In works such as Leo Tolstoy’s "Childhood" (1852) and Konstantin Leontiev’s "Khamid and Manoli" (1869), nineteenth-century Russian literature explores same-sex intimacy experienced by young men at ambiguous stages of their development into adulthood. Through their inclusion in anthologies like the 1993 volume “Out of the Blue: Russia’s Hidden Gay Literature” edited by Kevin Moss, such literary works have formed gay textual communities. This paper explores the contextual, narrative, and theoretical issues at play in claiming such works as part of a gay Russian literary tradition. It traces Western and Russian gay heritage projects centred around such literary works, reflecting on both their commonalities and divergences, and it asks what, if any, reading strategies might make room for the fraught and contradictory place such texts occupy in the history of queer emancipation in Russia.