To the outside world, Cassandra “Cassie” Ventura’s life alongside hip-hop mogul Sean “Diddy” Combs seemed like a dream. The R&B singer was often spotted gracing red carpets and glittering Hollywood parties, basking in the glow of Combs’ fame and fortune.
But behind the glitz and glamor, Ventura says she was trapped in a life of abuse, fear, and humiliation.
This week, Ventura, now married to personal trainer Alex Fine and eight months pregnant with their child, took the stand as the star witness in Combs’ federal sex crimes trial in Manhattan.
Her testimony painted a dark, harrowing picture of life behind closed doors with one of music’s most powerful figures.
“I was expected to have freak offs on my period,” Ventura testified on Tuesday, May 13. “Sean would expect it. I don’t think anyone wants to do that.”
Ventura described to jurors how Combs forced her to take part in what he called “Freak Offs” — encounters where male escorts were hired to have sex with her, often while Combs watched and filmed.
These encounters, she testified, sometimes involved deeply degrading acts.
Combs or one of the male escorts, she said, would urinate on her during these encounters. When Assistant U.S. Attorney Emily Johnson asked Ventura if she wanted this, Ventura responded firmly, “No. But there was no conversation. It was a turn-on for (Combs), so it happened.”
The R&B singer told jurors she often found herself “choking” because there was “too much urine in my mouth,” sometimes from both Combs and the escort at the same time.
“I don’t want anyone to urinate on me,” she added. “Sean would urinate in my mouth — not super often but often enough.”
Asked why she didn’t refuse, Ventura explained, “I was squeamish, high and in the moment with this man, so that’s what happened. There is not a whole lot of control you have with two men standing over you peeing. I thought it was obvious I didn’t want to do it.”
Once these so-called Freak Offs ended, Ventura said she was left to clean up hotel rooms littered with blood and urine.
Ventura also recounted her first uncomfortable encounter with Combs.
On her 21st birthday in August 2007, after a VMA event in Las Vegas, Combs kissed her for the first time.
“There was a 17-year age difference,” she testified. “I was really confused at the time, you know, new artist. I was pretty naive.”
Asked if she wanted the kiss, Cassie replied, “No, not on my birthday.”
Despite that early discomfort, Ventura admitted she stayed close to Combs.
“I wanted to be around Sean for the same reasons as everyone else at the time — this exciting, entertaining, fun guy who also happened to have my career in his hands,” she said.
As a self-described “total people-pleaser,” Ventura said she often complied with Combs’ increasingly disturbing demands, describing how he controlled every aspect of her life. “He controlled a lot of my life,” she said.
Combs allegedly introduced her to voyeuristic sex acts and forced her into numerous Freak Offs.
The humiliating encounters, she said, left her filled with “nervousness and confusion.” He would often record these sessions, referring to the footage as “blackmail materials.”
For years, Ventura said, she lived in fear that he would release them. “He had many resources to do that,” she testified.
Jurors were also shown chilling surveillance video from 2016, capturing Combs beating and kicking Ventura in the elevator bank of a hotel lobby.
Combs was arrested in September 2024 and pleaded not guilty to five counts, including sex trafficking, racketeering, and transportation to engage in prostitution. If convicted, he could face life in prison.
He has remained in custody at the Metropolitan Detention Complex in Brooklyn since his arrest.
In her opening statement, U.S. Attorney Emily Johnson told jurors that Combs allegedly used his wealth and influence to drug women and coerce them into degrading sexual encounters.
Ventura’s lawsuit, filed in 2023, accused him of a wide range of sex crimes.
Though it was settled the following day for an undisclosed amount, federal charges followed soon after, with more alleged victims coming forward.
Combs’ defense attorney, Teny Geragos, argued that Ventura’s relationship with Combs was consensual and that she chose to stay with him for more than a decade.
“She made a choice, every single day for years — a choice to stay with him, a choice to fight for him, because for 11 years, that was the better choice,” Geragos told jurors.
When she finally left, Geragos added, “she communicated it to him, and ran into the arms of another man — a physical trainer Combs had hired to train her.”
The trial continues with more witnesses expected to take the stand.
