Diddy Urinated on Girlfriend During 'Freak Offs'

Sean Combs performing at the eTalk Festival Party, during the Toronto International Film Festival, 2008. Photo by Richard Burdett under CC BY 3.0

When singer Cassie Ventura took the stand in Sean "Diddy" Combs' ongoing federal trial, the courtroom braced for impact. But few could have anticipated the disturbing and detailed allegations she would lay out. From sex parties to video blackmail, the revelations were relentless. As the trial unfolds in New York City, here are the biggest bombshells so far — all allegations, and none yet proven in court.

1. Cassie Describes 'Freak Offs' and Drug-Fueled Sex Parties

According to Ventura, Combs allegedly orchestrated multi-day sex parties called "Freak Offs" where she was directed to perform with male escorts while he watched, as reported by Business Insider. She testified that the events sometimes lasted for four days and involved heavy drug use including cocaine, GHB, MDMA, and mushrooms. Ventura said she took drugs to numb herself during the encounters.

2. Alleged Urination and Abuse During Sexual Encounters

Ventura alleged that she was urinated on during these "Freak Offs," often by Combs or hired escorts — sometimes both. She testified she never consented and described instances of choking due to the volume of urine in her mouth, calling the experiences degrading and traumatic.

3. Video Recordings and Alleged Blackmail Material

During her testimony, Ventura said Combs recorded these sexual acts without her full consent and later used the footage as "blackmail material," according to PEOPLE.

She described living in fear that the videos would be leaked to damage her career or reputation, particularly when their relationship soured or she tried to move on romantically.

4. The 2016 Hotel Assault Caught on Tape

One of the most public pieces of evidence was a surveillance video from a Los Angeles hotel, shown early in the trial. The footage captured Combs allegedly assaulting Ventura near an elevator. Ventura testified that she sustained a black eye, bruised lip, and multiple other injuries that night. Prosecutors claim Combs paid $100,000 to suppress the video — a move allegedly orchestrated to avoid public backlash.

5. Diddy's Alleged Death Threat Against Kid Cudi

Ventura also testified that when Combs discovered she was seeing rapper Kid Cudi in 2011, he exploded with rage and allegedly threatened to blow up Cudi's car. Prosecutors allege that Combs orchestrated an arson attack on Cudi's vehicle using a Molotov cocktail — a claim Cudi has publicly confirmed in past interviews.

6. A $20 Million Settlement and a Price for Silence

During the trial, Ventura revealed that she settled a 2023 civil lawsuit against Combs for $20 million. She said she initially asked for $30 million in exchange for the rights to a book she had written about their relationship. When Combs didn't respond, she filed the lawsuit alleging sex trafficking and abuse.

7. Dawn Richard Testifies About a Violent Attack Over Eggs

Singer Dawn Richard, a former member of Danity Kane, testified that she witnessed Combs violently assault Ventura in 2009 because she was too slow to cook eggs. According to Richard, Combs hit Ventura with a skillet, kicked her repeatedly, and dragged her upstairs by her hair. She also claimed, according to Business Insider, Combs warned them to stay silent, saying, "people go missing," before giving them flowers the next day.

8. Feds Seize Baby Oil, Drugs, and Blue Party Lights

When federal agents raided Combs' hotel suite at the Park Hyatt New York in September 2024, they found multiple bottles of baby oil, personal lubricants, and baggies of pink powder that allegedly tested positive for ecstasy. The items matched Ventura's description of what was typically used during the "Freak Offs," down to the blue lightbulbs used to illuminate the rooms.

9. Cassie Says Diddy Once Overdosed at the Playboy Mansion

Ventura testified that Combs once overdosed on opioids after attending a party at the Playboy Mansion. The incident occurred around February 2012, shortly after the death of Whitney Houston. She said she drove him to the hospital and learned later that he had taken a very strong opiate.

The allegations in the trial are extensive, graphic, and deeply troubling. Combs has pleaded not guilty to all charges, and the trial is ongoing. As more witnesses take the stand, further revelations may emerge. Until then, the public continues to watch closely — not just for justice, but for the truth.

References:8 Biggest Bombshells from Cassie's Shocking Testimony at Diddy's Sex Trafficking Trial | Diddy Trial: Biggest Moments from Week 1, Including Cassie's Emotional Testimony | The 8 Biggest Bombshells from the Diddy Trial — Including a 'Death Threat' Described by Danity Kane Singer Dawn Richard | The 11 Biggest Bombshells from the Diddy Trial — Including What Cops Found in His Hotel Room When He Was Arrested