A system and method of topically applying an anesthetic, or other medication, to one or both lips of the mouth. An applicator device is provided that has a curved first wall, a curved second wall, and a horizontal shelf that joins the first wall to the second wall. The first wall, the second wall and the horizontal shelf combine to define either one or two curved lip compartments. A volume of the anesthetic, or other medication, is placed within the curved lip compartments. The applicator device is partially placed in a persons mouth so that the second wall is positioned between the back of the lips and in front of the teeth. While in this position, the lip of the user passes into the curved lip compartment and is contacted by the anesthetic.