In a large bowl, whisk together the gluten-free instant vanilla pudding mix, whole milk, softened cream cheese, sweetened condensed milk, and vanilla extract until smooth and creamy. Use an electric mixer for best results.

In a separate bowl, whip the heavy whipping cream and powdered sugar until stiff peaks form. Be careful not to overmix.

Gently fold the whipped cream mixture into the pudding mixture until just combined. Be careful not to deflate the whipped cream.

Arrange a layer of sliced bananas at the bottom of your serving dish (a 9x13 inch dish works well).

Top the banana layer with a layer of gluten-free vanilla wafers. Break them if needed to fit.

Pour half of the pudding mixture over the wafers. Repeat layers of bananas, wafers, and then the remaining pudding mixture. Chill for at least 4 hours, or preferably overnight, before serving.