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‘On my period’: Shocking alleged sex demands

Picture: Elizabeth Williams via

Picture: Elizabeth Williams via

WARNING: Distressing content, strong language

The ex girlfriend of Sean “Diddy” Combs has broken down in tears as she told a New York court the only thing that made the star’s “humiliating” freak off sex parties bearable was that it was a chance for her to spend time with her increasingly distant partner.

“It was the only time I could have one-on-one time with him,” Cassandra “Cassie” Ventura said of the parties that always involved her having sex with men that Combs allegedly would choose.

On Tuesday, US time, the court also heard Combs’ procured a swimming pool of lube which Ms Ventura had to wade in until she “glistened” while a lurid series of emails were read out between the pair about the freak off parties.

She also alleged a litany of violent abuse, that Combs directed men to urinate on her during which she “choked” and demanded she have sex on her period leaving hotel sheets bloodied.

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

The case centres on allegations some participants were forced to take part in sexual encounters against their will

Combs could face life in jail for just the racketing charge, a minimum of 15 years for sex trafficking and a minimum of 10 years for transportation to engage in prostitution.

Combs denies all charges.

 

Cassie Ventura seen here ahead of her testimony in court. Picture: Backgrid
Cassie Ventura seen here ahead of her testimony in court. Picture: Backgrid


Sean ‘Diddy' Combs, far left, and lawyer Marc Agnifilo, second from left, listen as witness Cassie Ventura, far right, answers questions from assistant US Attorney Emily Johnson, centre, with Judge Arun Subramanian presiding in Manhattan federal court, Tuesday, May 13, 2025, in New York. Picture: Elizabeth Williams via AP
Sean ‘Diddy' Combs, far left, and lawyer Marc Agnifilo, second from left, listen as witness Cassie Ventura, far right, answers questions from assistant US Attorney Emily Johnson, centre, with Judge Arun Subramanian presiding in Manhattan federal court, Tuesday, May 13, 2025, in New York. Picture: Elizabeth Williams via AP

 

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

Heavily pregnant Ms Ventura, in a brown top and tan jacket, took to the witness stand on Tuesday.

At 19, she had signed to Combs’ Bad Boy records label.

She was in a relationship with Combs for 11 years which began when she was 21. Combs was 17 years her senior.

She said she was “naive” for being in a relationship with the producer and musician. But she insisted she was in love with Combs while also being aware of the power he had over her career.

Speaking softly throughout the day, Ms Ventura said she believed she was his girlfriend, but “in hindsight Sean Combs had many girlfriends”.

She told the jury that around six months after they began dating Combs said he was into voyeurism and wanted her to have sex with other men in sessions he called “freak offs”.

“I just remember my stomach fell to my butt,” she said of the request.

“But l loved him. I wanted to make him happy”.

She alleged she would be plied with drugs – such as ecstasy or cocaine – to enable the freak offs to happen with male escorts or dancers who were paid thousands of dollars per freak off session. She would dress in “sex store outfits” including high platform shoes.

It’s alleged Combs would mostly masturbate in the corner, directing Ms Ventura to have sex, but would sometimes have intercourse with his girlfriend.

Comb’s lawyers have insisted she was a willing participant.

 

Cassie Ventura and Sean Combs in 2017. Picture: Theo Wargo/Getty Images
Cassie Ventura and Sean Combs in 2017. Picture: Theo Wargo/Getty Images

 

Swimming pool of lube and baby oil

The alleged freak offs became an almost weekly affair.

“I would stay up for days on end having sex with strangers and taking drugs,” she said.

Ms Ventura knew most of the men she had sex with only by a pseudonym. There was “Daniel,” “Johnny” and one man known only as “The Punisher”. Combs’ preference was for black men to sleep with his girlfriend, she said.

Given Bad Boy released just one of her ten planned albums, Ms Ventura said organising the parties for Combs became her “job”.

“At a certain point I felt I didn’t have a choice,” she said about taking part, with Combs allegedly telling her he would leak images of her at the parties online.

A significant amount of the planning involved sourcing enough Johnson’s baby oil and Astroglide lubricant for Combs’ exacting requirements, Ms Ventura said.

“Baby oil was as important as everything else,” she told the court.

“We poured it all over our bodies until we were glistening. It was Sean’s preference”

If Ms Ventura or the men were getting “too dry,” she said Combs would demand they slather on more oil “to be more shiny”. If the oil ran out, a staff member would be told to buy more.

“There was a blow up pool full of lube and oil,” Ms Ventura said of one party in a hotel.

“I got in the pool with my outfit and shoes. It was dangerous, it was a mess. (But) I couldn’t say no.”

 

Cassie Ventura's husband, Alex Fine, at federal court in New York City on May 12. Picture: Angela Weiss/AFP
Cassie Ventura's husband, Alex Fine, at federal court in New York City on May 12. Picture: Angela Weiss/AFP

 

Freak off brings Ventura to tears

Ms Ventura was asked by prosecution lawyer Emily Johnson how she felt after the freak offs.

“It felt like that was all I was good for. I felt disgusted, humiliated.”

She said there was one thing she enjoyed about the freak offs – being with the increasingly distant Combs.

“The one-on-one time with him – it was the only time I could get with him”.

Blood and urine

Ms Ventura said on several occasions, Combs told men to urinate on her and also did so himself. A male escort had earlier told the court he had urinated on Ms Ventura but she had encouraged it.

“I didn’t want anyone to urinate on me,” she said.

“There was no conversation. It was a turn on for (Combs) so it happened.

“I was choking because there was too much urine in my mouth”.

She was asked by the prosecution why she didn’t protest the urination.

“There was nothing on my face that was reading I wanted to do that.

“I didn’t say no because I thought it was obvious I didn’t want to do it”.

She said it only stopped when, on the floor, wet, she put her hands up in the air to signal it should cease.

Ms Ventura also said urine would get on the sheets of the hotels where the parties frequently happened. But also blood.

“I was expected to have freak offs on my period,” she said of the blood.

“Nobody really wants to do that”.

 

CCTV footage of Combs beating Cassie Ventura in a Los Angeles hotel. Picture: CNN Exclusive
CCTV footage of Combs beating Cassie Ventura in a Los Angeles hotel. Picture: CNN Exclusive

 

‘Really need 2 f*** you’

The court was also shown an email exchange between Ms Ventura and Combs.

“I really need 2 f***,” Ms Ventura wrote.

Combs’ was said to have replied “So who u gonna f***, wanna call someone”.

“I wanna f*** you, are you crazy,” wrote Ms Ventura.

Combs said “just joking” in the exchange. But Ms Ventura said it was an example of his desire for sex parties more than sex with her.

In the same email trail, she said she wanted to talk about the parties to which Combs’ took badly and said her reticence was “predictable”.

Ms Ventura then told the court she quickly backtracked sensing Combs’ anger.

“I wasn’t going to say I didn’t want to do it anymore,” she wrote.

 

Quincy Brown, Chance Combs and D'Lila Star Combs, the children of Sean
Quincy Brown, Chance Combs and D'Lila Star Combs, the children of Sean "Diddy" Combs arrive for Sean Combs' trial at Manhattan Federal Court on Tuesday. Picture: Michael M. Santiago/Getty Images via AFP

 

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

Comb’s ‘crazy’ oral sex claim

Ms Ventura said Combs first kissed her in his hotel bathroom during a trip to Las Vegas in 2007 to celebrate her 21st birthday.

“I was really confused and naive. I didn’t want to kiss Sean. I cried and ran off.

“He had my career in his hands”.

A relationship ensued and at New York’s Trump Hotel, overlooking Central Park, he “introduced me to the idea of oral sex”.

“It was not something I did or understood.

“I went home and he made me feel crazy for not reciprocating,” she said.

“I was completely sexually inexperienced.”

Ms Ventura also discussed the violence Combs meted out to her, including in a now infamous CCTV recording in a Los Angeles hotel that made global headlines.

She said the abuse occurred “too frequently”.

“He would drag me, knock me over, stomp on my head when I was down. Busted lips, black eyes, bruised all over.

“It was always in the back of my mind I’d somehow be hurt.”

“His eyes would go black. The version of him I was in love with was no longer there”.

The proceedings are expected to last eight to 10 weeks.

Author: Benedict Brook in New York

Source: News Corp Australia Network:

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