In preparation for a demonstration of optical stochastic cooling in the Cornell Electron Storage Ring (CESR) we have developed a particle tracking simulation to study the relevant beam dynamics. Optical radiation emitted in the pickup undulator gives a momentum kick to that same particle in the kicker undulator. The optics of the electron bypass from pickup to kicker couples betatron amplitude and momentum offset to path length so that the momentum kick reduces emittance and momentum spread. Nearby electrons contribute an incoherent noise. Layout of the bypass line is presented that accommodates optics with a range of transverse and longitudinal cooling parameters. The simulation is used to determine cooling rates and their dependence on bunch and lattice parameters for bypass optics with distinct emittance and momentum acceptance.