Cassie Forced to Read Diddy ‘Freak-Off’ Texts Aloud in Sex Trafficking Trial Cross-Exam

Cassie Ventura was forced to read dozens of pages of explicit text messages aloud between her and former boyfriend Sean “Diddy” Combs during her cross-examination on the fourth day of the music mogul’s sex trafficking trial Thursday.

Combs’ defense attorneys including Anna Estevao, who was leading the questioning, focused on labeling the mogul’s behavior as consensual and part of a “swingers” lifestyle. According to the AP, Estevao began by having Ventura read “loving emails and text messages” the pair shared in the early stages of their relationship, including an August 2009 text message where Combs said to her, “I love you sooooo much it makes me cry.” She testified that she was in a relationship with the mogul and admitted she loved him at the time of the messages.

Estevao then moved on to the music mogul’s infamous “freak-offs,” which have been described as days-long, drug-fueled sex parties. These events are said to have involved Combs compelling women into taking drugs and having sex with male escorts while he watched and recorded.

“When do you want to freak off? Lol” a text message from Combs read in August 2009, per the AP’s reporting. Ventura replied, “I’m always ready to freak off.” Two days later, the conversation came up again with Combs saying, “I can’t wait to watch you. I want you to get real hott,” to which she replied, “Me Too, I just want it to be uncontrollable.”

Combs’ defense has maintained that the now-notorious group events were consensual and that these texts prove their case. After being asked to read the graphic text messages aloud, at one point Ventura asked for a break and Judge Arun Subramanian granted her request.

Ventura previously testified that she was forced to participate in these sexual encounters, which would often go on for days, and that she “hated” having sex with other men.

The singer expressed concern during the cross-examination that jurors were not hearing the full context of the messages that Estevao requested be read aloud. “There’s a lot we skipped over,” she said.

She also read messages where she told Combs she was not satisfied with their relationship and wanted it to be about more than sex. In an April 2010 email addressed to Combs she said, “I am really hurt by the way you deal with me, I don’t need your money, I need some attention.”

According to the AP, the content of the messages was also displayed on monitors in front of the jury box, prompting one female juror to shake her head at a particularly explicit text.

Later in the trial, according to multiple media reports, Estevao asked Ventura about the night Combs suffered from an apparent overdose from painkillers following a night at a sex club together in San Bernardino, California. Estevao pressed Ventura on the February 2012 incident, which happened after she went home and Combs partied at the Playboy Mansion. The rapper allegedly took a strong opiate and Ventura took him to a hospital where she was told he overdosed on painkillers.

Ventura testified that she thought Combs was an addict. She has also has been open about her own addiction to opioids and about their shared drug use throughout the relationship.

On Wednesday, Ventura testified that she developed an opioid addiction and considered suicide because of her abusive relationship with Combs. In order to recover from the sometimes days-long parties, in which she says she had sex with male escorts while Combs watched and recorded, the R&B singer said she relied on IV fluids, massages and opioids. Her reliance on the latter eventually developed into an addiction. “Opioids make me feel numb, which is why I relied on them so heavily,” she explained.

Combs’ defense claimed that he suffered from drug addiction as well and Estevao ended her Thursday cross-examination by asking Ventura if they had taken a “bad batch” of MDMA that preceded his 2016 assault on her at the Intercontinental hotel in Los Angeles. Ventura refuted the notion saying she had “no idea” if the MDMA was in fact laced with other drugs.

In Wednesday’s testimony, Ventura revealed that she received a $20 million settlement for the lawsuit she filed against him in November 2023. The suit was settled the next day and was soon followed by an avalanche of accusations of sexual abuse and assault from other alleged victims.

Ventura is one of four witnesses expected to testify against Combs, who is facing charges of one count of racketeering conspiracy, two counts of sex trafficking by force, fraud or coercion and two counts of transportation to engage in prosecution.

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