‘Freak-offs became a job’: Ex-girlfriend Casandra Ventura testifies in Sean ‘Diddy’ Combs trial

Warning: This article contains graphic details that may distress some readers.

New York: Casandra Ventura says her life became dominated by the drug-fuelled sexual encounters organised at the behest of her then-boyfriend and record label boss, Sean “Diddy” Combs, telling a jury the longest of these sessions, called “freak-offs”, lasted four days.

Cassandra Ventura, aka Cassie, and Sean “Diddy” Combs at the Met Gala in 2015.Credit: Charles Sykes/Invision/AP

Ventura, an R&B singer known professionally as Cassie, took the stand for the first time on Tuesday (Wednesday AEST) in Combs’ sex-trafficking and racketeering trial, in which he is accused of coercing women into sexually abusive and violent encounters with male escorts, aided by his staff.

Heavily pregnant and wearing a tan dress, Ventura, 38, told the jury that after following Combs from New York to Los Angeles as his girlfriend and an artist signed to his label, much of her time was spent recovering from the days-long sex and drug binges that took place in hotels, rather than making music.

In these sessions, which Combs had called “freak-offs” or “wild king nights”, Ventura would typically have sex with a male escort while Combs masturbated and sometimes recorded video, the court heard. Drugs and alcohol were also consumed.

“The freak-offs became a job where there was no space to do anything else, but try to recover,” Ventura told the jury. While they would typically last between 36 and 72 hours, “the longest one ever was four days”, she said. “Recovering from partying – that took a big chunk out of my life.”

The prosecution alleges Combs used his business and staff as a criminal enterprise to enable and cover up the transportation and coercion of women for sex, and blackmailed them into remaining silent.

The defence which, along with the prosecution, delivered its opening statement on Monday, acknowledged Combs had been violent to women and engaged in sexual fantasies, but said they were consensual participants in adult relationships.

Early days

In the morning session on Tuesday, the court heard Ventura met Combs in New York City in 2005 when she was a 19-year-old model, and had started recording a few songs. Combs was 17 years her senior and the owner of Bad Boy Records. In early 2006, he signed her to a 10-album deal, only one of which was ever produced.

In those early days, Ventura described Combs as a charismatic and sympathetic figure who looked out for her following “some rough [musical] performances”. They would socialise in similar circles, seeing each other once a month or every other month at New York nightspots.

The relationship began to turn sexual when Combs kissed her in a hotel bathroom during a trip to Las Vegas in August 2007, Ventura said. The trip coincided with her 21st birthday and the MTV Video Music Awards. Ventura described herself at the time as a new and naive young artist “who just didn’t know the lay of the land”.

She said that after the trip, Combs had invited her to hang out at hotels in New York while his apartment was being renovated, and introduced her to oral sex. They had intercourse for the first time during a trip to Miami in 2007, where she also voluntarily took ecstasy for the first time.

From then on, Ventura said she became like a “shadow” to Combs. She felt they had begun a monogamous relationship. Over time, she began to see abusive and controlling behaviour. She said he was an “incessant caller” and if she did not return his calls or messages, he would have his security guards and assistants track her down, sometimes showing up at her apartment. She also became aware he was involved with other women.

Ventura followed Combs to Los Angeles, as he wanted to be closer to his children from a previous relationship. She lived separately in apartments typically paid for by Combs, and described having a “stomach in knots moment” when he would sometimes show up unannounced.

Meanwhile, her music career was stagnating. Ventura told the court she had recorded hundreds of songs, but a second album never materialised through Combs’ record label. Asked whether she received compensation if an album was not released, she said: “You don’t. You barely received it when they got released.”

The first freak-off

In the afternoon session, Ventura told the court the first “freak-off” she performed for Combs occurred in one of his Los Angeles homes, about two to three months after he first raised the idea with her.

The encounter involved consuming alcohol and ecstasy, Ventura said, while at Combs’ direction she wore tall platform “stripper” shoes, an outfit from a sex store and a masquerade mask. “Every freak-off was directed by Sean,” she told the court.

Ventura said that at the time, “I was high, so there wasn’t too much feeling”. Afterwards, she felt dirty and confused, but pleased that Combs was happy and she “did something right”.

A freak-off would typically involve multiple sex sessions with the chosen male escort or multiple male escorts, Ventura told the court. Combs would watch either in the room or from a different room, sometimes using the FaceTime app. Sometimes he would also take part by having Ventura perform oral sex on him at the same time, she said.

Drugs – ecstasy, MDMA, cocaine, ketamine, marijuana and others – had helped her to stay awake for the entire freak-off, Ventura told the jury.

She said as the encounters became more frequent – weekly for a number of years – it was impossible to recall them all. “It just felt like it was all I was good for,” she said. “Doing this, it made me feel horrible, it made me feel worthless.”

Ventura said she did not want to participate in the freak-offs, though the court saw messages in which she had indicated to Combs that she did. She said she definitely brought up her real feelings about the encounters to Combs, but “treaded lightly”.

“I just didn’t want anything bad to happen,” Ventura said. She indicated she feared Combs’ violent rages, but also that he might find somebody else to participate in the sexual encounters with escorts. “When you really care about somebody, and you’re in love with them, you don’t want to disappoint them.”

In one email exchange between Ventura and Combs, she hinted at reservations about the freak-offs. Combs responded by calling her “predictable”. “He didn’t really care,” she told the jury.

‘He was directing’

Later in the afternoon, prosecutors asked Ventura about the freak-offs in painstaking detail. She said Combs insisted their bodies were oily and shiny, and the sessions involved large amounts of baby oil – up to 10 large bottles. On one occasion, at the Beverly Hills Hotel in Los Angeles, she said a small blow-up pool had been filled with baby oil and lubricant, and she climbed into the pool.

Defence lawyers objected to the length and repetitiveness of some of the prosecution’s questioning. “At this point, it’s getting a little cumulative,” one defence lawyer said.

Ventura told the jury the freak-offs created a significant amount of mess, including the walls and furniture, and towels soiled with lubricant and oil, and even blood and urine. “I was expected to have freak-offs on my period,” she said.

Combs’ fantasy involved her describing the sexual acts she undertook with the male escorts in detail, Ventura said – something she found awkward and humiliating, though it eventually became “normal”. She described trying to speed the process along because “I just wanted it to be over”.

The male escort would usually ejaculate on her body, she said. Then, when they were alone together in another room, Combs would ask her to spread it on his chest. If the escort ejaculated without Combs’ permission, they would get paid less, Ventura told the court. “This is his fantasy. He was controlling the whole situation, he was directing.”

When the jury was dismissed for the day, they had been hearing Ventura’s account of a freak-off that took place at the InterContinental Hotel in Century City, Los Angeles, in March 2016. Video of Combs assaulting Ventura in the hotel hallway has already been played to the jury (and was published by CNN last year).

In her telling, Combs had already hit her in the hotel room, and she had sustained a black eye. “I knew I had to get out. I just grabbed my stuff and ran out as fast as I could,” she told the jury. When he caught up with her in the elevator foyer, he threw her to the ground.

Asked by prosecutors how many times Combs had thrown her to the ground during their relationship, Ventura said: “Too many to count.”

The trial continues.

If you or anyone you know needs support, you can contact the National Sexual Assault, Domestic and Family Violence Counselling Service on 1800RESPECT (1800 737 732), Lifeline 131 114, or Beyond Blue 1300 224 636.

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