For the cakes:

2 cups granulated sugar
1 cup shortening
2 eggs
4 cups flour
2 tsp. baking soda
1/2 cup cocoa
1 2/3 cup milk
2 tsp vanilla

For the cream filling:

3 tbsp. flour
2 tsp. vanilla
1/2 cup milk
2 lb. powdered sugar (a.k.a. 10x sugar)
1 cup shortening
Chai Masala to taste

For the cake:

1.  Preheat oven to 350º
2.  In a large mixing bowl, combine 2 cups sugar, 1 cup shortening, and 2 eggs. Blend together until smooth.
3.  In a medium bowl, combine 4 cups of flour, 2 tsp. baking soda, and 8 tablespoons of cocoa. In a small bowl, combine 1 2/3 cup of milk and 2 tsp. vanilla.
4.  Alternate adding the dry and wet ingredients from medium and small bowls to the large bowl. About half at a time. Beating the mixture each time to combine ingredients.
5.  Mix batter until smooth. It should look like a mix between frosting and cake batter. Add more milk (or water) a teaspoon at a time if batter is too thick. You need to be able to scoop the batter like cookie dough so be cautious if adding extra milk.
6.  Spray cookie sheet (you'll need multiple) or line with parchment paper. Add batter to cookie sheet by the tablespoon. Space about one inch apart. Use 1/2 a tablespoon to create smaller whoopie pies.
7.  Bake for 8-9 minutes. Papa says the cakes are "ready when the tops spring back when touched." 
8.  Once cakes finish baking, remove from oven and transfer to a wire rack to cool completely.  

While cakes bake, prep filling.

For the cream filling: 

1.  In a large bowl, mix together 2lbs powdered sugar and 1 cup of shortening. 
2.  Add 3 tablespoons of flour, 2 teaspoons vanilla, and roughly 1/2 cup of milk.
3. Papa Pro Tip: add the milk a little at a time while mixing, until you achieve a thick but creamy frosting constancy. Be careful not to add too much milk or the frosting will be too runny to add to the cakes.
4.  Add chai masala to taste.
5.  Mix together until smooth and creamy.

Final step:

Sandwich desired amount of filling between two pieces of cake. Repeat and enjoy!

*You may have leftover cream/frosting depending on how many cakes your batch makes and how much cream/frosting you add to the cakes. 

(Pictured: Papa, Grams, and me circa 1992)