Male escort alleges disturbing details of what happened at Diddy’s ‘freak off’ parties during trial

The male escort claimed he had multiple encounters with Diddy and Cassie

A male escort spoke in the ongoing Diddy trial and gave his recollection of alleged meets with the producer and his then girlfriend Cassie.

Sean ‘Diddy’ Combs’ trial is well underway and the court has already heard extensively from his former partner Cassandra Ventura, known as Cassie, about his alleged actions while they were together.

Cassie spoke about the nature of her relationship with Diddy and went into great detail about what allegedly took place during his notorious ‘freak off’ parties.

Prosecutors believe it is during these parties that illegal actions took place.

Diddy was arrested last September while he was in New York and faces a whole host of charges, including racketeering and sex trafficking by force, fraud or coercion.

Diddy has denied all of the charges against him.

The escort spoke in the trial of the meet ups with Diddy and Cassie (Jeff Kravitz/FilmMagic)The escort spoke in the trial of the meet ups with Diddy and Cassie (Jeff Kravitz/FilmMagic)

The escort spoke in the trial of the meet ups with Diddy and Cassie (Jeff Kravitz/FilmMagic)

A male escort, who was known as The Punisher, real name is Sharay Hayes, spoke to the courtroom on May 20 and detailed his alleged experience interacting with both Diddy and Cassie.

He said that he was initially booked by Cassie who gave the name ‘Janet’ back in 2012 and told him he was wanted as a dancer for an event with friends.

However, when he arrived, he was informed that this was not what he would be doing.

Hayes said there were no other guests when he arrived and added: “She explained to me that she didn’t want me to actually dance.

“She explained to me that her and her husband liked to create a sexy scene that consisted of me and her mutually applying baby oil, applying it to ourselves and to possibly each other, and try to create a sexy environment that her husband would eventually come out to watch.”

Hayes claimed that he was hired between eight and twelve times for additional freak offs, with the last one happening March of 2015.

The male escort said Diddy would watch while he was intimate with Cassie(George Pimentel/WireImage)The male escort said Diddy would watch while he was intimate with Cassie(George Pimentel/WireImage)

The male escort said Diddy would watch while he was intimate with Cassie(George Pimentel/WireImage)

The escort also explained what Diddy’s role was during these meetings with Cassie.

He said: “[Diddy] would at some point come into the room, sit in the distance, gave subtle directions to Ms. Ventura based on…angles, lighting, positionings, and sometimes the sexual activity.”

Hayes was also asked about Cassie’s demeanor during these visits and how he perceived her feelings of being watched by Diddy.

He alleged that Diddy would give Cassie instructions while she had sex with him, and noted that he would see ‘a sigh’ or ‘a wince’ from her towards these directions at times.”

He commented that he was experienced as an exotic dancer and escort and ‘did not get any cues that there was a discomfort with what was going on’, when it came to Cassie.

He added: “It seemed like it was consensual as far as I was concerned.”

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Cassie describes what happened at Diddy's 'freak off' parties after prosecution revealed alleged urine act he made her doCassie describes what happened at Diddy's 'freak off' parties after prosecution revealed alleged urine act he made her do

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Cassie describes what happened at Diddy’s ‘freak off’ parties after prosecution revealed alleged urine act he made her do

Cassie has been speaking in court on Tuesday about Diddy’s alleged ‘freak off’ parties

Callum Jones

Callum Jones

Cassandra Ventura, known more commonly as Cassie, has detailed what happened at the alleged ‘freak off’ parties hosted by Diddy.

The rapper, real name Sean Combs, was arrested at the Park Hyatt hotel in Manhattan, New York last September, and has been charged with racketeering and sex trafficking by force, fraud or coercion – all of which he has repeatedly denied.

Combs has spent the past months at Brooklyn’s Metropolitan Detention Center before his trial began on Monday (May 12), with prosecution now having given their opening statements.

After the opening remarks on Monday, Cassie has taken to the stand on Tuesday (May 13) and described what happened at these alleged ‘freak off’ gatherings.

Explaining ‘freak-offs’, Cassie said they were ‘sexual encounter[s] called voyeurism’ where Combs would watch her have sex with another man.

Cassie has taken to the stand today (Emma McIntyre/The Hollywood Reporter via Getty Images)Cassie has taken to the stand today (Emma McIntyre/The Hollywood Reporter via Getty Images)

Cassie has taken to the stand today (Emma McIntyre/The Hollywood Reporter via Getty Images)

In court, Cassie recalled what happened when she was first introduced to these so-called ‘freak-off’ parties.

“I remember my stomach falling to my butt,” she said. “Just the nervousness and confusion… I had just turned 22.”

Cassie claims it involved hiring an escort and Combs would watch her with another man while directing them, as per the BBC.

She explained in court how she didn’t want to be involved, but ultimately did so because she ‘loved him [Diddy] very much’ and ‘wanted to make him happy’.

Cassie added: “The freak offs became a job. There was no time to do anything else but do them then try to recover. The longest was four days, significant periods of time.”

Cassie went on to tell the jury how she was scared to say no to the rapper and that physical violence was often on her mind.

She was also worried of ‘making him angry’ and told the court how Diddy blackmailed her with video of the ‘freak offs’ to get her to do more.

Diddy and Cassie pictured together in 2018 (Nicholas Hunt/Getty Images)Diddy and Cassie pictured together in 2018 (Nicholas Hunt/Getty Images)

Diddy and Cassie pictured together in 2018 (Nicholas Hunt/Getty Images)

Cassie also claimed she and Combs got in arguments that would ‘result in violence, dragging’, adding that he would ‘stomp [her] in the head if I was down’.

When asked how often Combs became violent with her, she responded: “Too frequently.”

She said Combs would ‘bash on my head, knock me over, drag me, kick me.’

A CCTV video also made public that went viral last year was also shown to jurors, which appeared to show Combs attacking her inside a Los Angeles hotel in 2016.

Cassie told the court the former couple were having a ‘freak-off’ that day, which she said she was introduced to during the first year of their relationship.

f you are experiencing domestic violence, please know that you are not alone. You can talk in confidence 24 hours a day to the national domestic violence helpline on 1.800.799.SAFE (7233) 24/7. You can find a list of local resources here.

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Every disturbing claim revealed at opening trial day of Diddy's sex-trafficking caseEvery disturbing claim revealed at opening trial day of Diddy's sex-trafficking case

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Every disturbing claim revealed at opening trial day of Diddy’s sex-trafficking case

One witness reported being ‘concerned for his life’

Poppy Bilderbeck

Poppy Bilderbeck

Warning: This article contains allegations of sex trafficking, abuse and assault which some readers may find distressing.

Sean ‘Diddy’ Combs’ trial has commenced with accusations against him laid out in the first day alongside two witnesses being called to the stand.

On September 16 2024, the 55-year-old was arrested at the Park Hyatt hotel in Manhattan, New York, after a grand jury indicted him.

Combs was ultimately charged with racketeering conspiracy, two charges of sex trafficking and two charges of transportation to engage in prostitution – the rapper having denied all charges.

And on Monday (May 12), his sex-trafficking trial commenced in Manhattan and details of the allegations against him were laid out in full in the opening statements.

Sean ‘Diddy’ Combs trial begins
Credit: ABC News
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Accusations against Sean ‘Diddy’ Combs outlined by the prosecution

When the indictment against the rapper was unsealed, it revealed Combs was accused of having ‘abused, threatened and coerced women and others around him to fulfil his sexual desires, protect his reputation and conceal his conduct’ alongside using ’employees, resources, and influence of the multi-faceted business empire that he led and controlled’ to ‘attempt to engage in, among other crimes, sex trafficking, forced labor, kidnapping, arson, bribery and obstruction of justice’.

The indictment describes the alleged abuse towards ‘women and other individuals’ as a combination of ‘verbal, emotional, physical and sexual’ and states the ‘physical abuse by Combs’ was ‘recurrent and widely known’, referring to the video of him and former partner Casandra ‘Cassie’ Ventura in a hotel corridor.

On the first day of Combs’ sex trafficking trial, prosectors focused on Ventura and another former girlfriend – who has remained anonymous.

Prosectors alleged Combs sexually abused women and ran a criminal enterprise, using violence and threats against Ventura’s career to get her to perform in so called ‘freak-offs’.

And two witnesses were brought to the stand by prosecutors.

Diddy's sex trafficking trial has commenced (Shareif Ziyadat/Getty Images for Sean 'Diddy' Combs)Diddy's sex trafficking trial has commenced (Shareif Ziyadat/Getty Images for Sean 'Diddy' Combs)

Diddy’s sex trafficking trial has commenced (Shareif Ziyadat/Getty Images for Sean ‘Diddy’ Combs)

Security guard from hotel where video of Combs assaulting Ventura was filmed

The first witness to be brought up following opening statements was Los Angeles police officer, Israel Florez.

Florez was working as a security guard at the InterContinental Hotel in California where the video of Combs assaulting Ventura was filmed in March, 2016.

He was the officer who responded to the altercation at the time, detailing how he was called about ‘a woman in distress on the sixth floor’, BBC reports.

The security guard alleges he went upstairs to find Ventura curled up in a corner covering her face and Combs in a towel and socks with a ‘devilish’ look on his face.

Florez says Ventura told him she wanted to leave but Combs said she wasn’t allowed and he then escorted the pair back to their room, leaving a foot in the door to make sure Ventura could get out before helping her down to the valet.

He also reports Ventura having a purple eye but refusing his offer to call police.

Florez also alleged when he and the hotel manager went back up to Combs that the rapper took the hotel manager’s phone in fear of being recorded alongside allegedly showing Florez a wad of cash which the security guard believed to be an attempt at a bribe – a claim denied by Combs’ defence.

The video – which was widely spread online – was played to the court despite the defence’s attempt to have it blocked and photographs from the aftermath of the incident were also shared.

Combs’ attorney Teny Geragos’ response to the video? Well, he argued ‘domestic violence is not sex trafficking’.

And then the second witness took to the stand.

A video shows Combs assaulting then-girlfriend Cassie Ventura (Johnny Nunez/WireImage)A video shows Combs assaulting then-girlfriend Cassie Ventura (Johnny Nunez/WireImage)

A video shows Combs assaulting then-girlfriend Cassie Ventura (Johnny Nunez/WireImage)

Witness claiming Ventura and Combs paid him to have sex with Ventura and detailing ‘freak-offs’

A 41-year-old named Daniel Phillip alleged he was paid $5,000 to have sex with Ventura while the rapper watched.

Phillip claimed he went to the meet-up at the Gramercy Hotel in the belief he was filling in for a male stripper co-worker at a bachelorette party but when he showed up he found himself with Ventura.

Phillip also weighed in on Combs’ alleged ‘freak-offs’ – claiming they would typically occur in New York hotel rooms or the rapper’s own residences.

Ranging from one hour to 10 hours, the witness told the court the meetings would sometimes see Combs masked and instructing him and Ventura what to do, the rapper allegedly recording the meet-ups.

One incident Phillip claims Ventura and Combs were in a next-door room and he heard what sounded like Ventura being beaten and left in tears alongside seeing the rapper allegedly drag Ventura by her hair, stating the reason he didn’t go to authorities was because he was ‘concerned for [his] life,’ BBC adds.

In defence of Combs, Geragos said he simply has ‘a bit of a different sex life’.

Details of the alleged 'freak-offs' were revealed too (Samir Hussein/Getty Images for Sean Diddy Combs)Details of the alleged 'freak-offs' were revealed too (Samir Hussein/Getty Images for Sean Diddy Combs)

Details of the alleged ‘freak-offs’ were revealed too (Samir Hussein/Getty Images for Sean Diddy Combs)

What Combs’ attorney has said

In response to the news of Combs’ arrest, his attorney Marc Agnifilo told UNILAD at the time: “We are disappointed with the decision to pursue what we believe is an unjust prosecution of Mr. Combs by the U.S. Attorney’s Office.

“Sean ‘Diddy’ Combs is a music icon, self-made entrepreneur, loving family man, and proven philanthropist who has spent the last 30 years building an empire, adoring his children, and working to uplift the Black community. He is an imperfect person, but he is not a criminal.

“To his credit Mr. Combs has been nothing but cooperative with this investigation and he voluntarily relocated to New York last week in anticipation of these charges. These are the acts of an innocent man with nothing to hide, and he looks forward to clearing his name in court.”

The trial is expected to last around eight weeks. If convicted, Combs faces up to life in prison.

UNILAD has contacted representatives for Combs and Ventura for comment.

If you’ve been affected by any of the issues in this article, you can contact The National Sexual Assault Hotline on 800.656.HOPE (4673), available 24/7. Or you can chat online via online.rainn.org.

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Cassie reveals effects from excessive drug use during alleged 'freak offs' had on her body at Diddy trialCassie reveals effects from excessive drug use during alleged 'freak offs' had on her body at Diddy trial

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Cassie reveals effects from excessive drug use during alleged ‘freak offs’ had on her body at Diddy trial

The singer told the court she abused drugs to dissociate from the alleged freak-off events

Poppy Bilderbeck

Poppy Bilderbeck

Warning: This article contains allegations of sex trafficking, abuse, assault and drug use which some readers may find distressing.

Cassie Ventura has detailed a time she ‘woke up in hospital’ amid her relationship with Sean ‘Diddy’ Combs and participating in the alleged ‘freak off’ parties.

On May 12, the sex trafficking trial of Sean ‘Diddy’ Combs began in Manhattan federal court – the rapper having been indicted by a grand jury and arrested in September last year.

The 55-year-old is charged with racketeering conspiracy, two charges of sex trafficking and two charges of transportation to engage in prostitution – the rapper having denied all charges.

Multiple people have been called to the stand including R&B singer and dancer Cassie – real name Casandra Ventura – a former partner of Combs.

The pair dated for around a decade – Ventura 19 years old at the time they first met and Combs 37.

Sean ‘Diddy’ Combs trial begins
Credit: ABC News
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Ventura has detailed allegations of rape and abuse alongside revealing what happened at Combs’ alleged ‘freak off’ parties.

Yesterday (May 15), Combs’ lawyer Anna Estevao cross-examined Ventura, honing in on the alleged drug use within the pair’s relationship.

The lawyer questioned whether Combs and Ventura had considered rehab, to which Ventura responded: “Rehab wasn’t really a thing during our relationship.”

Estevoa asked: “The freak offs were an opportunity for you to take drugs together?”

Ventura confirmed they were.

When asked if she ‘tried to get into a rehab’ called ‘the Golden Door’, Ventura added it was ‘a spa’.

“There was a time I lost all sense of smell and taste and woke up in a hospital with an IV in my arm – I tried then to get help,” she added.

It follows Ventura having spoken out about how she got through the alleged ‘freak off’ parties.

The pair dated for around a decade (Laura Thompson / New York Daily News via Getty Images)The pair dated for around a decade (Laura Thompson / New York Daily News via Getty Images)

The pair dated for around a decade (Laura Thompson / New York Daily News via Getty Images)

Ventura said she took ketamine during the alleged gatherings to dissociate from the sex acts she didn’t want to be involved in.

She told the court she did several drugs at a time and wouldn’t eat or sleep because of these alleged ‘freak off’ parties.

Ventura went on to state she had gastrointestinal issues, sores in her mouth and frequent urinary tract infections (UTIs) as a result.

And despite having ‘painful’ infections, Ventura claimed Combs still forced her to take part in the events – sometimes allegedly lasting multiple days, which would lead to her having to seek massages and IV fluids to help recover.

Ventura testified in court that when Combs wanted a ‘freak-off’, he would push until he got one.

If you want friendly, confidential advice about drugs, you can call American Addiction Centers on (313) 209-9137 24/7, or contact them through their website.

If you’ve been affected by any of the issues in this article, you can contact The National Sexual Assault Hotline on 800.656.HOPE (4673), available 24/7. Or you can chat online via online.rainn.org

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Topics: DiddyUS NewsCelebrity

Cassie reveals what she thought when Diddy asked her to join 'freak off' party for first time as she describes shocking detailsCassie reveals what she thought when Diddy asked her to join 'freak off' party for first time as she describes shocking details

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Cassie reveals what she thought when Diddy asked her to join ‘freak off’ party for first time as she describes shocking details

Cassandra Ventura was in a relationship with the rapper between 2007 and 2018

Ella Scott

Ella Scott

Warning: This article contains discussion of sexual harassment and domestic violence which some readers may find distressing

Cassandra ‘Cassie’ Ventura told a Manhattan courtroom yesterday (May 13) that she felt ‘confused and nervous’ when ex-boyfriend Sean ‘Diddy’ Combs allegedly invited her to join in on one of his infamous ‘Freak Off’ parties.

The trial of 55-year-old Combs, also known as his aliases Diddy, P Diddy and Puff Daddy, began in New York on May 12, where he faces charges of racketeering conspiracy; sex trafficking by force, fraud or coercion; and transportation to engage in prostitution.

The Bad Boy Records founder, who once served as the Notorious B.I.G.’s manager, is accused of having ‘abused, threatened, and coerced women and others around him to fulfil his sexual desires, protect his reputation, and conceal his conduct’ from at least 2008.

The trial of Sean 'Diddy' Combs comes after he was arrested at a hotel last September (John Lamparski/WireImage)The trial of Sean 'Diddy' Combs comes after he was arrested at a hotel last September (John Lamparski/WireImage)

The trial of Sean ‘Diddy’ Combs comes after he was arrested at a hotel last September (John Lamparski/WireImage)

It’s also alleged in a 14-page legal indictment that the father-of-seven held ‘Freak Off’ parties where prosecutors claim both male and female victims were induced into drug-fuelled, sexual performances.

If found guilty, the three-time Grammy winner faces up to life in prison if the jury convicts him on the racketeering charge.

He also faces a minimum sentence of 15 years for sex trafficking, and a maximum of 10 years behind bars for transportation of prostitution, if found guilty by the jury.

Combs, who was arrested at the Park Hyatt hotel last September, has repeatedly denied claims against him and is continuing to plead not guilty to the charges.

On the second day of the trial (May 13), Combs’s ex-girlfriend and American singer Cassie Ventura, 38, took to the witness box.

The ‘Long Way 2 Go’ singer, who was in a relationship with Combs between 2007 and 2018, told the courtroom how she was just 22 when she was allegedly asked to participate in a ‘Freak Off’ party for the first time.

She told the jury she was ‘confused and nervous’ about the event, claiming: “I just remember my stomach falling to my butt.”

Cassie Ventura and Diddy were in a relationship for over a decade (Johnny Nunez/WireImage)Cassie Ventura and Diddy were in a relationship for over a decade (Johnny Nunez/WireImage)

Cassie Ventura and Diddy were in a relationship for over a decade (Johnny Nunez/WireImage)

Ventura said she felt as if she couldn’t refuse her boyfriend, alleging she ‘didn’t know what ‘no’ could be, or what ‘no’ could turn into’ and that ‘[Combs] controlled a lot of [her] life’.

“Sean is a really polarizing person; he was charming,” Ventura said. “It’s hard to really be able to determine what you need when he’s telling you what he wants. I just didn’t know. I didn’t know what would happen.”

The Associated Press reports that Ventura feared videos of the ‘Freak Offs’ would eventually find their way to the internet.

It’s also said Combs would call her ‘predictable’ for not wanting to take part in the events that left her feeling ‘disgusting’ and ‘humiliated’, as per CBS News.

“The freak offs became a job. There was no time to do anything else but do them then try to recover,” she continued, before telling Assistant United States Attorney Emily Johnson the longest event took place over ‘four days’.

On the second day of the trial, surveillance footage of Combs beating the hitmaker inside a Los Angeles hotel in March 2016 was played to the courtroom.

The outlet reports that the video depicted Ventura with a bag at the hotel’s elevators and sees Combs rounding a corner before striking her and throwing her to the ground.

The footage then saw the accused kicking his ex-girlfriend before dragging her back toward their hotel room.

Defense lawyers had unsuccessfully tried before the trial commenced to get the video banned from court.

Cassie claimed the longest 'Freak Off' party lasted four days (Julia Beverly/Getty Images)Cassie claimed the longest 'Freak Off' party lasted four days (Julia Beverly/Getty Images)

Cassie claimed the longest ‘Freak Off’ party lasted four days (Julia Beverly/Getty Images)

However, prosecutors maintain the video is a piece of evidence in the case against Combs.

It’s understood that three hotel surveillance videos and two cellphone videos were shown to the 12-person jury inside the Daniel Patrick Moynihan U.S. Courthouse in New York City.

Ventura’s testimony comes after she alleged in a bombshell lawsuit in November 2023 that Combs had trafficked, sexually assaulted and physically abused her during their long-term relationship.

A day after the filing, the two ‘amicably’ settled the lawsuit, with USA Today reporting the hip-hop mogul’s team alluded to a ‘substantial eight-figure settlement’ in court documents.

If you are experiencing domestic violence, please know that you are not alone. You can talk in confidence 24 hours a day to the national domestic violence helpline on 1.800.799.SAFE (7233) 24/7. You can find a list of local resources here.

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Topics: Cassie VenturaDiddyCrimeUS NewsCelebrityMusic

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