Cut butternut squash in half and remove seeds. Place squash with the cut side down into a glass baking dish and add a small amount of water. Cover with plastic wrap and cook in microwave for approximately 20 minutes, or until very tender. Place in blender or food processor. Add 1 teaspoon of vanilla and mix until smooth and creamy. (Two cups of softened squash will make 2 pies.) Set aside to cool while preparing the remaining ingredients. Mix vanilla pudding according to package directions for pie, using 1 1/2 cups skim milk. Add remaining vanilla and sugar. Mix one packet of Dream Whip according to package directions. Combine squash, pudding and Dream Whip together and pour into pie crusts. Cool for 3 hours. Top with whipped cream and serve.