Sean ‘Diddy’ Combs’ former assistant claims he was ordered to have sex to prove his ‘loyalty’ to rapper

An alleged ex-assistant of Sean “Diddy” Combs claims the rapper once forced him to have sex with a woman to prove his “loyalty” during his employment with the disgraced mogul.

Phillip Pines, who allegedly worked as Combs’ senior executive assistant from 2019 to 2021, recalled being at one of Combs’ parties where he was allegedly pushed to drink alcohol when he claims Combs approached him with the proposition.

“I remember hearing the words: ‘Prove your loyalty to me,'” Pines claimed in a pre-taped interview airing Tuesday night following the final episode of “The Fall of Diddy” documentary, per the Hollywood Reporter.

“He grabbed me by the shoulders, kind of gave me a quick massage, like a coach would give a player that’s about to enter the game, and handed me a condom, pushed me to a girl that was on the couch, a guest.”

An alleged ex-assistant of Sean “Diddy” Combs claimed the rapper forced him to have sex with a woman to prove his “loyalty.” Getty Images for Sean Combs Phillip Pines, who allegedly worked for Combs from 2019 to 2021, claimed the music mogul grabbed him by the shoulders at a party, “handed [him] a condom [and] pushed [him] to a girl that was on the couch.” ID/Warner

The woman allegedly gave her consent to Pines before they engaged in sexual activity, which he claimed he agreed to in part because he feared retaliation from Combs.

“He got me. It was a circus. He did whatever he wanted, and we were just at his disposal. … He’s a predator,” Pines claimed.

“I mean that in a sexually charged way, in a manipulation way. He has an innate ability to make you feel comfortable and to make you do things for him that you would never do.”

At another point in in the interview, Pines claimed he wasn’t present for any of Combs’ alleged “freak-off” parties, which are expected to be mentioned in the rapper’s upcoming trial as he faces charges of sex trafficking, racketeering and forced prostitution.

“He did whatever he wanted, and we were just at his disposal. … He’s a predator,” Pines claimed of the musical artist in a pre-taped interview airing Tuesday night after “The Fall of Diddy” docuseries. ID/Warner Pines also claimed he had supply alcohol, baby oil and drugs for the Bad Boy Records founder’s alleged “Wild King Nights” parties. Bryan Bedder/CP/Getty Images

However, Pines claimed that he provided the hitmaker with various items for so-called “Wild King Nights” events, which allegedly took place in hotel rooms with young women.

“We usually had a laundry list of items that included lights, alcohol, marijuana, ketamine, Molly,” Pines claimed.

“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.”

“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,” Pines further claimed.

“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 filed a lawsuit against Combs in December 2024 for sexual battery, sexual harassment, sex trafficking and more. Getty Images Reps for Combs responded to Pines’ allegations in the lawsuit, saying the rapper is “confident he will prevail in court.” Getty Images for Sean "Diddy" Combs

In December 2024, Pines joined the long list of accusers suing Combs when he filed a lawsuit against the music mogul for sexual battery, sexual harassment, sex trafficking and more.

He also alleged in the suit that he cleaned up blood, bodily fluids and urine after Combs’ wild parties and then leave a generous tip for hotel employees in the hopes any damage would not be reported.

When asked for a response to Pines’ recent interview, reps for Combs directed Page Six to the rapper’s previous statement on Pines’ lawsuit.

“No matter how many lawsuits are filed, it won’t change the fact that Mr. Combs has never sexually assaulted, or sex trafficked anyone—man or woman, adult or minor,” the statement read.

“We live in a world where anyone can file a lawsuit for any reason. Fortunately, a fair and impartial judicial process exists to find the truth, and Mr. Combs is confident he will prevail in court.”