For men in the context of urban poverty in the Dominican Republic, Pentecostal conversion may lead to conditions of gender distress: frustration stemming from the challenges of reconciling the conflicting gender ideals of the church with those of the street. Drawing on ethnographic research conducted with members of a Pentecostal community in the town of Villa Altagracia, I discuss how many young men come to experience the initial trials of conversion as tormenting spiritual assaults on their manhood in the form of alluring succubi. At the same time, male converts adopt newly inspired antagonisms with women familiars whom they blame for their illicit desires. Elsewhere I have discussed the strategies Pentecostal men deploy in order to mediate the conflict between barrio masculinity and evangelical Christianity; here I am concerned with illustrating how this conflict is given personal and cultural expression and how the attending experience of gender distress and its symbolic elaboration shapes masculine identity and male subjectivity in the church and local faith communities. By focusing on male converts and their struggles to remain manly, this article contributes to a richer understanding of gender dynamics in Pentecostal churches and offers useful insight into how gender is variously troubled, performed, and remade through conversion and religious practice more broadly.