In a large bowl, whisk together the milk and sweetened condensed milk until combined. Sprinkle in the instant pudding, and mix until completely incorporated with no lumps remaining. Refrigerate for 5 minutes or until set.

Add 2 cups of cream, 2 tablespoons of sugar, and 2 teaspoons of vanilla to a bowl, then mix on high until stiff peaks form.

Remove pudding from the refrigerator then fold the whipped cream into it.

Peel the bananas and slice them into ½-inch thick coins.

To assemble, add a layer of cookies to the bottom of your trifle dish or a large serving bowl. Place a quarter of the pudding mixture over the cookies, then smooth using a spatula.

Add another layer of cookies then place a row of cookies set upright against the side of the dish facing out. Add a layer of banana slices on top. Add another quarter of the pudding mixture and smooth.

Continue layering with cookies, bananas and pudding until complete. Chill for three hours.

Whip the remaining 1 cup of cream, remaining 1 tablespoon of sugar, and remaining 1 teaspoon of vanilla until soft peaks form. Top the pudding with the whipped cream and pile any remaining cookies on top.