The development of electronic skins and wearable devices is rapidly growing due to their broad application fields, such as for biomedical, health monitoring, or robotic purposes. In particular, tactile sensors based on piezoelectric polymers, which feature self-powering capability, have been widely used thanks to their flexibility and light weight. Among these, poly(vinylidenefluoride-trifluoroethylene) (PVDF-TrFE) presents enhanced piezoelectric properties, especially if manufactured in a nanofiber shape. In this work, the enhanced piezoelectric performances of PVDF-TrFE nanofibers were exploited to manufacture a flexible sensor which can be used for wearable applications or e-skin. The piezoelectric signal was collected by carbon black (CB)-based electrodes, which were added to the active layer in a sandwich-like structure. The sensor was electromechanically characterized in a frequency range between 0.25 Hz and 20 Hz—which is consistent with human activities (i.e., gait cycle or accidental bumps)—showing a sensitivity of up to 4 mV/N. The parameters of the signal acquisition circuit were tuned to enable the sensor to work at the required frequency. The proposed electrical model of the nanofibrous piezoelectric sensor was validated by the experimental results. The sensitivity of the sensor remained above 77.5% of its original value after 106 cycles of fatigue testing with a 1 kN compressive force.