Men who have sex with transgender women (MSTW) currently constitute a gap in the research community’s understanding of male sexuality and sexual desire. In an effort to address this lack of knowledge, an ethnographic study of MSTW in New York City was conducted between December 2005 and May 2007, including in-depth interviews with MSTW (n = 15), key informant interviews (n = 13), and ethnographic observation of semi-private “tranny” parties held at various venues throughout New York City. The specific objectives were to: (1) describe the sex marketplaces and the sexual experiences of an ethnographic sample of MSTW in New York City and (2) describe the ways MSTW construct their sexual partnering practices and the meanings attributed to those practices in relation to varying social contexts (in and outside the sex marketplace). In this analysis, we described the MSTW sex market landscape in New York and identified three major recurrent themes in the ways that MSTW organized their sexual desire for TW transitioning from sex marketplaces to social spaces in their lives: (1) phallus-centric trade sex market focus; (2) relational-companionship market focus; and (3) specialized market focus. Although the findings from the study are not representative of the broader MSTW population, they represent an important step in amassing a body of knowledge about an understudied and underserved sex market upon which future research is needed.