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1.
When the Captain, your boss, is screwing the secretary and she's on the rag; he pulls out, and gives her a mushroom stamp on either cheek, hence; a Craiggedy-Ann, and then she laughs hysterically like the laugh whore she is!

Person 1: Now what is the secretary laughing at?

Person 2: The Captain just gave her a Craiggedy-Ann, she is such a freakin laugh whore!
by r-dog October 19, 2006
5 10

Words related to Craiggedy-Ann:

boink clown face on the rag rag raggedy-ann screw