The act of ejaculating in someone's eye, thus causing one eye to shut. Variations include saying "Arrr!" immediately after the eye closes to ensure proper scoring.
"I missed her mouth and inadvertantly gave her a JollyRoger"
Double-fisting so that the arm going into the vagina and the arm going into the anus are crossed. For effective movement, the crossed arms are held just below the head, thus creating the "Jolly Roger" similar in resemblance to the infamous buccaneer flag.
Avast matey! Let's head to the crows nest and strike the Jolly Roger!