Grease and preheat a round waffle baker according to manufacturer's directions.
In a large bowl combine cake mix, chocolate milk, eggs, butter, and peanut butter chips.
Pour 1/2 cup of batter in the center of the waffle baker. Close lid and bake until edges are crisp. Repeat with remaining batter. Cool completely on wire racks.
Meanwhile, transfer bananas to a quart-size re-sealable plastic bag. Mash until smooth.
In a large bowl beat cream cheese until light and fluffy. Add sugar and vanilla; beat until combined. Add heavy cream and beat until stiff peaks form. Fold in mashed bananas.
Lay a waffle on a cake stand or serving plate. Spread with about 1/2 cup banana whipped cream. Repeat with remaining waffles and whipped cream.
Meanwhile, pour hot cream over chocolate chips and let stand 3 minutes. Whisk until smooth and carefully pour over the top of the cake, allowing excess to drip over the sides. If desired, chill up to 1 hour.
To serve, top with berries and sprinkle with powdered sugar. To serve, take 3 to 4 layers off the top at a time and slice.