Diddy’s former girlfriend details pressure to take part in ‘hotel nights’

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 further claimed that a group of employees assisted in obtaining drugs to facilitate the extended encounters, referred to as "hotel nights" or "freak-offs," which caused her significant pain and recurring infections.

Prosecutors have charged Sean "Diddy" Combs, 55, with racketeering conspiracy, sex trafficking, and transporting individuals for prostitution. He has pleaded not guilty to all allegations.

As the trial enters its fifth week, defense attorney Teny Geragos argued that the government is overreaching by framing consensual adult relationships as criminal activity.

Prosecutors, however, aim to use testimonies like Jane’s to demonstrate that Combs’ actions were part of illegal conduct.

During her testimony, Jane described a 2023 “hotel night” in New York where she arranged for a male sex worker to fly from Atlanta to join her and Combs at the Trump International Hotel.

She covered the escort’s airfare and later ensured a cash envelope containing several thousand dollars was left for him at the hotel front desk.

Jane also alleged that Combs’s chief of staff, Kristina Khorram named by prosecutors as a coconspirator once instructed her to pick up drugs in Los Angeles and bring them to Combs’ Miami mansion.

Jane testified that she received the package from a member of Combs’ security team, packed it in her checked luggage, and discovered it contained ecstasy upon arrival.

She further stated that Combs frequently called on his assistants and security personnel to deliver drugs to the hotels where encounters with escorts took place.

One of the key charges, racketeering, requires prosecutors to prove that Combs operated a criminal enterprise and conspired to commit illegal acts as part of that operation.

By the time of the 2023 New York encounter, Jane said she had reached a point where she no longer wanted to take part in the "hotel nights." The couple had been together since 2021.

During the trip, tensions rose as they began "bickering" over the events, and Jane told Combs she was "done with this," she testified.

Combs initially reacted defensively but told her they didn’t have to continue. However, later that night, she still participated in one.

Prosecutors questioned Jane repeatedly about why she remained in the relationship despite describing feelings of being "disgusted" and "repulsed" after a rare occasion when she did not use drugs which she said she normally took to make the encounters feel less real.

When asked why she arranged the New York "hotel night" if she had just expressed she didn’t want to participate, Jane paused before saying it was difficult to answer and that she wanted to make her partner happy.

The prosecution also highlighted the financial ties between the two.

At the time, Combs was covering Jane’s $10,000 monthly rent, a support he continues to provide.

Jane testified that they had a “love contract” in which Combs agreed to pay her a monthly allowance of $10,000 for two years.

She claimed he used this financial support as leverage when she resisted participating in the hotel nights.

Jane also recounted planning an "all-star party" involving male escorts from previous encounters. While Combs was reportedly excited, Jane attempted to back out.

Prosecutors presented text messages exchanged between the two, including photos Jane sent to show she was unwell.

Mr. Combs replied with messages that Jane interpreted as veiled threats to cut off her financial support.

In 2024, toward the end of their relationship, Mr. Combs told her he had been unaware that the “hotel night” encounters upset her, claiming she never communicated her feelings.

However, after reviewing her messages and personal notes, Jane testified she had, in fact, expressed her distress.

In one text from November 2021, she told Mr. Combs she was hurt that he spent time with another woman despite only having “hotel night” encounters with her. She wrote, “I need a breather and a break from you. This doesn't make me feel good at all, your intentions are in plain sight.”

Jane also told the court that the “hotel nights” took a severe physical toll on her, causing frequent infections and pelvic pain she experienced “100% of the time” after the encounters. She admitted she likely did not inform Mr. Combs of these issues because she “didn’t want to indicate any negativity.”

Earlier in the trial, R&B singer Cassandra “Cassie” Ventura testified about similar drug-fueled sexual encounters with  Combs during their more than decade-long relationship.

She is expected to continue testifying next week, where Mr. Combs’ defense team will likely question her extensively about her time with the music mogul.