Context:

Cassie, a 38-year-old singer, testified in the ongoing sex trafficking trial against 55-year-old music mogul Sean 'Diddy' Combs, revealing when their relationship turned sexual. Initially signing with Bad Boy Records at 19, Cassie described her first encounter with Diddy, which involved an unexpected kiss on her 21st birthday. Despite a 17-year age gap, their relationship developed further through meetings at the Trump Hotel, where Diddy introduced her to oral sex and later, under the influence of drugs, they had sex for the first time on a boat in Miami. Cassie recounted feeling pressured and inexperienced, and mentioned that their relationship was discreet due to Diddy's personal life, including his relationship with the late Kim Porter. She also touched on later sexual experiences in their relationship, described as 'freak offs', which occurred after they began spending more time together post-Miami trip.

Dive Deeper:

• Cassie testified about her early interactions with Diddy during the second day of his sex trafficking trial, where she revealed their relationship began when she was 19 and signed to his label, Bad Boy Records, a deal which she only released one album under.

• Their romantic relationship started when Diddy kissed Cassie unexpectedly in a bathroom at the VMAs on her 21st birthday, leaving her confused and overwhelmed due to her naivety and inexperience in the music industry.

• Despite initially not wanting to engage in a romantic relationship, Cassie described how meetings at the Trump Hotel in Manhattan led to a more comfortable relationship, where Diddy introduced her to oral sex, though she did not reciprocate initially.

• Cassie recalled their first sexual encounter on a boat in Miami, where, under the influence of alcohol and ecstasy provided by Diddy, she felt euphoric and high, leading to their first sexual experience despite her lack of understanding of such relationships.

• The relationship was kept private for many years, as Diddy was concerned about public perception and personal matters, given his ongoing relationship with Kim Porter at the time their relationship became physical.

• Cassie described the pressure she felt to conform to the dynamics of their relationship and how her youth and inexperience left her struggling to comprehend the situation fully.

• She also mentioned the evolution of their intimate encounters into more elaborate 'freak offs', which occurred after they began spending more time together following their initial trip to Miami.

• Cassie is opening up about her first sexual interactions with Sean “Diddy” Combs.

• The 38-year-old pregnant singer spoke out during Day 2 of the ongoing sex trafficking trial. The 55-year-old music mogul was arrested in 2024 for alleged sex trafficking, prostitution, racketeering conspiracy, sex trafficking by force, fraud, or coercion, as well as transportation to engage in prostitution.

• During her testimony on the witness stand, Cassie revealed when she first met Diddy, and when their relationship became sexual.

• Keep reading to find out more…

• During her testimony, she described signing to his label Bad Boy Records at 19.

• “He was a larger-than-life musician, a fan of music, didn’t know too much about him personally,” she told jurors.

• “When I signed contract, I was 19, it was a 10- album deal, released an album later that year in 2006 in August.”

• She notably did not release another album under Bad Boy Records afterward, despite the 10-album deal.

• Cassie also explained how the romantic relationship began with Diddy allegedly kissing her in a bathroom at the VMAs on her 21st birthday.

• “I was confused, I was a new artist that didn’t know the lay of the land and things like that,” she said.

• “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.”

• Cassie, who has a 17 year age gap with Diddy, said she did not want to kiss him that day, but after meeting with him handful of times at the Trump Hotel in Manhattan where they discussed her music career, they “started to develop a comfortable relationship with each other.”

• During those meetings, he allegedly introduced her to the idea of oral sex, teaching her how perform it and giving it to her. When asked if she reciprocated, Cassie told jurors no.

• “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. 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.”

• Cassie then recalled having sex for first the first time with Diddy while high on drugs on a boat in Miami.

• “I was drinking wine, then started to take drugs, a blue dolphin ecstasy pill. Sean gave it to me, 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 recalled feeling “euphoric” on the drug. “You are just really high, sensitive to touch and all of your senses.”

• She also confirmed Diddy was in a relationship with the late Kim Porter when they started a physical relationship.

• She said after the Miami trip, they began to spend more time together, but their relationship “was not public for many years.”

• “He just didn’t want it to look bad, but also knew it was because of his children and personal things like his family,” Cassie said, confirming she was speaking about “Kim Porter.”

• She also discussed the “freak offs” that happened later in the relationship. See all the updates from Day 2 of the trial.