We present the results of simulations of occultation events for small TNOs with non-spherical shapes in the context of the Trans-Neptunian Automated Occultation Survey (TAOS II). We have developed an optimized software package to compute occultation shadows by small objects with non-circular apparent shapes (as may result from an intrinsic morphology or from the projection of a contact binary). The new simulator calculates diffraction features in the occultation shadows based on Fourier transformations, as well as resulting light curves as would be measured by the TAOS II survey system. We include effects such as the spectral type and finite angular size of the occulted star, and objects with projected 2D shapes such as those of the contact binaries, ellipsoids, non contact binaries and other customized shapes. For the event simulator we include reading direction relative to the object shape and and the impact parameter, resulting in a set of complicated diffraction profiles that are not present for simple spherical objects. We find that occultation events, especially by Trans-Neptunian Objects with diameters ~3 km may be misidentified or mischaracterized when not taking non-spherical shapes into account.