Baby oil, sexual desires and violence: What are Diddy’s ‘freak offs’ that have become a key part of his trial?
‘Freak offs’ or days-long, drug-fueled orgies were allegedly orchestrated by Diddy and involved his former longtime partner, Cassie.
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 Diddy’s junior, accused him of rape and repeated physical abuse throughout their decade-long relationship in a 2023 lawsuit. She testified for four days 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 judge ruled on May 14 that videos of the alleged incidents would not be made available to the media or public.
Diddy, 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 Diddy 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 Diddy was “really happy with me.”
The sessions also used “quite a bit” of baby oil because Diddy wanted them to be “glistening,” she said.
Ventura said Diddy 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 Diddy 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 Diddy’s 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 Diddy happy. While Diddy was pleased with her participation, she felt a mix of emotions when they were finished: dirty, ashamed, confused, but also relieved that Diddy 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, Diddy 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 Diddy watched
During the first day of the trial, prosecutors called on Daniel Phillip, a male escort who slept with Ventura while Diddy 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 Diddy 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.”
Ex-assistant talks Trump International and freak-off setup
David James, who worked for Diddy as an assistant from 2007 to 2009, testified on May 20 that Diddy’s favorite hotel in New York City was the Trump International.
“They knew me very well, they gave me a key," James said.
He also spoke about setting up hotel rooms for Diddy, which included his clothes, a toiletry bag allegedly filled with drugs, applesauce, Jell-O and Fiji Water.
Diddy took Obama-shaped ecstasy pills: ex-assistant
James also testified that Diddy’s alleged daily drug cocktail included ecstasy pills in the shape of former President Barack Obama’s head.
The disgraced mogul’s toiletry bag also allegedly consisted of Percocet, ecstasy, Viagra, weight loss pills, and sperm count supplements.
Another former assistant testifies about setting up ‘freak offs’
George Kaplan, a former executive assistant to rapper Diddy, testified on May 21 that his job included organizing Diddy’s homes and hotel stays, which often involved preparing rooms with items like candles, liquor, baby oil, and lube.
He said these setups, in cities such as Los Angeles, Miami and New York, were cleaned afterward to a "polished state."
Though Kaplan didn't refer to the events as “freak offs,” others have testified that such items were used during prolonged sexual encounters.
He also recalled once cleaning up an unknown brown powder. Kaplan suggested these tasks were done to protect Diddy from potential hotel leaks.