Use a small knife and cut around the edge of the oranges to loosen the fruit from the rind. Use a spoon and scoop the fruit out of the halves, reserving the juices. Place the orange halves, cut side up, in a 12-cup muffin tin. This will keep the oranges even when you fill with jello.
In a medium bowl, toss to combine raspberries, strawberries, peaches, pineapple and sugar. Place the black cherry jello in a medium bowl and pour over the boiling water. Whisk to dissolve the jello, about 2 minutes. Stir in 1/2 cup reserved orange juice, 1/4 cup cold water, red wine and triple sec.
Spoon about 2 tablespoons of the marinated fruit into each of the orange halves, then pour in the jello mixture to the top of the orange. Transfer to the refrigerator until jello is set, about 6-8 hours and up to overnight.
To serve, slice the oranges in half through the stem.