Casandra “Cassie” Ventura took the witness stand on Tuesday, May 13, to tell the world about the “most humiliating nights of her life” she allegedly suffered because of her ex-boyfriend, Sean “Diddy” Combs.
On the second day of the disgraced rapper’s trial, the 38-year-old singer exposed the dark secrets of Diddy’s notorious “Freak Offs” and how she was allegedly violated by Sean and numerous other people for years.
Cassie, who is currently eight months pregnant with her husband Alex Fine’s child, saw her arrested ex-boyfriend for the first time in court since their 2018 split.
Casandra “Cassie” Ventura took the witness stand on May 13 during the trial of Sean “Diddy” Combs
Trigger warning: this article contains details of exploitation, mistreatment, and physical violence that may be distressing to some.
Cassie broke down in court as she spoke about Diddy and the control he had over her life.
When she first met Diddy at the age of 19, Cassie saw the then-37-year-old rapper as a “larger-than-life entrepreneur, musician.”
She said during her testimony that their relationship changed during a trip to Las Vegas for her 21st birthday, when Diddy kissed her in the bathroom of his hotel suite, she recalled.
“Sean controlled a lot of my life, whether it was career, the way I dressed, everything, everything,” Cassie said in court. “I just didn’t have much say in it at the time.”
Cassie spoke about how Diddy controlled aspects of her life, including her clothing and her career
Among other questionable things, Cassie revealed that Diddy made her call him “pop pop,” which was what she used to call her grandfather.
“He wanted me to have a nickname for him … I thought it was weird and now I feel like it was disrespectful,” she said.
The singer testified that the Last Night rapper proposed the idea of “voyeurism” within the first year of their relationship, where he would watch her being intimate with another man.
“The nervousness and confusion on that moment. I had just turned 22,” she testified. “I didn’t have a concept of how that would be a turn on, but I also felt a sense of responsibility with him sharing something like that with me.”
“I was confused, nervous but also loved him very much and wanted to make him happy,” she added.
The Me & U singer said male escorts were hired for the “freak offs” so she could “perform” for Diddy, who would watch and “direct” her as she had intercourse with them.
The singer revealed details of how the rap mogul used to watch and “direct” her as she had intercourse with male escorts
Cassie said she quickly knew she didn’t want to engage in such acts, especially because it started to happen “regularly.”
“But I was in love and wanted to make him happy,” she said. “It got to the point I didn’t feel I had much of a choice. I didn’t really know what it could turn into.”
Describing herself as “super young, naive, a total people pleaser” at the time, she said she was worried that he would blackmail her with footage of the acts.
Cassie Ventura is visibly pregnant as she was sworn in to testify in Sean “Diddy” Comb’s trial Tuesday, May 13th.
Sketch (Jane Rosenberg/Reuters) pic.twitter.com/PMLiNnJ72m
— SKDoubleDub (@SKDoubleDub33) May 13, 2025
The recordings of the freak offs were described as “souvenirs of the most humiliating nights of her life,” according to Assistant U.S. Attorney Emily Johnson.
Cassie went on to reveal that copious amounts of baby oil was used during the freak offs.
“We poured it all over our bodies …” she said. “It was always heated… if [Sean] felt like you were too dry he’d let you know, you need to be glistening, you need to be shining.”
Recordings of the freak offs were described as “souvenirs of the most humiliating nights of her life”
During day 2 of the #DiddyTrial, #CassieVentura Described Freak Offs.
She said there was a kiddie “pool filled with baby oil” during an alleged event held at Montage Beverly Hills. Cassie also claimed she got into the pool upon #Diddy’s request. pic.twitter.com/RYF8lVKTTw— Aman Magazine (@Aman_Magazine) May 14, 2025
On one occasion, Diddy “choreographed” her to get into a pool of baby oil at a hotel in Beverly Hills.
Cassie revealed she would be “high” on illicit substances during the freak offs and committed the acts out of fear.
“I was expected to have freak offs on my period,” she said. “Sean would expect it. I don’t think anyone wants to do that.”
She even detailed being urinated on by Diddy or one of the male escorts during the freak offs.
“I was expected to have freak offs on my period,” Cassie said
Cassie said she would have to have intercourse “with strangers for days.”
They would go on for “36, 48 to 72 hours,” she said. “The longest one was four days, maybe even more than on and off breaks… a significant part of the week.”
The Long Way 2 Go singer accused Diddy of often becoming physically violent towards her.
“He would bash my head, knock me over, drag me, kick me, stomp me in the head when I was down,” she said in court.
She also revealed the backstory behind the infamous hotel footage, which captured Diddy violently hitting her and dragging her back to their hotel room.
The Me & U singer spoke about how Diddy would often turn physically violent
Live from New York#DiddyTrial …#CassieVentura’s husband personal trainer Alex Fine leaving court today.
He looks angry, rightfully so, as he became part of the courtroom conversation.
FULL WRAP UP AT 7P ET: https://t.co/FVSIryBxXV pic.twitter.com/yfSFwWqsKr
— Surviving The Survivor Podcast (@PodcastSTS) May 13, 2025
Cassie said she was trying to leave a freak off when the hotel surveillance cameras captured her running out of the room and trying to escape.
“I just knew I had to get out. I grabbed my stuff and ran out as fast as I could. I made it to the elevators, got my sneakers on. The next thing I was just thrown to the ground,” she said.
“Sean grabbed me by the back of my neck and threw me to the ground,” she added.
Diddy was arrested in 2024 and could face life in prison if he is convicted on all counts.
Cassie and Alex Fine share two daughters and are preparing for the arrival of their third child
Cassie went public with her romance with Alex in 2018 and tied the knot a year later.
They are currently parents to two daughters and are preparing for the birth of their third child.
“She was a kid and was in fear of her life,” one wrote online
