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

For your consideration by For your consideration
May 15, 2025
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Cassie Told Diddy She Was Ovulating When He Asked for Freak-Off, Agreed to Kissing
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Cassie To Diddy
I’m Ovulating, But We Can Kiss …
Response to Freak-Off Request

Published May 15, 2025 12:12 PM PDT

cassie diddy ovulation getty comp 4

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.

cassie diddy 2017 sub getty

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.

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

cassie ventura p diddy sub getty swipe

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.

p diddy cassie ventura court sub reuters swipe

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


Diddy Inside the Trail-INLINE-PROMO-watch-free

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

Published May 15, 2025 12:12 PM PDT

cassie diddy ovulation getty comp 4

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.

cassie diddy 2017 sub getty

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.

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

cassie ventura p diddy sub getty swipe

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.

p diddy cassie ventura court sub reuters swipe

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


Diddy Inside the Trail-INLINE-PROMO-watch-free

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.

related articles


    Diddy


    Cassie


    Crime & Arrests


    Hip Hop


    Sex


    Diddy Trial


    Fairly Legal

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