In a large bowl whisk together vanilla pudding and milk then refrigerate for at least 5 minutes.
Fold in condensed milk.
Reserve 1 cup of whipped topping then fold the remainder of the container into the pudding mixture. Place the pudding back into the refrigerator while you slice the bananas.
Once the bananas are sliced begin layering ingredients into a trifle bowl starting with the wafer cookies. Place ½ of the cookies on the bottom of the bowl. Next put half of the banana slices on top of the cookies. Finally add half of the pudding mixture to the bowl. Repeat these steps for the next layer ending with pudding.
Spread the reserved 1 cup of whipped topping on the top of the desert. Garnish with crushed cookies and banana slices.