Former rap mogul James "Jimmy Henchman" Rosemond claims in an affidavit that federal prosectors allegedly grilled him with awkward questions about the sex lives of different celebrities, including Diddy.

According to the Smoking Gun, Rosemond was interrogated by prosecutors during nine pre-trial proffer sessions. During his October 4, 2011 session, the Czar Entertainment CEO alleges that he was asked about Diddy's sexual proclivities and whether he engaged in sex with underage boys.

Normally, these interviews allow defendants to admit to past crimes without it being used against them in court. These off-the-record confessions often help a defendant cut a deal with the feds.

The 48-year-old music executive was convicted last year of running an elaborate multimillion-dollar drug-trafficking scheme throughout the U.S. with various associates. He faces a mandatory term of life in prison when sentenced in federal court on Oct. 25.

Rosemond, who used to manage rapper Game, gave no reason behind the questioning and claims that prosecutors rejected his deal because he wouldn't confess to crimes that he didn't commit.

Rosemond's former attorney, Gerald Shargel, contends that investigators were simply fishing for "trophies" when they questioned his client about celebrities' sex lives during the proffer sessions.

Prosecutors denied Shargel’s claims and said that Rosemond was untrustworthy and lied during the interrogation.