Preheat oven to 375 degrees. Spray 2 baking sheets with nonstick spray, or line with parchment paper.
In large mixing bowl, combine sugar and butter. Mix by machine or hand until fluffy. Add eggs, milk and vanilla and lemon extracts, and mix until smooth.
In medium bowl, combine cake flour, all-purpose flour, baking powder and salt. Stir until mixed. Add dry mixture to the wet in batches, stirring well after each addition. Using a soup spoon, place large spoonfuls of the dough about 2 inches apart on the baking sheets. Bake until edges begin to brown, 18 to 20 minutes. Cool completely.
Boil a cup or so of water in a small pot. Place confectioners’ sugar in large, heat-safe mixing bowl. Gradually stir in enough boiling water to the sugar to make a thick, spreadable mixture. You don't want to add too much because the icing will become too thin. Place the bowl over the boiling water, creating a double broiler. This will help keep the icing loose enough to coat the cookie.
Spread frosting on half of the flat side of each cookie. I tried this a couple of ways before getting it right. THe icing tends to become dry very quickly so I would dip the cookie half into your icing while it's over the boiling water. Let the excess icing drip off and lay flat. This will ensure that the icing stays smooth on the cookie and not splotchy.
Once you've finished with the vanilla, stir in the bitter or unsweetened chocolate until melted, as well as the light corn syrup.
Dip the other half of each cookie in the chocolate. It's ok if there's overlapping. The chocolate tends to dry out even quicker than the vanilla, to keep this from happening you can add some of the boiling water to the mixture. I would add it about 1/4 a cup at a time, stirring constantly. Continue doing this until the frosting reaches a shiny, loose consistency.
Let the frosting set. Store in an airtight container. Enjoy!
