Heat the olive oil in a large skillet over medium-high heat.
Add the ground sirloin and cook, crumbling the meat with a wooden spoon for 5-7 minutes or until the meat has lost all of it's pink color and has browned.
Stir in the garlic, oregano, and red pepper flakes and cook one more minute.
Pour 1 cup of the wine into the skillet and scrape up any browned bits.
Add the tomatoes, tomato paste, 1 Tablespoon salt and ½ teaspoon 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 and a splash of olive oil and cook pasta according the package directions on the box.
While the pasta cooks, finish the sauce. Add the nutmeg, basil, milk, and remaining ¼ cup of wine to the sauce and simmer for 8-10 minutes, stirring occasionally until thickened.
When the pasta is cooked, drain and pour into a large serving bowl.