Our study explores gender differences with respect to the widespread phenomenon of adolescent sexting. We first present an 18-month long case study conducted with a family whose adolescent daughter had engaged in sexting behavior. We then describe the results from two surveys conducted with college underclassmen. Consistent with the case study, the descriptive data emerging from our exploratory studies suggest that significant gender asymmetries emerge for adolescent sexters. Specifically, survey responses revealed that females (vs. males) were more likely to create (i.e., send) sexted content, while males (vs. females) were more likely to distribute (i.e., share) sexted content with others. In addition, consistent with sexual double standards, females were more likely to experience negative outcomes from sexting than males. We conclude with specific educational and policy recommendations, and a call for additional explorations of this and other related phenomena by those conducting research in the areas of gender differences, communications technology, and/or risky adolescent consumption.