Boyhood gender is a complex and often times misunderstood phenomenon. Difficult to measure and describe it is frequently, but incorrectly, equated with biological sex and thus portrayed as a dichotomous positioning of male or female. Few scientific inquiries have sought to understand the complex interplay of social, biological, emotional and developmental influences on gender behavior from discussions with boys themselves. The purpose of this interpretive study was to describe the meaning and experiences of gender in boys. First person, in depth individual interviews as well as field notes were the primary data sources. Eleven boys between the ages of eight and ten participated in this study. These boys understood gender by describing what boys do; primarily acts of physicality such as sports and games. Although they understood gender as a process influenced by others (parents and teachers) peers were the most salient. They presented themselves as active, agentic participants in how they come to learn about and subsequently embody gender. Rituals of gender behavior maintenance were identified in this study. Rituals of confirmation, punitive rituals, pollution rituals, and enforcement rituals all served as methods of promoting and enforcing boyhood gender. The results support boys who are typical in gender presentation experienced felt pressure to maintain conforming gender behavior and that boys who were atypical in gender presentation also experienced felt pressure to maintain conforming gender behavior. Both groups experienced felt pressure to avoid nonconforming behavior. Boys atypical in gender presentation experienced distress, both in maintaining conforming behavior and avoiding nonconforming behavior; whereas boys typical in gender presentation did not. Understanding the complex worlds of boys and gender is essential for providing holistic care, as well as creating safe and supportive healthcare environments.