This chapter examines the violations against role-playing games (RPGs), expectations of play patterns, and cultural conceptions of role-playing. It discusses the boundedness of play, games, and RPGs, and explains the concepts of transgression and deviance. The chapter describes three categories of transgressive role-play: adult play and imagination as deviant; violations of game rules and the concept of "game"; and, finally, violations of norms relating to the relationship between the player and the character. "Game" as a concept is a sociocultural artifact. In order to play games together, participants need to trust that they share similar enough ideas about how games are played and how involved one should become while playing. The chapter considers violations of the concept of game, specifically transgressing game rules, trust amongst players, and issues with involvement as well as boundedness and separation of playing from the quotidian.