In order to design a painless and mechanically durable micro syringe-needle system for biomedical applications, the study of insect stingers is of interest because of their elegant structures and functionalities. In the present work, the structure, mechanical properties and the mechanical behavior during insertion of wasp and honeybee stingers have been investigated. The non-invasive imaging tool, micro-computed tomography has been employed to reveal the 3D-structures of wasp and honeybee stingers. A quasi-static nanoindentation instrument was used to measure the nanomechanical properties. Both wasp and honeybee stingers have graded mechanical properties, decreasing along their longitudinal direction starting from the base. The computed tomography images and the measured material properties from nanoindentation were fed into a computational framework to determine the mechanical behavior of the stingers during penetration. The computation results predicted the penetration angle of +10° for the wasp stinger and −6° for the honeybee stinger, which mimics the practical insertion mechanism of both stingers. Based on this understanding, a wasp and honeybee stringer inspired micro syringe-needle design has also been proposed.