Mix entire contents of vanilla pudding mix, 3 Tablespoons chocolate pudding,1 tsp vanilla, and milk in a large bowl with a whisk. Set in fridge to chill 5-10 minutes.
Place Oreos in food processor and blend until they are fine crumbs (no large chunks). If you don't have a food processor, you can place them into a gallon-size freezer bag and smash using a rolling pin. This will take a bit of time, since you'll want to get rid of all large pieces.
Take the pudding from the fridge and mix in the crushed Oreos. The mixture will be dark gray/black. Now, fold in whipped cream being careful not to break down the whipped cream. It now is a lighter color but not quite gray.Place back in fridge to chill for at least one hour before serving.
To serve, spoon into a cake decorating bag fitted with a star tip (Wilton 1M) pipe on top of each cupcake in a swirl pattern. Top with a few edible pearl sprinkles.
This will frost 12-14 cupcakes.