Building on a study of three Nordic and Baltic digital sexual platforms, this article analyzes the perceptions of enjoyable sex and sexual belonging among 60 people, who self-identify as sexually liberal. In dialogue with Gayle Rubin’s formative work on sexual hierarchies and “good sex,” we explore our participants’ complex and often ambiguous sexual boundary work to delineate liberated sex. Independent of particular preferences (non-monogamy, BDSM, fetishism, and exhibitionism), liberated sex for our participants is definitionally enjoyable and articulated via an aspirational hierarchy based on willingness, diversity/variability, and self-reflexivity—partly set against national sexual imaginaries of vanilla normalcy, yet allowing vanilla some gradations and nuances.