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In a large bowl, beat together the softened cream cheese and powdered sugar until smooth and creamy.
Add the instant vanilla pudding mix and 2 cups of milk to the bowl. Continue to mix until everything is well combined and the pudding starts to thicken.
In a separate bowl, whip the heavy whipping cream until stiff peaks form. Gently fold the whipped cream into the pudding mixture until well combined.
In a 9x13-inch baking dish, lay down a layer of graham crackers to cover the bottom of the dish. Break them into smaller pieces if needed to fit.
Spread half of the cream mixture evenly over the graham crackers.
Add another layer of graham crackers on top of the cream mixture.
Spread the remaining cream mixture over the second layer of graham crackers. Finish by adding a final layer of graham crackers on top.
In a microwave-safe bowl, warm the chocolate frosting in the microwave for about 20-30 seconds to soften it. If it's too thick, add 1 tablespoon of milk to reach a pourable consistency.
Pour the chocolate frosting over the top layer of graham crackers, spreading it evenly with a spatula.
Cover the dish with plastic wrap and refrigerate for at least 4 hours, or preferably overnight.
Slice the cake into squares and serve chilled. Garnish with whipped cream or extra chocolate shavings if desired.