Slice tomatoes about 1/4 inch thick or less, and set aside.
On a large plate, combine flour, salt, pepper, and sugar. For a more savory flavor, use 1/4 cup or less sugar. Mix well.
In a large, deep cast iron skillet, heat just enough oil to cover one layer of tomatoe slices, about 1/4 of an inch. Get oil fairly hot, about 350 degrees when tested with a thermometer.
While oil his heating, dip each tomato slice into the flour mixture and coat both sides completely, gently pressing to make mixture stick.
Once oil is hot, carefully put each slice into the oil and fry until golden brown on both sides, flipping halfway through. This step is essential! Once fully browned, remove them to a plate and fry the next slices.
Once all the slices are fried, drain any excess oil from the skillet, return all the tomato slices to the skillet at once, and add slowly add the milk. Bring to a simmer and cook until the tomatoes break down and the mixture thickens, about 5-10 minutes.
This will make a thick, reddish gravy full of chunky tomatoes that is great served over mashed potatoes as a main dish. Makes 4-6 servings. Enjoy!