“That’s a difficult story” — Clayton Howard recounts how Cassie allegedly forced him to have s*x on her menstrual cycle, with Diddy watching

In Sean "Diddy" Combs' trial, several names of male escorts were mentioned in court. Clayton Howard, one of the male escorts allegedly hired by Combs to join "freak-offs" with his ex-girlfriend Cassie Ventura, has now filed a lawsuit against the former couple. The lawsuit was filed just days after Diddy was acquitted of s*x trafficking and racketeering charges.

Disclaimer: This article contains mentions of alleged s*xual assault and coercion. Reader discretion is strongly advised.

On July 3, TMZ reported on the lawsuit filed by Clayton Howard, in which the male escort accused Cassie and Diddy of drugging, manipulating, and traumatizing him for years. Howard was one of the male "entertainers" that prosecutors claimed the Combs transported across state lines for prostitution purposes.

Recently, the male escort appeared on an interview with The Art of Dialogue podcast and shared his experience. The first part of the interview was aired on July 11, 2025. The podcast channel dropped the third part on July 13, 2025.

In the interview, the male escort was asked if Cassie Ventura "forced" him into s*xual encounter during her menstrual cycle, to which Clayton Howard responded:

"She didn't put hands on me. She forced herself on me, by that's a difficult story, but it's not too hard to tell once you understand what happened. Um, she calls me for one encounter."

He further revealed in the interview that once Cassie called him to join for a "freak-off" while he was with his girlfriend. Howard claimed that he reluctantly went there as Diddy and Cassie were paying him well for the last few years.

Howard claimed that Cassie was under the influence of alcohol and alleged that she was "too aggressive," and they proceeded to engage in s*xual activity. He further revealed that after it ended, he turned on the side lamp and noticed blood all over, which left him extremely upset.

"Bro, it's blood everywhere. Blood on the sheets, blood on the floor underneath me, darkened bloodstains in my lap. So, the first thing I'm doing is I'm looking at her like, "Yo, what the hell?" And she pretends like, "Oh my god, I didn't know I had my period. It must have just came." But the way she said it and the smirk on her face, I said, "Yo, she lying." So, I got pissed," Howard said.

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What more did Clayton Howard claim about Diddy and Cassie in the podcast?

The male escort alleged in the podcast that Cassie Ventura drugged him once on the pretext that it enhances the s*xual experience. He also claimed that this led to unprotected s*x between them.

"The first time we had unprotected sex actually is the first time she drugged me with ecstasy...She shows me a purple E pill. Thick E pill, too. So basically, Cassie tells me that if I take this little bit of this substance with her, the sex is going to be amazing. It's going to go from like 1 to a 10," Howard alleged.

The male escort claimed that Diddy gave him "water money" and apologized on behalf of Cassie and told him that she allegedly knew she was on her period.

"[Diddy] comes back out and he looks me directly in the face. He says, "Yo, bro, listen. I'm sorry." He said, "She knew she was on her period. She wanted to have sex. We just came back from an event. She's mad drunk... Finally, he takes out a lot of money. He gives me the water money. He said, "Yo, man, accept this as my apology," Howard said.

He further claimed that Cassie called him in the morning the next day and apologized for her behavior and admitted that she knew about her period.

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On the contrary, according to E! Online, Cassie Ventura, during her testimony in Diddy's trial, alleged that the rapper would want her to take part in "freak-offs" even on her period.

Edited by Sriparna Barui