The sex-trafficking trial of Sean “Diddy” Combs has pushed the music mogul’s infamous “freak off” parties into the spotlight, with two witnesses divulging graphic details of the alleged sex-fueled parties.
“Freak offs” – or days-long, drug-fueled orgies allegedly orchestrated at the behest of Combs – would involve his longtime partner, Cassie Ventura, and male escorts hired to have sexual intercourse with her.
Ventura, who is nearly 20 years Combs’ junior, accused him of rape and repeated physical abuse throughout their decade-long relationship in a 2023 lawsuit. She testified Tuesday and Wednesday in Manhattan federal court about the alleged abuse.
While Ventura and another witness, male escort Daniel Phillip, detailed the “freak-offs” in their testimonies, the court is still weighing whether videos of the alleged incidents will be made available to the media.
Combs, 55, is facing a five-count indictment accusing him of sex trafficking, transportation to engage in prostitution and racketeering conspiracy. He was arrested in September 2024 after federal authorities alleged he and his associates threatened, abused and coerced victims “to fulfill his sexual desires” – through twisted “freak offs” or recorded sex performances he orchestrated.
Diddy has denied any wrongdoing and rejected a plea deal offer.
Here’s everything we know about Diddy’s “freak offs”:
What happened at the ‘freak offs’?
Combs’s “freak-offs” would often involve his former partner, R&B singer and model Casandra Ventura – also known as Cassie. Under his instructions, Ventura would engage in sex acts with male sex workers while Combs masturbated and filmed the encounters.
Ventura testified that she was barely 22 when Combs first asked her to participate in a “freak off,” which he introduced as “voyeurism” to her. She said the experience left her “confused” and “nervous,” but that she loved him and wanted to make him happy.
Now 38 years old, Ventura tearfully detailed the infamous “freak-offs, “shedding light on the turbulent and oftentimes violent relationship she shared with Combs during their decade-long relationship.
Days-long, drug-fueled and choreographed with ‘quite a bit’ of baby oil
Each “freak off” would last anywhere from 36 to 48 hours, with the longest Ventura ever participated in spanning four days, she testified. The singer and model became emotional talking about how the sexual encounters “became a job,” but said she felt relief after her first one because Combs was “really happy with me.”
The sessions also used “quite a bit” of baby oil because Combs wanted them to be “glistening,” she said.
Ventura said Combs would instruct her to apply more oil if he felt like she didn’t have enough on, and that they probably used 10 large bottles of Johnson’s brand baby oil each time. She described the “freak offs” as being orchestrated by Combs and a “very choreographed experience.”
During one “freak off,” a blow-up baby pool was filled with baby oil that Combs instructed Ventura to get into in her “outfit” and shoes, she testified.
“It was such a mess,” she testified. “I was like, ‘What are we doing?’”
According to Ventura, the baby oil would be heated up before the sessions in a sink full of hot water. If they ran out of lubricant during a “freak off,” Ventura said they would call someone on Combs’ staff or the hotel desk to bring more.
The sessions often lasted days and were always paired with drugs such as ecstasy, MDMA, marijuana, ketamine and alcohol.
Ventura said she relied on drugs to numb herself during the sessions, which she said she did not enjoy but participated in to make Combs happy. While Combs was pleased with her participation, she felt a mix of emotions when they were finished: dirty, ashamed, confused, but also relieved that Combs was “really happy” that she “did something right.”
“I just didn’t want to make him upset. I just didn’t want to make him angry and regret telling me about this experience that was so personal,” Ventura testified.
If Ventura indicated that she didn’t want to participate, Combs would become “dismissive,” she testified, later detailing his controlling nature over her life, and how she feared saying no would prompt him to leak “freak off” videos online.
When asked if there was anything she enjoyed about the “freak offs,” Ventura said through tears that she only enjoyed them for “the time spent with him.”
The male escorts who participated in the “freak offs” were found online and flown across the country to participate, she claimed. Each was paid between $1,500 and $6,000 for their participation.
Male escort testifies he slept with Ventura while Combs watched
During the first day of the trial, prosecutors called on Daniel Phillip, a male escort who slept with Ventura while Combs watched on multiple occasions.
Phillip said he first encountered a “freak off” when his boss asked him to dance at a bachelorette party at the Gramercy Park Hotel in New York City, but he never got to do a strip tease. Phillip said he was greeted by Ventura, who gave him $200 to sleep with her while her partner watched.
Phillip said he recognized the music mogul’s voice immediately, and told the court the rapper sat in the corner watching him and Ventura have sex.
Ventura gave him thousands of dollars after the encounter, which kicked off a series of similar encounters are ritzy hotels across New York.
At times, Diddy directed Phillip and Ventura to “slow down” or to “separate,” or even where Phillip had to ejaculate, he testified. These encounters lasted anywhere from one to 10 hours and Diddy would record some of them. At one point, Diddy asked Phillip for his driver’s license, “just for insurance” — a move that Phillip understood to be a threat, he told the court.
Phillip’s graphic description of the alleged sex parties paved the way for Ventura to testify on the second day — and for jurors to be shown security footage of Combs beating Ventura at a Los Angeles hotel.
Ventura later claimed that before the altercation, “We were having an encounter called a ‘freak off’ and I was leaving there.”
