We are two days into the racketeering, sex trafficking, and prostitution engagement trial against Diddy in New York City. Cassie was the third witness to take the stand behind a former hotel security worker and a male escort. Prosecution wasted no time getting into the graphic details of the singer’s relationship with Combs, from when it turned sexual to the infamous drug-fueled “freak offs.” From big bottles of baby oil to how long they lasted, here are all the details the internet has been begging for since Diddy’s arrest and bombshell indictment in September.
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Editor’s Note: This article contains graphic and sexually explicit recollections shared during trial testimony.
When Was Cassie’s First And Last Freak-Off?
In her testimony, Cassie said the first time Diddy kissed her was when she was 21 in Las Vegas, celebrating her birthday. At 22, she said they had sex for the first time on a boat in Miami, and soon after, he introduced her to oral sex before ultimately bringing up the “freak offs” topic.
The first freak off she took part in occurred at his home in Los Angeles with a paid male sex worker, Cassie testified. It was 2008, and she was still 22. The Las Vegas stripper was supposed to dance and have intercourse with the singer.
As for how many freak offs she participated in, Cassie also testified that there were too many for her to recall them all. The prosecution noted in opening statements that Diddy also labeled the encounters “Wild King Nights” and“Hotel Nights.” Cassie said her last freak-off session with Diddy was in 2017 or 2018.
Wiping away tears, she explained that those encounters provided some of her only one-on-one time with Diddy. Cassie said she was engaging in “freak offs” weekly. The final one occurred in 2017 or 2018.
— TheShadeRoom (@TheShadeRoom) May 13, 2025
How Long Did The Diddy’s Freak Off Sessions Last?
Casandra testified that freak offs with Diddy “became a job.” They happened every week, and recovery from them also cut into her focus on her career. She recalled that the longest freak off she’d been a part of lasted four days, with others lasting between 36 and 48 hours. Afterward, she said she needed to recover from dehydration, fatigue, and drug use. Cassie recalled that she later began consuming different drugs, from ecstasy to Special K, GHB, MDMA, and mushrooms, to dissociate from the “freak offs.”
Just before the break, Cassie testified that the longest “freak off” she participated in with Diddy lasted four days.
“The freak-offs became a job,” she said, adding that other encounters sometimes went on for 36 to 48 hours.
She testified the marathon sessions often left her…
— TheShadeRoom (@TheShadeRoom) May 13, 2025
The freak offs also led to extensive damage to hotel rooms. Cassie said on the witness stand that a freak off at the Intercontinental in New York was the most expensive one she recalled. She noted that the whole room had to be redecorated as a result.
What’s The Real About Diddy & Baby Oil?
According to Cassie, Diddy’s freak offs were a”very choreographed experience,” and baby oil played a major part. The singer said Sean Combs would call her out if she “looked dry” and demand that she re-oil her body. Sometimes that would happen every five minutes or so, Cas said.
Diddy allegedly had the baby oil bottles heated in warm sink water in preparation. In their opening statements, the prosecution also alleged the producer would set up hotel rooms in the U.S. and overseas with specific lighting, extra linens, and baby oil and lubricant. Meanwhile, in her testimony, Cassie described one such instance where Diddy allegedly had an inflatable pool filled with baby oil and lubricant in the middle of a hotel room. She was instructed to get inside it with her outfit and shoes on. Additionally, Cassie testified that up to 10 large bottles of baby oil were used in one freak off.
“It was such mess,” Cassie said on the stand. “It was like, ‘What are we doing?’”
Aside from baby oil, Diddy used candle wax and involved male sex workers for voyeurism in the freak offs. Voyeurism involves one person observing and gaining sexual pleasure from watching an unsuspecting person engage in sensual or sexual acts.
Were Male Sex Workers Involved In Diddy’s Freak Offs?
The short answer is yes. A male stripper, Daniel Phillip, was the second witness to take the stand on Monday’s first day of testimony (May 12). He admitted that he received payment for sexual intercourse with Cassie at the Gramercy Park Hotel in 2012. Phillip said Diddy was disguised in a white robe, bandana over his face, and a baseball cap, but he recognized his voice. Meanwhile, Cassie allegedly wore a red wig, stockings, and sunglasses. He, too, mentioned that Diddy commented on the amount of baby oil in the act not being enough.
In another instance, Cassie said Diddy sent away an escort who couldn’t perform.
Who Paid Escorts Involved In Sex Parties?
According to the producer’s ex-girlfriend, Diddy employed “safe escorts.” That is the phrase Diddy allegedly used to describe workers who weren’t cops or who wouldn’t talk to the police. Cassie added that a security guard delivered cash payments to escorts, or Diddy brought the funds to the freak-offs.
Baby Oil Aside, Did Diddy Enjoy Pee Play?
In short, Cassie testified that Diddy continued to demand pee play between her and sex workers, despite her objections. She said that she did NOT enjoy being urinated on, and called the act “disgusting.” “I didn’t want anyone to urinate on me,” Cassie testified. Still, it happened “often enough,” the singer said on the stand.
“No one could think I wanted it,” she said after describing an instance where she choked on the bodily fluid during a freak off.
Was The Viral 2016 Hotel Hallway Beating About A Freak Off?
It appears so. In the viral video of Diddy beating her in a Los Angeles hotel hallway, Cassie said she was walking away from a freak off.
Did Diddy Record These Freak Offs?
Cassie testified that Diddy recorded the freak off sessions and sent them to Cassie’s devices or had them on his. She said she asked him to delete the “disgusting” footage because she didn’t want anyone to see it, but isn’t sure he ever did. Additionally, she said he sometimes watched “freaks off” via FaceTime.
Cassie testifies to feeling dehumanized and objectified by men, with some sessions being watched by Diddy via FaceTime. Recordings of the sessions sometimes appeared on Cassie’s devices, which she would delete, calling them “disgusting” and expressing a desire for no one ever to…
— TheShadeRoom (@TheShadeRoom) May 13, 2025
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