David Bridges
We are currently witnessing the unfolding of a high-profile trial involving Diddy, focusing on serious allegations of racketeering, sex trafficking, and prostitution in New York City. Cassie has emerged as the third witness to testify, following a former hotel security personnel and a male escort. The prosecution wasted no time diving into the explicit details concerning the singer’s tumultuous relationship with Combs, detailing when their relationship turned sexual and the notorious drug-fueled encounters dubbed “freak offs.” From extravagant bottles of baby oil to the duration of these escapades, we have compiled all the information the public has eagerly anticipated since Diddy’s shocking arrest and indictment in September.
RELATED: Cassie Provides Testimony on Her Allegedly Abusive Relationship with Diddy, Revealing Shocking Encounters (LIVE UPDATES)
Editor’s Note: This article contains graphic and sexually explicit content based on trial testimonies.
Exploring Cassie’s Initial and Final Encounters of the “Freak-Off” Phenomenon
During her testimony, Cassie revealed that her first kiss with Diddy occurred when she was just 21 years old, while they were celebrating her birthday in Las Vegas. By the age of 22, they engaged in sexual activity for the first time aboard a boat in Miami, which quickly led to her introduction to oral sex and subsequently to the topic of “freak offs.” Cassie recounted that her inaugural freak-off took place at Diddy’s residence in Los Angeles with a hired male sex worker, occurring in 2008 when she was still only 22 years old. The event involved a Las Vegas stripper who was meant to perform and engage in intercourse with the singer.
When asked about the number of freak-offs she participated in, Cassie stated there were too many to accurately remember. The prosecution highlighted during their opening statements that Diddy referred to these encounters as “Wild King Nights” and “Hotel Nights.” Cassie stated that her final freak-off session with Diddy occurred around 2017 or 2018, marking a significant point in her life.
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
Understanding the Duration of Diddy’s “Freak Off” Sessions
Cassie described her experiences with Diddy’s freak-offs as having evolved into a regular occurrence, stating that they became a sort of job for her. These events transpired weekly and significantly impacted her ability to focus on her career. She recalled that the longest freak-off she was part of lasted an astonishing four days, while others spanned between 36 to 48 hours. Following these intensive sessions, Cassie often needed time to recover from dehydration, extreme fatigue, and the effects of drug use. She disclosed that she began experimenting with various substances, including ecstasy, Special K, GHB, MDMA, and mushrooms, to help her dissociate from the strenuous freak-off experiences.
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 aftermath of these freak-offs also led to considerable damage in hotel accommodations. Cassie testified that one particularly extravagant freak-off at the Intercontinental in New York was the most costly, requiring the entire room to be redecorated due to the extensive mess left behind.
Unveiling the Role of Baby Oil in Diddy’s Freak Offs
According to Cassie, Diddy’s freak-offs were highly orchestrated events, with baby oil playing a pivotal role. She recalled that Combs would call her out if she appeared to be “dry” and would insist that she reapply the oil to her body. This demand could occur as frequently as every five minutes, demonstrating the meticulous nature of these encounters. Allegedly, Diddy would have the bottles of baby oil warmed in sink water beforehand to ensure they were ready for use. The prosecution also claimed that Diddy would meticulously prepare hotel rooms both domestically and abroad, equipping them with tailored lighting, extra linens, baby oil, and lubricants. In one instance, Cassie recounted a particularly bizarre occasion where Diddy had an inflatable pool filled with baby oil and lubricant set up in the middle of a hotel room, instructing her to enter while still fully clothed. Cassie testified that as many as ten large bottles of baby oil could be utilized in a single freak-off.
“It was such mess,” Cassie said on the stand. “It was like, ‘What are we doing?’”
Along with baby oil, Diddy incorporated candle wax into these sessions and involved male sex workers for voyeuristic purposes. Voyeurism is defined as one individual gaining sexual pleasure from observing another engaged in sexual acts without their knowledge.
Confirming the Involvement of Male Sex Workers in Diddy’s Encounters
The answer to whether male sex workers were involved is a clear yes. A male stripper named Daniel Phillip was the second witness to testify on the first day of proceedings (May 12). He admitted to receiving payment for sexual activities with Cassie at the Gramercy Park Hotel in 2012. Phillip described how Diddy disguised himself with a white robe, a bandana covering his face, and a baseball cap, yet he recognized Diddy’s distinct voice. Cassie was purportedly dressed in a red wig, stockings, and sunglasses during that encounter. Phillip mentioned that Diddy commented on the insufficient amount of baby oil used during the act.
Furthermore, Cassie recounted an instance in which Diddy sent an escort away for being unable to perform.
Who Was Responsible for Compensating the Escorts at Diddy’s Parties?
According to Cassie, Diddy referred to the escorts he employed as “safe escorts,” a term he allegedly used to describe individuals who were not affiliated with law enforcement or who would not report to the police. She further revealed that a security guard was typically responsible for delivering cash payments to these escorts, or that Diddy himself would bring the funds directly to the freak-offs.
Examining Diddy’s Interest in Pee Play During Freak Offs
In her testimony, Cassie stated that Diddy had an ongoing interest in pee play, often involving her and other sex workers, regardless of her evident discomfort with it. She explicitly mentioned that she did NOT find being urinated on enjoyable, labeling the act as “disgusting.” “I didn’t want anyone to urinate on me,” Cassie asserted, yet noted that such incidents occurred “often enough” during the freak-offs.
“No one could think I wanted it,” she said after describing an instance where she choked on the bodily fluid during a freak off.
Connecting the Dots: The 2016 Hotel Hallway Incident and the “Freak Offs”
It appears that the infamous viral video depicting Diddy assaulting her in a hotel hallway in Los Angeles was indeed linked to a freak-off. Cassie testified that she was walking away from a freak-off at the time of the incident, illustrating the disturbing nature of their relationship.
Did Diddy Document His Freak Off Sessions?
Cassie disclosed that Diddy recorded their freak-off sessions, often sending the footage to her devices or keeping them on his own. She recounted requesting that he delete the “disgusting” recordings, expressing that she did not want anyone to see them, although she remained uncertain if he ever complied. Additionally, she highlighted that he sometimes viewed their freak-offs via FaceTime, further emphasizing the invasive nature of their relationship.
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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