This essay -- written autobiographically as a confession -- charts uncomfortably and reflexively salient experiences and emotions of a queer educator of color. It unveils and analyzes unresolved feelings as messy examples in his journey as an urban school teacher, as a graduate student, and eventually as a university academic and administrator. In particular, it foregrounds the pleasure-pain dynamic that will be addressed, although often intertwined, separately for fuller exposition and examination. Drawing interpretive and methodological insights from women of color feminism, the essay enacts a theorizing from the personal to work against facile understanding of the cultural politics of identity and emotion. Rather, it marks a queer of color critique that is grounded in feminist theorizing as a framework and language for a more livable and humane world.