During the late Ming Dynasty, Feng Meng-long (1574-1646) mentioned stories of Hua Mu-lan, Zhu Ying-tai and Huang Chong-gu in the preface to his work “Li Hsiu-qing Being Brother to the Chaste Woman Huang Shan-cong” in the 28th chapter of the Short Story Collection~from Ancient to Present. It depicts Huang Shan-cong who made a living by vending incense with her father. This story is pivoted around four females in disguise as male roles, both in its preface and ending. Although not created by Feng Meng-long, the theme featuring a cross-dressing heroine can be found in literary works in the Wei Jin Nan Bei, Tang and Ming Dynasties, which could serve as a focal point to observe the relationship between the changing cultural conceptions and the weakening of moral codes. In addition, Feng Meng-long proposed his views on female virginity, romantic love and intelligence, which differed dramatically from the mainstream thinking of his time. Clearly, Feng attempted to strike a balance between the conflicting moral codes and the proposed affection codes. With a perspective on gender and culture, this paper first explores how the mainstream of gender ideology had defined gender differences and dress code since the Pre-Qin Era, to review the varying interpretations of connotations of gender disguise in different times. Then, the connotations of cross-dressing in the story “Li Hsiu-qing Being Brother to the Chaste Woman Huang Shan-cong” and the differences underlying the females in disguise as males, and vice versa, in Feng’s works were also delved into. The final section of this paper discusses the significance of the text in relation to its time.