At Diddy Trial, Ex-Girlfriend Cassie Details “Disgusting,” “Humiliating” “Freak-Off” Sex

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During a sex trafficking and racketeering trial in New York on Tuesday, Cassie Ventura, Sean “Diddy” Combs’ ex-girlfriend and the person whose complaint initiated a federal investigation into the rap mogul, detailed what were referred to as his “freak-offs.” This investigation ultimately led to Combs’ arrest on a five-count indictment, with Cassie being identified as Victim-1.

On Tuesday, Ventura testified that the 2016 video showing Combs attacking her in the InterContinental Hotel’s hallway in Los Angeles depicts her attempting to escape from an unexpectedly violent altercation they called a “freak-off.” She informed the court that prior to this incident, she had a major movie premiere approaching and had expressed her excitement about participating in a freak-off with Combs but was concerned it might harm her physically before the event. In the courtroom, Ventura recollected, she was struck in the eye by Combs, causing facial bruising; at that moment, she hurriedly left the room while he was either in the bathroom or on the phone. The jury watched the footage of the brutal attack for a fifth time over two days.

On Monday, during the initial statement at Combs’ trial, it was highlighted that Ventura’s presence marked a six-year reunion for the former intermittent pair who had been together for over a decade following Combs’ signing to Bad Boy Records. During her testimony on the first day, a heavily pregnant Ventura vividly recounted instances of repeated violent episodes and sexually explicit encounters in drug-filled hotel rooms that she claims were both forced upon her and initiated by Combs as a victim of his abusive and manipulative behavior.

For two decades, federal prosecutors allege that music and fashion mogul Sean “Diddy” Combs has mistreated women, trafficked sex workers, and illegally transformed his business into a criminal organization. In September, he was apprehended in Manhattan and has been imprisoned at a Brooklyn detention center since then. According to a five-count indictment, Combs is accused of crimes including sex trafficking, racketeering, and facilitating prostitution. He has maintained his innocence, denying all charges against him, asserting that he’s not guilty of any crimes he’s been accused of.

On Tuesday, Prosecutor Emily Johnson spent 7 hours grilling Ventura regarding her past relationship with Combs. During her time at Bad Boy Entertainment, she claimed her manager was essentially powerless as all decisions needed Combs’ approval. Ventura further testified that for the first three years of their connection, Combs’ assistants managed her finances and she communicated with them daily, often discussing Combs’ emotional state. Their conversations frequently revolved around Ventura’s physical appearance and body.

Ventura emphasized that he valued how I looked, stating, ‘My appearance was significant to him.’ We frequently discussed maintaining a specific physique during that period.

Occasionally, when Combs didn’t approve of my actions, he would discipline me by having his team confiscate my belongings – my jewelry, car, you name it. At times, they even evicted me from our shared apartment. The role of Combs’ staff in their interactions with me and the alleged crimes he is accused of are vital for the federal authorities to establish the racketeering aspect of their indictment and prove that a criminal organization was indeed operating.

In the afternoon session, Johnson shifted the discussion towards unusual topics with Ventura, where he was grilled about the male escorts involved in the situation, their hiring methods by Combs and sometimes Ventura through platforms like Craig’s List and Cowboys for Angels; details on the substances used at these events, which she testified included ecstasy and MDMA, ketamine, GHB, and psychedelic mushrooms, along with descriptions of their effects; a description of the escalation of sexual activities during these events; and the embarrassment of being asked to perform an act humiliating enough to involve being urinated on, at Combs’ behest.

During a lengthy interview, Ventura was queried about and provided details regarding certain sexual acts that she felt uncomfortable performing for Combs. She frequently paused and requested two afternoon breaks as the questions became more explicit. When asked why she persisted in participating in and even organizing these encounters, which she referred to as “freak-offs,” Ventura responded: “That’s an intriguing question. I wanted to bring him joy.

In my perspective as a devoted fan, every “freak-off” was meticulously orchestrated by Sean. He had a clear vision of where everyone should be, down to the lighting and other details. As the sessions progressed, we found ourselves inexorably drawn closer, eventually needing to apply oil on each other. This revelation about the baby oil was uncovered during a federal raid at his home last year.

Testifying, she stated that Combs desired both her and the hired escort to appear “shimmering.” She revealed that approximately 10 large bottles of baby oil were used during each occasion they referred to as a “freak-off,” and on one particular instance, a baby pool was filled with it. The damages to hotel rooms in New York, Los Angeles, and Miami were immense, she asserted.

During these prolonged sessions, lasting from several hours to even four days, there was a gradual escalation of intimate activities between Ventura and her male companion, who was hired for this purpose. Initially, it involved mutual masturbation, followed by oral sex, and eventually progressed to sexual intercourse. Combs orchestrated every step of these events, determining the setup of lighting that began as soft candlelight but evolved into vibrant multi-colored LEDs. The music mogul would observe these proceedings, often engaging in self-pleasure while issuing commands. These instructions, Ventura testified from the stand, were sometimes so intense they caused the escorts to lose their erections. This was allegedly due to Combs making changes within the room or hearing his distinctive voice, as she clarified.

After each meeting, Ventura and Combs would depart, choosing to indulge in drugs or share quiet moments apart from the crowd in a secluded space. This pattern recurred frequently, with a revolving door of companions. In a heart-wrenching moment during court proceedings, Ventura tearfully confessed that the only aspect she enjoyed about these encounters was “the time spent with him,” feeling that these were the rare instances when they truly connected while together.

Ventura stated, ‘I was filled with revulsion and shame. At the moment, I lacked the ability to articulate just how awful I truly felt, and I found it impossible to share my feelings with anyone.’

Photos of multiple male escort individuals were presented in court, with Ventura identifying them and detailing their involvement in “contests.” It was mentioned that some of these men regularly attended such events, and one of them was famously referred to as “The Punisher,” a term that was brought up during the court proceedings.

Initially, combs started recording the “freak-offs” without notifying her or seeking her approval, Ventura testified. He further stated that her devices were utilized on occasion, “because they were available,” and if she discovered them later, she would promptly delete them. She expressed that having these videos on her phone made her feel uncomfortable as they were “distasteful” and “embarrassing.

At some point, Ventura was questioned about why she didn’t just skip performing for Combs, and how she managed to avoid participating in the so-called “contests of weirdness.

She clarified that she was cautious not to offend or anger him by discussing the matter, but would approach it delicately when she did bring it up, often resorting to emails instead. Her intention was to avoid any potential misunderstandings or negative outcomes. The trial, which started this week, is expected to last for eight more weeks.

On Tuesday, Judge Arun Subramanian refused a joint plea from the media to screen seized “freak-off” videos in open court for reporting purposes. He explained his decision by expressing concern that doing so might retraumatize Ventura and another accuser of Diddy. The jury’s verdict concerning Combs’ guilt is largely dependent on the coercive nature of the “freak-offs,” which prompted the press to request access to aid in informing the public about the content of the video evidence.

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2025-05-14 02:55