Step 1
Preheat oven to 375 degrees F (190 degrees C). Cut and set aside 25 pieces of plastic wrap about 5 inches square.
Step 2
For cookies beat 1/2 cup of vegetable shortening 2 cups of milk 2 cups of sugar the eggs and 2 teaspoons of vanilla extract together in a large mixing bowl until smooth and creamy. In a separate bowl whisk the 4 cups of flour with both amounts of unsweetened cocoa baking soda and salt until thoroughly combined. Beat the flour mixture into the wet ingredients just until smooth.
Step 3
Scoop up the batter by teaspoons and drop onto ungreased baking sheets in small round dollops about 2 inches apart. Recipe should make about 50 cookies. The cookies will rise and expand a lot.
Step 4
Bake in the preheated oven until the cookies are set in the middle 8 to 10 minutes. Allow to cool on baking sheets for several minutes before removing to finish cooling on racks.
Step 5
To make the filling place 1 cup milk in a microwave-safe measuring cup and cook in microwave until hot but not simmering 1 to 2 minutes. Pour the heated milk into a large mixing bowl. Add the cup of room temperature butter 1 cup of vegetable shortening 2 cups of sugar 2 tablespoons of flour 2 teaspoons of vanilla extract and the marshmallow creme. Beat the mixture on high speed until the frosting is fluffy 5 to 10 minutes. At first the frosting will appear lumpy but keep beating.
Step 6
To fill the cookies choose 2 cookies that are about the same size and spread about 1 1/2 tablespoon of the frosting onto the flat bottom of a cookie. Top with the other cookie flat side down and wrap the filled cookie in a sheet of plastic wrap. Place the filled cookie into the freezer. Repeat with remaining cookies and frosting wrapping each whoopie pie in plastic wrap and freezing.
Step 7
To serve remove whoopie pies from the freezer and allow to thaw until very cold but not frozen 10 to 15 minutes.