Diddy's assistant recalls sickening moment he was ordered to have sex to prove his 'loyalty', bombshell doc reveals

Diddy's former personal assistant has described the sickening moment the disgraced hip hop mogul ordered him to have sex with a girl to prove his 'loyalty'.

Phillip Pines broke down in tears while recounting the moment Diddy grabbed him by the shoulders during one of his notorious sex parties and gave him a massage like a 'coach would give a player'.

Diddy handed Pines a condom and told him 'Prove your loyalty to me,' referring to himself as 'King' as he motioned towards a girl in the room.

Pines told Investigation Discovery that he reluctantly 'performed for a bit' and then ran out the room when Diddy - who had been drinking and partying all day - wasn't looking anymore.

The shocking interview features in 'The Fall of Diddy', a documentary screening on Max and discovery+ with Pine's interview available from Tuesday night.

Pines sued Diddy last month for sexual battery, sexual harassment and other claims.

The lawsuit stated that Pines worked for Diddy between 2019 and 2021 and the rapper treated him 'like an animal playing fetch in order to prove his loyalty'.

Diddy, 55, whose real name is Sean Combs, is currently in jail awaiting trial on sex trafficking and racketeering charges.

He denied all the claims, including those made by Pines.

In the documentary, Pines said that loyalty was 'everything' to Diddy and that the only reason he got so close to him was by doing his every bidding.

The moment he had to 'prove himself' was 'something I won't forget', Pines said.

'My life changed and I've never really recovered from it', he said tearfully.

According to Pines, Diddy had been drinking all day and he was asked to set up for the next stage of the party with alcohol, marijuana cigarettes, alcohol and drugs.

But then things turned dark very quickly.

Pine said: 'I took a shot (drink) with them. That was his way of making sure you felt comfortable.

'I 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.'

Fighting back the tears, Pines said: '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, 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?

'I didn't know what to do.

'She gave me consent, yeah, nodded her head and I performed for a little bit and then I ran out of there as soon as I didn't see him in my sight anymore.'

Pines explained he didn't say no because he had seen previous employees be physically assaulted if they stood up to Diddy.

'I saw how angry he could get from the simplest thing,' he said. 'I thought to myself if I don't do this I don't know what's going to happen'.

Looking back, Pines has a 'great sense of remorse' and felt a 'bomb would explode' if he spoke up about his harrowing experience.

Openly crying, he said: 'I come from a Christian background and I lean on those morals heavily.'

Among the other revelations in the documentary are damning text messages sent to Pines by Kristina Khorram, chief of staff at Combs Enterprises, who has been likened to Ghislaine Maxwell - the top recruiter for the late pedophile Jeffrey Epstein.

Diddy's lawyers have denied he engaged in sex with any minors.

Pines says that Khorram and Diddy were so close it was like they were in a 'marriage'. A video shot by Pines showed Diddy toasting Khorram as 'my soul sister'.

Khorram would be the one to text Pines to set up a hotel room or a room in one of Diddy's luxury homes for what he knew as 'Wild King Nights' - prosecutors have called such parties 'Freak Offs'. 

Pines said that these events needed a 'laundry list' of things including ketamine, marijuana, mushrooms, baby oil, male libido supplements and Astroglide - a lubricant. 

One text from Khorram detailed what was needed for a party read: 'Gatorade, 5 bottles of blue water, 3 bottles of chlorophyll, Okay did the seasonal circos (Ciroc vodka), 5 Deleon (tequila), 2 each of wine.'

Another text referred to a string of prescription drugs including Zolpidem, a sedative, and Cialis, which is used to treat erectile dysfunction but has been known to be used as a party drug.

A message sent to Pines read: 'Lorazepam - give him (3), Zolpidem - give him (2), Cialis - give him (3) 5mg, Clonazepam - give him (5).'

A third text from Khorram asked for: '2 Whispering Angel Rose, 1 Astroglide, 2 Baby oil'.

Another sent in March 2021 read: 'Hey! PD needs a drop off of the following please: 4 of those young coconuts, 7 bottles baby oil, 7 bottles of astroglide, his Apple TV'.

The message went on to say Pines may have to visit some adult stores to get the supplies. 

The documentary also features several voice memos sent to Pines by Diddy.

One of them says: 'Phil I need some Cialis', referring to the erectile dysfunction drug.

Another said 'give me 20 Xanax please' while a third said 'I need a Plan B', referring to the morning after pill to avoid pregnancy.

In other voice memos, Diddy said 'I need 10 Adderall' and asked for Pines to bring him 'the mushroom capsules, the microdose'.

One of Pines' jobs was to clean up the mess after the Wild King Nights, including doing 'emergency cleanup', which meant that Diddy had wrecked a hotel room.

'That was one of the hardest things to do,' Pines said. 'When you get there, you see the wreckage, the stains, the used condoms, the baby oil half used, Astroglide oozing down the sizes of the bottle and you have to pick it up. Broken glass, urine, blood, stains on the furniture.

 'I kid you not, you could slip because there was baby oil all over the floor. There would be baby oil surrounding the bathtub and there would be a bathtub full of water. You'd reach down to unplug and you'd feel the baby oil at the top'.

Pines shuddered as he said that you could 'only imagine' what had been happening in the room hours earlier.

He said: 'It's disgusting. It's a little triggering because the smell of baby oil is something I don't ever want to smell again.'

In the film, Pines said that one time he saw Diddy being violent towards a girl and ordered her to take off her hoodie so she was topless.

According to Pines, he covered the woman with his jacket and bundled her into an Uber.

Another time he had to drive a woman to her hotel and she was 'visibly shaking' and said she had 'never done anything like this before'.

Pines says that Diddy's life 'was a circus, he could do whatever he wanted'.

He said: 'He's a predator and I mean that in a sexually charged way, a manipulation way. He has an innate ability to make you feel comfortable and do things you would never do.'

When Diddy hosted 'Red Light parties' - rooms filled with red lights because he allegedly thought it made people think about sex - Pines said he became a 'stark' and 'heavy' person.

'That was my experience, everybody's experience who knew him beyond the lights and cameras,' Pines said.

'It's dark around him, it's very dark.'

The finale for The Fall of Diddy premieres tonight beginning at 9pm ET on ID and streams on Max and discovery+.