Understanding the frictional properties of phosphorene is essential for reliable fabrication and sustainable operation of phosphorene-based nanotechnology devices. Although recent studies have revealed that phosphorene exhibits anisotropic frictional characteristics, the detailed mechanisms are not well analyzed, and the influence of some experimental parameters (e.g., spring stiffness, tip load force, and tip size), which are very sensitive to atomic frictional forces, were not considered. This study was carried out to address the above shortcomings. The anisotropic frictional behavior of phosphorene and its detailed mechanism were analyzed using potential energy profiles. Also, the effects of spring stiffness and tip load force on the stick-slip behaviors were investigated. Furthermore, we studied the sub-nanoscale stick-slip behavior during the nanoscale slip motion. The nanoscale and sub-nanoscale stick-slip phenomena were originated from the tip's behavior of passing over the bond between the phosphorus atoms and over the puckered honeycomb structure along the zigzag and armchair directions. We utilized a simple one-dimensional model to explain the energy profiles. The influence of tip size on the stick-slip behavior was also examined and found related to the initial nanoscale slip velocity. As the tip diameter decreased, a high-frequency sub-nanoscale stick-slip phenomenon and shorter nanoscale slip duration were identified.