Preheat your oven to 400°F and line a large baking sheet with parchment paper for easy cleanup.
In a large bowl, toss the trimmed asparagus with olive oil and black pepper until evenly coated.
Divide the asparagus into 8 equal bundles. Wrap each bundle with a strip of bacon, starting from the middle and making sure to slightly overlap the bacon to secure it.
Place the bacon-wrapped asparagus bundles seam-side down on the prepared baking sheet.
Bake in the preheated oven for 22 to 28 minutes, or until the bacon is crispy and the asparagus is tender. The exact cooking time will depend on the thickness of the bacon and the asparagus, and your desired level of crispiness.
Serve the bacon-wrapped asparagus warm or at room temperature, and enjoy!