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Hugh Hefner's ex-girlfriend Kendra Wilkinson detailed what she saw during Diddy's infamous parties

Home> Celebrity

Published 16:32 26 Oct 2025 GMT

Hugh Hefner's ex-girlfriend Kendra Wilkinson detailed what she saw during Diddy's infamous parties

The Girls Next Door star moved into the Playboy Mansion with Hefner after meeting at his 78th birthday party in 2004

Ella Scott

Ella Scott

Warning: This article contains discussion of sexual assault allegations which some readers may find distressing.

Ex-Playboy model Kendra Wilkinson revealed that she'd been to 'one or two' of Sean 'Diddy' Combs' parties and spoke about what she saw.

On May 5, the trial of 55-year-old rapper Diddy, who was charged with sex trafficking, racketeering and transportation to engage in prostitution last year, began.

The rapper has plead not guilty to the charges against him and has repeatedly denied all allegations of wrongdoing.

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The star was detained at the Metropolitan Detention Center in Brooklyn, New York, after his arrest on September 16, 2024.

Diddy, who was denied bail numerous times, is charged with hosting parties, known more commonly as ‘Freak Offs’, where he'd allegedly force sex-trafficking victims to engage in group sex acts.

Sean 'Diddy' Combs' trial began earlier this week (Shareif Ziyadat / Contributor / Getty)
Sean 'Diddy' Combs' trial began earlier this week (Shareif Ziyadat / Contributor / Getty)

An indictment reads: "After Freak Offs, Combs and the victims typically received IV fluids to recover from the physical exertion and drug use."

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Prosecutors have also accused the Bad Boy Records founder of recording sex acts - sometimes without the victim's knowledge - during these ‘freak offs’. Judge Arun Subramanian, who has been on the federal bench since 2023, will preside over the Diddy case.

One famous face who has confirmed that she'd attended a couple of P Diddy parties in the past is Kendra Wilkinson, one of Hugh Hefner’s former girlfriends.

In an interview with KIIS FM host Jackie 'O' Henderson, Wilkinson was asked about 'going to P Diddy's parties back in the day'.

She replied: "I remember just going to like one or two, but again, like I had a great time in my youth.

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Kendra Wilkinson admitted to attending a couple of Diddy's infamous events (Paul Archuleta / Contributor / Getty)
Kendra Wilkinson admitted to attending a couple of Diddy's infamous events (Paul Archuleta / Contributor / Getty)

"Like, I didn't really see anything. Like I never saw anything really bad happening around me. Sex is sex, in my opinion."

When asked if she saw anything abnormal to that of a typical 'Hollywood party,' Wilkinson responded: "Look, you're going to the Playboy Mansion. You know, there's girls topless in the grotto.

“Don't we already know that. [...] [The Mansion] was pretty nasty. You know, there was dog poop everywhere and Hef [Hefner] would wobble by and just pick it up with his bare hands."

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Wilkinson has previously spoken out about how Playboy 'really messed [her] whole life up'.

She ultimately resolved about her experiences with Diddy: "I'm not saying that something bad didn't happen. I'm saying that, you know, nothing bad ever happened to me."

A timeline of events leading to Sean 'Diddy' Combs' trial

November 2023: Cassie Ventura files a civil lawsuit against Sean 'Diddy' Combs

Musician and Diddy's ex-partner, Cassie Ventura, filed a lawsuit accusing him of rape and years of abuse. She said he used his power to 'set the groundwork' for a 'manipulative and coercive romantic and sexual relationship.' The lawsuit was settled out of court the day after for an undisclosed amount.

February 2024: Another lawsuit filed

Music producer Rodney ‘Lil Rod’ Jones filed a lawsuit alleging Combs 'sexually harassed, drugged and threatened him', as reported by NBC. Combs' lawyer Erica Wolff quickly fired back at Jones' claims saying: "Mr. Jones’s lawsuit is pure fiction — a shameless attempt to create media hype and extract a quick settlement."

March 25, 2024: Federal raids

Diddy's properties in LA, Miami and New York were raided by Homeland Security after they served search warrants in the early hours of the morning. The raid was in connection with a sex trafficking investigation - which is one of the charges Diddy is facing.

May 17, 2024: Assault video released

CNN released a video which showed Diddy attacking ex-partner Cassie Ventura in the hallway of a hotel. The video is said to be from 2016. The video mirrors the assault allegations Cassie made in her lawsuit against the disgraced music mogul.

May 19, 2024: Public apology

Diddy posted a video to his Instagram and Facebook accounts, apologising for the assault on Cassie. He said in part: "So difficult to reflect on the darkest times in your life, sometimes you got to do that. I was f**ked up.

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"I mean I hit rock bottom, but I make no excuses, my behaviour in that video is inexcusable. I take full responsibility for my actions in that video, I'm disgusted."

September 16, 2024: Federal arrest

Combs was arrested in Manhattan after a grand jury indicted him on charges of sex trafficking and racketeering. Diddy is charged with racketeering conspiracy, two charges of sex trafficking and two charges of transportation to engage in prostitution, as reported by the BBC. These also include accusations of kidnapping and drugging his victims.

October 10, 2024: Trial date set

A federal judge set May 5, 2025, as the start date for Diddy's trial.

February 21, 2025: Diddy's defense Attorney quits

Anthony Ricco, one of Diddy's defense attorneys withdrew from the high profile case citing an inability to continue effectively representing him. He said at the time: "Under no circumstances can I continue to effectively serve as counsel for Sean Combs, consistent with the ABA Standards for Criminal Justice.

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"While I am aware that the Local Rule requires that an application for withdrawal of counsel is supported and granted 'only upon a showing by affidavit or otherwise of satisfactory reasons for withdrawal,' there are sufficient reasons (related to the protections afforded by the attorney/client privilege) for brevity in my application for withdrawal as counsel in this case."

May 5, 2025: Trial begins

Jury selection commenced in Manhattan federal court, marking the official start of Diddy's trial.

Featured Image Credit: Kyle and Jackie O Show

Topics: Diddy, Hugh Hefner, Crime, Celebrity

Ella Scott
Ella Scott

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