In large skillet over med heat add the oil and coat pan. When the oil is hot add the tomato slices and season with salt and pepper. Cook until softened, 1 or 2 min. per side. Transfer to a plate.
Brush the bread on both sides with some of the oil and set 2 or 3 tomato slices onto 21 of the bread slices. Grate the gouda over the tomato and top with the remaining bread.
Wipe out the saute pan and place it over med heat. When the pan is hot, add the sandwiches and cook until the bread is golden brown 2 0r 3 minutes. Turn the sandwiches over and grill the other side another 2-3 minutes. Serve immediately.