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The ruin of Matapena Community as a community for pesantren literature activist in 2014 does not end the reproduction of pesantren literature with its pesantren cultural problems as a spiritual journey in planting self-identity in alternative medias with popular genres. This article discusses discoursive contestation of self-identity in two pesantren literary works; Sensei, Assalamualaikum Desu! by Diyana Millah Islami and Menggapai Kosong by Izzul Muttaqin. Construction of Self-identity in the literary works engages to the contestation of self-identity discourse in the real world and the cyber world of the writers as milenial generations. Through theory of representation by Stuart Hall, I choose consructionist approach with Foucauldian discoursive model to analyze the works. The result shows an overlapping of in-between-ess as an absolute ideological negotiation of religion with the open-ness of the millenial gen that limitless in time and space. Technology and latecapitalism facilitate the fluidity of time and space boundary presented in the easthetic works.