Preheat the oven to 425 degrees F (220 degrees C).
Mix white sugar, brown sugar, and flour in a large bowl. Add softened butter, 1 cup heavy cream, eggs, and vanilla; mix until well-blended. Pour into 2 unbaked pie shells.
Bake in the preheated oven for 10 minutes, then reduce temperature to 350 degrees F (175 degrees C) and continue baking until center is set, 45 to 50 minutes.
Whip 1 cup heavy cream in a mixing bowl and add sugar gradually until stiff peaks form. Gently fold in bourbon. Serve pie slices with dollops of whipped cream.