In this paper, we comprehensively present new advancements towards the working-principle, algorithm, prototype setup and experimental characterization and feasibility demonstration of a new aircraft helmet mounted display aiming system. More specifically, we describe detailed design methodology and algorithm of an eye tracking based HMD aiming system. We also present a proof-of-concept prototype and conduct experiment tests in lab environment to characterize the performance of the proposed system. Lastly, through a comparison with related works, we demonstrate the advantages of the proposed HMD system for free head movement and no additional light source required.