Cassie’s explicit messages with Sean ‘Diddy’ Combs read aloud to jury

R&B singer Cassie was forced under cross-examination to read to a jury her sexually explicit messages with former boyfriend Sean “Diddy” Combs, some of which showed her expressing enthusiasm for encounters with other men at Combs’ behest that she previously said she “hated doing”.

Lawyers for Combs are seeking to portray Cassie as a willing participant in his sexual lifestyle and say that, while he could be violent, nothing he did amounted to a criminal enterprise.

Combs denies all the allegations and has pleaded not guilty to federal sex trafficking and racketeering charges.

Prosecutors say he exploited his status as a powerful music executive to violently force Cassie and other women to take part in these encounters with sex workers, which he called “freak-offs”, and of using his network of employees to facilitate illegal activities, which is a key part of the racketeering charge.

Messages between Combs and Cassie – both romantic and lurid – were the focus of the fourth day of evidence in Manhattan.

Defence lawyer Anna Estevao read aloud what Combs said while Cassie recited what she wrote to him.

Cassie, whose legal name is Casandra Ventura, read numerous explicit messages, including some in which she described in graphic detail what she wanted to do during the freak-offs.

At one point, she asked for a short break from the readings, which Judge Arun Subramanian granted.

In August 2009, Combs asked her when she wanted to have the next episode, and she replied “I’m always ready to freak off.”

Two days later, Cassie sent an explicit message and he replied in eager anticipation.

She responded: “Me Too, I just want it to be uncontrollable.”

Combs’ lawyers have insisted that all the sex at the freak-offs was consensual.

Later that year, however, she had also sent Combs messages that she was frustrated with the state of their relationship and needed something more from him than sex.

As the messages were read, Combs appeared relaxed at the defence table, sitting back with his hands folded and his legs crossed.

The courtroom was packed with family and friends of Combs, journalists and a row of spectator seats occupied by Cassie’s supporters.

While reading more affectionate conversations, Cassie said that Combs was charismatic, a larger-than-life personality.

“I had fallen in love with him and cared about him very much,” she said.

Ms Estevao spoke gently during the questioning, which at times had such a friendly tone that they seemed like two girlfriends chatting.

Cassie, however, did complain once that jurors were not hearing the full context of the messages the defence was highlighting, saying: “There’s a lot we skipped over.”

As the messages were read, Combs appeared relaxed at the defence table, sitting back with his hands folded and his legs crossed.

The courtroom was packed with family and friends of Combs, journalists, and a row of spectator seats occupied by Cassie’s supporters including her husband.

The 38-year-old Cassie – who is in the third trimester of pregnancy with her third child – has held up well in the witness box.

She cried several times during the previous two days of questions by the prosecution, but for the most part has remained composed and matter-of-fact as she spoke about the most sensitive subjects.

The Associated Press does not typically name people who say they have been sexually abused unless they come forward publicly, as Cassie has.

During a break, Combs stood at the defence table, huddling with his lawyers, holding a pack of Post-It notes in one hand and a pen in the other.

At one point, he turned to the gallery and acknowledged a few reporters who were studying his demeanour.

“How you doing?” he asked.

Combs’ daughters were not in the courtroom on Thursday as the explicit messages were read and shown to the jury.

Jurors leaned forward in their seats to follow along as the messages were displayed on monitors in front of them in the jury box.

One woman shook her head as a particularly explicit message was shown.

A man stared intently at the screen, pressing his thumb to his chin.

Other jurors appeared curious and quizzical, some looking at Cassie or jotting notes.

Cassie’s evidence on cross-examination was in contrast to Wednesday, when she described the violence and shame that accompanied her “hundreds” of encounters with male sex workers during her relationship with Combs, which lasted from 2007 to 2018.

While prosecutors have focused on Combs’ desire to see Cassie having sex with other men, she said that she sometimes watched Combs have sex with other women.

She said Combs described it as part of a “swingers lifestyle”.

Ms Estevao asked Cassie directly whether she thought freak-offs were related to the swingers lifestyle.

“In a sexual way,” Cassie responded, before adding: “They’re very different.”

Cassie said on Tuesday that Combs was obsessed with a form of voyeurism where “he was controlling the whole situation”.

The freak-offs took place in private, often in dark hotel rooms, unlike Combs’ very public parties that attracted A-list celebrities.

She said she sometimes took IV fluids to recover from the encounters, and eventually developed an opioid addiction because it made her “feel numb” afterwards.

When questioned by Ms Estevao, Cassie agreed that Combs once communicated to drug dealers in Los Angeles to stop delivering drugs to her, and he suggested she get treatment.

Cassie said Combs only wanted her to do drugs with him, not friends.

She alleged on Wednesday that Combs raped her when she broke up with him in 2018, and that he kept her locked in a life of physical abuse by threatening to release videos of her during the freak-offs.

Cassie sued Combs in 2023, accusing him of years of physical and sexual abuse.

Within hours, the suit was settled for 20 million dollars (£15 million) – a figure Cassie disclosed for the first time on Wednesday – but dozens of similar legal claims followed from other women.

Combs, 55, has been jailed since September.

He faces at least 15 years in prison if convicted.