"It felt like what, is this fun for him?" — Diddy's former personal assistant alleges rapper forced him to have s*x to prove his loyalty

Rapper Sean Diddy Combs' former personal assistant, Phillip Pines, alleged that Diddy forced him to have s*x with a guest to prove his loyalty. The alleged incident took place at one of Combs' parties.

In an interview with journalist Mara S. Campo for the investigative docuseries, The Fall of Diddy, Phillip Pines shared details about what allegedly went on during the rapper's frequent parties. He recalled one particular incident that he will "never forget" when the rapper asked him to "prove himself."

Pines said in the interview that Diddy was usually always drinking before one of his freak-off parties. The former assistant claimed that the rapper offered him alcohol ahead of the alleged incident.

“I took a shot (of alcohol) with them. That was his way of making sure you felt comfortable. go back to the office, sit there, get summoned again, take a shot, take a shot. He’s out of his mind. He’s in rare form as we would call it. I remember hearing the words prove your loyalty to me, (your) King," Pines recalled.

Pines then alleged that Combs forced him to indulge in s*xual activity with another woman guest and continued:

"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, pushed me to a girl that was on the couch, a guest. I froze before it took place, I didn’t know what was happening. In the moment it felt like what, is this fun for him? Is this a test for entertainment, does he know he’s doing this? Is he that gone?"

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Pines added that he "didn't know what to do" for a while but claimed that the girl allegedly gave her "consent" to the act. The former assistant alleged that he "performed it" for a little while before running out of the place. Pines was also spotted crying on camera while narrating the alleged incident.

Phillip Pines reportedly worked for Diddy between 2019 and 2021. The former assistant is one of the multiple people who've filed a lawsuit against the rapper.

In his December 2024 lawsuit, Pines accused Combs of alleged s*xual battery, s*xual harassment, and s*x trafficking and claimed his job duties included enabling the rapper's alleged illegal activities.

Phillip Pines claims Diddy often gave him a "laundry list" of questionable items

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In his interview on the docuseries, The Fall of Diddy, the rapper's ex-assistant Phillip Pines made multiple claims about his time working with the former. He said:

“We usually had a laundry list of items that included lights, alcohol, marijuana, ketamine, Molly. You have mushrooms on the top there … baby oil and astroglide [lubricant] are very important; candles, incense, Apple TVs, electronics, computers, iPads. Obviously there was, you know, male libido supplements, stuff like that."

Pines further claimed that he had never personally witnessed one of Diddy's alleged 'freak-off' parties. For those unaware, Combs reportedly held alleged 'freak-offs' or White Parties where multiple industry heavyweights would be present.

These parties were allegedly known for involving s*xual activity and drugs with everyone wearing white clothes.

However, Phillip Pines mentioned witnessing alleged "Wild King Night" events. He claimed Diddy took advantage of these less-famous women during these events at hotels.

“A lot of times, there were girls that were under the radar, didn’t have a lot of influence. I think that speaks to the type of situations people were put in. A lot of times, you have [Combs] with a young female, and there’s a power dynamic there. A more impressionable girl is easier to reel in, as opposed to somebody who might be a celebrity who’s not going to do too much of that, or give some pushback," Pines said.

Journalist Mara S. Campo asked the former assistant whether Diddy broke any laws as claimed in the multiple lawsuits filed against him.

For context, the lawsuits against Combs include various charges including r*pe, s*xual harassment, s*x trafficking, and racketeering.

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Pines did not give a clear answer to Campo's question and mentioned that he had not witnessed enough of the alleged Wild King Nights parties to judge whether the acts involved were consensual or not.

The former assistant then recalled one incident where an upset young woman had to be escorted back to her hotel.

“I remember a time when Diddy told me to come up and grab one of his guests’ bags, take it out to the car and drive her to her hotel. I don’t know what took place. All I can say is that when I had brought her down to the car, she was shaky. Physically shaken. Didn’t look like how she had looked the night before. She said something to the effect of, ‘I’ve never done like anything like this before,’” Pines alleged.

Phillip Pines further recalled that Combs would often ask him to do "emergency cleanups" after Wild King Nights parties. The rapper allegedly did not want to raise suspicions among hotel staff about these parties and almost always "destroyed" the rooms after the events.

In another incident, Pines narrated that Diddy allegedly physically assaulted one of his female guests in Florida. The rapper reportedly "kicked the woman twice" after an argumentative discussion with her. He also ordered her to take off her hoodie, leaving the woman "topless."