Shocking full testimony of male escort who claims he was paid by Diddy to sleep with his girlfriend: Court is told of rapper’s ‘vile sex act, awkward “role-play” sex encounter and bizarrely specific instructions on how and where to orgasm’

A male escort testifying in the Sean ‘Diddy‘ Combs sex trafficking trial in New York has delivered a graphic account of how he was regularly paid thousands of dollars by the rap superstar to have sex with his then-girlfriend. 

Daniel Phillip, 41, took to the stand for an hour yesterday afternoon to allege how Combs paid him up to $6,000 each time to take part in orchestrated sexual relations with R&B singer Casandra ‘Cassie’ Ventura. 

Diddy would often direct their encounters, forcing them to engage in awkward ‘role play’ before giving Mr Phillip specific instructions on when and where to orgasm, the male escort alleged. 

He said Combs routinely instructed him to massage baby oil all over Cassie and have sex with her while the rapper performed a sex act on a chair in the corner. 

On one occasion, Combs allegedly instructed Mr Phillip to orgasm inside Cassie, with Mr Phillip mentioning that the pair rarely used condoms. 

The escort said he ‘pretended’ to orgasm and was subsequently asked repeatedly by Combs whether he was ‘sure’ he had done so inside her. 

He also claimed to have witnessed Combs physically abuse Cassie on multiple occasions and added that the music mogul once gave him MDMA, according to a court report by Variety. 

Mr Phillip’s testimony came after the court heard how Combs, 55, forced women to take part in drug-fuelled sex parties which went on for days while he filmed them. 

For decades, the music mogul ran a ‘criminal enterprise’ built around trafficking victims, with his ‘inner circle’ helping to cover up his offences, prosecutors told the opening of his trial in New York.

He once stamped on a girlfriend’s head, dangled one woman from a balcony and allegedly tried to set fire to another man’s car, it was claimed.

The musician and businessman ‘viciously attacked’ women who resisted taking part in the sex parties, known as ‘Freak Offs’, or otherwise upset him, jurors were told.

In a bombshell admission, Combs’s lawyers told the court he had beaten up some of his girlfriends – but insisted he was not guilty of sex trafficking.

They admitted he was ‘kinky’ and that his conduct had been ‘horrible, dehumanising and violent’, but claimed it was all driven by jealousy and too many drugs.

Mr Phillip was the second witness to give evidence. He described in graphic detail how he would take part in ‘Freak Off’ parties with Cassie and Diddy that could last for up to ten hours. 

He claimed he first met Combs and Ms Ventura in 2012 when he was asked to perform a striptease at a bachelorette party in Manhattan’s Gramercy Park Hotel. 

Mr Phillip said he expected to meet a group of women and was instead greeted by Cassie, who asked him to have sex with her. Combs is said to have been sitting in the corner with his face concealed by a bandana, but Mr Phillip said he recognised the rapper’s voice.

Cassie is said to have told Mr Phillip that Combs was ‘not gay’ and assured the male escort he would not be touched by the rapper.

That encounter was allegedly the first of many that took place over the subsequent two years until early 2014 in which Mr Phillips said he was routinely asked to engage in sexual relations with Ms Ventura as Diddy watched on, both one-on-one and as part of the rapper’s ‘Freak Off’ parties. 

The escort said Combs on multiple occasions videotaped him having sex with Cassie on a cellphone and a camcorder. He also gave graphic descriptions of the sex acts he was asked to perform.

He claimed Ms Ventura once asked him to urinate on her, and added that the rapper once directed the pair of them through a role-playing game. ‘We were not very good at that at all,’ he said. On occasion, Combs would switch places with Phillip to engage in sexual intercourt with Ms Ventura, 

Mr Phillip recalled another occasion when Combs had called Ms Ventura from another room – but when she told him to wait a second, Combs came out and Mr Phillip says he saw a liquor bottle fly past her.

Diddy was alleged to have hit Cassie before grabbing her by the hair and dragging her out of the room.

Mr Phillip said: ‘She was screaming, and he pulled her into the bedroom. I could hear what sounded like him slapping her. She was screaming, ‘I’m sorry! I’m sorry!’ 

Mr Phillip added Combs said to Ms Ventura: ‘B****, when I tell you to come, you come now. Not later.’ 

The escort alleged that in one incident at the Jumeriah Essex House Hotel in New York, he heard slapping and screaming sounds coming from a closed bedroom. 

Cassie later exited crying and sought comfort from Mr Phillip, kissing and hugging him without instruction, which the escort said she had never done before.

He claimed to have asked her why she was staying in the ‘abusive relationship’ with Combs, only for her to say she was ‘OK’. Mr Phillip went on to allege that Combs later came back into the room to watch them have sex. 

Mr Phillip also told the court that he felt he was threatened by Diddy. 

Though Diddy never struck him, Mr Phillip said the rapper once took a photograph of his driver’s license and told him it was ‘just for insurance, just in case’. 

‘I understood it to be he was threatening me,’ Mr Phillip told the court, much to the chagrin of Diddy’s lawyers.  

The escort added he was offered MDMA, also known as ‘ecstasy’ or ‘molly’, by Combs – but was not forced to take it. 

Combs was once worth nearly $1billion and had a string of hits on his Bad Boy Records label in the 1990s, including his 1997 chart-topper with singer Faith Evans, I’ll Be Missing You.

But in September last year, he was arrested – months after Cassie sued him for sexual assault in a civil case.

Combs’s downfall was hastened by the release of a devastating video of him beating Ms Ventura in the corridor of a hotel in Los Angeles in 2016.

The video, which was first broadcast by CNN last May, was played in full to the trial and Ms Ventura, 38, who is heavily pregnant, is expected to testify.

Combs denies racketeering conspiracy, two charges of sex trafficking and two charges of transportation to engage in prostitution. He faces life in jail if convicted.

Prosecutor Emily Johnson said the trial would hear testimony from victims who ‘will tell you about some of the most painful experiences of their lives. The days they spent in hotel rooms, high on drugs, dressed in costumes to perform the defendant’s sexual fantasies’.

Opening the case, she told Manhattan Federal Court: ‘This is Sean Combs. To the public, he was Puff Daddy or Diddy, a cultural icon, a businessman, larger than life. But there was another side to him, a side that ran a criminal enterprise.

‘During this trial, you are going to hear about 20 years of the defendant’s crimes. But he didn’t do it alone, he had an inner circle of bodyguards and high-ranking employees who helped him commit crimes and helped him cover them up.

‘Kidnapping, arson, drugs, sex crimes, bribery and obstruction. These are just some of the crimes the defendant and his inner circle committed again and again. You’re going to hear about all of them during this trial.’

Prosecutors described a horrific claim made by Ms Ventura, who said she was left ‘feeling like she was choking’ when Combs allegedly made an escort urinate in her mouth during a ‘Freak Off’.

Ms Johnson also told the court about an incident where the rapper was ‘on the hunt’ for Ms Ventura because she was seeing another man.

The prosecutor said: ‘When he finally found her, he did what he had done countless times before: he beat her brutally. Kicking her in the back and flinging her around like a rag doll. All of that violence was not enough though.

‘The defendant had to make sure he had control over Cassie once again so he threatened her. The defendant told Cassie that if she defied him again, he’d publicly release the video of her having sex with a male escort he kept as blackmail. Souvenirs of the most humiliating nights of her life.’

But Combs’s lawyer Teny Geragos countered that prosecutors were trying to twist the star’s romantic relationships into a racketeering and sex trafficking case.

‘Sean Combs is a complicated man, but this is not a complicated case. This case is about love, jealousy, infidelity and money,’ she said in her opening statement.

Ms Geragos accused the alleged victims of filing lawsuits against Combs as a ‘money grab’.

‘Ask yourself why are they making this allegation now? What is their motive? For many of them, the answer is simple: money,’ she told jurors.

The prosecution’s first witness was Los Angeles police officer Israel Florez, who in 2016 was a security guard at the InterContinental Hotel in LA when the CCTV of the assault on Ms Ventura was filmed.

He said he was called to help a ‘woman in distress’ on the sixth floor, where he found Cassie sitting in the corner covering her face while Combs was slouched in a chair wearing just a towel with a ‘devilish’ look on his face.

‘She was scared,’ Mr Florez added. ‘She was in the corner, hood on, covered up. I couldn’t see her face, she was pretty much in the corner.’

Mr Florez also told the court he used his phone to film the assault video from the hotel security monitor to show his wife.

‘If I had told my wife what had happened, she wouldn’t have believed me,’ he said.

During the hearing, six of Combs’s children could be seen sitting nervously in the public gallery two rows back from the front. They included his twin daughters D’Lila and Jessie, daughter Chance and his sons King and Justin.

Combs’s mother Janice sat in the middle of them wearing a black blazer with sunglasses and bright orange hair.

The rapper walked in wearing a crew neck, light grey sweater and light grey trousers. He smiled at his family and made a heart symbol with his hands before hugging his lawyers and shaking the hands of his jury consultant, Linda Moreno.

Before sitting down, Combs blew one of his sons a kiss.

Over the course of the two-month trial, jurors are expected to hear testimony from three or possibly four of the rapper’s female accusers, as well as former employees who prosecutors say helped to arrange and cover up his actions.

Just selecting the jury caused a headache after the prosecution and defence both struck out a string of potential jurors.

Combs’s lead counsel, Marc Agnifilo, claimed that the prosecution’s veto of potential jurors was discriminatory because seven out of the nine people they rejected were black.

But Judge Arun Subramanian rejected the claim, saying prosecutor Maurene Comey had given ‘race-neutral reasons’ to explain each rejection.

About 150 potential jurors were vetted before the final 18 were selected, including six reserves. They will remain anonymous, but include an investment analyst, a massage therapist, a scientist, an architect and a United Nations worker.

Born in New York and raised by a single mother, Combs went on to live in mansions in Miami and LA and host lavish parties for the cultural elite in destinations such as the Hamptons and Saint-Tropez in France.

Among the artists he helped launch were Mary J Blige, Mariah Carey and Jennifer Lopez, whom Combs once dated.

The trial continues.