1 Line 9-inch square baking pan with foil. Spray foil with no stick cooking spray. Place chopped chocolate in large bowl. Set aside.
2 Bring sweetened condensed milk and cream to simmer in medium saucepan on medium heat, stirring frequently with wire whisk. Pour over chopped chocolate. Let stand 1 minute. Whisk until chocolate is melted and mixture is smooth. Stir in orange extract. Pour into prepared pan.
3 Refrigerate 4 hours or overnight until firm. Cut into 36 squares. (May be made ahead. Store chocolate mixture, tightly covered, in pan in refrigerator up to 2 weeks. Bring to room temperature before cutting into squares.)
4 To assemble chocolate on a stick, thread a marshmallow half and a chocolate square onto each lollipop stick. Wrap each hot chocolate on a stick in plastic wrap or small cellophane bag. (May be assembled up to 2 days ahead.)
5 To serve, stir hot chocolate on a stick into 8 ounces hot milk.