A former assistant of Sean ‘Diddy’ Combs has revealed unsettling details regarding the infamous parties hosted by the disgraced hip-hop mogul. As the documentary The Fall of Diddy approaches its conclusion, Phillip Pines shares an emotional narrative about the controversial rapper’s sexually charged gatherings, indicating that he felt compelled to demonstrate his “loyalty” to Diddy in a deeply troubling manner.

Pines recounted an incident where Diddy instructed him to engage in sexual activity with a woman at one of these events, asserting his dominance by referring to himself as the ‘King’ who controlled everything. According to Pines, he reluctantly acquiesced and “performed for a bit” before discreetly exiting the room when Diddy, who was heavily intoxicated and immersed in the party atmosphere, turned his attention elsewhere.

Diddy and chief of staff had ex-assistant at their beck and call

The former assistant alleged that both Diddy and his chief of staff, Kristina Khorram, had him arrange accommodations for what they termed ‘Wild King Nights,’ which legal documents have labeled as ‘Freak Offs.’

The preparations for these explicit gatherings involved a detailed list of required items, including ketamine, marijuana, baby oil, mushrooms, male enhancement supplements, and the lubricant Astroglide, among others. Additionally, Pines was tasked with the cleanup after these events, often being called upon for “emergency cleanup,” which typically indicated that Diddy had left the room in disarray.

Phillip Pines experienced sexual battery during his employment with Diddy

The latest episode of Investigation Discovery’s docu-series, The Fall of Diddy, which became available on Tuesday night, reveals a disturbing incident that Pines endured while working for the controversial artist. Pines stated, “My life changed and I've never really recovered from it,” reflecting on the distressing moment when he felt compelled to demonstrate his loyalty to Diddy, who placed immense value on allegiance. In a lawsuit filed in December 2024, Pines highlighted that he was employed by the rapper from 2019 to 2021, accusing him of treating him “like an animal playing fetch” to validate his loyalty.

Recounting the events of that day, Pines noted that Diddy had been drinking heavily while he was instructed to prepare for a party that would involve even more alcohol and drugs. “I took a shot with them. That was his way of making sure you felt comfortable,” Pines explained. “I remember hearing the words prove your loyalty to me, (your) King.”

“He grabbed me by the shoulders, gave me a massage like a coach would give a player that's about to enter the game, handed me a condom, and pushed me toward a female guest on the couch.

“I froze before it took place; I didn't know what was happening. In that moment, I wondered if this was some sort of entertainment for him, or if he was genuinely unaware of his actions.”

Diddy's ex-assistant complied out of fear for his well-being

Feeling powerless, Pines was uncertain how to respond. Although the woman consented, he claims to have “performed for a little bit,” before fleeing the scene as soon as Diddy was out of sight.

Pines has filed a lawsuit against Diddy for sexual battery, harassment, sex trafficking, and other inappropriate demands, characterizing him as a “predator… in a sexually charged way, a manipulation way.”

In a recent documentary interview, Pines reveals his apprehension about discussing his traumatic experiences, having witnessed Diddy physically assaulting other employees who opposed his demands. He characterized the task of cleaning up after the Wild King Nights as “one of the most challenging responsibilities.”

Harrowing insight into Diddy's freak-offs

“Upon arrival, one is confronted with the aftermath: the debris, stains, used condoms, partially emptied baby oil bottles, and Astroglide seeping from the sides of the containers, all of which must be collected. There was broken glass, urine, blood, and stains on the furniture,” he recounted.

“I assure you, the floor was so slick with baby oil that one could easily slip. Baby oil would be found around the bathtub, which was filled with water. When reaching down to unplug it, one would encounter the baby oil floating on the surface.” He now admits that the scent of baby oil serves as a distressing reminder of the unsavory activities that transpired behind closed doors, which one could “only imagine.”

The founder of Revolt is currently incarcerated, awaiting trial on charges of sex trafficking and racketeering.

The finale of The Fall of Diddy will premiere on ID on January 28 at 9 p.m. ET, with subsequent streaming available on Max and Discovery+. The forthcoming exclusive 30-minute interview with Phillip Pines will further elaborate on the explosive four-part series. Journalist Mara S Campo conducted this interview with Combs' former senior executive assistant, marking the first occasion he has publicly addressed the allegations against his former employer on camera.

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