A wireless earpiece assembly configured to physically contact a user substantially exclusively at an outer ear location of a user's ear when in use. For example, the outer ear location may be an ear lobe providing the assembly with an appearance of an earring. The assembly is configured to distribute a significant portion of its bulk away from the isolated location of a user's ear for long term user comfort without sacrifice of audio or communicational integrity. The wireless earpiece assembly simultaneously eliminates extraneous wiring in order to optimize the un-encumbering user-friendly advantages afforded by wireless technology.