Preheat oven to 350 degrees F. In a medium size bowl, cream together shortening and sugar. Add eggs, milk, and vanilla.
In a separate bowl, mix dry ingredients (flour, baking powder, and salt). Slowly mix dry ingredients into the wet mixture until you form a large dough ball. Refrigerate for 30 minutes.
Lightly flour your countertop. Roll the dough balls out until ½ inch to ¾ inch thick. Cut the dough into shapes using a cookie cutter. Place cookies on a lightly greased cookie sheet.
Bake at 350 degrees for about 8-10 minutes. Cookies should still be soft when you take them out, but not doughy. (Don't overcook or they will be hard!)
In a small bowl, mix together cream cheese, powdered sugar, and vanilla. Beat until smooth, then fold in the Cool Whip and stir well. Spread a thin layer of the cream cheese frosting over the cooled sugar cookie. Place fruit on top. Serve immediately!