Heat a large stockpot over medium-high heat. Add oil and 3 popcorn kernels; cover. Once they pop, add remaining popcorn kernels; cover, and shake pot. Cook until a few more kernels start to pop.
Add confectioners' sugar, and cook, covered, shaking pot, until kernels stop popping, about 2 minutes. Add maple sugar, and remove from heat. Let stand for 5 seconds, then stir to coat. Transfer to a bowl. Add 3/4 teaspoon salt and 1/4 teaspoon pepper; toss to coat.
Storage: Popcorn can be stored in an airtight container for 1 day.