A novel wingman-based estimation and guidance concept is proposed for a sensorless pursuer. The pursuer is guided towards a maneuvering aerial target using proportional navigation (PN) guidance law. The wingman is assumed to acquire bearings-only measurements of the target and to accurately track the wingman-pursuer relative position. The pursuer-target relative states, needed for the pursuer guidance law implementation, are estimated from the available data to the wingman. The proposed state estimator is implemented using extended Kalman filter equations and transformed wingman's measurements into the moving pursuer frame. Analytical observability analysis of the proposed wingman-based measuring concept suggests an optimal wingman trajectory in terms of the wingman-pursuer relative geometry. The resulting wingman trajectory ensures maximum observability of the pursuer-target line-of-sight (LOS) angle, which is a crucial parameter needed for the PN guidance law implementation. The resulting trajectory can be directly related to the well-known LOS guidance concept. Monte Carlo simulation results validate the analytical findings and demonstrate the potential of the proposed concept.