EXCLUSIVE: Radar's Diddy 'Freak Off' Files — We Reveal the Most Revolting Secrets of Rapper's Kinks Including 'Gay Play' and 'Watersports'
An escort has revealed the kinky requests of Cassie Ventura and Sean 'Diddy' Combs.
June 25 2025, Published 3:10 p.m. ET
One of Sean 'Diddy' Combs' sexual escorts has given RadarOnline.com an exclusive inside look at the disgraced rap mogul's "kinks and fetishes" he was asked to fulfill at his infamous "freak off" parties.
Clayton Howard said he was shocked by some of the alleged requests, including one that he said seemed to answer the question about Combs' long-debated sexuality.
Combs' trial is wrapping up.
As Combs' sex trafficking trial enters its final phases, one of the 55-year-old's top former "freak off" partners has shared his personal experiences with the rapper and his then-girlfriend Casandra 'Cassie' Ventura.
In his explosive new tell-all book, Cassie: Victim or Co-conspirator, Howard, who went by the name "Dave" during his sexual sessions with the couple, claimed Ventura initially hired him under the instructions that the two were to have sex while her "husband" watched and pleasured himself in the corner of a hotel room.
Howard claimed he "worked" for the couple for nearly a decade but did not have much interaction with Combs at the start, as the rapper would sit quietly in the corner with various articles of clothing wrapped around his face to conceal his identity.
It took nearly a year, but once he discovered the mystery figure in the shadows was Combs, the alleged requests became increasingly more graphic from both music stars.
Sexual Preferences
Clayton Howard spent a decade as one of Combs' personal escorts.
Howard claimed Combs tried to get him to have anal sex with the rapper but does not think this makes him gay.
"He's definitely bisexual," Howard claimed to Radar in an exclusive interview.
He claimed most nights "Diddy wanted to watch me masturbate for hours. I couldn't watch another man masturbate for a minute, but he sat there for hours watching my body as he masturbated to please himself. This always made me uneasy."
Often, Howard would begin having sex with Ventura, while Combs would allegedly tag in later in the session. One time, the escort speculated Combs was trying to seduce him.
"He had me stand in front of him as he was giving Cassie oral sex," Howard claimed. "He kept positioning his anus right in my line of sight while he had me stand in front of her."
Seduction Techniques
He said the rapper tried to seduce him.
As Howard would adjust his position to try to steer clear of Combs, he realized the rapper was presenting himself – much like a horny animal would to a prospective mate.
"He kept trying to move. He kept positioning me in his line of sight," he claimed. "He was trying to manipulate me into thinking his anus was a vagina."
Cassie's Requests
Ventura wanted Howard to pee on her.
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Howard claimed Ventura had her own kinky requests as well.
"Every time I saw her for probably the first year or two she would beg and try to seduce me to urinate on her, which was weird to me because she's a beautiful girl," he claimed.
The escort would repeatedly politely decline her requests and tell her "he was not that kind of lover," which she accepted willingly and eventually stopped asking.
Howard did one day ask about her kinky desire to be peed on.
He claimed: "She liked the way the warm urine felt running down her chest and her body."
