Combine berries, sugar, and orange liqueur in a large, nonreactive bowl and stir to coat the fruit. Let rest at room temperature, stirring occasionally, for 1 hour, so the mixture releases its juices.
Meanwhile, butter a 1-quart bowl and line it with enough plastic wrap so at least 6 inches is hanging off on all sides. Press the plastic wrap into the bowl so there are no air bubbles.
Line the inside of the prepared bowl with brioche slices, cutting them as necessary to fit snugly. (You may have to overlap the slices, and you should have a few left over to cover berries.) Set aside.
Once the fruit has rested, pour the berries and juices into the brioche-lined bowl, pressing down so they all fit. Top with remaining brioche, taking care to cover exposed berries. Press firmly on the top bread pieces to flatten them and push the juices into the bread. Cover the bread with the overhanging plastic wrap and place a plate (small enough to fit just inside the bowl) on top. Put 6 to 7 pounds of weight on the plate (large cans of tomatoes work well), and place the bowl in the refrigerator for 24 hours.
To unmold the pudding, remove the plate, unwrap the plastic, invert the bowl onto a serving platter, and lift off the bowl. Remove the plastic wrap and serve the pudding sliced, with whipped cream and additional berries if desired.
Beverage pairing: Doisy-Daëne Sauternes, France. Something sweet and racy will be nice with this dessert, and any number of sweet wines could work. In this case, a good choice is Sauternes. Its peach, pear, and apricot flavors will complement but not mimic the berries, and it has the weight and richness to hold up against the cream.
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