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Pain in the hole 

When you're a Judge and you're assigned Enoch Burke.
I have Enoch Burke on my court list, he's gonna be some pain in the hole.

rude slang An especially irritating, aggravating, or obnoxious person, thing, act, or situation. Primarily heard in Ireland.

pain in the ass hole 

Often used in the gay community used to refer to someone who is hung causing immense damage to your rectum
Dear God, I was out with Kevin last night. He's a huge pain in the ass hole.