Are there any consequences for his actions, such as removing a favorite tv show or video game privileges etc.? Your ability to stay firm in redirecting him to bed without confrontation is admirable. You have to be consistent so that he knows that you mean business and giving in and letting him stay up or sleep with you would seriously undermine what you are trying to accomplish. One suggestion is to have him repay your time. In other words, for however long it takes you to finally get him into bed and asleep is time that you would have otherwise used for doing whatever you do at that time, whether it be resting, sleeping, doing laundry etc. So for however long that is, then the next day during "his" time for recreation, instead he must do a chore or something for the amount of your time that he wasted. It is a consequence in a way, but also teaches responsibility and appreciation for others time and duties. Good luck! I hope this helps.
