This paper explores the comparative material on gender identity, sexuality, and cultic prostitution within the context of ancient Mesopotamian and North-West Semitic cultures, focusing on the Inanna/Ishtar cult and Canaanite practices. The analysis delves into the enduring nature of the Ishtar cult across millennia and its syncretism with other cultures, particularly during the Greco-Roman period. The study highlights the gender-bending aspects of the Inanna/Ishtar cult, including the roles of transgender priests and ritualistic cross-dressing practices. It also investigates the concept of cultic prostitution, examining the terms קְּדֵשִׁים (qᵊdēšîm) and קְּדֵשׁוֹת (qᵊdēšôt), often translated as “sacred prostitutes,” and their roles within the religious and social contexts of the time. Based on a detailed analysis of biblical passages and comparative material from Mesopotamia and Ugarit, the paper explores the functions and perceptions of these cultic personnel. It addresses the scholarly debate on whether these terms denote actual cultic prostitution or refer to a broader category of temple functionaries who may have engaged in sexual activities outside their official duties. The paper also considers the implications of these practices for understanding the intersection of sexuality, religion, and social norms in the ancient Near East. By synthesizing textual evidence and modern interpretations, the study aims to comprehensively understand how gender and sexuality were perceived and ritualized in ancient religious practices and their portrayal in biblical literature.