In a large bowl, beat the softened cream cheese until smooth.
Gradually add the powdered sugar, mixing well.
Fold in the whipped topping until fully incorporated.
In another bowl, whisk together the chocolate pudding mix and milk for 2 minutes.
Allow the pudding to set for about 5 minutes.
Combine the pudding mixture with the cream cheese mixture and blend thoroughly.
In a trifle dish or a large bowl, layer half of the crushed Oreos at the bottom.
Spread half of the pudding mixture over the Oreos.
Add another layer of the remaining crushed Oreos.
Top with the remaining pudding mixture and smooth out the top.
Finish with crushed Oreos and gummy worms for decoration.
Refrigerate for at least 2 hours before serving.