A former girlfriend of Sean “Diddy” Combs, testifying for a second day at his criminal trial under the pseudonym “Jane”, described how she felt pressured to engage in sexual encounters with male escorts while he watched, despite her expressing they upset her.
She also alleged a network of employees helped procure drugs for the lengthy encounters, known as “hotel nights” or “freak-offs”, that left her in pain and with frequent infections.
Prosecutors have charged Mr Combs, 55, with racketeering conspiracy, sex trafficking, and transportation to engage in prostitution.
He has pleaded not guilty to all charges.
At the beginning of the trial, now in its fifth week, defence attorney Teny Geragos said the government had overstepped with its charges and are trying to portray consensual sex between adults as evidence of crimes.
With Jane’s testimony, prosecutors are seeking to provide evidence that the music mogul’s activities were criminal.
In one “hotel night” encounter in New York in 2023, Jane testified that she invited a male sex worker to fly from Atlanta, Georgia, to New York City to join her and Mr Combs for an encounter at the Trump International Hotel.
Jane paid for his ticket, she testified, and afterward, she worked to ensure that an envelope containing several thousand dollars was left for the escort at the front desk.
On another occasion, the woman testified that Mr Combs’s chief of staff Kristina Khorram allegedly instructed her to pick up drugs from Los Angeles to bring to Mr Combs’ Miami mansion.
Ms Khorram has been named by prosecutors in court as a co-conspirator to Mr Combs, and could potentially testify.
Jane told the court that she picked the package up from a member of Mr Combs’ security, put it in her check-in luggage and flew to Miami, where she discovered it contained ecstasy.
She also said she often saw Mr Combs call his assistants and security to bring drugs to the hotels where they had their encounters with escorts.
One of the charges Mr Combs faces is racketeering. In order to prove that, prosecutors have to show that he was running a criminal enterprise and conspiring to commit crimes.
By the time of the 2023 New York encounter, Jane said she realised she no longer wanted to participate in these “hotel nights”. The pair had been together since 2021.
During the trip, the two began “bickering” about them and she told Mr Combs she was “done with this”, she said.
Mr Combs was defensive, she said, but told her they didn’t have to continue. Still, later that night, she joined him for one.
Prosecutors asked the woman several times why she stayed in a relationship with Mr Combs, even as she described feeling “disgusted, repulsed” after one rare encounter where she did not take drugs, which she said she took to make them seem less real.
A federal prosecutor asked why she arranged the “hotel night” in New York if she had just told Mr Combs she no longer wanted to participate.
Jane paused for a long time, at first saying it was hard to answer. She wanted to make her partner happy, she said.
Prosecutors introduced the pair’s financial ties. At the time, Mr Combs was paying Jane’s $10,000 per month rent, which he continues to do to this day.
Jane testified that the pair made a “love contract” in which Mr Combs agreed to give her a monthly $10,000 allowance for two years. The rapper would hold the money over her head if she resisted hotel nights, she testified.
She said one week, she was planning an “all-star party” with male escorts from their previous encounters.
Mr Combs said he was “hyped”, but Jane eventually tried to back out. Prosecutors showed the jury texts between the two, where Jane sent photos to prove she was not feeling well.
Mr Combs responded with messages she interpreted as threats to cut her off financially.
In 2024, near the end of their relationship, Mr Combs told her that he had not known the hotel night encounters upset her and that she had not told him.
But in reviewing her messages and notes from their relationship, Jane said she realised she expressed her unhappiness.
In one exchange, she told Mr Combs she was upset that he had spent time with another woman after only engaging in a “hotel night” with her.
“I need a breather and a break from you,” she texted him in November 2021. “This doesn’t make me feel good at all, your intentions are in plain sight.”
She also testified on Friday that the “hotel nights” took a physical toll on her.
She told the court that she frequently contracted infections, and felt pelvic pain “100% of the time” following the encounters.
Jane recalled she “probably” did not tell Mr Combs about these physical issues “because I just didn’t want to indicate any negativity”, she said.
Earlier in the trial, R&B singer Cassandra “Cassie” Ventura took the witness stand, describing similar drug-fuelled sex encounters with Mr Combs, who she dated for more than a decade.
She will continue to face questioning next week, with Mr Combs’ defence attorneys likely to be grilling her extensively about her time with the rap mogul.
