This dissertation examines the ways five contemporary Asian-American authors portray their protagonists' attempts to construct viable masculine subjectivities contravening popularly sanctioned, institutionally dictated possibilities for social iterability. In each novel, depictions of prostitution and the prostitute as tropes illustrate subordinated, often `failed,' masculinities. Critical attention is called for because prostitution and prostitutes feature prominently and illustrate the existing dearth of representational vehicles available to Asian-American authors to discuss disenfranchisement from U.S. mainstream society while not employing, but arguably exploiting, another group of marginalized individuals to fully realize the gravity of their grievances. In each chapter, the ways Asian-American men are specifically impacted when prevailing social mores and internalized racism make self-actualization nearly impossible is explored through the particular ways prostitutes are deployed to enable readers to begin thinking about the effects upon men whose sexuality and gender have been racialized, while race has also been gendered and sexualized. This investigation includes works about hetero- and homosexual men, in both national and transnational contexts. The goal is not to solve the dilemma posed by the formation of alternative ways of being in the world, but to begin creating a representational lexicon reflecting less anxiety about not meeting the conventional definition of manhood and not silencing those who, in unique ways, have experienced a form of social death. This dissertation essentially asks how we begin the process of democratizing identity formation in literature.