As the high-profile legal proceedings against music mogul Sean “Diddy” Combs unfold, prosecutors are bringing to light a series of deeply disturbing allegations that center around his relationship with singer and model Casandra “Cassie” Ventura. The latest testimony has painted a dark and troubling portrait of their time together, with the most shocking claims emerging from what prosecutors referred to as “freak-off” parties — exclusive and secretive sexual events orchestrated by Combs.
On the stand this week, lead prosecutor Emily A. Johnson revealed a harrowing account of what Cassie allegedly endured during her relationship with Combs, detailing how she was coerced into degrading and traumatizing acts. One of the most graphic claims involved a supposed incident in which an escort was made to urinate into Cassie’s mouth — an act that Johnson said Cassie was forced to submit to, despite her clear discomfort and refusal.
“She knew it was not something she wanted to do,” Johnson told the court. “She did it because she was in love with him, because she was afraid, and because she didn’t believe she had a choice.”
This explosive testimony is part of a broader legal battle that began after Combs was indicted by a grand jury following his arrest in September at the Park Hyatt Hotel in Manhattan. Since his arrest, the 55-year-old Bad Boy Records founder has remained in custody. Observers noted his graying hair and noticeably subdued demeanor during the latest court session, a stark contrast to his larger-than-life persona in the entertainment industry.
The ‘Freak-Off’ Allegations
At the heart of the allegations are what have been described as “freak-offs” — private, often multi-person sexual encounters reportedly arranged by Combs. According to the prosecution, these events frequently involved paid escorts and were filmed by Combs himself, who often participated as a voyeur. Cassie, who had a romantic and professional relationship with Combs for over a decade, is said to have been a central figure in these encounters.
In one particularly chilling moment during court proceedings, Johnson quoted Cassie as saying she “felt like she was choking” during an incident where an escort urinated in her mouth at Combs’ behest. This incident, prosecutors argue, exemplifies the level of psychological and emotional control Combs allegedly exerted over her.
The prosecution has also indicated that Cassie is prepared to testify directly to the jury. Her anticipated testimony could provide further insight into her experiences and the power dynamics of her relationship with Combs.
“Ms. Ventura is willing to speak in her own words about what happened,” Johnson added. “She wants the truth to be known.”
A Decade-Long Relationship Under Scrutiny
Cassie and Combs’ relationship dates back to the mid-2000s. They met when Cassie, then 19 years old, signed with Combs’ label, Bad Boy Records. He was 37 at the time. Over the next several years, their relationship would evolve from professional to romantic, though it was marked by frequent breakups and reconciliations.
The age and power imbalance in their relationship has been noted by both legal experts and advocacy groups, with many pointing out that Combs’ influence over Cassie began when she was still a teenager entering a male-dominated industry. Critics argue that the label owner-artist relationship only deepened the imbalance, giving Combs not just emotional leverage, but also professional control over Cassie’s career.
While Cassie has previously alluded to abuse in their relationship — most notably in a now-settled 2023 civil lawsuit that detailed allegations of rape and repeated physical abuse — this is the first time such graphic and explicit details have emerged in a criminal courtroom.
