Surfactants play a critical role in bottom-up nanotechnologies due to their peculiar nature of controlling the interfacial energy. Since their operational mechanism originates from the molecular-scale formation and disruption processes of molecular assemblies (i.e., micelles), conventional static-mode atomic force microscopy has made a significant contribution to unravel the detailed molecular pictures. Recently, we have successfully developed a local solvation measurement technique based on three-dimensional frequency-modulation atomic force microscopy, whose spatial resolution is not limited by jump-to-contact. Here, using this novel technique, we investigate molecular nanomechanics in the formation and disruption processes of micelles formed on a hydrophobic surface. Furthermore, an experiment employing a hetero-nanostructure reveals that the nanomechanics depends on the form of the molecular assembly. Namely, the hemifusion and disruption processes are peculiar to the micellar surface and cause a higher energy dissipation than the monolayer surface. The technique established in this study will be used as a generic technology for further development of bottom-up nanotechnologies.