When people think of gender and sexuality studies within the frame of Ottoman literature, very prestigious works on Ottoman poetry come to mind immediately. However, there are also some relatively fewer studies on prose in terms of gender and sexuality. I desire to add another to this corpus of quantitatively few but qualitatively significant works on gender and sexuality in Ottoman prose literature. Therefore, in this paper, I closely examine the first seven stories in an anonymous manuscript collection of stories entitled Kitāb-ı Ḥikāyāt, registered under the catalog number 06 HK 4074 in the collection of Ankara Adnan Ötüken Provincial Public Library. I approach these stories from a gendered perspective by doing a close reading to reveal the literary representations of women in these narratives. While doing so, I will keep in mind that gender is a socially and historically constructed concept and focus on how gender, sexuality, age, social class, and political and legal status influence the representations of women created by an Ottoman male elite, which will also enable me to make a holistic analysis of different kinds of womanhood in Ottoman prose stories. Thus, I classify women in the narratives as old women, lesbian-like women, and female slaves. This paper aims to contribute to the studies of Ottoman literature by studying a hitherto unexamined miscellany containing prose stories in Ottoman Turkish by other scholars. It also seeks to contribute to gender and women studies by examining these narratives from a gendered perspective. Since Ottoman literary and cultural studies adopting gender analysis will help us understand the perceptions of gender in Ottoman society, tracing characters outside today’s heteronormative order will enable us to raise new questions about renegotiating meanings of gender and sexuality in pre-modern periods and add to our knowledge of gender history in the Ottoman context.