Preheat oven, if using, to 400 degrees F.
Lightly coat asparagus spears in extra-virgin olive oil. Season the asparagus with black pepper. Take a quick count of the spear tips. Divide the total number by four. Gather that number of spears and use a slice of bacon to wrap the bundle and secure the spears together. Repeat with remaining ingredients.
To grill, place bundles on hot grill and cover. Cook 10 to 12 minutes until bacon is crisp and asparagus bundles are tender.
For oven preparation, place bundles on slotted broiler pan. Bake 12 minutes.
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