3 (1.5 fluid ounce) jiggers creme de cacao
2 (1.5 fluid ounce) jiggers vodka
1 (1.5 fluid ounce) jigger vanilla-flavored vodka
1 cup crushed ice, divided
1/4 cup granulated sugar, or as needed
1 wedge orange
Combine creme de cacao, vodka, and vanilla-flavored vodka in a cocktail shaker. Secure lid on shaker and shake vigorously.
Spread sugar onto a flat plate wider than your martini glasses. Run the orange wedge along the lip of each martini glass to assure it's moistened all the way around; dip martini glasses in sugar to coat.
Divide remaining ice between the martini glasses. Strain the cocktail into the glasses.