In a medium bowl, stir pudding and milk and set aside. Beat whipping cream and sugar until peaks form. Add about 1/4 of the whipped cream to the pudding and gently fold it in to lighten it. Fold the remaining whipped cream into pudding and serve in small bowls or cocktail glasses on an underliner plate. Place a few berries on each dessert to garnish and serve a few cookies on the underliner plates.