In this paper, we present the existing content sharing paradigms along with some advanced sharing use cases that are not feasible with the existing technologies. For satisfying these use cases, we propose a new system that allows content sharing in a totally user-centric manner, meaning that users can select the people they want to share their content with and just let the system handle all the lower level device, network bearer and content transfer technologies, which best fit each sharing occasion. The system feasibility is proved in two dimensions, firstly by a technical prototype implementation in a laboratory environment, and secondly via usability studies with non-expert users, for gathering their input and feedback on the interface and preferred interaction with such a system.