Virtual worlds have drawn the attention of many individuals because of the alleged opportunities to make anything and to be anyone. Yet, recent writing on the subject suggests that creative opportunities in virtual worlds, especially those for children, are not equal. Against this backdrop, we turn to both designed affordances for creativity and ground-up creative play developed by children in a comparably open virtual world for tweens (children on the cusp of adolescence, aged 9–13), Whyville.net. We consider three forms of creative play, ranging from the socially acceptable to the socially transgressive. First, we examine avatar design, a form of creative expression provided by the designers of Whyville. Then we review language play through flirting, a peer-developed form of play allowed but not designed for by Whyville’s creators. Finally, we reflect on cheating as a transgressive yet creative form of play that pushes back on the intended culture of playing science games in Whyville, adding elements of collaborative agency to an otherwise single-player consumption of games. In the discussion, we consider what these forms of creative play mean for designing for creativity, using virtual worlds in local educational contexts, and pushing back against constraining discourses of safety and protection.