The concern with a "digital divide" has been transformed from one defined by technological access to technological prowess--employing technologies for more empowered and generative uses such as learning and innovation. Participation in technological fluency-building activities among high school students in a community heavily involved in the technology industry was investigated in a study of 98 high school seniors enrolled in AP-level calculus. Findings indicated substantial variability in history of fluency-building experiences despite similar levels of access. More and less experienced groups were defined based on their breadth of prior experience. Males and females who were classified as more experienced utilized a broader range of learning resources and were more likely to learn from out-of-school classes and distributed resources such as online tutorials and reading material. Gender differences emerged with respect to participation in certain activities such as computer programming, even when controlling for overall breadth of experience and an analysis of course-taking history helped explain why. Four times as many males as females had taken a programming class. Analysis of reasons for taking courses indicated that the majority of females who chose to take programming did so with the encouragement of family members. Both confidence and interest were related to experience, though the relationship differed for males and females. These results are discussed with respect to a multi-context framework for the development of technological fluency.