During a recent court hearing, heavily pregnant Cassie Ventura emotionally recounted distressing experiences of alleged abuse and inappropriate sexual behavior by former music executive Sean ‘Diddy’ Combs.
Approaching the witness box with caution, Ventura, who was just a fortnight away from her due date, composed herself before sharing her testimony. She was dressed in a form-fitting brown bodysuit that accentuated her significant baby bump.
Meanwhile, Combs, clad in gray attire, attentively watched as Ventura took her place in the stand, knowing that her words could have a significant impact on his future, potentially leading to a lengthy prison sentence.
But star witness Ventura did not look his way on the second day of the blockbuster trial and appeared to avoid locking eyes in the tension-filled New York federal courtroom.
It is the first time she has been anywhere near Combs since the 2018 funeral of another of his exes, singer Kim Porter – mother of three of his children.
At times she dabbed her eyes with a tissue as tears welled up while giving evidence.
Cassie’s eye-raising testimony about Diddy’s ‘wet’ fetish had her detailing the routine of a freak off, Ventura said it would begin with oil and touching then progress through oral sex to full intercourse. ‘I often tried to speed it up,’ she said.
During one session, Diddy ‘choreographed’ Ventura getting into a pool of baby oil at a hotel in Beverly Hills in a full outfit purchased from a sex shop and heels. She said she didn’t want to do it ‘especially in a hotel room’, but that she couldn’t say no because it ‘would have been all bad’.
At various points throughout her testimony, Cassie Ventura would dab her eyes with a tissue as tears welled up while giving evidence
Diddy kids including his three daughters and sons watched on in shock as Ventura detailed the horrific sex acts she went through with strangers in Diddy’s ‘orchestrated’ freak offsÂ
Ventura was seen looking stoic as she made her way to court, as she is set to come face to face with her abusive ex, Diddy, on Tuesday
Cassie also detailed how the Freak Offs would go down, saying: ‘First sex act, masturbating and looking at each other – I would be looking at the escort and they would be looking at me. I would describe what I saw in detail. That is what turned (Combs) on… his fantasy.
‘It was always awkward… sitting describing someone’s penis to another male was pretty awkward and humiliating but eventually it became normal. It would lead to intercourse.’
Ventura said sometimes both the escort and Combs would have sex with her, other times the fallen mogul would ‘just watch’.
She added: ‘If I was having intercourse with an escort, Sean would walk up and have me give him oral sex.’
Asked if the escorts ejaculated, the star witness replied: ‘Yes, usually when it was OK for them per Sean. But if they did then Sean and I would go into the next room and he’d want me to put the semen on his body… usually on his chest, on his nipples’.
If escorts ejaculated without being given permission by Combs they were paid less, said Ventura.
Cassie told how he made her call him ‘Pop Pop,’ the name she called her grandfather:Â ‘He wanted me to have a nickname for him, Ventura said. ‘I thought it was weird and now I feel like it was disrespectful.’
And in a wobbling voice she explained that when he got violent, the look in his eyes would shift into something unrecognizable.
Diddy watching as Cassie is sworn in as a prosecution witness during his second day at court on Tuesday. This was the first time the former couple had seen each other since Kim Porter’s funeral
Cassie heading to court for the Diddy case in NYC. She was wearing close-fitting brown bodysuit that showed off her large bump on the stand, and is just two weeks away from giving birth
Cassie and Diddy first met in 2005, when she was 19 and he was a 39-year-old superstar (Pictured: New York, 2006)Â
Asked about the violence in her 10-year relationship with the disgraced hip-hop titan, Billboard 100 singer Ventura said: ‘He would bash me on the head, knock me over, drag me, kick me, stomp me in the head if I was down.
‘I’d get knots in my forehead. Busted lips, swollen lips, swollen eyes… whites of eyes would be red. Bruises all over my body.’
Prosecutor Emily Anne Johnson asked 38-year-old Ventura: ‘How frequently physical.’ She replied: ‘Too frequently.’
Her horrific testimony comes a day after the court heard how Harlem-born Combs, 55, forced women to take part in drug-fueled sex parties he dubbed ‘freaks offs’ and went on for days while he filmed them.
He has denied sex trafficking by force, racketeering conspiracy and prostitution for what prosecutors have said was a decades-long criminal enterprise in which ‘he called himself the king’.
Ventura told the Manhattan court: ‘Within the first year of our relationship Sean proposed to me this idea, this sexual encounter that he called voyeurism where he’s watch me in sexual activity with a third party, specifically another man.
Sighing as she recounted in slow and halting speech, she added: ‘It entails the hiring of an escort and setting up this experience so that I could perform for Sean.
‘It involved Sean being able to watch me with the other person and actually direct us on what we were doing sexually.’
Ventura, who is expecting her third child with former personal trainer husband Alex Fine, said when Combs suggested the freak offs ‘I remember my stomach falling to my butt’Â
Diddy’s defense says he is guilty of domestic violence but not of sex-trafficking or racketeering, and that the government is targeting him for his sexual preferences
Ventura, who is expecting her third child with former personal trainer husband Alex Fine, said when Combs suggested the freak offs ‘I remember my stomach falling to my butt.
‘The nervousness and confusion on that moment. I had just turned 22. I didn’t have a concept of how that would be a turn on, but I also felt a sense of responsibility with him sharing something like that with me.
‘I was confused, nervous but also loved him very much and wanted to make him happy.’
Ventura, who was signed by Combs to his Bad Boy Records label as she began her singing career, said she agreed to a freak off.
More followed and ‘pretty quickly I knew that it wasn’t something I wanted to be doing. Especially as regularly as it became. But I was in love and wanted to make him happy.
‘Got to the point I didn’t feel I had much of a choice. I didn’t really know what it could turn into.’
Sighing again, she said: ‘At this point Sean controlled a lot of my life, career, the way I dressed, everything. And I didn’t feel I had much say in it… being super young, naive, a total people pleaser.
‘Over time it turned into the fact there was blackmail material to make me feel if I didn’t do it, it would be hung over my head or these things would become public.
While on the stand, Ventura was visibly nervous, biting her lip as she agreed with prosecutor Johnson that any ‘blackmail materials’ would be photos and videos of the freak offs
The singer, who gently rubbed her baby bump during testimony, told the court that the physical violence Diddy inflicted on her could be triggered by just a look she gave him
 ‘It was always in the back of my mind I’d be hurt by him. Sean is a really polarizing person. Also very charming… I just didn’t know what would happen.’
Ventura then bit her lip nervously as she agreed with prosecutor Johnson that any ‘blackmail materials’ would be photos and videos of the freak offs.
The singer, who gently rubbed her baby bump during testimony, told the court she first hooked up with Combs as a 19-year-old and signed a 10-album deal in 2006.
They began a relationship, but she was ‘completely sexually inexperienced’ and ‘I didn’t even have the vocabulary for some of the things we talked about.’
But she wanted to be around him, telling the court: ‘For the same reason as everyone else. Just this exciting, entertaining, fun guy that also happened to have my career in his hands. It felt special. Not a lot of people got that kind of time with him.’
The pair had sex on a boat in Miami and ‘I would say we were together… after that. Now I known in hindsight I became one of his girlfriends….’
For a while Ventura said she soaked up the lifestyle.
‘I really fell in love with him. We had fun. It was my first adult relationship, or I thought it was. It was so different to anything I can imagine. His lifestyle was much different than mine,’ she told the court.
They were last photographed together during the Met gala in May, 2018. Ventura said on the stand that she was ‘sexually inexperienced’ when she began their relationship, which she alleged Diddy took advantage of
Cassie’s husband Alex Fine (left) – a personal trainer that Diddy hired for her before going public with their relationship in 2018 – threatened to ‘beat the f***’ out of Diddy in texts sent after she demanded $30 million from him, the court heard today
The couple share two girls together and have a third child on the way
But then Combs allegedly started tightening his grip.
‘I began to experience a different side of him,’ Ventura recalled. ‘His abusive side, very controlling over my life, the things I wanted to do. But there’s still love there.
‘Control was everything. From the way I looked to what I was working on that day, who I was speaking to. Control was an all-around thing to a certain point.’
Combs’ moods ‘varied depending on what was going on. It could change at the drop of a conversation, a bad conversation that I had nothing to do with.
‘At certain times I knew it wasn’t even about me…. the next thing I was getting hit in the face.
‘If I wasn’t smiling at him the way he wanted… I just looked a certain way he didn’t like. Maybe I was a brat, or something, he would let me know I need to fix my face or watch my mouth.’
Ventura paused to regain herself, then continued: ‘Psychological was every day, not know what he was going to be when he woke up that day…. that was a lot, someone constantly telling you who to be.’
She admitted being jealous of Combs’s other women in an environment which she intimated she was too young to understand.
The video that led to Diddy’s downfall – which was aired by CNN in May 2024 – shows Combs, wearing only a white towel, punching, kicking and throwing Ventura to the groundÂ
Judge Subramanian said he could make the ‘freak off’ videos and photos public despite pleas from Ventura to keep them under wraps
‘I was insanely jealous,’ she said. But also super young, I didn’t get it all. I didn’t get that he was him.
‘As he would say, ‘I’m Puff Daddy and Puff Daddy has many women, he like the company of women’. I had to learn that over time.’
Confusingly, Ventura added: ‘He made me feel like we were in a monogamous relationship. He expected that of me, so I assumed that of him. He would say, I’m not dealing with anyone else, it’s just us.’
The witness moved to Los Angeles where her career began to be ‘stifled’ around 2012, and she began a heavy partying lifestyle.
But also ‘the freaks offs became a job where there was no space to do anything else but to recover and try to feel normal again.’
‘The partying was staying up for days on end, taking drugs and other substances, drinking. Having sex with strangers for days.’
The freak offs ‘ranged anywhere from 36, 48 to 72 hours. The longest one was four days, maybe even more than on and off breaks… a significant part of the week.’
As her music career faltered, Ventura was earning between $7,500 and $20,000 for hosting events in LA clubs and also modeling, the court heard.
Diddy made a heart with his hands as a gesture to his kids who returned to the courtroom – despite walking out yesterday as prosecution witness revealed explicit details of their father’s sexual encounters
But Combs still exerted control by taking away things he had paid for such as a car or apartment if the mood suited him, she said. Items would be removed for ‘as long as I was being punished’.
The freak offs continued and one evening terrifying potential gun violence came into play, the court heard.
Combs kept weapons in New York, Los Angeles, Miami and Alpine, New Jersey, Ventura said. He also had an intense rivalry with Death Row Records boss and former NFL player Suge Knight.
‘Suge and I were having a freak off at one of his homes in LA and I remember we were chilling at D Rock came in and said Suge was down… the hill and they quickly packed up and drove down there,’ she said.
‘I was crying. I was screaming, please don’t do anything stupid… really nervous. I didn’t know what it meant or what they were going to do.
‘It was like I wasn’t even there. They put on a bunch of black clothes, went in the safe, grabbed guns. Next thing I knew they were in the SUV just whipping down there.’ She did not say what happened next.
Prosecutor Johnson turned the testimony back to freak offs and voyeurism. Ventura said she can’t remember the name of the first escort involved and that she took ecstasy supplied by Combs.
Three of Diddy’s kids and his mother Janice walking back into court after the lunch break
Ventura walking out of the courtroom past Diddy after testifying on the second day of his trial
She had to wear an outfit bought from a sex store and high platform shoes – plus a masquerade mask. After the first session ‘I was high but there wasn’t too much feeling.
‘It was a mixture of dirty and confusion with, OK he’s really happy with me I did something right. I didn’t know we were going to do it more frequently.
‘They became almost weekly. It became, depending on where we were… weekly for a consistent amount of years. The drugs honestly helped. Ecstasy and molly (MDMA). We started to other drugs like cocaine later on.’
Ventura said she felt ‘disgusted, pretty horrible about myself. I was humiliated’ by the freak offs.
Her voice breaking and close to tears, she continued: ‘I couldn’t talk to anybody about it’. Combs ‘would be violent, his look would change’. Fighting for words, she said: ‘I wouldn’t know what would happen.
‘Best way (to describe Combs), his eyes go black. the person I was in love with was no longer there.’
Reaching for a tissue, she added poignantly: ‘I did feel very close to him. As sad as it was, it was the only time I could get.
Now sobbing, she said: ‘I never wanted him to feel I judged him, but I wanted him to know (it) made me feel horrible, made me feel worthless, like I didn’t haven’t anything else to offer.’
Despite reservations, Ventura said she also went along with having her nipples pierced and also a piercing ‘that sits on your clitoris. Sean’s suggestion. He actually came with me’.
Diddy’s kids had to sit through Ventura’s testimony where she detailed their father’s ‘nipple’ fetish and how he went with the singer to get a piercing on her clitorisÂ
Ventura testified that the ‘freak offs’ could last from ’36, 48 to 72 hours’ and that the longest one she was involved in lasted four daysÂ
One of Combs’ particularly sick requests, Ventura alleged, was to have a male escort urinate on her and in her mouth during freak offs.
‘Sometimes he himself (Combs) or he would have the escort urinate on me… there was no conversation. It was a turn on for him, so it happened.’
When asked if she had wanted this, she said a firm ‘no’, describing it as ‘humiliating is anyone was there to see it.
‘It was disgusting, it was too much, overwhelming’. In an indication of the procedure, she said she was choked and ‘I was laid on the floor in a position I couldn’t easily get out of.’
Asked if she was able to ask the escort to stop, she replied: ‘I put my hands up and Sean saw and told him to stop. Only thing I could do laying on the floor… too much urine in my mouth.
Prosecutor: ‘Did you want Sean to urinate on you?’
Ventura: ‘I didn’t want anybody to urinate on me.
‘I was squeamish immediately and high and in the moment with this man, so that’s what happened.
Cassie testified that when Diddy was told with Death Row Records boss and former NFL player Suge Knight (pictured) was in the area, he grabbed his guns and hopped in an SUV, bolting off to an unknown location Â
‘There’s not a whole lot of control… taken that many drugs and being on the floor with two men peeing on you.’
Ventura also revealed hotel rooms booked for freak offs would end up covered in blood, urine and baby oil, with the latter ‘all over the walls’.
The freak offs in New York hotels included sessions at the Gramercy, Trump Hotel and an Intercontinental, she said. In Miami and Miami Beach, it was the Mandarin Oriental, Fontainebleau and Setai. For LA, they happened at the Beverly Hills Hotel and Shutters on the Beach.
Ventura said former Bad Boy executive Toni Fletcher sometimes booked the room, occasionally she would. She used the alias Jackie Star, while Combs used the name Frank White or Frank Black.
The main supplies were huge amounts of Johnson’s baby oil, condoms and Astroglide sexual lubricant.
The oil ‘was just as important as everything else. We poured it all over our bodies (so they were) glistening,’ Ventura said. ‘It was always heated… if he (Combs) felt like you were too dry he’d let you know, you need to be glistening, you need to be shining.’
It was ‘a very choreographed experience. One time there was a blow-up pool and it was filled with oil. I got in with my outfit and my shoes, it was quite dangerous.
Explaining the presence of blood, she replied: ‘I was expected to have freak offs on my period.’
Ventura also revealed hotel rooms booked for freak offs would end up covered in blood, urine and baby oil, with the latter ‘all over the walls’ when the session was finished
Ventura also named several Diddy staff members she claimed would arrange the freak offs including Kristina Khorram (pictured) who was named by others as the ‘fixer’ for the rapper
Ventura also named several Diddy staff members she claimed would arrange the freak offs – including his ‘trusted assistants’ Kristina Khorram and Neil Dominic.
Khorram was previously named by others as a ‘fixer’, who allegedly helped Diddy set up the orgies.
‘Everything from scheduling to what kind of mood he was in,’ Cassie said when asked what she discussed with Khorram. ‘I talked to [Khorram] about a lot. She knew a lot of my personal things.’
Ventura also claimed Diddy’s security guard, R. Rock ‘used to take away her things as punishment’ on the mogul’s direction. She also said the guard would come find her when she tried to hide from Diddy.
Khorram – once referred to as the ‘Ghislaine Maxwell to (Diddy’s) Jeffrey Epstein – has not been accused of any wrongdoing or charged with any crimes. However, several ‘high ranking supervisors’ are mentioned, but not named, in a criminal indictment against the rapper.
Ventura gave a dramatic account of the infamous 2016 hotel hallway surveillance video that showed her trying to leave a freak off in the now closed InterContinental Hotel in Century City. It revealed Combs, wearing only a towel, punching, kicking and dragging her.Â
When she chose to leave, she ‘grabbed what I could and Sean followed me into the hallway and grabbed me up, threw me on the ground, kicked me, tried to drag me back to the room, rook my stuff’.Â
She said attending a move premiere in the following days and wanted to be careful about her looks.
‘We were having a freak off, and Jules was one of the escorts. In the middle of it there was a lot drinking and partying.Â
Ventura also gave her account of what happened during the infamous 2016 hotel video and said it started when she tried to leave a Freak OffÂ
Diddy’s mom Janice Combs, 82, who sat through graphic evidence about her son’s harrowing alleged crimes yesterday, arrived later
‘I’m not sure what happened. I got hit by Sean and had a black eye and at that point all I could think about was getting out of their safely. I had my premiere and didn’t want to mess it up.Â
‘I just knew I had to get out. I grabbed my stuff and ran out as fast as I could. I made it to the elevators, got my sneakers on. The next thing I was just thrown to the ground.
‘It was really fast. I ran out without any shoes. It was faster. Sean grabbed me by the back of my neck and threw me to the ground.’Â
Ventura looks uncomfortable as the footage is played. She says Combs is pulling her back to the room and when asked how many times has, he thrown her to the ground, she replied: ‘Too many to count.’Â
Referring to her staying down, she added: ‘I covered my face and stayed there. I didn’t want him to do any more damage than he’d already done. It felt like the safest place to be (on the ground). He was dragging me around the corner.’Â
Earlier, the court heard defense attorney Anna Estevao Ventura’s reveal husband Alex Fine allegedly threatened to ‘beat the f***’ out of Combs in texts after she demanded $30million from him.
Fine, 32 – who turned up at the courtroom this morning – allegedly sent the message before his wife filed her civil lawsuit accusing him of rape and sexual assault that started the whole prosecution process.
Both sides agreed Fine had to leave the courtroom during her version of events when it reaches 2018.
Combs was brought to court from the Metropolitan Detention Center in Brooklyn. He made a hand gesture to his three sons and three daughters who returned to the courtroom – despite walking out yesterday as prosecution witness revealed explicit details of their father’s sexual encounters.
His 82-year-old mother Janice, who sat through graphic evidence about her son’s harrowing alleged crimes yesterday, arrived later.
The fallen mogul was arrested in September last year after his mansions in Los Angeles and Miami were raided by federal authorities.
Also earlier, Diddy’s defense attorney Marc Agnifilo brought into play the question over the freak off videos and photos, which are currently sealed.
He told Judge Arun Subramanian: ‘There is no aspect to any of the videos that is not in the nature of adult pornography.
Daniel Phillip, 41, (pictured) took to the stand this morning to resume the lawyers’ cross-examination. Yesterday, he told the jury he was paid to have sex with Cassie as Diddy watched
‘That’s what it is. It’s people who are nude, who are having sex or about to have sex. It’s all sexually explicit.
‘Our application is that the visual images and the audio is within the purview of the sealing order. It’s a privacy issue. It’s not insignificant that this is in the nature of pornography.’
The judge said he could make the videos and photos public despite pleas from Ventura to keep them under wraps.
Prosecutor Johnson said that all the materials were ‘entirely sexually explicit’ and involved nudity.
She said that nobody planned to clear the courtroom during the evidence and that Cassie’s lawyers had already objected to the material being public.
Evidence started with male escort Daniel Phillip resuming his testimony from the day one – and revealing how he lost his erection with Ventura after she’d suffered a violent confrontation with Combs at the Essex House hotel in New York City while he was with them.
He said Combs and Ventura went to a bedroom where there was screaming. The singer came out and jumped in his lap. ‘She was shaking uncontrollably, obviously afraid,’ he told the court.
‘We started talking for a while before we ended up kissing.’ The pair were ‘moving’ in the direction of sex, and he had an erection. But at that moment Combs walked in, and he lost it.
Phillip, 41, has alleged he was paid $6,000 each time to have orchestrated sex with Cassie as Combs watched.
Defense attorney Xavier Donaldson grilled the escort on his personal attraction to Ventura and suggested he might have been jealous of the rapper.
Phillip said he believed he had established a ‘bond’ with the singer but denied it was a relationship. ‘I was attracted to her and had she given me the chance to date her, I absolutely would,’ he told the court.
After the violence at the Essex, he said: ‘I wanted to really help her but there was nothing I could do. I was completely shocked. She was afraid. I could see she was really afraid. I could see in her face she was crying a lot.
‘She went to grab my shoulders, that’s how we started, with an actual hug. I was just completely messed up; I could not engage.’
