Flexible tilting skin contacting devices are disclosed herein. In some embodiments, an apparatus includes an applicator that is to contact skin surface, and a base connectable or detachable from the applicator. The applicator comprises first, second, and third portions. The second portion is disposed between and connected to the first and third portions along the rotation axis of the applicator. The first portion comprises an outwardly curved disc with at least one tip protruding from a major surface of the first portion, the second portion comprises an elastomeric material configured to flex proportionately in response to respective contact pressure on the at least one tip with the skin surface during rotation of the first portion, and the first portion is to tilt in a plane different from a rotation plane associated with the rotation axis in accordance with the flexing of the second portion.