Joshua Goldman
Joshua Goldman
min read · June 11, 2025 · Entertainment

Diddy's Bizarre NBA Roleplay Fantasy: Inside the Sexual Thrills with Michael Jordan and More

Diddy's ex-girlfriend who's testifying under the pseudonym 'Jane' said she believed the Freak Offs the rap mogul asked her to participate in was a way of exploring his sexuality since he was 'too ashamed' to engage in sexual acts with a man

SEAN COMBS' WILD Sexual Fantasy: A Twisty NBA Roleplay That Got Him In Trouble!

In a shocking turn of events, rapper and entrepreneur Sean Combs - aka Diddy - has been accused of leading a twisted game of sexual fantasy with his ex-girlfriend, "Jane" (real name not disclosed). The bizarre scenario, which involved Diddy casting himself as Michael Jordan, his ex-girlfriend as Kobe Bryant, and another man as Shaquille O'Neal, was revealed in court yesterday during the fifth week of Diddy's sex trafficking trial.

According to Jane, who testified under a pseudonym, the hip-hop mogul's obsession with "cuckold" scenarios might have been a way for him to live out his bisexual fantasies without actually engaging with men - because he was too ashamed to do so openly.

Diddy played Michael Jordan

Jane described the lavish sexual roleplay sessions they attended during their relationship as being filled with extravagant and over-the-top sexual fantasy, where participants gave each other nicknames inspired by legendary basketball stars. But that's not all - Jane also claimed that Diddy was so addicted to sex with her that he gave her the nickname "Crack Pipe"!

The testimony emerged during Jane's cross-examination as Diddy's lawyers sought to show how close she was to him, whose real name is Sean Combs, and undermine her claims that she felt "obligated" to participate in these Freak Offs because he was paying her $10,000 a month rent for her Los Angeles home.

Diddy denies all charges of sex trafficking, but it's clear that his wild sexual fantasies have gotten him into some serious trouble!

When their relationship became problematic, Jane stumbled upon the word 'cuckold', which she said aptly described Diddy and his tendencies to watch her engage in sexual acts with the escort

Jane told defense lawyer Teny Geragos during cross-examination that she still loved Diddy. The rap mogul smiled and nodded his head despite being reprimanded by the judge about reacting when the jury is present

Kobe Bryant and Diddy ran in the same circles before the Laker's untimely death  in a 2020 helicopter crash. Bryant attended Diddy's 50th birthday party with wife Vanessa

Diddy performed at Shaq's Funhouse during Super Bowl Weekend in 2020

Diddy's mother Janice Combs has been consistently present at the trial and walked into the Manhattan Federal Courthouse on Tuesday

Trainer Paul Arthur was the third member of the group's 'trifecta' who played the role of Shaq in their bizarre Freak Offs. He also has been named by Cassie Ventura as a male escort she slept with

Dozens of bottles of Astroglide were found when Diddy's Miami home was raided. Jane claimed that Diddy was so addicted to sex with her that he gave her the nickname 'Crack Pipe'

Jane said towards the end of their relationship, Diddy's drug use began to take a toll on his body and that he looked like he had 'jaundice'