In a large bowl, stir together the tomatoes, olive oil, kalamata olives, capers, basil, Greek oregano, garlic, salt, and several grinds of black pepper. Let stand at room temperature, stirring occasionally, for several hours, or at least while you cook the pasta. Cook the pasta in a large pot of boiling salted water, stirring often, until slightly undercooked. Drain in a colander. Spoon off some of the tomato sauce juice and put it into the empty pasta pot, then set it over medium-low heat, add the drained pasta, and toss until the juices are absorbed. Add the pasta to the bowl of sauce and toss to combine. Season to taste and serve, passing the freshly grated cheese at the table. Hunks of warm crusty bread to sop up the sauce are optional.