The fatigue failure mechanism of bending fretting for cyclic softening material 6061-T6 aluminum alloy was researched by experiment and finite element method. The influence of cyclic load on bending fretting fatigue was researched and the damage characteristics under different cycles was discussed experimentally though SEM images. In the simulation, a normal load transformation method was employed to obtain a simplified two-dimensional model used for simulating the bending fretting fatigue from a three-dimensional model. An advanced constitutive equation with the Abdel–Ohno rule and isotropic hardening evolution was transplanted into ABAQUS by UMAT subroutine to consider the ratchetting behavior and cyclic softening characteristics. The peak stain distributions under various cyclic loads were discussed. Additionally, the bending fretting fatigue lives and crack initiation locations referring to a critical volume method were estimated using the Smith–Watson–Topper critical plane approach and reasonable results were obtained.