Adolescent sexting is a serious public health concern and is associated with adverse psychosocial outcomes, including depression, anxiety, low self-esteem, declining academic performance, and health problems. Effective prevention of sexting requires a comprehensive and deep understanding of the multiple contexts whereby sexting is likely to occur. The present study explores individual and contextual risk and protective factors that are associated with sexting behavior among a large sample of adolescents. Participants were high school students in midwestern U.S. (N = 2501; LGB n = 309, 76.4% female; non-LGB n = 2192, 47.4% female) who completed self-report measures of sexting and risk (e.g., pornography exposure, impulsivity) and protective (e.g., social support) factors. Path analysis models were conducted with the sexting outcome for groups of LGB and non-LGB students. Among LGB students, results indicated a significant association between sexting and parental monitoring (b = −0.08, p < 0.01); pornography exposure (b = 0.13, p < 0.05); dating partners (b = 0.01, p < 0.01); bullying perpetration (b = 0.17, p < 0.001); and delinquency (b = 0.13; p < 0.001). Among non-LGB students, significant associations were found between sexting and alcohol/substance use (b = 0.05, p < 0.001); bullying (b = 0.08, p < 0.001); and delinquency (b = 0.06, p < 0.001). Moderation analyses suggest that parental monitoring may have a buffering effect between sexting and several risk factors. Recommendations for practitioners include considering the protective factors of sexting perpetration and encouraging appropriate levels of parental monitoring and the continued importance of bullying and alcohol and drug prevention programming to decrease risk factors of sexting perpetration.