Line the bottom of a 9x13 baking dish with the vanilla wafer cookies.
Add a layer of mandarin orange segments.
Add the cream cheese, condensed milk to a mixing bowl, beat with an electric mixer until smooth.
Add the dry pudding mix, vanilla, and milk. Beat until fully combined then set aside. Wash and dry the mixer blades if you are using fresh cream.
In another mixing bowl, add the whipping cream and beat until soft peaks form, then add the powdered sugar and beat until stiff peaks form, then set aside 1 1/2 cups.
Take the remaining whipped cream and fold that into the pudding mixture. OR fold in two containers of Cool Whip. I used Cool Whip.
Spread the pudding mixture evenly over the oranges.
Top the pudding with the reserved whipped cream OR another container of Cool Whip. Cover and place in the fridge for at least 4 hours, or overnight.
To serve, slice into serving size pieces, top each serving with a mandarin orange segment if desired.
Enjoy.