Preheat oven to 325 degrees F. Butter three 8" cake pans with 1 1/2-inch-high sides.
Line bottoms with parchment paper round; butter parchment. Place chocolate in l bowl set over saucepan of simmering water. Stir until melted and smooth.
Whisk all purpose flour and next 4 ingredients in medium bowl. Using electric mixer, beat brown sugar, butter, and vanilla in large bowl to blend. Add eggs 1 at a time, beating well after each addition. Beat in warm melted chocolate.
Mix in dry ingredients in 2 additions alternately with buttermilk in 1 addition. Divide batter among prepared pans.
Bake cakes until tester inserted into center comes out clean, about 23 minutes. Cool cakes in pans 10 minutes. Turn cakes out onto rack; peel off parchment.
Cool cakes completely. Can be made 1 day ahead. Wrap cakes in plastic and store at room temperature.
In a large mixing bowl beat the shortening, butter, creamer and vanilla. Gradually beat in the confectioners sugar.
Add in enough water until frosting reaches desired consistency. To make chocolate frosting, beat in cocoa powder to taste or to achieve the desired chocolatey-ness.
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