To investigate the friction behaviors of elastomer and polyacetal writing tips sliding on various textured glass surfaces, the influences of the pitch size and height of sub-millimeter to millimeter sized texture on friction were examined via reciprocating friction tests. The friction coefficients of each writing tip could be systematically varied by changing the pitch and height of the texture. These changes in friction were based on the relationship between the convex-concave shapes and the contact parts of the writing tip, and hence, influence the adhesive, abrasive, and deformation frictions. By inducing a surface texture with a pitch smaller than the contact area of the writing tip, the friction coefficient could be reduced effectively. By inducing a surface texture with a larger height, the friction coefficient of the elastomer could be increased due to deformation friction. These behaviors indicate the possibility of controlling the friction by changing the parameters such as the pitch and height of the textured glass surfaces.