1 1/2 fluid ounces rum
1 1/2 fluid ounces triple sec
3 tablespoons pickled chutney (such as Branston®)
1 1/4 ounces Brie cheese, or more to taste
1 cup ice cubes, or as needed
1 dash Worcestershire sauce, or to taste
1/2 ounce wedge Stilton cheese, or as desired
Combine rum, triple sec, pickled chutney, and Brie cheese in a blender; pulse 1 or 2 times to combine. Add ice cubes and blend until drink is slushy, 1 to 2 minutes. Pour drink into a martini glass; top with Worcestershire sauce and garnish glass with Stilton cheese wedge.