In a mixing bowl, combine flour, sugar, salt and baking soda; cut in shortening. Knead in buttermilk. (The dough will be sticky, but don't add extra flour; biscuits won't be as light and fluffy.)
Roll out and cut with a biscuit cutter; place biscuits on a greased baking sheet with sides just touching. Brush with butter. Bake at 450 for 10-12 minutes or until the tops and bottoms are light brown.
Meanwhile, for gravy, peel and cut tomatoes into a bowl, reserving the juice. In a sauce pan, melt butter; add flour and stir until browned. Gradually add water. Stir in tomatoes and juice. Add milk, salt and pepper; simmer for 15 minutes.
Serve over hot biscuits. Yield: about 10 biscuits and 3 cups gravy.
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