Jurors in the trial of hip-hop mogul Sean ‘Diddy’ Combs were reportedly left stunned after viewing explicit images from the so-called “Freak Off” sex parties allegedly orchestrated by the music icon.
The courtroom in New York fell silent as jury members were shown five still photographs of these private events on screens, images which were kept hidden from the public. Reactions among the jurors were telling: one male juror raised his eyebrows, while a female juror appeared visibly unsettled, swallowing hard and shaking her head.
Combs’ ex-girlfriend, R&B singer Casandra ‘Cassie’ Ventura, testified in a subdued tone as she described the five images, which showed her with three male escorts. One photograph depicted Ventura alongside an escort named Greg in the midst of a “Freak Off.” Ventura, 38, explained she was wearing high heels and had baby oil applied to her skin.
To protect her privacy, the court restricted viewing of the images to Ventura, the jury, Combs and his legal team, and the prosecution.
The images were presented on the third day of Combs’ trial. The 55-year-old, a three-time Grammy winner and one of hip-hop’s most prominent figures, faces serious allegations connected to these parties.
Ventura, testifying for a second day, detailed the physical toll of attending multi-day sex parties, describing the experience as “hell on my body.” She revealed she suffered repeated, painful urinary tract infections (UTIs) throughout their decade-long relationship due to the demanding “Freak Offs.”
The singer also recounted injuries sustained from having sex for up to four days straight. She spoke about frequent arguments with Combs, whom she began dating in 2006 when she was 19 and he was 17 years her senior.
Among the incidents she described was an altercation at the InterContinental Hotel in Los Angeles in March 2016, where Combs allegedly assaulted her — an event captured on CCTV. Ventura said Combs subsequently sent her a barrage of text messages pleading, “Call me,” “Help,” and “If you don’t pick up you’ll never hear my voice again.”
Despite his claims of impending arrest, neither police involvement nor hotel security intervention was reported.
Ventura also testified that Combs later showed up at her apartment, forcefully banging to get in and causing chaos. The jury was shown a photograph of her injuries from being dragged across the floor, including a swollen lip and black eye. Photos from a few days later at a film premiere showed Ventura wearing sunglasses to conceal the bruising.
She further testified about an incident in 2013 before a trip to Canada’s OVO music festival, where Combs allegedly attacked her while she was asleep. Friends intervened to restrain him, but Ventura sustained a significant cut above her left eye. Combs’ security staff reportedly took her to a Beverly Hills plastic surgeon for stitches. Afterwards, she sent Combs a photo of the wound with the message, “So you can remember.”
During testimony, Ventura identified 13 male escorts from a binder of photographs, in addition to six she had named the previous day, whom she said she was forced to have “Freak Offs” with.
She described the serious medical issues stemming from these encounters, including stomach problems linked to drug use and frequent UTIs. Ventura said the parties were often back-to-back, forcing her to participate while infected, enduring intense pain and burning sensations.
Ventura claimed Combs threatened to release videos of her participating in these parties, at one point even playing them during a flight with other passengers nearby. Fearing public exposure and having to face her family, Ventura said she felt trapped.
The court also heard allegations that Combs attempted to damage the car of another man Ventura dated. She said Combs became enraged when he learned in late 2011 that she was seeing rapper Kid Cudi (Scott Mescudi). Combs allegedly threatened to harm both Ventura and Mescudi, leading her to end the relationship.
“It was too much,” Ventura said. “Too much danger, too much uncertainty.”
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