This paper discusses the conditions and representations of womanhood and manhood as portrayed in the Ottoman literature of the late sixteenth century. For the study, the compilation of stories, Bed?yiü?l-?s?r, by Cin?n? (d. 1595), a member of the Ottoman literati is chosen. The work of Cin?n?, according to his own account as well as other contemporary sources, was written down upon the request of the Sultan, Murad III, who asked Cin?n? for stories yet untold. In his attempt to please the Sultan, Cin?n? came up with this very entertaining prose-work that is full of stories about beautiful and evil women, marvels, martyrdom, and rightly religious behaviors. In most cases, the women are the most elaborately described characters of the stories causing the destruction of men. The compilation which is full of vivid and colorful stories revealing men and women from different classes, relations, and manners has been appropriate for the goals of the paper as the stories reflect the plurality of the conditions of manhood and womanhood in a late sixteenth century Ottoman literary work. The intended goal in questioning the manhood and womanhood in fiction is to provide an alternative framework for studies on early Ottoman literature in general and representation of women and men in literary works in particular. Most of the available studies of literature focusing on portrayals of women argue that the male authorship was strongly misogynic, and women were either misrepresented or not represented at all as characters. They claim that the visibility of women deteriorated with the urban conditions of an institutionalized Empire, and the women were silenced in this strongly patriarchal setting. It is true that most of the women described in the stories in detail were of "evil-nature," however they had their agency over the course of their lives, unlike most men who in the stories are depicted as following women blindly. The women were the "others," but remarkably, men were the "others" of women, too. The paper claims that it is almost impossible to talk about a prototypical "Ottoman man" or "Ottoman women" in such a multifaceted context and aims to contribute to the available works on Ottoman literature by providing a multilayered perspective on gender, introducing and analyzing various types and characters of a work of sixteenth century fiction, notably, both men and women.