Three days into the racketeering, sex trafficking, and prostitution engagement trial against Diddy, the testimonies were already beyond explicit. 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 10-year relationship with Sean Combs. And Casandra Ventura aired it ALL, from when things turned sexual to the baby oil used in hotel parties. Here are the BOMBSHELL details Casandra shared about the infamous “freak offs.”
Editor’s Note: This article contains graphic and sexually explicit recollections shared during trial testimony against Sean ‘Diddy’ Combs.
RELATED: From Freak-Offs To Stompings, Cassie Testifies In Trial About Alleged Violent Relationship With Diddy (LIVE UPDATES)
When Was Cassie’s First And Last “Freak Off?”
In Tuesday’s (May 13) testimony, Cassie said the first time Diddy kissed her was when she was 21. At the time, she was in Las Vegas, celebrating her birthday. At 22, she said they had sex for the first time on a boat in Miami. Soon after, he introduced her to oral sex before ultimately bringing up the “freak offs” topic. Voyeurism was a common theme in the “freak offs.” That involves a person observing and gaining sexual pleasure from watching others engage in sensual or sexual acts.
The first “freak off” she took part in occurred at his home in Los Angeles with a paid male sex worker, Cassie testified. That was months after he had suggested the idea. It was 2008, and she was still 22. The Las Vegas stripper was supposed to dance and have intercourse with the singer. In opening statements, prosecutor Emily Johnson noted that Diddy also labeled the encounters “Wild King Nights” and “Hotel Nights.”
As for how many “freak offs” she participated in, Cassie first testified that there were too many for her to recall. During her continued prosecution testimony on Wednesday, she said, “Impossible to know. Hundreds?” Cassie said her last “freak-off” session with Diddy was in 2017 or 2018. She said she has not been involved in “freak offs” since the relationship ended in 2018.
On the stand, she repeatedly said she did not want to be involved in “freak offs,” calling them humiliating and emotionally overwhelming.
How Long Did The Diddy’s “Freak Off” Sessions Last?
Casandra testified that “freak offs” with Diddy “became a job.” They happened every week. She recalled that the longest “freak off” she’d been a part of lasted four days, with others lasting between 36 and 48 hours. Sessions also didn’t end before the escorts “finished,” Cassie said, recalling at least two instances where that happened.
Where Did The Sex Parties Take Place?
The “freak offs” happened at Diddy’s homes or hotels across the U.S. and overseas. Sometimes the
“Wild King Nights” or “Hotel Nights” led to extensive, expensive damage to hotel rooms. Cassie said on the witness stand that the most expensive one she recalled was a “freak off” at the Intercontinental in New York. She noted that the whole room had to be redecorated afterward.
Diddy also allegedly attended sex clubs in Los Angeles and Las Vegas, sometimes in the company of Cassie and escorts. On one occasion, he allegedly had sex with an escort’s girlfriend.
Who Was Responsible For Finding & Paying Sex Workers?
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. She said she never contacted escorts independently, but was directed to respond to ads on Craigslist and Backpage when in New York. Cassie added that a security guard delivered cash payments to sex workers, or Diddy brought the funds to the “freak-offs.”
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 was involved with Diddy and Cassie for about two years, and paid for sexual intercourse.
On one occasion, he was hired to have sex 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 wanted extensive use of baby oil during the act, and complained when it wasn’t enough. In another instance, Cassie said Diddy sent away an escort who couldn’t perform.
During her second day of testimony for the prosecution, Cassie also identified several male sex workers Diddy allegedly employed. “Islander” was from the site Latin Men, and participated in “freak offs” in Los Angeles, and maybe Vegas. Other names included Tommy, Greg, and Jonathan in Miami, and one man she couldn’t identify in a photo but said looked “familiar from the freak-offs.”
Attorney Johnson shows Cassie various photos of male escorts asking, "Who’s this?"
Cassie: “Islander. He was on Latin Men. We used him in LA and maybe Vegas.”
“Who’s this, 2A-616?”
Cassie: “We called him Tommy.”“Who is this?”
Cassie: “Greg, an escort in Miami.”“Who’s this?”…
— TheShadeRoom (@TheShadeRoom) May 14, 2025
What Did Cassie Say About Diddy & Baby Oil?
According to Cassie, Diddy’s “freak offs” were a “very choreographed experience,” and baby oil played a significant role. 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 added.
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?'”
He also allegedly instructed Cassie and male escorts to rub oil on each other and masturbate, requiring her to describe escort penises. “Describing somebody’s penis to another male was awkward and humiliating,” Cassie stated, per Variety. Afterward, there was oral sex and intercourse, with Diddy sometimes joining in when he wasn’t observing. Candle wax was also sometimes used in the acts.
Diddy Also Allegedly Demanded Pee & Semen Play In “Freak Offs”
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.
Urine aside, Diddy also allegedly requested that escorts ejaculate on Cassie’s body. Other times, Diddy allegedly asked her to put the semen on “his chest and nipples,” per Variety.
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. The singer also alleged that he used these recordings to threaten her into silence and staying with him.
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
What Happened After The Freak Offs?
After the “freak offs”, the singer said she needed to recover from dehydration, fatigue, and drug use, using IVs, chef-cooked food, and massages. All of this allegedly cut into her career duties and music production. Cassie recalled that she later began consuming different drugs, from ecstasy to Special K, GHB, MDMA, and mushrooms, to dissociate from the “freak offs” before, during, and after.
During her second round of testimony, Cassie also said she took opiates “often.” She also contracted UTI infections to the point that anti-bacterial medicines “didn’t work anymore.” Nonetheless, Diddy allegedly demanded she perform with infections, which caused burning, and with sores on her tongue and mouth, contracted from the “freak offs.”
Was The Viral 2016 Hotel Hallway Beating About A Freak Off?
In the viral video of Diddy beating her in a Los Angeles hotel hallway, Cassie said she was walking away from a “freak off.” After she left the room, surveillance footage shows Sean Combs kicking and dragging Cassie, as well as throwing a glass vase at her. Minutes later, a security guard intervened. The guard was the first witness to testify in the trial, and alleged that he declined a cash payment from Diddy to keep quiet and instead instructed the couple to return to their room. The Department of Justice has since released the full 15-minute video. It has no audio.
Full unedited 15-minute video of Diddy attacking Cassie in a hotel hallway, during a freak off in 2016 was released by the Department Of Justice. pic.twitter.com/OTgV5se6Pa
— DomIsLive NEWS (@domislivenews) May 14, 2025
