Sprinkle a line of shredded cheese across the bottom third of a tortilla and set a hot dog on top. Starting at the same end, roll the tortilla around the hot dog. Place the pup seam side down on a baking sheet coated with cooking spray. Brush with olive oil. Bake at 375° until golden brown, about 20 minutes. Use tongs to hold the pup and slide a lollipop stick or skewer into one end. Serve with your child's favorite hot dog toppings.