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This is a slang term used mainly between gay or gay-friendly people. It refers to the asshole or anus which is located between a human's buttocks (i.e. ass, bootie). Thus we get bootie hole, or the hole in your bootie. The use of this term implies that both the person speaking it and the other person in the [conversation] are reasonably [knowledgeable] and accepting concerning anal sex. So it is best to confine your use of this term to gay tolerant locations such as gay bars where gay identification will not earn you a punch in the face. [Straight acting] males may pretend to be puzzled.
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