To 3qt mixing bowl, add sweetened condensed milk and whipped cream cheese then whisk until well combined.
Add instant pudding mixes and whole milk then whisk until pudding mixes are fully dissolved and pudding starts to thicken.
Add cinnamon + nutmeg to pudding then whisk until well-combined.
Using a sharp knife, cut bananas into round but firm slices.
To trifle bowl, start with adding a layer of cookies until bottom is covered and there's no room for more cookies.
For the next layer, add half of the sliced bananas and ensure the cookie layer is completely covered.
For the next layer, add half of the pudding and spread it around until it forms an even layer and the whole bananas are completely covered.
Use additional cookies to form a moat around the layer of pudding.
For the next layer, add half of the whipped topping into the cookies moat and spread it around until it forms an even layer on top of the pudding and the pudding is completely covered.
Repeat steps until all of the cookies, whole bananas, pudding and whipped topping have been used up.
Placing remaining cookies in storage bag and crush into crumbs using a mallet or rolling pin.
Sprinkle crumbs on top of final whipped topping layer until it is well-coated.
Cover bowl and chill in refrigerator overnight before serving (optional).