The present paper is devoted to a theoretical analysis of sliding friction under the influence of in-plane oscillations perpendicular to the sliding direction. Contrary to previous studies of this mode of active control of friction, we consider the influence of the stiffness of the tribological contact in detail and show that the contact stiffness plays a central role for small oscillation amplitudes. In the present paper we consider the case of a displacement-controlled system, where the contact stiffness is small compared to the stiffness of the measuring system. It is shown that in this case the macroscopic coefficient of friction is a function of two dimensionless parameters—a dimensionless sliding velocity and dimensionless oscillation amplitude. In the limit of very large oscillation amplitudes, known solutions previously reported in the literature are reproduced. The region of small amplitudes is described for the first time in this paper.