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It is [unfortunate] that most people do not search for original sources. All you have to do is check with the final authority on the Spanish Language, the Royal Academy and you will get this word as [originally] meaning the male reproductive member or penis. It may have been later applied by sailors to describe the top mast lookout point in [reference] to an undesirable place to be in or thing to have but more than likely initiating with the negative connotation which applies when referring to said member in undesirable situations.
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