Sunday, September 21, 2025
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Cassie Told Diddy She Was Ovulating When He Asked for Freak-Off, Agreed to Kissing

Artistes

Artistes
Cassie To Diddy
I’m Ovulating, But We Can Kiss …
Response to Freak-Off Request

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Diddy asked Cassie if he had her permission to set up a freak-off … and then she told him she was ovulating … but appeared to agree on going forward with it if things remained PG.

The interesting exchange was raised Thursday while Cassie was being cross-examined by Diddy defense attorney Anna Estevao, who was going over text messages between the former couple.

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Diddy texted Cassie, asking permission to set up “freaky fun,” and her response was limited to one word — “Ovulation” … which sounds like a clear “no” to sexual intercourse. She previously testified Diddy did not want the male escorts using condoms with her during freak-offs.

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Diddy texted Cassie, asking if they could “kiss a lot,” and she agreed.

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Cassie asked Diddy which hotel would they be meeting at, and testified she offered to go to a sex shop, the Pleasure Chest, to stock up on sexual supplies … including lubricants and outfits.

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Diddy texted Cassie to “have fun, impress me” on her way to the sex shop.

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Prosecutors claim Diddy was coercing Cassie into participating in freak-offs … but it appears his defense is using cross-examination to show things between them were consensual.

This exchange happened in the summer of 2017 … towards the end of their relationship.

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