Allegations regarding Milwaukee Brewers star Ryan Braun’s alleged cheating may extend beyond the baseball diamond. In a “request for admissions” submitted as part of his ongoing defamation lawsuit, former friend Ralph Sasson claims that the disgraced slugger cheated on all of his girlfriends, including current fiancée Larisa Fraser.

Sasson requests that Braun make 48 separate admissions of guilt regarding various indiscretions that occurred throughout the pair’s friendship. The court document asks Braun to admit to having used steroids since playing at the University of Miami, accepting his $105 million contract extension under false pretenses, and to various “infidelities” in his romantic life, especially those involving Fraser, his fiancée.

“Admit that YOU have engaged in infidelities in every amorous relationship YOU have engaged in including YOUR current relationship with Ms. Fraser,” Sasson requests of Braun in the document. Braun has been engaged to Fraser, a professional model, since at least November 2012,” sports blog Busted Coverage reported.

According to Sasson’s defamation lawsuit, he and Braun were close friends for 16 years, attending “junior high, high school, and college at University of Miami together.” Their friendship was so close that, when Braun was tested positive for performance-enhancing drugs in 2011, he asked Sasson, a law student, to assist in his defense.

Sasson claims that Braun, along with his agent, Onesimo Balelo, offered to pay him $5,000 in exchange for his help in acquiring background information regarding Dino Laurenzi Jr, the man responsible for collecting Braun’s positive urine sample. According to the plaintiff, the information he obtained was crucial in Braun’s successful appeal of the 2011 PED charges.

However, Sasson alleges that their relationship deteriorated when Braun refused to pay the $5,000 that the pair had agreed upon as a fee, putting Sasson and his wife in “dire financial straits,” according to court documents. The lawsuit claims that Braun only agreed to pay the money when Sasson threatened to sue for breach of contract. Braun then defamed the plaintiff to the pair’s mutual friends.

Sasson’s requests of admission for Braun aren’t limited to the claims that he cheated on fiancée Larisa Fraser. The full list of Sasson’s demands can be viewed here, while his official defamation complaint can be viewed here.