In a large non-stick skillet (a 12-inch diameter works well), sauté the prosciutto over medium heat until crisp, about 4-5 minutes, stirring often. Remove to a plate.
Add 1 tablespoon olive oil to the pan, and then add the shrimp in one layer. Raise the heat to medium-high, season lightly with salt and pepper (I use about 1/4 teaspoon each at this point), and cook for 3-5 minutes, flipping occasionally, or until the shrimp are opaque and just barely cooked through the center. Remove to a plate. (To keep the prosciutto crisp, place the shrimp on a separate plate.)
Add the remaining tablespoon of oil to the pan, followed by the asparagus and another pinch or two of salt and pepper. Cook the asparagus for another 3-5 minutes, stirring regularly, or until crisp-tender. Precise cooking time will depend on thickness of spears.
Return the shrimp to the pan, sprinkle the Parmesan over top, and stir to evenly coat. Sprinkle with the reserved prosciutto, remove from the heat, and serve immediately.