Diddy Trial: Ex Testifies About Drugs, Male Escorts

A woman who dated Sean “Diddy” Combs from January 2021 to August 2024 broke down in tears on the witness stand as she recounted enduring three-day sex sessions with male escorts that were allegedly arranged by Combs.

Testifying under a pseudonym, “Jane” said Combs pressured her into participating in these so-called “hotel nights,” drug-fueled sexual performances that closely resemble the “freak-offs” that Casandra “Cassie” Ventura described. Jane said she told Combs multiple times that she did not want to have sex with other men, and that he was “dismissive” of her concerns. An audio recording from a hotel room in which Jane asked that an escort wear a condom was played in court. In the recording, Combs is heard brushing off Jane’s request. Jane testified that on another occasion, Combs looked at her and said, “You better not ask for a fucking condom” as an escort prepared to begin intercourse with her.

Jane described one “hotel night” that involved three rounds of sexual intercourse with one escort over the course of 18 hours. Immediately afterward, Combs allegedly left the hotel. Jane said she was “so high” from ecstasy given to her by Combs and felt “lonely.”

Jane said “hotel nights” became nearly a weekly occasion in her relationship with Combs. The longest “hotel night” Jane remembers having lasted more than three days without sleep. She said the shortest of such encounters lasted 12 hours, and a typical “hotel night” spanned 24 to 30 hours.

On one occasion, Jane testified, she performed a “hotel night” without taking drugs. After having sex with two male escorts, she went to the bathroom and threw up. As a third escort entered the hotel room, she recalled Combs telling her, “You’ll feel better now that you’ve thrown up. Let’s go.”

In a text message from September 2023 that was read in court, Jane told Combs, “I don’t want to play this role in your life anymore … it’s dark, sleazy and makes me feel disgusting.”

Jane’s testimony began on Thursday afternoon, when she told the jury that she met Combs while on a girls’ trip in Miami in 2020. At the time, Combs was romantically involved with one of Jane’s friends, and he invited them on a boat and to his house. She called him “Ernie” and he called her “Bert,” nicknames based on the “Sesame Street” characters.

Jane and Combs started a romantic relationship in January 2021, and Jane found him “super charming,” “passionate” and “larger than life.” She told him that she had previously been in a relationship with one of his friends, and that she had a child with someone Combs disliked.

A month later, Combs took Jane on a trip to the Turks and Caicos Islands, when he allegedly gave her the drug ecstasy 10 times over the course of nine days. Over the next few months, they met up every other week and had lots of sex. She said Combs often gave her cash payments, sometimes up to $10,000, as a loving gesture.

Things changed in May 2021, when Combs began opening up to Jane about his sexual fantasies. Early one morning, they had been up for 24 hours straight on ecstasy and MDMA, and they were having sex for nearly 15 hours while watching pornography. “He really wanted me to fantasize or talk about other men,” Jane said. She recalled Combs saying, “I can make this fantasy a reality,” and, within a couple of hours, he brought her to a hotel room that was being set up by assistants.

Combs hired a male escort named Don to come to the hotel, and he had Jane dress up in lingerie and “big stripper heels,” as she called them. Jane described being high on drugs as Combs instructed her to pour baby oil on Don and then perform oral sex on him. Things escalated, and soon enough Jane was undressing and having intercourse with Don. After he ejaculated, she had sex with Combs. Jane said this experience “exhilarated” her because “it was taboo.” “I had a good time with my partner,” she said.

But “that night opened a Pandora’s box in our relationship,” Jane said. “It was a door I was unable to shut.”

Soon, having sex with other men became 90% of her time spent with Combs, Jane said. These “hotel nights” could involve multiple rounds of sex with male escorts and with Combs, and they could span up to 30 hours without sleep. Jane said she told Combs “many times,” both in writing and verbally, that she did not want to have sex with other men, a concern that Combs allegedly brushed off.

When Jane moved from the East Coast to Los Angeles in 2021, Combs paid her $10,000 rent. When she expressed hesitancy about his sexual preferences, Combs insinuated that they could break up and he would stop paying her rent, she testified. Thus, she said she felt “obligated” to “perform” for him. In the September 2023 text, Jane told Combs that she felt the “hotel nights” were “the only reason you have me around and pay for the house.”

Earlier in the trial, Combs’ longtime ex-girlfriend Ventura alleged that over the course of 11 years, Combs used violence and threats of blackmail to coerce her into “freak-offs,” drug-fueled sex parties with male escorts that lasted days at a time.

Combs is pleading not guilty to charges of sex trafficking and racketeering. If convicted, he faces a possible life sentence in prison.