This paper focuses on the works of a very colorful figure from the Early Modern Ottoman world of literature, S̱ābit (d. in early 1710s), in order to trace the representation of men, women and their relationship with a special focus on the language and metaphors used in their depictions. S̱ābit’s two mes̱nevīs used in this paper share a similar and simple plot: There is a charming and ruthless beloved who does not respond to the lover’s feelings. The lovers are passionate men trying every possible way to reach the beloved. As all the common paths of attracting the beloved are vain, they trick the beloved and take advantage of him/her sexually. In both narratives there is no poetic justice, as the men are not punished. The beloved are totally silent throughout the both narratives and there is no clue what happens to them afterwards. It is widely accepted that S̱ābit introduced a new set of vocabulary and images to Ottoman Classical Poetry. In S̱ābit’s stories, sexual intercourse is narrated with very clear and graphic images. The stories selected for this presentation challenge the norms of the courtship and the desired union with the idealized beloved. They turn the courtship into a trick, and the union into a rape - thus they violently challenge the established norms of mes̱nevī. The expressions of obscene/erotic content are of particular interest for the purposes of this paper, because they are an integral part of this genre in spite of the disregard of many scholars. S̱ābit, while challenging the established ideals of the “Classical” literature, still made use of the traditional imagery and metaphors, nevertheless he expanded its boundaries with witticisms, connotations, proverbs and puns. Obscene and erotic content was an integral part of their narrative, and created the humorous effect that aims at entertaining the readers/audience. The reaction of the addressee is very hard to determine; they might consider these as skillful literary descriptions, humorous witticisms, graphic and arousing displays, or disgusting content. It is important to realize that S̱ābit creates a humorous and grotesque world in his path of seeking originality, and he challenged the boundaries of the language and content. In that, he was obviously successful, proven by the people he inspired, by the widely scattered copies of his manuscripts, and especially by the very fiction and language he created.