Sean ‘Diddy’ Combs trial: Diddy, Cassie Ventura’s graphic sessions with ‘The Punisher’

A male escort, known as “The Punisher,” has told jurors in watering detail about his sex parties with Cassie Ventura and Sean “Diddy” Combs.

WARNING: Graphic content

A male stripper has gone into graphic detail about a string of sex sessions he was hired to take part in involving Sean “Diddy” Combs and the star’s then-girlfriend Cassandra Ventura.

Sharay Hayes, a male escort known professionally as “The Punisher,” gave evidence in Combs’ extortion and sex trafficking trial on Tuesday, US time.

The rapper, 55, has pleaded not guilty to all charges. He faces life in prison if convicted.

Mr Hayes also revealed how a slip-up inside a hotel room - a TV displaying the message “Welcome Sean Combs” - first revealed the identity of his celebrity client.

Also giving evidence on Tuesday, Ms Ventura’s mother Regina said she felt “physically sick” when she received an email demanding thousands of dollars to prevent a sex tape of her daughter being released.

One of Combs’ former staff members also took the stand, blasting the musician’s own lawyers for asking a “crazy question”.

Pregnant Cassie Ventura and her husband Alex Fine are seen here in New York City on May 19, 2025. Picture: Elder Ordonez/INSTARimages/Media Mode

‘The Punisher’ reveals sex sessions

Mr Hayes said he got the nickname “The Punisher” playing on New York basketball courts. But it was useful in his career as an exotic dancer, typically for birthdays and bachelorette parties.

He said that in late 2012 he received a call from a “Janet” who he later found out was Cassie Ventura.

He testified he was asked to come to New York’s Trump International Hotel at 2.45am to dance for a group of friends. When he arrived he saw “Janet” was wearing a dressing gown and nothing else.

He said he was given $US800, four times his usual rate, and asked to create a “sexy scene” with her and her “husband”.

This was his first experience of Combs’ now infamous “freak-off” parties.

Around the hotel room were bottles of baby oil. Ms Ventura, he said, rubbed baby oil into her skin and told him to do the same.

“I was specifically told to try not to look at or communicate with her husband,” Mr Hayes told the court.

“The man then came out and he was nude but for a veil. You could only really see his eyes. I noticed at times he was masturbating.”

Mr Hayes said the man was holding Astroglide lubricant.

MORE: ‘Freak off’: Diddy cops $50m insult in major blow

Sharay Hayes aka “The Punisher”. Picture: Instagram

”The Punisher” said he was summoned by Cassie Ventura to the Trump Hotel in New York. Picture: Instagram.

After the session was finished, Ms Ventura – whose identity, like the man, he didn’t know – asked him if he wanted to “finish”, which he took to mean climax. He declined, he said, because he wanted to remain “professional”. He then left with a further $1200.

But the couple appeared to like “The Punisher” because they hired him on a further eight to 12 occasions which would go on for hours at time, he claimed. During these sessions, Combs would direct the pair, often making them move to a different position or moving a candle that lit them.

The escort and stripper would perform sex acts on Ms Ventura, he said.

But on the final occasion he met the pair, Mr Hayes said, Combs’ behaviour meant he couldn’t get an erection.

Mr Hayes claimed that Combs said he was “ready” for him to have sex with Ms Ventura in an “assertive” and “aggressive” tone. The escort said he performed oral sex. But then Combs began throwing condoms and cash on a sofa near to them. Combs actions, he said, meant he wasn’t able to perform to Combs’ instructions.

Mr Hayes has written a book about erectile dysfunction called In Search of Freezer Meat.

Combs’ trial is underway in New York City. Picture: Elizabeth Williams via AP

He faces life in prison if convicted. Picture: Jordan Strauss/Invision/AP, File

Slip-up reveals Diddy’s identity

Mr Hayes said that at first he was unaware of the couple’s identity. But one slip-up saw the mystery revealed, he alleged.

In a hotel suite he was told to wait prior to the freak off beginning.

“The hotel TV was on and it said ‘Welcome Sean Combs’,” he told the court.

“Then I looked on his social media and I recognised Cassie Ventura.”

After a while, Mr Hayes said, Combs dispensed the veil and his secret identity and simply wore a baseball cap during the sessions.

Comb’s former assistant lashes Combs’ lawyers

Combs’ former “trusted assistant” David James returned to the stand on Tuesday.

While there he had a dust up with Combs’ lawyers.

He testified that on one occasion he had gone out to buy burgers for Combs from Los Angeles’ famous Mel’s Diner.

When he and another staff member Damien Butler, known as “D-Roc”, had parked at the diner they came across rival music producer Suge Knight. Knight founded Death Row Records and is in prison for voluntary manslaughter.

While he and D-Roc were in the diner, Mr James said, several additional cars turned up and guns were produced suggesting they were in danger. The pair then fled back to Combs’ LA mansion.

Defence lawyer Marc Agnifilo asked Mr James if he had left D-Roc at the diner.

“That’s a crazy question,” said Mr James.

“Why would I leave D-Roc at the diner when guns were being passed around.

“That doesn’t make any sense.”

On another occasion during his cross-examination, Mr Agnifilo said “that’s a bad question”.

“I agree,” snapped back Mr James.

David James is a witness for the prosecution. Picture: John Lamparski/Getty Images/AFP

MORE: Jailed Diddy’s wild $98m move exposed

Mr James also told the court that when his boss was in Miami he recorded in the same studio that Pharrell Williams and Will Smith used.

“He would go where Pharrell was working. Will Smith had a studio,” Mr James said.

Cassie’s parents Rodrick and Regina Ventura depart the Manhattan Federal Court. Picture: John Lamparski/Getty Images via AFP

The mother of Combs’ ex-girlfriend, Cassie Ventura will also testify on Tuesday. Picture: Chris Pizzello/Invision/AP File

Cassie’s mother tells court she was blackmailed by Diddy

Ms Ventura’s mother Regina Ventura also testified on Tuesday.

The jury was shown an email from her daughter around Christmas 2011 claiming she was being blackmailed by Combs.

“Threats have been made to me by Sean ‘Diddy’ Combs relating to 2 (sic) explicit sex tapes of me.

“He also said someone would hurt me and made a point it would not be by his hands and he would be out of the country when that happened”.

Regina Ventura said she was told Combs was demanding $US20,000 to be “recouped” from Cassie because he found out she was seeing rapper Scott Mescudi, also known as Kid Cudi. He is due to give evidence this week.

“I was physically sick,” said Ms Ventura when she read the email. “The sex tapes threw me.”

She said they had to remortgage her house to pay the money and then a staff member of Combs’ Bad Boy Records gave her the details to wire the money too. But five days later, the money came back.

Originally published as Sean ‘Diddy’ Combs trial: Diddy, Cassie Ventura’s graphic sessions with ‘The Punisher’