In this paper I try to focus on cross-dressing in literary texts in the Late Ming period—Sanyan (三言) edited by Feng, Menglung (馮夢龍) and Erhp’ai (二拍) written by Ling, Mengch’u (凌濛初) . I try to adopt Cross-Dressing research in Gender Studies, Kate Millett’s theory in Sexual Politics and Semiology to discuss the gender and culture implications in cross-dressing. In ancient China, the power structure model based on “male esteem” (Nantsun Nupei 男尊女卑), “male dominance” (Nanchu Nuts’ung男主女從) predominated. Cross-dressing has been considered “loosened” the tight grip of such dominance. The expression of it in forms of perversion of sex role and action, however, still shows opinionated interpretations. By comparing the texts, male and female cross-dressing, one detects different purposes and consequences. In short, male cross-dressing always leads to sexual violation against the female sex; however, female cross-dressing usually leads to variable consequences almost all positive in moral, ethical, and social terms. This leads to conclude that male editors and writers’ writing cross-dressing texts, on the one hand, still copy the real situation between male and female, on the other hand, male editors and writers have created some new “Images of Women” by cross-dressing’s inspiration. After all, “Clothing” is something “outside”, and it is a constructed semiotic system. “Gender” is some kind of “performance”, and it is constructed by culture. It is the human being who is being dressed is the true subject. We’re looking forward to building up some kind of culture having respect for any genders.