Diddy Trial Day 2: Pee pee, paranoia, and poolside punishment

Cassie Ventura’s chilling testimony details a decade of control, coercion, and “Freak Offs” disguised as love. As disturbing footage looms, Diddy’s lawyers scramble to spin the narrative.

Sean "Diddy" Combs watches as his former girlfriend Casandra "Cassie" Ventura is sworn in as a prosecution witness before U.S. District Judge Arun Subramanian at Combs' sex trafficking trial in New York City, New York, U.S., May 13, 2025 in this courtroom sketch.

just in case you missed our coverage of Day 1.

First off, we want to show grace to every victim involved in this case

Sexual violence, and any violence for that matter is not something to play around with. And we hope that justice is fairly sought for the sake of the victims involved.

Now that this is out the way, Day 2 was a shitshow. Basically, we got a front row seat to a Freak Off crash course we weren’t ready for. And boy did Cassie show us the way.

She served up a play-by-play of her “humiliating” relationship with Combs, including claims that he urinated in her mouth, forced her to carry a gun while high on mushrooms, and recorded their encounters as “blackmail materials.” 

Let that sink in. She also testified about being punished like a child (no phone, no laptop) and treated like a sexual accessory for several day-long sex benders that left her dehydrated and drugged out.

Oh, and let’s not forget the baby oil kiddie pool. No literally. Cassie recounted a kiddie pool at one point being filled with Diddy’s infamous Diddler oil. Totally normal stuff. Right?

Meanwhile, Combs’ legal team is busy insisting this is all just kink-shaming and that maybe, just maybe, the jury is being swayed by Cassie’s very pregnant presence. Real smooth guys. What a great time to be a man.

1,000 bottles of baby oil and not a single alibi

If you thought the baby oil pool was just a one-off freaky breakdown, think again. According to prosecutors, a raid on Combs’ properties turned up 1,000 bottles of the stuff—enough to lube up an entire party at St. Bart’s (that’s a whole other story). 

Now. Diddy’s lawyer, of course, had some things to say. For one, he disputed the amount of oil, because why not defend your client’s oil usage?

Cassie also testified that refusing Diddy’s demands wasn’t really an option. She described the vibe as “do it or deal with the consequences.”

Gun in the purse, mushrooms in the system, fear in the air

In one especially deranged detour, Cassie testified that during a Freak Off in L.A., Diddy got word Suge Knight was nearby. Naturally, the only logical response was to pack up the orgy and go hunting. Cassie says she was crying, begging him not to do anything stupid—so naturally, she was handed a gun and told to hold it in her purse while high on mushrooms. 

Because nothing says “responsible adult” like combining psychedelics with loaded firearms. She had no idea why she had the gun, except to feel “terrified”—a feeling that apparently came standard in Diddy’s circle of trust.

Freak offs as a job

Once Cassie Ventura took the stand, the prosecution wasted no time painting a picture of psychological warfare masquerading as a relationship. Ventura testified that Diddy kept her under 24-hour surveillance and would “punish” her by having his security team take away her phone and laptop.

No warning, no timeline. Just digital silence until he decided she’d earned access to the outside world again. When asked what else he took from her, she replied: “My self-confidence.”

She told the court how Combs micromanaged her appearance, from her French-tipped nails to her gym routine—specifically to prep her for the infamous “Freak Offs.” 

These were elaborate sex setups involving escorts, drugs, and role-play scenarios that lasted up to four days. She said she’d be left dehydrated and recovering afterward, noting that “the Freak Offs became a job.”

“I was confused. I was naive. And he had my career in his hands.”

Ventura recounted how Combs first kissed her on her 21st birthday in Las Vegas — a moment she described as deeply uncomfortable.

“I didn’t want him to,” she told the court, adding that she was already in a relationship at the time. But saying no to someone who controlled her record deal didn’t feel like an option.

The two would later meet at the Trump International Hotel in Manhattan, where Ventura says Diddy initiated oral sex, despite the 17-year age gap and her reluctance.

She testified she didn’t reciprocate. “He made me feel crazy for that,” she said. “But I didn’t understand. I was in a relationship with someone else.”

From there, Ventura described how Diddy began recording their intimate moments, allegedly calling the footage his “blackmail materials.” He had the means to distribute it, she claimed, and that knowledge kept her in a constant state of fear and compliance.

She also dropped a damning note about her music career: Ventura signed a 10-album deal with Bad Boy Records in 2006 — and only one ever came out. The implication? Her music was never the priority — control was.

Damage control in designer suits: The defense fires back

Diddy’s lawyers came out swinging, focusing on Phillip, the male escort Ventura testified she was made to hire and perform with during the infamous “Freak Offs.”

The goal? Paint Cassie as the one in control.Attorney Xavier Donaldson pressed hard:

  • “Did she pay you?” — Yes.

  • “Was she drunk or high?” — No.

  • “Was she in complete control?” — I can’t say that, Phillip replied.

That last answer? Not the win the defense was hoping for.

The subtext here was clear: they wanted to show that Ventura had agency, that this was a consensual experience — not coercion. But Phillip’s hesitation undercut the narrative. If anything, it reinforced that this wasn’t some wild, consensual Hollywood kink party — it was a performance with layers of pressure, power, and manipulation.

Then came the pregnancy pivot.

Marc Agnifilo, one of Combs’ lead attorneys, argued that Ventura’s visibly 8-and-a-half-months pregnant appearance might unfairly sway the jury. His request? That she be seated in the witness box before jurors enter, so they wouldn't witness her walking, breathing reminder of womanhood and vulnerability.

He told the judge, “Pregnancy is beautiful and wonderful. It is also a source of potential sympathy.” Translation: “Please don’t let her belly cost us the case.”

Our thoughts

Cassie Ventura’s testimony wasn’t just about salacious details — it was about power. Controlled routines. Carefully orchestrated humiliation. And a man who allegedly weaponized wealth, fame, and loyalty to manipulate nearly every corner of her life.

While Diddy’s team tries to frame it all as consensual, the prosecution is sketching a much darker portrait — one where sex wasn’t intimacy, but currency. Where love came with surveillance. Where punishment meant silence, and the price of speaking up is everything.

As the trial continues, one thing is clear: this isn’t about gossip anymore. It’s about accountability.

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