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

Trim asparagus spears by removing the woody bottom parts of the stems with a sharp knife.

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 whole stem of each spear should be wrapped, except for the tip.

Arrange wrapped asparagus spears on the lined baking sheets, making sure that there is plenty of room between the spears. Do not overlap them, as this will cause them to cook unevenly.

Brush each spear with the olive oil and season with black pepper.

Place baking pans with prepared spears under the broiler and cook for 4-5 minutes. Remove pan carefully, turn the spears over, and broil the other side for another 2-3 minutes. Cooked spears should be tender and prosciutto will be crisp.

Remove spears from the broiler and place on wire cooling racks to allow excess grease to drain away. Dab with paper towels to further remove grease from cooked prosciutto.

Repeat until all spears are cooked.

Serve hot and enjoy!