Heat 2 tablespoons of olive oil in a large skillet over medium-high heat. Add the onion and sauté for 3 minutes.
Add the ground beef 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.
Carefully pour 1 cup of the wine into the skillet, stirring to scrape up any browned bits.
Add the tomatoes, tomato paste, 1 tablespoon salt, and 1/2 teaspoons pepper, stirring until combined. Bring to a boil, lower the heat, and simmer for 10 minutes, uncovered.
After 10 minutes add the basil, cream, and the remaining 1/4 cup wine to the sauce and simmer for 8 to 10 minutes, stirring occasionally until thickened. After 10 minutes add the parmesan.