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Heat 2 tablespoons of olive oil in a large (12-inch) skillet over medium-high heat. Add the ground sirloin and cook, crumbling the meat with a wooden spoon, for 5 to 7 minutes, until the meat has lost its pink color and has started to brown. Stir in the garlic, oregano and red pepper flakes and cook for 1 more minute. Pour 1 cup of the wine into the skillet and stir to scrape up any browned bits. Add the tomatoes, tomato paste, 1 tablespoon salt and 1 ½ teaspoons pepper, stirring until combined. Bring to a boil, lower the heat and simmer for 10 minutes.
Meanwhile, bring a large pot of water to a boil, add a tablespoon of salt, a splash of oil and the pasta, and cook according to the directions on the box.
While the pasta cooks, finish the sauce. Add the nutmeg, basil, cream and the remaining ¼ cup wine to the sauce and simmer for 8 to 10 minutes, stirring occasionally until thickened. When the pasta is cooked, drain and pour into a large serving bowl. Add the sauce and ½ cup Parmesan and toss well. Serve hot with Parmesan on the side.