Mix the pudding according to box directions, adding 1/4 cup more milk. You want it to thicken, but not as thick as pudding when it sets up. Whip in sherry (optional) and vanilla; and store in fridge.
Slice the pound cake into 1/2-inch slices, anticipating two slices per serving. (Optional: using a pastry brush or your fingers, sprinkle the tops of the slices with sherry. Damp, but not wet.)
Spread a generous coating of fruit preserves on the top of each slice (approx. 2 tablespoons per slice). Place 1 slice of pound cake on each serving plate. Top with fresh fruit and drizzle pudding over all.
Place second slice on top of first slice. Repeat with fruit and then pudding. Allow the pudding to drizzle over the sides and puddle on the plate.
Top each serving with whipped topping. Place the extra pudding on the table either in a creamer or your gravy boat with ladle. If you wanted to get really fancy, you could top with some shaved chocolate or crushed toffee bar.