In a heat proof bowl combine the chocolate milk and chocolate chips. Place the bowl over a medium size pot filled with simmering water. Continue to simmer water until the chocolate completely melts. Stir until combined.
In a stand mixer (or blender) combine the chocolate mixture, banana, and extracts. Mix until combined.
Add the prepared whipped cream and mix until smooth.
To make 1 cup of whipping cream all you need to do is mix 1/2 cup of heavy cream and about 1 teaspoon of sugar in stand mixer until it's fluffy.
Now pour into a metal container, or plastic if you don't have metal, and place in the freezer for at least 4 hours, preferably overnight.
Remove a few minutes before serving.
Serve with a big old chocolatey-banana smile!