Trim the asparagus of the woody ends. Place on a sheet tray and drizzle with olive oil. Season with freshly ground black pepper and salt.
Wrap bacon slices around each asparagus spear. Skewer both ends of asparagus on each side to secure the bacon. Add 3 to 4 asparagus to each skewer.
Grill skewers on direct heat until the asparagus is tender and the bacon is crisp about 15 minutes; halfway through the grilling flip the asparagus. Transfer to a platter, remove the skewers and serve.