Prepare the cake per the instructions on the box in a 9x13-inch pan.
Once the cake has cooled slightly, use the end of a wooden spoon to poke holes randomly in the cake. In a medium bowl, combine the sweetened condensed milk and half and half. Pour that over the cake ensuring to fill the holes with the mixture.
Next, combine the pudding mix and milk together in a medium bowl (it can be the same bowl you used before) and mix well. Allow the pudding to set slightly (about 5 minutes) then pour the pudding over the cake making sure to fill the holes. Cover and refrigerate for 3 to 4 hours or even better, overnight.
When ready to serve, pour the whipping cream into a large bowl and whip using a hand mixer or in stand mixer until frothy. Add the powdered sugar a tablespoon at a time until it reaches your desires sweetness. Whip until you get stiff peaks then spread the whipped cream over the cake. Top with the fruit as desired.