A ritualistic study of Gender and Sexuality has very often been performed within the classrooms and enthusiastically discussed outside them, along the lines of the South Asian heritage. But when it comes to the discussion of desire of the sexual identities, their strengths, weaknesses, likes and dislikes, a vague and non-committal aura very often surrounds those deliberations. In the late 18th Century when S.T. Coleridge stated that the great mind is androgynous, he set the corner stone for Virginia Woolf and other critics of the 20th century to base their observations on androgyny. Going back into the mythological past the paper will discuss the power and passion of Shikhandi, or Amba the princess of Kasi reborn as a girl with all the female genitalia, and grows up into a male, acquiring the male sex organ. We will see how androgyny is defined and performed today, whether it is only in the form of mythological legacies or whether transgenders in their individual frames and forms do achieve a voice that embody characteristics of both genders simultaneously, an androgynous consciousness that can speak, despite the South Asian culture’s-imposed inferiority of women. Or are transgenders today ‘evaluated as pathologically evil, deranged, abnormal, strictly within a system of meaning-generation,’ that is to say since they are neither heterosexual nor procreative, they are condemned to the invisible. I will attempt to look at transgender (androgynous mind) and how they are situated in the society (unstable and contested?), by evoking the ancient texts and practices and analyzing the present-day realities. The paper will also unfold the historicity of sexual identities even as it focuses on Transgender in South Asia.