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

Published | Updated

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.

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.

051525_tmz_live_diddy_kal
CROSS-EXAMINATION BEGINS
TMZ.com

Cassie On Diddy Yes, We Were Swingers

Published | Updated

Diddy's defense says his sexual preferences are part of a swingers lifestyle, and Cassie just testified that they did some swinging.

Cassie is being cross-examined by Diddy's defense attorney Anna Estevao, and she confirmed she had conversations with Diddy about a "swingers lifestyle" when they were in a relationship.

The singer says she experienced swinging firsthand when she accompanied Diddy to sex clubs ... watching him have sex with other women multiple times -- which sounds like a reversal of the freak-offs, where a previous witness said Diddy would watch her have sex with a male sex worker.

051525_tmz_live_diddy_kal
CROSS-EXAMINATION BEGINS
TMZ.com

SZA Ask and You Shall Receive ... Gifts Fan Free Tickets, Onstage Shoutout

Published

SZA's all about adding to her loyal fans' "Good Days" ... 'cause she made one lucky dude's day by giving him free pit tickets to her show -- and shouting him out onstage.

The singer-songwriter took the stage at Gillette Stadium in Foxborough, Massachusetts earlier this week during the "Kendrick Lamar and SZA: Grand National Tour" ... and, during the performance, she leaned forward into the pit to wish her new pal Michael well.

051525_sza_kal
SHOUTOUT FROM SZA
TikTok / @tehemichael, Instagram / @tehemichael_

Check out the clip ... SZA leans forward, waves and says "Hi, Michael" before dancing across the stage -- going from playful to businesslike in no time at all.

Cassie To Diddy 'I'm Always Ready To Freak Off' ... Text Shown To Jurors

Published | Updated

Cassie expressed to Diddy that she was excited to participate in freak-offs ... at least based on a text message between the exes that was just read in court.

The singer is being cross-examined by Diddy's defense team, and jurors on Thursday were shown a slew of graphic and sexual text messages from their relationship.

In one message, Cassie tells Diddy ... "I'm always ready to freak off, it can be whenever." The text was a BlackBerry message to Diddy on August 5, 2009 ... about 2 years into their relationship.

051525_tmz_live_diddy_kal
CROSS-EXAMINATION BEGINS
TMZ.com

Diddy Trial Defense Begins Cross-Examination of Cassie ... Questions About Early, Loving Relationship

Published | Updated

The fourth day of testimony in Diddy's NYC federal sex trafficking trial began Thursday with Cassie taking the stand again ... with Diddy's defense team's turn at cross-examining her after two days of the prosecution's questioning.

Sean "Diddy" Combs' defense attorney Anna Estevao asked Cassie to read a text she sent to Combs years ago ... Cassie read it out in court, "I love you, smiley face, I'll fly anywhere for you, I love you, Cass."

Affectionate messages from Diddy were also shown to the jury from early in their relationship ... which Cassie described on the stand this morning as "loving."

"I'm a very lucky woman, I miss you so much," she said, reading from one of the exchanges.

051525_tmz_live_diddy_kal
CROSS-EXAMINATION BEGINS
TMZ.com

Chris Brown Arrested In England Over Alleged Bottle-Tossing Incident

Published | Updated

Chris Brown is in trouble with the law again -- the R&B singer was arrested Thursday in the United Kingdom over a bottle-throwing incident at a nightclub two years ago ... TMZ has confirmed.

Brown was taken into custody at a hotel in Manchester, England early Thursday morning on suspicion of grievous bodily harm, according to law enforcement sources.

The Sun reported Brown was busted hours after he flew into town on a private jet, landing in Manchester Airport.

chris-brown
BLAST FROM THE PAST
TMZ.com

Diddy Trial Photos of 4 Sex Workers Seen By Jury ... As Cassie Testifies For A Second Day

Published | Updated

More is being revealed by the minute on Day 3 of the Diddy sex trafficking trial ... federal prosecutors broke out photographs of 3 sex workers and one victim -- and showed them all to the 12 jurors.

Assistant United States Attorney Emily Johnson displayed the faces of the sex workers/victim on monitors for the jurors, starting with a picture of victim "Mia," who was allegedly raped by Diddy.

Then Johnson showed the jury two more photos -- one of sex worker Jules and another of Jules and Cassie together. A fourth photo showed Cassie and male escort Dave, as well as a fifth photo of Cassie and another sex worker named Greg.

Diddy Trial Highlights Cassie Back On The Stand ... Freak-Offs, Violence, Rape

Published | Updated
Screenshot 2025-05-14 145107
DAY 3 WRAP-UP

Cassie had a lot to say in her second day of testimony in the Diddy criminal trial ... testifying about freak-offs, physical abuse, suicidal thoughts and rape.

The prosecution's star witness was back on the stand Wednesday and she told the jury about the first time Diddy beat her and how he showed her footage from the freak-offs and threatened to release them.

douglas-wigdor-kal-05-14-2025
STRONG DAY FOR CASSIE
TMZ.com

She testified about the end of their relationship in 2018 ... telling jurors how he took her home after a nice closure conversation and then raped her on the living room floor.

Diddy Sued Raped Me With Tootsie Roll-Sized Penis

Published | Updated

Diddy raped a woman at his Manhattan apartment, but the woman said she was actually relieved when he whipped out his penis ... because she knew it wouldn't hurt that much due to a lack of length and girth -- at least according to a new lawsuit.

The Bad Boy Records founder is being sued by a Jane Doe who claims they met in May 2001 ... she says they hung out a few times without incident at his Manhattan recording studio, night clubs and a restaurant -- but things went south in July 2001 on their fourth meeting.

She claims after a night out at the club, Diddy took her back to his apartment ... leading her to his bedroom, where he locked the door and pushed her down onto the bed on her back, placing his hand around her throat and telling her, "I'm going to suck the life out of you."

Famed Defense Attorney Jose Baez How to Cross-Examine Cassie ... Tough Task for Diddy's Lawyers

Published | Updated
051425_jose_baez_kal
HOW TO COUNTER CASSIE
TMZ.com

The jury in Diddy's federal sex trafficking trial is hearing highly compelling testimony from Diddy's ex-girlfriend Cassie -- but, a very famous defense attorney has some ideas about how to effectively grill a pregnant woman on the stand.

Jose Baez, Casey Anthony's defense attorney in her 2011 murder trial, joined us Wednesday on "TMZ Live" to break down strategy for Diddy's defense team ahead of their cross-examination of Cassie.

Many think the case will rise or fall on the defense's cross-examination of Cassie -- but Baez says it shouldn't.

50 Cent Jeweler Sorry For Using Name, Image To Sell Chains ... I Won't Do It Again!!!

Published

50 Cent is getting an apology from a jeweler in New York City who was being sued by the rapper for allegedly using Fiddy's name and face to sell knockoffs of his famous crucifix chain ... and 50's case against him has been dismissed.

Maksud Agadjani from TraxNYC posted an apology to 50 Cent on all of his social media platforms ... and taped a printed out version of the statement to a storefront in the Big Apple.

In the apology, Agadjani says he's "writing to express my sincere and heartfelt apology" and he acknowledges using 50's name, image and other IP rights to "advertise, market, and sell my jewelry products without your permission."

Diddy Trial Cassie Reveals How Much $$$$ She Got In Lawsuit Settlement

Published | Updated

One of the biggest mysteries in the Diddy-Cassie saga was answered at the music mogul's federal criminal trial Wednesday ... Cassie settled her lawsuit against Diddy for a whopping $20 million!

Federal prosecutor Emily Johnson was grilling Cassie on Day 2 of her testimony at Diddy's sex trafficking trial in NYC when the questioning turned to a book she wrote about the alleged abuse she suffered at the hands of Sean "Diddy" Combs -- her former longtime boyfriend.

051425_diddy_cassie_unedited_kal_v2
THE FULL, UNEDITED VIDEO
Department of Justice

Cassie testified that her mom helped her write a "book with chapters," which she wanted Diddy to read. She testified she sent the chapters to Diddy through her attorney, but Diddy didn't take her book seriously.

Cassie Diddy Raped Me After We Split ... I Tried to Hurt Myself!!!

Published | Updated

More fireworks from the Cassie Ventura testimony in the Diddy case ... she told the jury Diddy raped her on the floor of her own home after they broke up -- and she later tried to hurt herself because she couldn't take all the pain.

The singer testified Wednesday that in August 2018 they had a closure conversation to shut the book on their relationship ... meeting at a restaurant in Malibu, where Diddy was being nice, playful and romantic. She said he drove her home and forced sex on her.

Cassie told the jury Diddy's eyes went black as he raped her on her living room floor.

Tory Lanez Stabbed After Contacting Megan Thee Stallion's Team ... Team Says Kelsey Harris Was The Shooter!!!

Published | Updated
051425_tory_lanez_presser_kal_v2 5/14/25
CONVENIENT TIMING...
TMZ.com

Update

3:47 PM PT -- Alex Spiro tells TMZ ... "Tory Lanez was tried and convicted by a jury of his peers and his case was properly adjudicated through the court system. This is not a political matter -- this is a case of a violent assault that was resolved in the court of law."

As he recovers from the brutal prison stabbing, Tory Lanez's reps held a press conference to claim Megan Thee Stallion's ex-BFF Kelsey Harris is the one who should be locked up for the 2020 shooting!!!

Several constituents for Unite The People addressed the media on Wednesday in Downtown L.A., and the org's lead legal consultant, Walter Roberts, claims a bodyguard by the name of Bradley James overheard Kelsey admitting to actually firing the gun that shot Megan.

James allegedly heard Kelsey say she fired the gun 3 times, in which Tory grabbed her arm and knocked it down, causing the weapon to fire 2 times more.

Cassie Diddy Flipped Over My Kid Cudi Relationship

Published | Updated

Cassie Ventura says Diddy freaked out on her after finding out she was hooking up with Kid Cudi ... threatening her with a wine opener and telling her he would release a video on Christmas showing her participating in a "freak-off."

The singer testified in court Wednesday that Diddy found out she was seeing Kid Cudi in 2011 when he went through her phone during a freak-off.

051425_diddy_cassie_unedited_kal_v2
THE FULL, UNEDITED VIDEO
Department of Justice

Cassie told the jury Diddy found an email about Cassie taking her toiletry bag to Kid Cudi's place ... and he put a wine opener in his hand and threatened her.

Florida Man Trump Hotel Shooter's Diddy Sex-for-Hire Claims Resurface

Published
051425_jonathan_oddi_kal
ENCOUNTERS WITH DIDDY & CASSIE
NewsNation

Details of Diddy's alleged "freak-offs" have been coming out in public for months ... and now a man who shot up a Trump hotel in Florida years ago and made wild claims about Diddy and Cassie at the time is seeing his story re-examined in context.

Jonathan Oddi -- who's currently incarcerated in Miami -- dropped some sensational allegations in an exclusive "Banfield" segment on NewsNation Tuesday night, claiming he had been hired years ago by Diddy as a "sex slave" to get it on with Cassie ... and some of his assertions are similar to previous reports about the couple's proclivities.

051425_jonathan_oddi_surveillance_kal MAY 2018
SHOOTOUT WITH COPS

In May 2018, a masked Oddi walked into the Trump National Doral Miami Hotel and Resort and fired his Glock pistol a bunch of times into the ceiling, then draped an American flag over the front desk and started breaking computers ... and when responding officers showed up, he fired at them, prompting a massive shootout with five cops. He fired at least 16 times ... and was arrested after being shot in his legs.