When you decided to have a homosexual experience with another male/female and have to lubricate your partner.
It can also be used to explain how someone became a homosexual.
The origin of this word dates back to the late 60's when sexual experimentation was socially allowed. I was used among teens back then when first experimenting with anal sex. It lost its use during the 80's when new terms like ]rim job] and cumcake started to be put into circulation. During the modern era it has became a popular nick name for blatant homosexuals.
One night I was having a sleep over with my friend and we decided to jiggly yo wiggly each other. This lead to many occurred situations after that.
Did you see billy last night? I hear he was jiggly yo wiggling a classmate of his during the camping trip and that lead to him coming out of the closet.