look up any word, like hipster:
 
1.
A sex act in which a penis is place under the armpit of the receptive partner, as the receptive partner masturbates the penis by moving their arm up and down as the penis is thrust in and out of the cavity created by the arm movement.

"Winging it" refers to the position of the arm--hooked at the elbow with the hand up near the chest--and the movement of the arm--the elbow moving outward in response to the thrust of the penis--mimicking the flapping of bird wings.

The term also has a double meaning as it tends to be done in a group sex situation when no other orifices are available, i.e., you have to wing it with finding something to penetrate.
At the gangbang, her hands and various orifices were occupied so the other participants in the event chose to wing it since her armpits were still available.
by GaystThingSinceGayCame2GayTown December 08, 2010