Ex-Girlfriend and Alleged 'Diddy' Victim Testifies How 90 Percent of Their Sex Involved Other Men

Yahoo

21 hours ago

A woman federal prosecutors are calling a victim of Sean 'Diddy' Combs took the stand at his federal trial in lower Manhattan on Thursday, telling the court that during their three year relationship, which lasted up until his September arrest, 90 percent of their time together was during drug-fueled, days-long 'freak-offs' where she was coerced into performing sex acts with male sex workers.
The woman, who is being referred to as Jane Doe during the trial to protect her identity, is the latest woman brought forth by federal prosecutors in the Southern District of New York to explain how the feds say the once powerful rap and fashion mogul used his companies and loyal staff as a criminal enterprise to coerce and control women, who he would blackmail and manipulate into performing in 'freak-off' sex marathons, which the near-billionaire would often film while masterbating. Combs has pled not guilty to all charges in the feds' five-count indictment, which includes sex trafficking, racketeering and transportation to engage in prostitution.
More from The Hollywood Reporter
Diddy Trial: Forensic Video Expert and Cassie Ventura's Best Friend Bolster and Hinder Prosecution's Case
Diddy Trial Sees Heckler Disrupt Court as Judge Learns Anonymous Witness' Name Leaked Online
Sean "Diddy" Combs Paid to Hide Cassie Beating Video Because He Feared Career Ruin, Witness Says
Taking the stand after court had returned from the day's lunch break, Jane Doe revealed early in her testimony that prior to connecting romantically with Combs in 2021, she was involved with a man whom Combs has history and a tense relationship. She said she met the rap world icon in Miami at a party she attended with a group of girlfriends, one of whom was casually dating Combs at the time; since his 2018 split with R&B singer Cassie Ventura, the federal prosecutors' star witness. Combs has been involved with several women at once, a fact that Doe told the jury was known to her as the relationship's inception.
Over her first few hours of testimony on Thursday afternoon, Doe painted a picture of the couple's meet-cute and easy segue into a more serious relationship, which grew over phone calls, texts and FaceTime video calls. In fact, their relationship saw a boom when Doe's friend, who was dating Combs, got engaged and moved to Europe. Soon, she told the court, Combs swept her off her feet with a trip to Turks and Caicos and the Bahamas over 15 days. The two enjoyed the relaxing island and dinner on their hotel suite's balcony, where they enjoyed viewing sunsets together. She recalled how he even bought her a bracelet that spells out L-O-V-E. Their sex life was the two of them; she was smitten.
'I really fell head over heels for Sean,' she said, adding that it was OK for her that he was also seeing other people because she really liked him. 'I understood that on his end, it was never a monogamous relationship.
One small hiccup on the trip, she recalled, came when Doe was handed an ecstasy pill by Combs and ended up so gobsmacked by the mind-bending drug that she doubled over in the sand and had to be taken into a tepid shower; over the remainder of the 15-day trip, Doe said she took Ecstacy 10 more times in smaller increments that were pieced out by Combs.
The questioning prosecuting attorney on Thursday quickly moved on to the moment that the relationship soured for Doe, when she asked her to recall for the court the night of March 21, 2021, when she was asked to participate in her first 'freak-off' with Combs, which were also referred to as 'hotel nights' at times. After Combs' assistants had set up the hotel suite, Doe said, she would dress in racy lingerie and high-heeled shoes. That was when Combs told her someone was coming: a male escort named Don, who Combs said he knew. The encounter as described by Doe followed a familiar trajectory, one described by Ventura a few weeks ago when she testified about her 'freak-off' experiences: the woman and escort would pour baby oil onto each other's bodies (12 bottles one time, she said); the two begin touching; Doe begins to perform oral sex on Don as Combs watches, masterbating. From the witness, Doe said that it was her that 'tried to move things along' into the suite's bedroom. Combs protested when Doe asked to use a condom, she explained to the court, but he soon provided one and Don and Doe began to have sex.
Doe said that her initial experience performing a 'freak-off' hotel night with Combs made her 'happy' and that 'it was taboo.'
'I just thought that it was a night of fun; I didn't think that we'd be doing it again,' she told the court, at that point holding back tears. 'I think that night opened a Pandora's Box in our relationship and I was never able to shut it. It just completely set the tone for our relationship moving forward.'
Doe told the court when asked to give a percentage figure by federal prosecutors that after May 2021, 90 percent of the sexual experiences she had with Combs involved other men. The rapper, Doe told the court, suggested they have a hotel night the very next time the two saw each other.
'I just wanted to satisfy my partner,' she said of participating in the freak-offs.
As their relationship stretched into months, Combs began to give large sums of money to Doe, whose work marketing brands on her social media accounts was dwindling. He handed her $10,000 after their initial trip to Turks and Caicos as she'd missed out on some work while on the trip with him; later, he'd typically give her $5,000 or $6,000 incrementally. As was the case with Ventura, he began to pay for her apartment; Doe said this was a reason she felt compelled to participate in 'freak-offs' even when she started to not enjoy them.
'I felt obligated to perform because my partner was paying my rent,' she explained.
An attempt she had planned to earn her own money by launching an Only Fans account, where she would appear in lingerie and bikinis, could have helped out with a sense of independence — as she told Combs, a friend had claimed she'd brought in $4 million in a year doing a Just Fans page. But Combs, she testified, was having none of that, telling her, 'Let's just give it time.' Prosecutors believe this constitutes coercion to keep Doe financially dependent on him so he could control her and force her into his sexual fantasies.
At a point, Doe says, she asked Combs if they could stop doing 'freak-offs' altogether. His response, she told the court, was to threaten her livelihood and home.
'He would just say things like, 'If you want to break up, that's fine. You have three months left on the house because I'm not about to be paying rent,'' Jane recalled Combs saying.
Doe's testimony will continue on Friday as the prosecution begins to eye the resting of its case.
Best of The Hollywood Reporter
Most Anticipated Concert Tours of 2025: Beyoncé, Billie Eilish, Kendrick Lamar & SZA, Sabrina Carpenter and More
Hollywood's Most Notable Deaths of 2025
Hollywood's Highest-Profile Harris Endorsements: Taylor Swift, George Clooney, Bruce Springsteen and More