Commercial sex is a risky business and men who buy sex engage in a form of voluntary risky behaviour. Using Stephen Lyng’s notion of edgework, this qualitative study examines Hong Kong men who buy sex in Hong Kong/China and argues that these men’s engagement can be understood as a form of leisure edgework which balances risk and pleasure by negotiating the boundary between order and chaos. This article concludes that men buying sex can be seen as a form of resistance to normative companionate sexuality and the skills they exercise are key cultural principles needed in late-modern society. Edgework therefore plays an important role in modern intimacy, especially in shaping masculinity and men’s sexual scripts.