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Picture holeing

The art of printing off a picture of someone online, cutting a hole in same, and using this for placing your penis in while you masturbate. Or, for women, cutting a hole where a mans penis should be and placing her dildo through same.
Hey Chris, your sister wont hook up with me so I spent all last night picture holeing her.
Picture holeing by doc88LAG February 14, 2012
To tamper with one's hole, particularly, the asshole.
PERSON 1: I'm going to the bathroom to do some holeing.
PERSON 2: Okay.
Holeing by HoleDude69 June 29, 2017
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!
Holeing by FungusAmongUs August 18, 2013

candy holein 

The act of pushing a nerds rope (or similar candy) out of a butthole while the other person deepthroats it, then pushes it back inside.
"Honey why did you by so many nerds ropes?"
"Oh baby, we'er gunna try candy holein tonight"
candy holein by Pikachuandme October 12, 2017
to hide in a hole with a good friend when you are down in the dumps
damn, my gramma josephina died, wanna go holeing
holeing by lisa November 12, 2002

Holeinator 

Where you fuck a girl in the ass and fist her at the same time.
Me and this one girl did the Holeinator all night long!