We are now two days into the high-profile trial concerning Diddy, facing serious allegations of racketeering, sex trafficking, and prostitution in New York City. Cassie took the stand as the third witness, following testimony from a former hotel security personnel and a male escort. The prosecution wasted no time delving into the graphic nuances of the singer’s tumultuous relationship with Combs, detailing how their interactions escalated from friendship to a sexual dynamic filled with notorious drug-fueled “freak offs.” From the excessive use of baby oil to the duration of these escapades, we’re uncovering all the shocking details that have captivated the internet since Diddy’s arrest and explosive indictment in September.
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Editor’s Note: This article contains graphic and sexually explicit recollections shared during trial testimony.
Unveiling the Timeline: Cassie’s First and Last Encounters of Freak-Offs
During her gripping testimony, Cassie revealed that the first time Diddy kissed her was on her 21st birthday while they were celebrating in Las Vegas. By the age of 22, she recounted that they had sex for the first time on a boat in Miami. Shortly thereafter, he introduced her to oral sex, leading to the controversial topic of “freak offs.” The initial freak-off experience Cassie participated in took place at Diddy’s home in Los Angeles, where a paid male sex worker was involved, occurring in 2008 when Cassie was still just 22 years old. The Las Vegas stripper was hired to dance and engage with the singer in sexual acts.
When asked about the frequency of these freak-offs, Cassie disclosed that there were far too many for her to remember them all. The prosecution, in its opening statements, mentioned that Diddy referred to these encounters as “Wild King Nights” and “Hotel Nights.” Cassie stated that her last freak-off session with Diddy occurred sometime around 2017 or 2018.
Wiping away tears, she detailed that those encounters provided some of her only one-on-one time with Diddy. Cassie stated that she was engaging in “freak offs” on a weekly basis, with the final one happening in 2017 or 2018.
— TheShadeRoom (@TheShadeRoom) May 13, 2025
Examining the Duration: How Long Did Diddy’s Freak Off Sessions Last?
Cassie testified that engaging in freak-offs with Diddy had become more like a job than a choice. These events occurred weekly, and the aftermath often interfered with her focus on her career. She recounted that the longest freak-off she endured lasted an astonishing four days, with others typically ranging from 36 to 48 hours. Following these extended sessions, she often found herself in need of recovery due to dehydration, extreme fatigue, and drug use. Cassie admitted that she began using various drugs, including ecstasy, Special K, GHB, MDMA, and mushrooms, as a means to dissociate from the overwhelming nature of 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 extended to 36 to 48 hours.
She testified that these marathon sessions often left her…
— TheShadeRoom (@TheShadeRoom) May 13, 2025
The aftermath of these freak-offs also resulted in significant damage to hotel rooms. Cassie revealed during her testimony that one particular freak-off at the Intercontinental in New York was the most costly one she remembered, necessitating a complete redecoration of the room due to the chaos that ensued.
Exploring Diddy’s Unique Preferences: The Role of Baby Oil in Freak Offs
Cassie disclosed that Diddy’s freak-offs were meticulously choreographed events, with baby oil playing a crucial role in their execution. She explained that Sean Combs would often call her out if he noticed she “looked dry,” insisting that she reapply baby oil to her skin, sometimes every five minutes. Allegedly, Diddy would even heat the baby oil bottles in warm water to ensure they were ready for use. The prosecution mentioned in their opening statements that Combs went to great lengths to prepare hotel rooms in the U.S. and internationally, including specific lighting, extra linens, baby oil, and lubricants. Cassie described a particular instance where Diddy had an inflatable pool filled with baby oil and lubricant set up in the middle of a hotel room, insisting that she get inside while still wearing her outfit and shoes. She testified that up to 10 large bottles of baby oil were utilized during a single freak-off.
“It was such a mess,” Cassie remarked on the stand. “It was like, ‘What are we doing?’”
In addition to baby oil, Diddy incorporated elements like candle wax and recruited male sex workers for voyeuristic purposes during the freak-offs. This practice involves one individual observing and deriving sexual gratification from watching another engage in sensual or sexual acts without their knowledge.
Understanding the Involvement of Male Sex Workers in Diddy’s Encounters
Indeed, male sex workers were involved in these freak-offs. A male stripper, Daniel Phillip, took the stand as the second witness on the first day of testimony (May 12). He confessed to receiving payment for sexual intercourse with Cassie at the Gramercy Park Hotel back in 2012. Phillip shared that Diddy was disguised in a white robe, with a bandana covering his face and a baseball cap, but he recognized his voice. Meanwhile, Cassie reportedly wore a red wig, stockings, and sunglasses during the encounter. Phillip also recounted that Diddy commented on the amount of baby oil used during the act, stating it was insufficient.
In a separate instance, Cassie mentioned that Diddy dismissed an escort who failed to meet his expectations.
Clarifying the Payment Process for Escorts at Diddy’s Parties
According to Diddy’s former girlfriend, he referred to the escorts he hired as “safe escorts,” a term he used to describe individuals who were not law enforcement officers and were unlikely to report anything to the police. Cassie further elaborated that a security guard typically delivered cash payments to these escorts, or Diddy personally brought the funds to the freak-offs.
Investigating Diddy’s Interest in Pee Play During Freak Offs
In her testimony, Cassie revealed that Diddy maintained a demand for pee play involving her and the male sex workers, despite her vocal objections. She expressed her discomfort with the act, labeling it as “disgusting.” “I didn’t want anyone to urinate on me,” Cassie asserted during her testimony, yet she stated that this occurred “often enough” for it to be a recurring theme.
“No one could think I wanted it,” she added, recounting an incident where she choked on the bodily fluid during a freak-off.
Connecting the Dots: Was the Viral 2016 Hotel Hallway Incident Linked to a Freak Off?
It appears that way. In the widely circulated video depicting Diddy physically assaulting her in a hotel hallway in Los Angeles, Cassie indicated that she was leaving a freak-off when the incident occurred.
Did Diddy Record His Freak Off Sessions with Cassie?
Cassie testified that Diddy took recordings of their freak-off sessions, which he either sent to her devices or stored on his own. She mentioned that she requested him to delete the “disgusting” footage, not wanting anyone else to see it, but she expressed uncertainty about whether he complied. Additionally, she noted that he sometimes watched the freak-offs live via FaceTime.
Cassie testified to feeling dehumanized and objectified by men, revealing that some sessions were watched by Diddy through FaceTime. She stated that recordings of the freak-offs would occasionally appear on her devices, which she would delete, labeling them as “disgusting” and expressing a strong desire for no one to ever see them…
— TheShadeRoom (@TheShadeRoom) May 13, 2025
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