Let your butter soften at room temperature. Line 18 muffin cups with cupcake liners. Preheat your oven to 375 degrees.
CUPCAKES -- Whisk together flour, sugar, cocoa, soda, and salt in a large bowl.
Add oil, water, and vinegar to the dry ingredients. Whisk till smooth.
Divide cake batter between the 18 liners, filling them about half full. Bake at 375° for about 16-19 minutes. (Start the filling while the cupcakes bake.)
Let cool in pans for five minutes, then remove to a wire rack. Cool completely.
FILLING -- Whisk together flour and milk in a medium saucepan. Cook and stir over medium heat till thick and creamy like pudding. Cool completely. (I like to place my pan in a sink filled with about 3” of ice water to speed things up.)
In a medium bowl, beat butter and sugar till creamy. Add milk mixture and vanilla. Beat for 5-7 minutes, or till smooth, thick, and creamy. It may look curdled at first, but keep beating and it will eventually turn out.
FROSTING -- Beat butter and cocoa till smooth. Add salt, powdered sugar, and about 2 tablespoons of the cream. Beat till smooth, adding more cream as needed to reach desired consistency.
ASSEMBLE -- Scoop filling into a piping bag with a large round tip. Poke a hole in the top of each cupcake and fill with about a tablespoonful of filling.
After all the cupcakes are filled with creamy goodness, pipe the chocolate frosting on the tops of the cupcakes using a large star tip. Enjoy!!
Notes
Cupcakes can be stored in an airtight container at room temperature for 3-4 days.