To open the concept of gender to its oscillations, this chapter turns to the works of the sculptor Anish Kapoor, in particular to his sculpture titled “Memory”, 1 and to the work of French artist Louise Bourgeois. I find Kapoor’s and Bourgeois’ work captivating in their capacity to invoke terror and awe, fullness and emptiness, tenderness and violence. Their work seems to capture the threshold between body and psyche, the “extimate” (Lacan, 1992, p.139) zone imagined by Lacan where the body and its surroundings, inside and outside meet and coalesce. The tubular, concave, slippery objects turn us on, stimulating our sexuality into being, inviting desire and repulsion associated with bodily orifices. We want to grab, touch, caress or turn away in disgust. In turn, we feel watched and grabbed, teased and laughed at by these objects, seeming resistance to meaning and accessibility. Art and literature bring us closer to the fluttering states of our beginnings, where the boundaries between inside and outside, passivity and activity are murky. Through Kapoor’s work, I want to show the inherent tensions in approaching the transsexual body as an enigmatic object. Confronting the obscurity of enigmatic objects returns us to the moment of emergence of our subjectivity where the interplay between experiences of pleasure and pain and presence and absence set our sexuality in transit and inaugurated the work of presentation. The elusive temporality mobilized by this strange and estranging encounter gives rise to conflicts around knowledge, love and truth. As we get closer to Kapoor’s installations we may wonder: what is behind the object? Can we get inside it? What will I make from what I don’t understand?