Use an electric or stand-up mixer when making the pudding, cream cheese mixture, and homemade whipped cream. You don’t have to wash the beaters between steps because they will all be mixed together.
In a large bowl, whisk together the gluten-free instant vanilla pudding mix and whole milk until fully combined. Let it sit for 5 minutes to thicken slightly.
In a separate bowl, beat the softened cream cheese until smooth and creamy. Add the sweetened condensed milk and vanilla extract, beating until well combined and lump-free.
In a third bowl, whip the heavy whipping cream and powdered sugar on high speed until stiff peaks form. This is your homemade whipped cream.
Gently fold the cream cheese mixture into the prepared vanilla pudding. Then, gently fold in the homemade whipped cream until just combined, being careful not to deflate the mixture.
To assemble: In a large serving bowl or individual dishes, layer gluten-free vanilla wafers, sliced bananas, and the pudding mixture. Repeat layers, ending with a layer of pudding. Chill for at least 4 hours, or preferably overnight, before serving to allow the flavors to meld and wafers to soften.