Preheat oven to 400°F.
Divide the asparagus spears into 12 bundles.
Wrap one piece of bacon around each bundle, starting about 1/2 inch from the bottom of the tips. Secure the bacon-wrapped spears with a toothpick.
Lay the bundles in a low-sided casserole dish coated with extra virgin olive oil. Season with salt and pepper.
Transfer the dish to the oven and roast until the spears have begun to wilt and the bacon looks fully cooked, about 20 minutes (or until bacon and asparagus are fully cooked).
Remove the toothpicks before serving.