ANSWERS: 2
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I can think of two uses for the phrase. Being frightened: Saying someone filled their boots, it refers to what would happen if you pooped your pants severely, it would flow down and fill your boots. Possible deviation of "Filling his Shoes": Like taking someone's place or role. "He was a great leader. Do you think you can fill his boots?" I can't find any reference in my books on origin of this one.
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The one which seems to make the most sense are these - On Sunday it was mentioned by one of the experts on the Antiques Roadshow. Someone had brought in a silver inlaid leather flask and was told that in Nelson's time such vessels were known as 'boots'. To have as much wine as they wanted they were told to 'fill your boots'. I must admit though, I can't find any other reference to it. At the HMS Victory museum in Portsmouth UK, you can buy a thick leather cup lined with pitch. This is a replica of the sailor's mug used on board in Nelson's time, and it was used (among other things) for the rum ration when issued. This cup is called a "boot", and when things were good and you got an extra rum ration, sailors were told "Fill Yer Boots"! http://www.funtrivia.com/askft/Question72214.html
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