At the bottom of each glass, add 2-3 tablespoons of hot fudge. In a blender, combine milk, ice cream, vanilla extract, bourbon, and about 1/4 cup of hot fudge. Blend until smooth and creamy. Pour into glasses and top with bourbon whipped cream + another tablespoon of hot fudge.
Whip ingredients together in an electric mixer until soft peaks form. Top shakes.