Dissolve the instant espresso in the fresh espresso and let cool while preparing other ingredients.
Preheat oven to 325°F. Line standard sized cupcake pans with baking liners (will make 16).
In the bowl of a stand mixer, combine the sugar, flour, baking powder, baking soda and salt. Using the paddle attachment, beat in the butter until it forms powdery crumbs.
In a separate bowl mix the eggs, sour cream, oil, vanilla and coffee extract. Add to the dry ingredients and mix just until combined. Slowly add espresso. Batter will be thin. Divide among cupcake liners, filling each cup about halfway full. Bake for 15-18 minutes or until a toothpick inserted in center comes out with just a few dry crumbs. Let cool in pans on wire rack.
For the frosting:
Dissolve the instant espresso in the brewed espresso. Chill completely in the refrigerator.
Beat chilled espresso, sweetened condensed milk, pudding mix and coffee extract until well blended. Set aside in refrigerator while preparing whipped cream.
Beat cream until stiff peaks form. Fold into pudding mixture. Scoop into pastry bag and chill until thickened. Pipe onto cooled cupcakes.