Diddy’s former escort claims freak offs became ‘evil’ over time

Shawn Dearing came forward to support Cassie Ventura’s testimony against Diddy.

Words by Charley Ross

Diddy

A former escort who allegedly worked for P Diddy has made several claims into what being part of his now infamous ‘freak-off’ parties was really like.

In an exclusive interview with People, Dearing alleged that there was a shift in tone of the freak-offs over time, that their mood became more sinister. ‘I just would say overall, the tone was a little darker towards the last times I’d seen them,’ he said. ‘I got to see the dark side of things.’

He went on to make allegations about Diddy’s ex-girlfriend and singer Cassie Ventura’s attitude towards participating. According to Dearing, he felt like Ventura was thinking ‘I’m here, I have to perform. Let’s do this.’

‘It was more of a “doing this to please him” type of spirit overall,’ Dearing said. ‘I can tell when the energy was different.’ He described Ventura as “playing her role”.

Dearing added: ‘It was evil … and she was under that.’

He went on to allege what he felt Ventura’s place and purpose was within the freak-offs, and claimed she wasn’t able to control the situation, calling it a ‘beast’.

‘In my opinion, in that situation, she didn’t know if this was a beast she could control or not anymore,’ he said. ‘So she was along for the ride, because she had to, because who knows? Who knows where this beast is going, and there’s no way to tame it.’

Cassie and Diddy

This comes after Ventura was reduced to tears while testifying in court for Diddy’s trial – which has now entered its fifth week – where he stands accused of sex trafficking, racketeering, and transportation to engage in prostitution. He has pleaded not guilty to all charges and has been jailed without bail.

Ventura has alleged that Diddy coerced her into participating in the ‘freak-offs’ – which have been described by prosecuting lawyers as ‘elaborate and produced sex performances’ – through threats of blackmail and physical violence. He denies these allegations.

Ventura alleged that she ‘had to’ do the ‘freak-offs’, despite explicitly stating on the stand that she did not want to do them.

Dearing alleges that he was first hired by Diddy around 10 years ago in late 2014 or early 2015 through elite male escort site Cowboys4Angels. He confirmed that he did not know Diddy’s identity as a client beforehand. 

He claims he was booked for ‘more than a dozen’ sessions with Diddy and Ventura, which he says would take place in one of two LA locations, a bungalow at The Beverly Hills Hotel or a condo off Sunset Boulevard.

Dearing left escorting in 2017 and moved home to Hawaii, and alleges that he was approached again by Diddy who asked him to work, which he declined. 

‘I just kind of had to do a lot of personal soul searching, in a sense,’ he explained. ‘I stepped away from [the freak offs], realising it was darker. Because honestly, I do care about these ladies. So I had to step away.’

Dearing says that he is on ‘a different path these days’, and that he ‘never thought that [escorting] was part of my life plan’. He describes being unfazed when it comes to what others think of him – he faces a certain amount of public scrutiny after his photo and alias was revealed by prosecutors in court.

‘The truth is, I don’t care what anyone says about me,’ he said. ‘If people would want to think negative thoughts about me, that’s on them.’ Most importantly, Dearing’s decision to go public with his allegations was to be an ally to Ventura, he says, noting that he wanted to lend ‘some credence’ to her testimony in court.

‘i had to do a lot of soul searching.’

This week, a different ex-girlfriend of Diddy’s testified under an alias (Jane) that she also took part in sex acts with male sex workers at his request. She described feeling more loved by him when she participated, but now feels regret at doing so as it felt like a ‘cuckold’ lifestyle.

She alleges that the sex acts were choreographed by Diddy and turned into marathons and often included drugs, and occurred weekly. Jane alleged that she was ‘under a lot of emotional pressure’ due to her desire to please Diddy and stay in a relationship with him.

‘I resent him for leading me into the lifestyle he led me to,’ Jane said. ‘I resented the way he went about introducing me to this lifestyle.’

She testified in court that she began therapy three months ago, and went back on arrangements to meet with Diddy’s lawyers. After starting therapy, Jane describes having reflected on the ‘hotel nights’ spent participating in these sex marathons, even though she only wanted to have sex with Diddy, but that the reasons were ‘becoming more and more clear’ as she continues with therapy.

She initially described feeling ‘something very special’ when it came to illicit sexual meetings with Diddy, and didn’t want to judge him because she ‘really wanted to just go along with these things because if I can be my partner’s escapes then I would be’.

Jane also alleged Diddy acts violently towards female sexual partners in order to fulfill his own desires in an earlier court testimony. Diddy denies all allegations against him.

Photo: Getty