Sex work in India is generally equated with female sex workers and people mostly believe that this is the only reality. This paper takes institutionalised compulsory heterosexuality as the starting point and locate male sex workers in this structure. Though male sex workers are male (outer social reality) their work is to cater to male clients and take on the roles as desired by clients in a same-sex sexual encounter. This situation means that the life-course of male sex workers is characterised by dialectic of transgression and conformity resulting from conflict derived from both masculine and feminine self-representations. This whole imitation involves a medley of identity forms. One is an enchantress, seductress who is ready to play any role to satisfy her/his client. This enchantress then switch role to play a devoted son, a doting father and a husband with family. This paper attempts to understand how sexuality is culturally produced in multiple ways and how male sex workers negotiate these culturally determined sexual scripts. This negotiation is marked by constant tension to behave in a culturally appropriate manner. Thus one aims to understand how male sex workers contest, reproduce and modify masculinity in their everyday interaction with clients, partners, wives and significant other. There are multiple hierarchies in their expression and negotiation of masculinity. This paper is based on 34 in-depth interviews of male sex workers who sell sex to men and sometimes to women in Mumbai and nearby cities. For fieldwork, one approached GAURAV, a community-based organisation of MSMs and MSWs working in Mumbai. Of the 34 male sex workers 17 identify themselves as bisexual, 9 as gay, 5 as kothi and 3 as versatile.