Diddy trial updates: Rapper 'dressed as Muslim woman in BURQA to disguise himself during first 'freak off' with "Punisher" escort'

The veil Diddy wore to disguise himself during a 'freak off' with an escort known as 'The Punisher' was an Islamic burqa, his trial was told Tuesday.

A burqa, also called a niqab, covers the entire face, only leaving the eyes showing under a fabric grill.

'I could not see his face,' male performer Sharay Hayes said of the first time he met Diddy and Cassie, in 2012.

'He had what the Muslim women wear, where their face is completely covered and you could only see his eyes,' he adde, according to The New York Post.

'The Punisher' said he had between eight and 12 total encounters with the couple.

He said he'd also met with them at Essex House, a luxurious hotel on Central Park South, just a stone's throw from the Trump International Hotel.

Hayes added that as Combs became more comfortable in his presence, he switched from wearing a veil to a baseball cap.

To hear all the explosive testimony from singer Cassie Ventura and the other witnesses in Sean 'Diddy' Combs' trial, tune in to Daily Mail's hit podcast The Trial.

From sworn testimony to video evidence and the rapper's every subtle move, our team of journalists take you inside the courtroom of the world's biggest celebrity case.

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Ash Armand, a former star on the reality TV show Gigolos, was among the escorts identified by Ventura as having been hired for the freak-offs.

The Showtime series followed the life of Armand - legal name Akshaya Kubiak - and other escorts who worked for Cowboys4Angels, which was frequently used by Ventura and Diddy.

Kubiak was sentenced to eight to 20 years in prison after pleading guilty to voluntary manslaughter and mayhem over the July 2020 death of Herleen Dulai.

Dulai, 29, was beaten to death after she and Kubiak took psychedelic mushrooms together at his home, according to an arrest warrant obtained by the Las Vegas Review-Journal.

Kubiak claimed he 'blacked out' and had no recollection of attacking Dulai, who died of blunt force trauma and strangulation. The coroner ruled her death a homicide.

The former Gigolos star initially faced a murder charge, but accepted a plea in September 2021. He was sentenced to prison in December that year.

The rapper Kid Cudi is on the witness list for the prosecution for Wednesday.

Cassie previously testified that Diddy threatened to hurt her and Cudi after he learned they were dating.

Cassie said she began a brief relationship with Kid Cudi 'during a rough patch' with Diddy.

She claimed Diddy went through her phone and found emails between her and the American rapper and became enraged.

Diddy allegedly placed a manual corkscrew in between his fingers and lunged at her, according to the lawsuit and she ran away to stay with Kid Cudi, according to the suit.

Cassie later returned and the music executive allegedly hit her several times, and then kicked her in the back as she tried to run out the door, the filing claims.

During Paris Fashion Week, she claims Diddy told her he was going to blow up Kid Cudi's car and that he wanted to make sure he was home with his friends when it happened.

'Around that time, Kid Cudi’s car exploded in his driveway,' the lawsuit stated.

When asked what he found in Diddy's home last year, agent Gannon said: 'Parts of AR-15 rifles, sex toys and Astroglide.'

The jury then saw images of the magazines which the agent said were loaded with bullets.

Gannon said the serial numbers had been cut out, which would make it ‘impossible’ to trace them.

The Homeland Security agent was one of the officials who searched Diddy's Miami mansion in March 2024.

Gerard Ganon began his testimony Tuesday by saying authorities decided to go into the property after learning that 'Mr. Combs and his family were flying out of the country.'

The agent said there was a pier in Diddy's Star Island mansion and they had to monitor it while they investigated him to make sure he did not use it to escape the law.

Diddy's former assistant David James said on Tuesday his job sometimes required him to ensure that hotel rooms where Combs stayed under the name 'Frank Black' were stocked with the musician’s comforts, including fresh underwear, an iPod, apple sauce, vodka, baby oil, Viagra and condoms.

There were also surprising moments, James said, like one in 2008 when Combs asked him to bring an iPod from his Miami home to a hotel room.

Upon entering, James said he saw Cassie on the bed with a white comforter pulled up to her neck and an unfamiliar naked man running from the room.

Before the jury arrived Tuesday, Diddy's lawyer Marc Agnifilo tried to persuade Judge Arun Subramanian to disallow the testimony, saying it was 'purely prejudicial' because it illustrated the wide difference between the financial status of the Ventura family and Combs.

The judge allowed it though, saying the threats to release sex tapes and harm Cassie made it an instance of 'potential extortion.'

An escort known as The Punisher said on the stand that sometimes he struggled to perform during sex sessions with Cassie and Diddy - and the experience inspired him to write a book titled 'In Search of freezer Meat.'

At times I experienced anxiety so there were times I struggled getting and maintaining an erection.

When asked why, he replied: 'a sexual scenario with a woman’s partner present actively giving directions was not the norm for me so it created discomfort that could affect me and my performance.'

The male performer saidhe took Viagra and Cialis - 'anything that I thought could help me perform. It was a lot of pressure.'

Defense lawyer Teny Geragos took a novel approach to defending Combs in her opening statement.

She conceded the hip-hop impresario has a 'bad temper' and is prone to violent outbursts that are often fueled by alcohol, jealousy and drugs.

But she maintained that while his actions might have warranted domestic violence charges, they aren’t proof he engaged in sex trafficking and racketeering — the charges he faces.

Geragos argued that Combs’ sexual habits were part of a swinger lifestyle involving consenting adults and reminded jurors that “kinky” sexual predilections don’t equate to sex trafficking.

'Sean Combs is a complicated man. But this is not a complicated case,' she said. 'This case is about love, jealousy, infidelity and money.'

Defense lawyers, during their cross-examination of Cassie last week, sought to cast the musician as an enthusiastic participant in the sex marathons.

'I’m always ready to freak off,' she wrote in one 2009 message read in court.

Later that year, however, Cassie expressed frustration with the state of their relationship and told Combs she needed something more from him than sex.

In a 2017 text message, Cassie told Combs: 'I love our FOs when we both want it,' using the initials of freak-off. On the stand, Cassie explained: 'I would say loving FOs were just words at that point.'

Cassie testified Tuesday that the mercurial music mogul — powerful, abusive and controlling — beat her mercilessly and ordered her to have “disgusting” sex with strangers during drug-fueled, multi-day marathons he called 'freak offs.'

Cassie, whose legal name is Casandra Ventura, sniffled and dabbed her eyes with a tissue, sighed heavily and paused to compose herself through about five hours of testimony at Combs’ sex trafficking trial.

The singer told jurors that his demands for her to engage in sometimes-revolting sex acts — sometimes as he watched from another room via FaceTime — left her feeling 'heavily objectified.' But, she said, she endured them because she was in love with Combs.

When she did try to leave, she said, Combs punished her — most notably in a 2016 assault captured on a security camera at a Los Angeles hotel. In the video, played in court for a fifth time, Combs is seen hitting, kicking and attempting to drag her back to their room.

Judge Arun Subramanian provisionally denied a joint application by news outlets for the videos to be played in open court and be described by the media.

He agreed with a prosecution argument that playing them would 'revictimize' Ventura and one of the unnamed female victims who will testify later iun the trial.

The judge also denied an alternative proposal to allow three pool reporters to stay in court when they were played, and share reports with other outlets.

“I’m not seeing any case that would suggest in any way, shape, or form that images or videos of these types of acts that are alleged to be sexual abuse would be required to be shown in open court when they pose the obvious risk of revictimization,' he said.

Robert Balin, the lawyer who argued on behalf of the press, earlier said the First Amendment was 'at its zenith' in the case.

He argued it was important 'people, though the press, be able to see justice is being done'.

Balin said the best evidence of whether the sex acts in the 'freak offs' were coerced - which underpinned the prosecution's case - were the videos themselves.

The application was only ever to view the videos and describe them, not for the footage to ever become public.

Escort Sharay Hayes described his first encounter with Diddy and Cassie to the court on Tuesday.

'There was an area for me to sit and her to sit and there were little bowls of water and bottles of baby oil,' he said of the meeting at the Trump International Hotel on Central Park West.

'Ms Ventura got on the sofa opposite me and I followed, mimicked what she did. She got a bottle of baby oil and started pouring it on herself and I did similar.

'A few minutes (later) I could see her husband enter the room. The man was nude but I could not see his face, there was a veil I could see he had a bottle of astroglide.

At some point the man stood up and left the room, Ms Ventura follow him out.'

He said he was paid an additional $1,200 when he was done.

When asked, the witness said he had between eight and 12 total encounters with the couple.

He said he'd also met with them at Essex House, a luxurious hotel on Central Park South, just a stone's throw from the Trump International Hotel.

Hayes added that as Combs became more comfortable in his presence, he switched from wearing a veil to a baseball cap.

I was hired sometime in late 2012 to create a sexy scene, sexy erotic scene for them on occasion.

He said he met the couple at the Trump hotel in Manhattan.

'[Cassie] explained her and her husband liked to create a sexy scene that consisted of me and her mutually applying baby oil to ourselves and each other and create a sexy environment and her husband would eventually come out to watch.

'Once she explained (this) she handed me a stack of money and instructed to change into underwear or a towel. It was $800.'

'I was told to no acknowledge her husband, not to look at him, no communication between me and him.'

Sharay Hayes, also known as 'The Punisher', operates a male dancing service in New York City.

Cassie named him as one of the escorts she and Diddy hired for sex.

He also previously struggled with erectile dysfunction, detailing his battle with 'sex, self-worth, and mental health' in a book titled In Search of FREEZER MEAT: A Story of the Male Mental Health Crisis Caused by Erectile Dysfunction and the Only True Cure No One is Talking About...a Penis Implant.'

The book, released in September 2022, details anonymous accounts of his encounters with Diddy and Cassie, labeling them as a 'married wealthy couple.'

'I use personal stories, where I try to make light of issues, comical references,' Hayes said in his testimony.

He explained that six and a half out of 180 pages anonymously cover his 'freak offs' with Diddy and Cassie.

Diddy's lawyers told the court they did not have questions for Regina Ventura after the prosecution ended their direct examination.

Regina told the court about various incidents where she saw Diddy turn aggressive.

She said she once called police after Diddy took Cassie's phone.

She also said one time in 2012 Diddy became enraged out of nowhere after one of his employees, Mia, laughed.

We were standing around talking casually, laughing and [Mia] was laughing and all of a sudden he didn't’ want her too and he asked her what she was laughing at.

She shrunk, went pale and looked very shaken and afraid.

Diddy was rubbing his shoulders and blocking on his hands during witness testimony on Tuesday.

At one point he appeared frustrated as he tried to make a point to his attorneys.

The judge eventually adressed the tempetaure in the room - 'we’re going to try to get the temperature turned up a few degrees. I’ve been told it’s complicated. I’m freezing in here with you.'

Regina Ventura testified that Diddy demanded that Cassie pay him $20,000 after he learned she was dating rapper Kid Cudi.

She said she and her husband tok out a home equity loan because 'that’s the only way we could get the money' and they were scared for Cassie's safety.

'[Diddy] was angry he’d spent money on her and she’d been with another person.

'His bookkeeper emailed me the wire information. I went to the (bank) and wired the money to the account.'

Regina said the money came back about 'four to five days later.'

Cassie's parents are seen arriving to court Tuesday.

Regina Ventura took the stand for the prosecution on Tuesday, saying she met Diddy after her daughter Cassie signed to his label in 2006.

Prosecutors showed the jury a text exchange from December 23, 2011, from Cassie.

The text read: '[Diddy] is going to release two explicit sex tapes of me, one on Christmas Day, maybe before or right after and another one some time after...

He will be having someone hurt me and (Kid Cudi) physically.'

Regina Ventura said: 'I was physically sick. I did not understand a lot of it. The sex tapes threw me. I didn’t know the other person but I knew he was trying to hurt my daughter.'

During cross-examination, Diddy's former assistant David James told the court that the mogul demanded he had ketchup for all of his meals.

'Ketchup was a big item he always needed for his food. It was to create a consistent environment which held,' David said on Tuesday.

'Ketchup in the UK is not similar to the Ketchup in America,' David told the court.

'[Diddy] would be not happy.'

The court also heard that Diddy likes to put 'applesauce on cheeseburgers.'

James is seen below in a court sketch.

Six of seven of Diddy's kids showed up to court last week, but none were present on Monday or Tuesday.

The mogul's sons three sons endured all of the harrowing testimony by Cassie last week, but his twins girls and eldest daughter Chance stopped attending mid-week.

Twins Jessie and D'Lila put their father's legal woes aside for the evening as they danced the night away in matching dresses for their high school prom night.

It's not clear why Diddy's sons did not show up to court on Monday as they did throughout last week.

The mogul's former assisstant David James told the court that he often had to bring Diddy's supplies to different hotels all over the world.

He said the Trump International hotel in New York was the mogul's 'favorite.'

'Trump International, they knew me very well, they gave me with a key,' James said when asked how he prepared the hotel rooms for Diddy's arrival.

Witness David James told the court that he quit as Diddy's assistant after an incident involving the mogul's rival Suge Knight in 2008.

James said Diddy's friend D-Roc noticed Knight at a famous diner in LA and approached him.

Knight then allegedly asked D-Roc: 'What you doin' in my city?'

Diddy's team then went back to the mogul's house.

Diddy then allegedly grabbed three guns and instructed James to drive back to the diner.

'This was the first time as his assistant that I realized my life was in danger. I told them I want to leave but give six months notice so I could train the next assistant,' James told the jury on Tuesday.

Richard said on the stand Monday that Diddy punched Cassie in the stomach during a private argument at a West Hollywood restaurant in 2010.

She claimed several celebrities were at the dinner, including Usher, Ne-Yo and superstar music executive Jimmy Iodine.

'Mr Combs punched Cassie in the stomach,' Richard told the jury.

'They were having a private conversation, we were all sitting eating at the tables together. Some of Bad Boy label mates, some celebrities were in the room.

'They were secretly arguing [and] he punched her in the stomach.

Richard added: '[Cassie] immediately bent over and he told her to leave, I could see him point out and she went out.'

Diddy's former assistant David James said he once took ecstasy and went to a Diddy New Year's Eve party.

'I was also drinking Ciroc that night,' he said.

'Normally I’m very straight edged, don’t have much emotion. I was dancing, Diddy bopping all around the party... I was just vibing, enjoying myself.'

A few days later, Diddy confronted him with a video of him dancing at the party, James claimed.

'[Diddy] said I’m going to keep this footage in case I need it. It was so out of character for me it would be embarrassing if he released that footage to the public.'

Diddy's former assistant David James told the court he applied to work for the mogul because he wanted a career in fashion.

James was emotional, crying, as he described his first days working for Diddy.

He said one of the executives at Bad Boy Entertainment told him his job was to please the mogul.

'I remember sitting at her desk and there was a picture of Mr Combs on the wall,' James told the court Monday.

'She pointed at the wall and said this is Mr Combs kingdom. We’re all here to serve him.'

Diddy's former assistant is being questioned about an incident Cassie Ventura mentioned during her time on the stand involving Suge Knight.

Cassie claimed Diddy one left her during a freak off at his Los Angeles home to confront rival record executive Suge Knight at Mel’s Drive-In, a landmark diner nearby.

'R-Rock came in and said Suge was down at a diner. Sean drove over there.... I cried, said don't do something stupid,' Cassie said.

'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. I saw them get dressed and leave the house.'

Knight, 59, was the CEO of Death Row Records while Sean 'Diddy' Combs, 54, was the CEO of rival company Bad Boy Entertainment.

Their beef began in the mid 90s as East Coast and West Coast rappers became entangled in a heated battle that shook up the hip-hop scene.

Diddy's former assistant told the court the mogul always traveled with a medicine back that contained about 30 pills.

'Some Advil, Tylenol,' David James said.

'He had water pills to help him lose weight, viagra, pills that helped increase his sperm count.'

James said Diddy would take percocets throughout the day and ecstasy at night.

When asked, James said one of the ecstasy pills Diddy took 'was in the shape of former president Obama's face.'

Regina Ventura arrived in Manhattan federal court on Tuesday to take the stand for the prosecution against Diddy.

She walked into the courtroom with her husband, Rodrick Ventura.

She is expected to testify about witnesses Diddy's alleged abuse and threatening of Cassie, his ex-girlfriend and main accuser.

Cassie named David James as one of the assistants who facilitated the alleged Freak Offs.

James worked as a personal assistant for Diddy from May 2007 to May 2009, the court heard on Monday.

Diddy's former assistant David James told the court he applied to work for the mogul because he wanted a career in fashion.

James was emotional, crying, as he described his first days working for Diddy.

He said one of the executives at Bad Boy Entertainment told him his job was to please the mogul.

'I remember sitting at her desk and there was a picture of Mr Combs on the wall,' James told the court Monday.

'She pointed at the wall and said this is Mr Combs kingdom. We’re all here to serve him.'

Sean 'Diddy' Combs longtime rival Suge Knight sensationally warned that President Donald Trump would pardon the disgraced music executive if he's convicted of sex trafficking and racketeering.

The imprisoned co-founder of Death Row Records made the bombshell allegations on Wednesday, hours after Diddy's ex Cassie Ventura addressed the duo's feud during her testimony in his criminal trial.

'That's me, a selfie of me with a fat lip,' the singer replied when asked about a photo entered as evidence last week.

The image, taken after Diddy assaulted Cassie in the hallway of an LA hotel, was released to the public on Monday.

Cassie said she took it while on an Uber on her way home following the filmed 2016 assault.

She said she texted Diddy saying: 'I have a premiere for the biggest thing I’ve ever done in my life on Monday. You are sick for thinking it’s OK to do what you’ve done. Please stay away from me.'

The rapper reportedly then claimed he was getting arrested.

Cassie said her then-best friend, model Kerry Morgan, became upset when she saw her face and called police.

Cassie said she chose to not report who had assaulted her when police showed up because she wanted to protect Diddy.

'In in that moment I didn’t want to hurt him that way. Just too much going on. A lot for me in that moment. I wasn’t ready.'

Sean 'Diddy' Combs blew a kiss to his mom and made a heart with his hands as she led his family into the courtroom to support him in his racketeering and sex trafficking trial.

The disgraced music mogul's criminal trial kicked off in Manhattan's federal court on Monday, eight months after he was first arrested and hit with a host of charges.

His family, led by his mom Janice, have been steadfast in their support of the 55-year-old.

Diddy took his seat by the defense on Tuesday in a blue sweater.

He shook hands with his attorneys as he came in the federal courtroom.

The mogul is allowed to wear his own clothes to the trial but with some conditions.

He can only have up to five pairs of pants, shirts and socks and only two pairs of shoes - with no laces.

Sean 'Diddy' Combs' legal team introduced salacious text messages from ex-girlfriend Cassie Ventura that claimed the R&B singer 'loved' Combs' infamous 'freak-offs.'

Diddy's lawyer Anna Estevao used the messages in court on Thursday in an effort to paint Cassie, 38, as a willing participant in the drug-fueled sex sessions that could last up to four days.

'I love our FOs when we both want it,' she wrote in one missive, adding: 'I want to Freak Off right now LOL. I want to have fun with you.'

Diddy replied: 'Let me know if you want to have a late night. Jules is available. If you're not into that NP. We can just do a thing. Love you.'

Cassie simply replies with a 'love you' back.

Diddy asks: 'If you're not super horny wtf?'

'Horny. Of course I am,' said Cassie.

The first week of Sean 'Diddy' Combs' sex trafficking trial saw a litany of bombshell claims and evidence unveiled before the Manhattan courtroom in New York.

R&B singer Cassandra 'Cassie' Ventura delivered horrifyingly graphic testimonies alleging that the music mogul physically and psychologically abused her over more than a decade from 2007-2018.

The 38-year-old detailed the regular beatings she allegedly experienced, the rapper's use of blackmail and scare tactics to coerce and manipulate, depraved sex acts she claims she was forced to participate in - and the medical toll she suffered as a result.

Morgan, 39, who is set to take the stand Monday, was mentioned by Ventura last week during her testimony.

The R&B singer told the court that her ex-boyfriend threw a wooden hanger at her then best friend, giving her a concussion.

Ventura also mentioned the alleged incident in the 2023 lawsuit she filed against Combs, where she accused the disgraced rapper of putting her through years of a 'cycle of abuse, violence and sex trafficking.'

The alleged incident between Morgan and Combs led to a settlement between the two, and Ventura also paid additional money to 'resolve the dispute between her close friend and her abusive and controlling boyfriend,' legal documents stated.

Following the alleged ordeal, the Me & U singer's relationship with Morgan, a model,  became 'strained,' per the filing.

Richard told jurors at Diddy's sex trafficking trial on Monday that the hip-hop mogul threatened to kill her if she told anyone she saw him physically abusing his longtime girlfriend.

Richard testified that Combs made the threat the day after she witnessed the Bad Boy Records founder punch and kick Cassie Ventura after taking a swing at her with a skillet. Richard said he told her and another woman who saw the attack that “we could go missing” if they didn’t stay quiet.

Assistant U.S. Attorney Mitzi Steiner asked Richard what she took 'we could go missing' to mean.

'That we could die,' Richard responded, saying she was shocked because all of this happened just as she was beginning to record with Diddy — Dirty Money, a musical trio with Combs and another R&B singer.

Cassie told the court last week that, while she was packing to go to Drake’s music festival in Canada, Diddy scuffled with her friends and threw her into a bed frame.

Cassie said she suffered a 'pretty significant gash' above her left eye. Diddy's security personnel brought her to a plastic surgeon in Beverly Hills to get the wound stitched up.

Afterward, she texted Diddy a photo of her injured face and wrote: 'So you can remember.'

Diddy replied: 'You don’t know when to stop. You pushed it too far. And continued to push. Sad.'

Cassie then described a photo of her where she is with rapper French Montana at the festival in Canada.

Incendiary images shown in Sean 'Diddy' Combs' trial reveal the disgraced rap mogul was preparing for a hotel 'freak off' despite knowing he was about to be arrested, prosecutors say.

The shocking images were shown to jurors as Diddy's ex-girlfriend Cassie testified at his federal trial on Monday - after she previously alleged how she was coerced into a life of manipulation and abuse.

On Monday, prosecutors brought up a set of images taken by law enforcement when Diddy was arrested at the Park Hyatt Hotel in Midtown Manhattan in September 2024.

Cassie said last week that when she went home for Christmas in 2011 with bruises from an altercation with the hip-hop mogul, she lied and told her mother it was the first time he’d hit her.

'I couldn’t hurt her like that,' Cassie testified. 'And it was terrifying. It’s not normal, constantly being bruised up by the person you love — who says they love you.'

Jurors saw photos showing a large, dark bruise on Cassie’s lower back and other bruises on her shoulder and thigh that she said she sustained in the altercation.

Incendiary images shown in Sean 'Diddy' Combs' trial reveal the disgraced rap mogul was preparing for a hotel 'freak off' despite knowing he was about to be arrested, prosecutors say.

The shocking images were to jurors as Diddy's ex-girlfriend Cassie testified at his federal trial on Monday - after she previously alleged how she was coerced into a life of manipulation and abuse.

On Monday, prosecutors brought up a set of images taken by law enforcement when Diddy was arrested at the Park Hyatt Hotel in Midtown Manhattan in September 2024.