This paper presents the real-world implementation and field validation of a user-Aware, smart bidirectional electric vehicle (EV) charging system, developed for the Mobilities for EU and DymoBat projects in Dresden. Building on previous scenario-based modeling and simulation frameworks, the system takes a critical next step: enabling the transition from conceptual pilots to operational deployment in city contexts. To support increasing demands for grid flexibility and clean urban mobility, our solution couples real-Time user and vehicle telemetry with a centralized optimization platform, achieving data-driven charging and discharging decisions. The architecture integrates a wireless On-Board Diagnostic II (OBD-II) interface and an open communication middleware node with a 5G campus network to furnish early, pre-connection access to vehicle state-of-charge, even before the vehicle is plugged in. Simultaneously, a tablet-based human-machine interface captures user preferences such as desired departure time and energy needs which inform optimization logic alongside grid conditions and mobility trends. A key innovation is the closed-loop, multi-level communication architecture that links the user, the EV, the bidirectional charging station, and the grid control center, leveraging the Open Charge Point Protocol (OCPP) for seamless system integration. This design synthesizes software, embedded hardware, and networked components to deliver real-Time, driver-inclusive charging management. Field deployment at Ostra Sport Park, located in the Dresden Ostra District, confirms the operational feasibility of the system, demonstrating improved load balancing and robust vehicle-To-grid (V2G) operation in practice. By enabling early data acquisition and proactive system management, the framework sets a benchmark for positive energy districts (PEDs) and climateneutral city initiatives across Europe. This work represents the core technical result of Dresden s pilot for the Mobilities for EU project, advancing the applied engineering and user-centered integration needed for the next generation of urban e-mobility systems.