In a gripping courtroom appearance, Cassie Ventura opened up about her tumultuous relationship with Sean “Diddy” Combs, revealing the emotional turmoil and fear that surrounded her as she testified in a civil lawsuit against the music mogul. Her statements highlighted the complexities of their dynamic, particularly regarding the infamous “freak off” sex sessions, during which she claimed she was coerced into participating.
During her testimony, Ventura, now 38 and heavily pregnant with her third child, recounted the moment she sued Combs in November 2023, knowing full well it could have devastating effects on his illustrious career. “I could understand that,” she said when questioned by Combs’ defence attorney, Anna Estevao, about the potential repercussions of her allegations being publicised.
Ventura went into detail about the extravagant measures she used during these encounters, often donning wigs and masks in an attempt to remain “discreet.” Initially, she had joined Combs’ record label Bad Boy in a strictly platonic capacity but soon found herself ensnared in a web of escalating emotional and physical complexities.
Reflecting on their early interactions, Ventura reminisced about her 21st birthday, when Combs, then 37, gave her her first kiss. “I guess you could say I was an up-and-coming star,” she remarked, reminding the court of her burgeoning career as both a model and a singer, which had begun to flourish by 2007.
As the trial shifted towards more explicit content, the jury was provided insight into the complex messages exchanged between the two during their 11-year relationship. Many of these messages, laced with sexual innuendos, illustrated a relationship marked by both affection and a troubling power dynamic. In one exchange, Ventura expressed nervousness about being reduced to merely fulfilling Combs’ sexual fantasies, which she described as a source of distress.
The account of the so-called “freak offs,” sessions that Ventura described as involving “hundreds” of encounters with male escorts while under the influence of substances, has played a significant role in the trial. Under questioning from Estevao, Ventura recounted moments where she felt compelled to please Combs, who she believed expected her to engage in such activities to maintain harmony in their relationship.
Despite the troubling claims she made on the stand, Ventura was adamant about her love for Combs, recounting how their relationship evolved. “It was fast, scary,” she explained, referring to her whirlwind romance with the music mogul. Yet, she acknowledged seeing a gentler side to Combs, stating he could be “sweet” and “attentive.”
As the court deliberated on the graphic messages showcased by the defence, Judge Arun Subramanian halted proceedings to address objections about the explicit nature of the evidence being shared, placing further attention on the sensitive content surrounding Ventura’s allegations.
For the prosecution, the urgency was apparent, with court officials expressing a desire to expedite Ventura’s testimony given her advanced pregnancy. Lead prosecutor Maurene Comey urged for her questioning to conclude swiftly, fearing the risk of her going into labour before the trial’s conclusion this weekend.
As legal representatives from both sides work to untangle Ventura’s complex narrative of love, betrayal, and fear, the trial continues to draw public interest, raising questions about the nature of celebrity relationships and the power dynamics that can often ensnare individuals within them.

