual acts at the events; and the humiliation of being urinated on at Combs request. 

Ventura was questioned on and described, frequently pausing and asking for two breaks in the afternoon as the questions drew out, the lurid details of what she explained were sex acts she did not want to perform but did to please Combs. Asked why she continued to do and even arrange “freak-offs,” Ventura replied: “Good question. I wanted to make him happy.”

“Every ‘freak-off’ was directed by Sean. He knew specifically where he wanted everyone to be, the lighting and such,”  she said, then describing the famous baby oil that was discovered at his home during a federal raid last year. “So over that first session, we just kind of, like, ended up getting closer and closer, then eventually had to put oil on each other.” 

Combs, she testified, wanted her and the hired escort to be “glistening.” A total of 10 large bottles of baby oil were used every “freak-off,” she said, and one instance saw a baby pool filled with it. Damages to some of the hotel rooms in New York, L.A. and Miami were astronomical, she said. 

“Freak-offs” would last hours or up to four days, with a progression of mutual masturbation between Ventura and the male escort who’d been hired, then to oral sex and then finally to intercourse. It was Combs who directed every moment, chose and directed his staff on setting up lighting, which started as candlelight but progressed to multi-color LEDs. The rap mogul would watch this all unfold and masturbate while barking orders, which frequently would lead the escorts to lose their erections, Ventura said from the stand. This was the result of Combs adjusting something in the room or hearing the sound of his recognizable voice, she explained. 

When the sessions ended, Ventura and Combs would exit and spend time doing drugs or being quiet together in a separate room; it often would repeat, again and again, with a new escort. Breaking down in tears, Ventura told the court when asked that the only thing she liked about the “freak-offs” was “the time spent with him,” and she felt that these were the only moments she really had with him while they were together. 

“I felt disgusted. I was humiliated. I didn’t have the words to put together at the time how horrible I really felt, and I couldn’t talk to anybody about it,” Ventura added.

Headshots of several male escorts were shown to the court as Ventura named them and explained the frequency of their participation in “freak-offs.” Some of the men became regulars, she said; one of the men was known as “The Punisher,” the court heard.  

Combs eventually began to film the “freak-offs” without informing her or asking for her consent, Ventura testified, adding that her devices were used at times, “because they were there,” and if she saw them later, she would immediately delete them. She said having them on her phone made her feel terrible as the videos were “disgusting” and “humiliating.” 

At one point, Ventura was asked why she did not merely not perform for Combs and what she did to stop having to participate in “freak-offs.” 

“I didn’t want to upset him or make him angry with me for even sharing it,” she explained. “But I would just tread lightly when I brought it up. Sometimes I would email him about it. I didn’t want anything bad to happen.”

Ventura’s testimony will continue on Wednesday. The trial is set to last eight weeks. 

On Tuesday, Judge Arun Subramanian denied a joint application from the news media for the “freak-off” videos seized by the feds to be played in open court so they can be described by media outlets. In his decision, he said that this would retraumatize Ventura and another Diddy accuser. Much of the decision for the jury around Combs’ guilt hinges on the coercive nature of the “freak-offs,” so the press sought the ability to help the public understand what was in the video evidence.