Line a large bowl (about 6 to 8 cup capacity) with plastic wrap. Cut the bread into diagonal halves and arrange them, puzzle-like, into the bottom and up the sides of the bowl.
In a large saucepan, heat the fruit, sweetening sugar and port and cook until the fruit is tender and beginning to burst, but still holds its shape, about 5 minutes. Remove from the heat and cool slightly. Using a slotted spoon, spoon the fruit into the bread-lined bowl, and spoon most of the juices over the fruit. Reserve the remaining cooking juices.
Top the fruit with a flat layer of the remaining bread, so that the fruit is completely covered. Cover with the plastic wrap and place a plate over the top. Add 2 heavy cans or a 2-pound weight to the plate and let sit at least 8 hours, or overnight, refrigerated.
In a large bowl, whip the cream until soft peaks just begin to form. Add the 1/4-cup sugar and whip until almost stiff.
To serve, remove the weights and plate and unwrap. Place a large serving plate on top of the bowl and gently invert. Shake gently to release the pudding onto the plate and remove the plastic wrap. Spoon the reserved fruit juices over the top and serve with sweetened whipped cream.
Yield: 6 to 8 servings