Combine marshmallow and milk in a small saucepan and cook over low heat. Stir occasionally until marshmallows are melted. Add all 36 unwrapped Hershey's kisses and stir constantly until chocolate is melted. Remove from heat and bring to room temperature. Take heavy cream and beat to soft peaks then add vanilla and confectionary sugar and continue beating until almost stiff peaks form. Fold 2/3 cup of whipped cream into chocolate mixture. Fill the mixture into mugs or parfait glasses about 3/4 the way to the top. Put into refrigerator and let set for 3-4 hours. Spoon/pipe reserved whipping cream and top with a kiss.