Preheat broiler to high. Line a large, rimmed baking pan with parchment paper and set aside. 

Cut each strip of prosciutto in half lengthwise. Wrap each trimmed asparagus spear with a strip of prosciutto, starting just below the tip and wrapping toward the bottom. 

When finished, the entire spear should be covered, except for the tip. 

Arrange wrapped asparagus spears on a lined baking sheet, leaving plenty of room between the spears. Use a second pan or work in batches, if necessary. Brush each spear with olive oil and season with freshly cracked black pepper, to taste. (Avoid adding excess salt because the prosciutto is naturally salty). 

Place baking pan with prepared spears under the broiler and cook for about 4-5 minutes. Remove pan from oven and carefully turn each spear before placing it back under the broiler. Broil for another 2 or 3 minutes, or until the prosciutto is crispy and the asparagus is tender. 

Remove spears from the baking sheet and place it on a wire cooling rack to allow excess grease to drain. Dab lightly with a paper towel, if desired. Transfer spears to a serving tray and serve immediately.