to relax - via sexual intercourse, the use of a dildo, fist, or other object - an anus to the point where it will remain open, at least for a short while, when the penis or dildo is removed. This is a desirable goal in certain kinds of fetishist anal play, e.g. the open anus is considered visually exciting, or it can be urinated in, used during scat play, etc. Sometimes "medical" devices, such as a speculum, are used to keep the anus open for similar purposes.
Definitions include: the more outgoing person in a pair. Origin: refers to folk-rock 1960s duo Simon and Garfunkel. Art Garfunkel, who did not write or play an instrument, arguably was the better singer of the two. He was also more personable/talkative. In a way, the "sidekick" of Simon. See also Simon.