This thesis examines poems and anecdotes about xiaohuan 小鬟 (little chignon) written by literati of the Song宋 (960－1279). The first chapter of this paper provides a brief history of household courtesans and the popularity of xiaohuan. The second chapter includes eleven poems and one anecdote on xiaohuan. All works are translated and followed by a critical analysis. Through a close reading of these works, I will examine the imagery of xiaohuan in the Song literary context, bring to light the major motif of the works, and reveal the reasons that contribute to literati's penchant for xiaohuan. The imagery of xiaohuan is based on their tender age. Poets use flowers to metaphorize xiaohuan's lithe, slim, short, and delicate figures. A major characteristic of the xiaohuan's youth is their inability to understand qing情 (affection) and this relative innocence and absence of desire becomes a major part of their representation. Consequently, their youth and virginity rather than their beauty are strongly stressed in the poems. This may be explained by poets' desire for longevity, pursued through the "Techniques of the Bedchamber," or fangzhong shu房中術, which suggests intercourse with pre-pubescent girls would bring men longevity or even transmutation.