The paper presents asymptotic modeling of reciprocating sliding wear with increasing contact zone under a prescribed constant normal load. The wear contact problem is formulated within the framework of the two-dimensional theory of elasticity in conjunction with Archard’s law of wear. It is shown that the asymptotic modeling approach, which maintains the experimentally-related feature of contact pressure in the steady-state regime, leads to simple but sufficiently accurate analytical approximations. In particular, simple closed-form approximations are derived for the planimetric wear, half-width of contact zone, and wear scar profiles. The obtained analytical results have been compared with finite-element simulation results published in the literature, and a good correlation was revealed between the analytically predicted and numerically simulated worn profiles in the case of fretting when there is no stick zone between the contacting surfaces.