Fractures provide preferential flow paths and establish the internal “plumbing” of the rock mass. Fracture surface roughness and the matedness between surfaces combine to delineate the fracture geometric aperture. New and published measurements show the inherent relation between roughness wavelength and amplitude. In fact, data cluster along a power trend consistent with fractal topography. Synthetic fractal surfaces created using this power law, kinematic constraints and contact mechanics are used to explore the evolution of aperture size distribution during normal loading and shear displacement. Results show that increments in normal stress shift the Gaussian aperture size distribution toward smaller apertures. On the other hand, shear displacements do not affect the aperture size distribution of unmated fractures; however, the aperture mean and standard deviation increase with shear displacement in initially mated fractures. We demonstrate that the cubic law is locally valid when fracture roughness follows the observed power law and allows for efficient numerical analyses of transmissivity. Simulations show that flow trajectories redistribute and flow channeling becomes more pronounced with increasing normal stress. Shear displacement induces early aperture anisotropy in initially mated fractures as contact points detach transversely to the shear direction; however, anisotropy decreases as fractures become unmated after large shear displacements. Radial transmissivity measurements obtained using a torsional ring shear device and data gathered from the literature support the development of robust phenomenological models that satisfy asymptotic trends. A power function accurately captures the evolution of transmissivity with normal stress, while a logistic function represents changes with shear displacement. A complementary hydro-chemo-mechanical study shows that positive feedback during reactive fluid flow heightens channeling.