From symbolic castration, plus-de-jouir and traversing the fantasy, this essay aims at analyzing Slavoj ?i?ek’s key category, jouissance, a product of symbolic castration. The identification of symbolic order can simply lead to plus-de-jouir in pain. Attempting to traverse the fantasy for jouissance, a subject will encounter death drive. While providing meaning for the being of subjects, jouissance is always-already separated from subjects who, in a sense, expect to be fooled by jouissance without pleasure, which is, paradoxically, associated with castration, pain and death. In seeking jouissance, literature finds its own territory.