Sean “Diddy” Combs’ trial took another intense turn Thursday as Cassie Ventura was cross-examined by his defense attorney, Anna Estevao. One of the more eye-opening moments involved a text exchange about a planned “freak-off” — and Cassie’s one-word response: “Ovulation.”
Cassie and Diddy’s Texts Revealed in Court
During questioning, Diddy’s lawyer presented text messages from 2017 — near the end of the couple’s relationship — in which Diddy asked for Cassie’s permission to arrange some “freaky fun.” Cassie responded with just one word: “Ovulation” — which the defense implied was a sign she didn’t want to have unprotected sex.
Cassie previously testified that Diddy did not allow male participants in these freak-offs to use condoms. Her response about ovulating seemed to serve as a boundary
Cassie Seemingly Agreed—But With Conditions
Despite the warning, Diddy replied asking if they could “kiss a lot,” and Cassie agreed. The singer also texted Diddy about which hotel they would meet at and offered to visit the Pleasure Chest, a known sex shop, to pick up lubricants and outfits.
According to testimony, Diddy encouraged her to “have fun” and “impress me” on her way to the store.
Consent vs. Coercion: The Core Legal Debate
Prosecutors argue that Diddy used coercion and manipulation to involve Cassie in these sex acts, dubbed “freak-offs.” However, Diddy’s legal team is using cross-examination and text evidence to paint a different picture — one suggesting that Cassie’s participation was consensual, even near the end of their relationship.
Context: Summer 2017 and the Decline of Their Relationship
This incident reportedly happened in summer 2017, just months before Cassie and Diddy parted ways. It adds another layer of complexity to the case, as the court tries to determine whether consent was freely given — or if Cassie felt she had no real choice.
