Butter a 7 1/2- to 8- by 11-inch baking dish.
Line the bottom with a layer of bread, cut to fit.
Make another layer of bread to fit on top, then lift out top layer and set aside.
Sprinkle half the cheese over the bread in dish.
Scatter tomatoes and olives on top of cheese.
Cover with reserved bread and sprinkle with remaining cheese.
Beat eggs to blend with milk.
Pour over cheese, moistening entire surface, then sprinkle with pepper.
Cover with plastic wrap; chill at least 4 hours or until next day.
Bake, uncovered, in a 350° oven until edges of strata are lightly browned and center is firm when gently touched, about 50 minutes.
Cool 10 minutes, then cut strata into squares.