Add chocolate milk ingredients to a blender and blend until creamy and smooth, adjusting flavor/level of sweetness as desired. Transfer to a serving glass or jar and refrigerate to chill.
Rinse blender and add cherry milk ingredients. Blend until creamy and smooth, then taste and adjust flavors/sweetness as needed.
Add a few ice cubes to your serving glasses and top with cherry milk (or do it in the reverse order). Drink immediately.