whoops hole Share definition Flag used to describe accidental anal sex, or deliberate anal sex, the later is often followed by a hey what are you doing...? whoops i've been trying to get anal for months, so what did you do.I used the whoops hole as cover whoops hole by jaffaw July 18, 2009 0 0 Get merch Get the whoops hole mug. Buy Now — $32.95 See more merch