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2.
to hide in a hole with a good friend when you are down in the dumps
damn, my gramma josephina died, wanna go holeing
by lisa November 12, 2002
 
1.
To deliver an affectionate/deserved romping of your woman's undercarriage.

One thing to note about a holeing that separates it from traditional intercourse is that neither oral/fore -play is prerequisite. This generally leads to a rather "rough-and-tumble" atmosphere where each and every relational dispute will find resolution in some hole or another.
Steve: Martha, could you check the calendar and see when our last holeing session was?

Martha: Well Steve , it says a week ago but I'm still having trouble walking!
by FungusAmongUs July 09, 2013