Grease a baking dish or sheet pan with nonstick spray and preheat oven to 350°F. (You can alternatively line pan with foil, if desired.)
Pat sausages dry, then wrap each sausage with a piece of bacon and secure with a toothpick.
Add brown sugar to a large zip-top bag. Add a few of the bacon wrapped sausages and shake to coat. Remove sausages, place on prepared pan, and repeat with remaining sausages.
Season sausages with black pepper, if desired.
Bake until bacon has browned, 30-35 minutes. If crispier bacon is desired, broil for a few minutes to brown. Enjoy!