Cassie details first time she had sex with Diddy as she describes what happened at 'freak off' parties

Warning: this article discusses sexual assault and domestic abuse which some readers may find distressing.

The trial of Sean 'Diddy' Combs has entered its second day in New York, with several witnesses taking to the stand as the US rapper stands accused of sex trafficking, racketeering conspiracy and transportation to engage in prostitution.

The 55-year-old has denied all charges made against him, with both the prosecution and his defence team having made their opening statements in court, as US Assistant attorney, Emily Johnson, claimed that Combs ran a 'criminal enterprise' with help from an 'inner circle' of employees.

Meanwhile, the rapper's defence argued that while Diddy was 'physical' and a 'drug user', he was not guilty of a 'federal crime'.

Diddy's ex-girlfriend, Cassandra 'Cassie' Ventura, has since taken to the stand to issue her testimony. Cassie had previously taken her ex-boyfriend to court after alleging sexual abuse and domestic violence before a settlement was reached in 2023.

The 38-year-old has since provided details about her first time having sex with Diddy, as well as what allegedly happened at the so-called 'freak-off' parties.

Cassie and Diddy together in 2018 (Taylor Hill/Getty Images)

Speaking in court, she suggested (via Sky News) that the two were on a boat in Miami, and that she was 'drinking wine' and started to take drugs, namely a 'blue dolphin ecstasy pill', which she claims Combs 'gave to her'.

"I had never taken it before. I was just out of it, laughing, didn't know what it was until a little bit later." she said.

Ventura also claims that Combs was in a relationship with Kim Porter, with whom he shares three children, at this time, where she added that their relationship wouldn't go public for 'many years'.

She added: "He just didn't want it to look bad, but also knew it was because of his children and personal things like his family."

Ventura also discussed how Combs allegedly kissed her on her 21st birthday and later introduced her to the concept of oral sex.

Combs was first arrested last year (Dave Benett/Getty Images for TAO Group Hospitality)

She said (via NBC News): "I was confused, I was a new artist that didn't know the lay of the land and things like that. I wasn’t used to an executive or anyone being that forward that way with me, in a more than friends way, a sexual way, a romantic way. I remember running out and back to my hotel and telling someone about it."

Ventura claims that she did not want to kiss him, and further revealed that she went to see him a few times to discuss her music career, where she claims he brought up giving her oral sex, which she said she didn't reciprocate.

"He made me feel crazy for not reciprocating, at the time I did not understand that kind of relationship and I was in a relationship with someone else," she continued. "I was just so young and did not have the vocabulary for some of the things we talked about. I was just trying to understand it, just completely inexperienced at that point."

She was also asked about why Combs allegedly started the 'freak-offs', to which she said: "Within the first year of our relationship, he proposed this idea. This sexual encounter that he called voyeurism where he would watch me be in intercourse with a third party, specifically with another man.

“Eventually it became a job for me, pretty much, so I knew if it was something he wanted me to do, I had the contacts to set it up and get a hotel room and all of that, but in the beginning, Sean set it up. He was in charge."

The trial continues.