Place 3 pitted cherries in each of 4 dessert bowls - set aside.
Place the rest of the pitted cherries in a measuring cup. Add enough milk to bring the level up to 2 c.
Put the milk and cherries in a blender. Add the flavoring and cornstarch. Puree.
Roughly chop the chocolate. Pour the cherry mixture into a saucepan, add the chocolate, and place over low-medium heat.
Stir constantly until the chocolate melts and the pudding thickens.
Once the pudding is fully thickened, pour it carefully over the cherries in the bowls. Let cool.
Refrigerate until serving.