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Similar to "A tall [glass of water]" (tall woman with long legs and beautiful features.) "A tall glass of milk" is used to describe more particuarly a tall [white woman] (or a fair woman of European decent) with long sculpted legs and a [brick house] body. This term is used usually by (older, pimp-ish) black men - hence why the glass is filled with milk rather than water. (Water could mean any race/color.)
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