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Home / World

Diddy trial: Lawyers reveal Cassie Ventura‘s texts about freak-offs

By Benedict Brook
news.com.au·
15 May, 2025 10:15 PM5 mins to read

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Sean Combs’ lawyers have grilled ex-partner Cassie Ventura uncovering texts including one where she said he was 'always ready' for sex parties. Photo / Getty Images

Sean Combs’ lawyers have grilled ex-partner Cassie Ventura uncovering texts including one where she said he was 'always ready' for sex parties. Photo / Getty Images

  • The jury in Sean “Diddy” Combs’ trial saw graphic texts between him and Cassandra Ventura about “freak-off” parties.
  • Ventura claimed she was coerced into the parties, but Combs’ defence presented texts suggesting her willingness.
  • Combs faces charges including sex trafficking and racketeering, which he denies; Ventura remained composed during cross-examination.

WARNING: Graphic content

The jury in the New York trial of Sean “Diddy” Combs has seen graphic, sexually explicit texts exchanged between the star and then-girlfriend Cassandra Ventura, some regarding his now infamous “freak-off” sex parties.

The sex sessions would involve Ventura having sex with male sex workers while Combs watched and sometimes participated.

On Thursday (US time), Combs also seemed more animated than previous court appearances; taking notes while Ventura was cross-examined.

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His defence team also sought to throw doubt on Ventura’s claims she was naive sexually when she began dating Combs, pointing out she was already in a relationship with an “older man”.

Singer Ventura is the star witness in Combs’ trial where he is charged with transportation to engage in prostitution, sex trafficking and racketeering.

Combs could face life in jail for just the racketeering charge. He denies all charges.

Ventura began her second day of questioning by Combs’ lawyers on Thursday. Despite the graphic and deeply personal subject matter, she remained composed.

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The court had heard earlier testimony from Ventura, who dated Combs for 11 years from 2007, that she initially agreed to take part in the freak-offs because she was naive and in love with the musician and producer.

But she later felt cajoled and blackmailed into continuing with the frequent and often days-long drug-fuelled sex parties.

However, Combs’ defence produced texts and emails on Thursday from Ventura saying she was “always ready” for a freak-off several years after the sex parties began.

And when, in these text message exchanges, she did question the freak-offs it was suggested it was more to do with the level to which Combs loved her than the sex sessions themselves.

Diddy and Cassie were in a relationship. Picture / Instagram
Diddy and Cassie were in a relationship. Picture / Instagram

In court, Combs’ lawyers revealed romantic texts from 2009. He would often call her “baby girl” or “BG” and her nickname for him was “Pop Pop”.

“I love you so much. It makes me feel like I can’t wait until we don’t have to care anymore,” one text from Ventura to Combs read.

His lawyers said that message showed how keen Ventura was to go public with their relationship, which had been under wraps.

“Pop pop, I really miss you,” she wrote.

“Me too baby,” replied Combs. “Damn I can’t wait to see you again.”

‘Wanna be nasty’

In August 2009, two years after she and Combs started dating and around a year and a half after the freak-offs began, Combs texted Ventura asking “when do you want to freak off?”

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“I’m always ready to freak off, LOL,” replied Ventura.

In court she said her texts seeming to approve of freak-offs were “just words at that point”.

Further messages from around the same time were more sexually focused.

“There are things I want to do for you and to you,” wrote Combs in December 2009.

“I wanna be nasty for you.”

The jury were also shown texts from 2012 of Combs asking Ventura if she was “horny” and her replying “you like it when I moan”.

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“One of my favourite times is when we freak off and we make love after,” he wrote.

“I love when we make love after,” she replied.

Janice Combs. Photo / AFP
Janice Combs. Photo / AFP

Ventura asks for break

The court was shown even more graphic texts about sexual positions and Ventura describing male genitalia.

“I can’t wait to watch you,” wrote Combs, about his girlfriend having intercourse with another man.

“I want you to get real hot.”

Ventura replied: “Me too. I want to be uncontrollable.”

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Another explicit text the singer wrote – in which she graphically described what she couldn’t “wait” for her then-boyfriend to do to her – finally pushed her over the edge.

Ventura immediately asked the judge for a break after the raunchy text was read. The singer – who is eight months pregnant – was seen grabbing her belly with both hands at the time.

Her husband, Alex Fine – who is the father of her children – was in the courtroom.

‘Dirty, grimy’

Nonetheless, not all of Ventura’s communications with Combs about freak-offs were positive.

In 2009, after Combs said he wanted to “get nasty” Ventura said she needed to feel she “trusted” the star “beyond it being just sexual”.

“The last time was a mistake,” she said, referring to a sex party.

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“It made me feel dirty and grimy, not sexual and sensuous.

“That’s the reason I go back and forth in my mind with wanting and not wanting to do freak offs when we’re so in love.”

Ventura wrote that initially freak-offs “felt right” but later “I get nervous I’ve just become the girlfriend that you get your fantasies off with and that’s it”.

Earlier in the week, Ventura has given testimony where she claimed she was “sexually inexperienced” when she met Combs. She said Combs “introduced me to the idea of oral sex” at the Trump International Hotel in New York.

“It was not something I did or understood.”

But defence lawyer Anna Estevao raised the fact that Ventura had already been in a relationship with music producer Ryan Leslie.

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“It wasn’t the first time you’d been dating an older man, right?” she asked.

Ventura conceded she had been in a romantic relationship immediately before Combs.

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