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1
Preheat oven to 425 degrees and butter and flour two 8-inch round cake pans.
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2
In a medium-sized bowl, sift together the cocoa powder, flour, baking powder, and 1/2 cup of sugar. With your fingers, mix the butter in until it ranges in size from small pebbles to grains of sand.
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3
dd the milk and mix with a fork to incorporate. The dough will look like a mess, shaggy and lumpy. But don't worry; it will bake up just fine.
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4
Pour half of the dough into each pan and use a spatula to spread it evenly to the edges of the pan. Bake until a toothpick comes out clean, 10 to 12 minutes. Let the shortcakes cool in the pan for about 30 minutes.
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5
While the cakes are cooking and cooling, prepare the orange sauce. Using a small sharp knife, slice the top and bottom off each orange. Resting the orange on a cutting board on one of the cut ends, cut off the peel from top to bottom making sure to remove all of the pith. Cut out each section of the orange by cutting between the white section dividers, which I just learned are called carpels. Reserve the carpels and any pulp. Repeat this for the remaining oranges.
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6
Using your hands, squeeze the juice from the pulp and carpels into a small bowl. At this point, your hands will be red with the juice of the oranges. By the time you are finished washing up the dishes after making the cake, though, the color will have rinsed off and your hands will have returned to their usual hue.
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7
Pour the juice and half of the orange sections into a small stockpot. Add 2 tablespoons of sugar. Cook the sauce over medium heat, stirring occasionally, until it thickens, about 15 minutes. Set aside to cool. When the sauce has cooled, stir in the remaining orange sections.
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8
Whip the cream with a mixer until it holds soft peaks. Add the remaining 2 tablespoons of sugar and vanilla and mix for a few more seconds.
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9
After the cakes have cooled, remove them from their pans by running a knife around the sides of the pans and turning them out onto a serving plate. Once assembled with the cream and sauce, the cake will need to be eaten immediately (such hardship!) so if you are not eating it all at one meal, cut slices of the cake first and assemble individual servings.
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10
Place the first layer on a serving plate. Spoon the orange sauce over the bottom layer and top with a couple of tablespoons of whipped cream. Add the top layer. If you like, add another dollop of whipped cream, and drizzle a bit of the sauce on top.
