Scant research has sought to explore the development of dimensions of sexual orientation among Black bisexual male adolescents (BBMA). Understanding how sexual attractions, behaviors, and identities evolve among BBMA over time is crucial to understanding the most appropriate support strategies to provide during this developmental period. We sought to understand and describe the sexual orientation development experiences in a sample ofBBMA overthe course of 1 year. We further sought to understand the sociocontextual factors that may play a role during this development process. Fifteen BBMA, aged 15–19 years, were interviewed about sexual debut experiences (baseline) and were re-interviewed three times over a 1-year period about sexual attractions, behaviors, and identity at each follow-up point. A three-person team used inductive open coding to analyze each participant’s data set. The mean Kinsey scale score for the sample was 2.93 (SD = 1.2) most closely translating to“heterosexual/gay-equally.”A case study analysis was used to identify themes related to sexual attractions, behavior, and identity over time, within and across participants. Among the sample of young men, two unique groups were identified based on self-reported sexual identity and experiences of same- and other-sex sexual attractions and behaviors over time. The first group consisted of seven young men who consistently described their sexual identity as bisexual from baseline to the final follow-up. These young men also described similar experiences related to same- and other-sex sexual and romantic attractions and more consistently described same- and other-sex sexual behaviors. The second group consisted of eight young men that described changing sexual identity and same- and other-sex sexual romantic attractions overtime. Participants described sociocontextual factors such as religion, masculinity, and homophobia played during their development. Findings from this study underscore the complexity of sexual orientation development and sociocultural factors and expectations that may influence sexual identity and behavior among BBMA.