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Diddy trial: Cassie Ventura claims Sean Combs raped as they were breaking up

Sean ‘Diddy’ Combs’ ex-girlfriend Cassie Ventura has made shock claims about the physical toll of his “freak off” parties. WARNING: Graphic content

Sean ‘Diddy’ Combs trial: Sordid details of alleged sex parties revealed

WARNING: Graphic content

The ex-partner of singer and musician Sean “Diddy” Combs has told a New York court shocking claims that he raped her on her living room floor as the pair were breaking up.

Cassandra “Cassie” Ventura said Combs’ “didn’t even notice” her as she said no and cried.

The allegation came at the end of two days of gruelling testimony by Ms Ventura conducted by federal government lawyers as they build their case against Combs.

Diddy’s alleged hotel assault captured in horrific video

Jurors in the Downtown Manhattan court were also shown images from Combs’ notorious alleged “freak off” sex parties. These were so explicit, the public gallery and media were not permitted to view them.

Additionally on Wednesday, Ms Ventura told the court medicines to combat STDs stopped working as she had contracted so many during the estimated hundreds of freak offs she felt compelled to take part in.

She also said Combs threatened to release sexual images of her from “iPads full of skeletons,” that he beat her so badly on one occasion his own security guard began crying, and that her now husband had to stop her “walking into traffic” because of the pain of her previous relationship.

She also revealed for the first time the multimillion dollar settlement she received from Combs in a 2023 civil case.

Cassie Ventura, right, walks out of the courtroom past Sean Diddy Combs after testifying in Manhattan federal court, Tuesday, May 13, 2025, in New York. (Elizabeth Williams via AP)
Cassie Ventura, right, walks out of the courtroom past Sean Diddy Combs after testifying in Manhattan federal court, Tuesday, May 13, 2025, in New York. (Elizabeth Williams via AP)

The singer is the star witness in Combs’ trial where the US government has charged him with transportation to engage in prostitution, sex trafficking and racketeering.

Combs could face life in jail if he is found guilty of just one of the charges.

He has pleaded not guilty and his lawyers have claimed Ms Ventura was a willing participant in sex parties.

A heavily pregnant Ms Ventura took to the stand for a second day of prosecution questioning on Wednesday.

She claimed she gave into Combs’ demands for her to have sex with other men, while he watched on, because she was a naive 22 year old when they started dating, she loved him and her career as a singer was dependent on his record label.

However, as the sex sessions became more degrading, including Ms Ventura allegedly being urinated on and told to have sex on her period, she said she felt unable to tell Combs she no longer wanted to take part.

Diddy and Cassie in happier times. Picture: Instagram
Diddy and Cassie in happier times. Picture: Instagram

MORE: ‘Freak off’: Diddy cops $50m insult in major blow

She said she had so much sex in the freak offs, which could last days and were often weekly, that she suffered from “burning” urinary tract infections.

Ms Ventura said the UTIs became so frequent she was eventually immune to antibacterial treatments.

The sheer amount of oral sex she performed also left her with sores on her tongues from “friction in her mouth”, Ms Ventura claimed.

MORE: Jailed Diddy’s wild $98m move exposed

Janice Combs (L), mother of Sean
Janice Combs (L), mother of Sean "Diddy" Combs and her grandson King Combs (R), depart Manhattan's Federal Court in New York City on May 13, 2025. (Photo by Leonardo Munoz / AFP)

Security guard cried

The jury was shown multiple confronting images including a gash on Ms Ventura’s eyebrow and a black eye which she said was the result of an attack by Combs who was her partner for 11 years.

She detailed one alleged incident that occurred in Las Vegas when Combs was hosting a party.

Ms Ventura said she was talking to a manager when “Sean tapped me on the shoulder and told me to go in the next room”.

“There he beat me up,” she told the court.

“I was trying to run away and make it into the bathroom, to close and lock the door.

“He was kicking me, punching me and I was screaming.

“It ended when security came into the room”.

Ms Ventura said a security guard of Combs’ began crying when he saw the state she was in

“I had black eyes and a golf ball sized knot on my forehead”.

Sean
Sean "Diddy" Combs attends the 2022 Billboard Music Awards at MGM Grand Garden Arena on May 15, 2022 in Las Vegas, Nevada. (Photo by Frazer Harrison/Getty Images)

‘Raped me on the floor’

She had earlier said that there were two versions of Combs. The violent Combs would emerge as “his eyes would go black – the version of him I was in love with was no longer there”.

On Wednesday she referenced that version of Combs when she alleged she was raped at the end of their relationship in 2018. At the time she was already dating her then personal trainer and now husband, and father of her children, Alex Fine.

Ms Ventura said she and Combs went for dinner and had a “closure conversation”.

“Sean was nice, romantic vibes, laughing, playful”.

After dinner, he drove her home.

“He came in, nothing unusual, and then he raped me on the floor,” she alleged.

“The eyes were black, he wasn’t himself, the laughing wasn’t there. I remember crying, it was very fast. (But) he continued, I don’t know if he even noticed.

“When I said no, he continued.

“He ejaculated inside of me and then got up and left.”

Sean Combs celebrates his Fabulous 50 Dinner Party at his private residence in Miami in 2004. Pictured: Sean Combs BACKGRID.
Sean Combs celebrates his Fabulous 50 Dinner Party at his private residence in Miami in 2004. Pictured: Sean Combs BACKGRID.

Ms Ventura admitted to having sex with Combs on one more occasion after the claimed rape. When asked by prosecution lawyer Emily Johnson why she slept with him again, Ms Ventura replied: “We’d been together for 10 years. You don’t just turn feelings off”.

‘IPad of skeletons’

On Wednesday, the prosecution showed the court various messages between Combs and Ms Ventura.

In one 2019 back and forth, after the pair had broken up, Combs said he had “iPads full of skeletons” of Ms Ventura.

She said he appeared to be referencing the many videos of her having sex with male sex workers.

However, in a reply to Combs she said that what she had was “way deeper than iPads,” meaning potential revelations about the abuse she suffered from.

Cassie Ventura's husband Alex Fine departs the New York court. (Photo by John Lamparski/Getty Images)
Cassie Ventura's husband Alex Fine departs the New York court. (Photo by John Lamparski/Getty Images)

‘Walked into traffic’

Ms Ventura said she had to undergo rehab and trauma therapy after spending a decade with Combs.

She has since had two children with husband Mr Fine and another baby is due imminently.

But she said she was so affected by her past she tried to commit suicide.

“I was shooting a music video and I had these horrible flashbacks,” she told the court.

“I went home super late and the kids were asleep. And I said (to Mr Fine) ‘you can do this without me, you don’t need me any more’

“I couldn't take the pain anymore.

“I tried to walk out of the front door into traffic (but) my husband would not let me”.

Massive settlement in civil case

Ms Ventura also revealed the mammoth settlement she received from Combs after her civil case in 2023. In that case she accused Combs of rape and physical abuse.

The lawsuit lasted just one day when Combs agreed to settle.

At the time the amount was kept under wraps. But in court on Wednesday, Ms Ventura said Combs and his companies paid her $US20 million ($31 million).

Originally published as Diddy trial: Cassie Ventura claims Sean Combs raped as they were breaking up

Original URL: https://www.heraldsun.com.au/entertainment/celebrity-life/sean-diddy-combs-trial-ex-cassie-ventura-to-testify-again-on-day-three/news-story/566d03b79f926d3ccdfe8e799e94fe88