XBOX enforcement penalties for original and licensed XBOX content. How that can be right...

If you recently transferred content to a new console, you can play the content on your new console if you sign in using the gamertag that originally purchased the content. If you want to use the transferred content without signing into Xbox LIVE or
with a different gamertag, you’ll need to transfer the content licenses to your new console. For information on how to do this, see Xbox 360 Digital
Rights Management.

Usually how it works is the license that is transferred is the console license. Which means that the console which has the license can be used offline with other profiles (including your own). Your other console can also use your content so long as the
original gamertag which purchased the content is logged into Xbox live (even if another profile wants to use the content)

This is the answer you are looking for and how DLC add on's work. Please read all.

What is "Digital Rights Management"?

Digital Rights Management (DRM) technology is used by content providers such as Xbox LIVE Marketplace to control how game and video files are used and distributed. Xbox LIVE Marketplace sells and rents DRM-protected videos, games, and add-in content that
are covered by media usage rights that allow specific uses of that content.

When you purchase content, you receive a license to use that content. The license has two parts: the system license and the local license. The system license applies to the gamertag that purchases the content, and the local license applies to the console
where you first downloaded the content

Can I transfer a content license from one Xbox 360 console to another?

Yes, you can transfer content licenses from one console to another once every four months.

If your console was recently repaired or if you’ve purchased a new console, use the license transfer option on your console to transfer content licenses. Here’s how:

1.On your console, sign in to Xbox LIVE using the gamertag that you used to purchase the content.

•Don't know your gamertag? See Download, move, or delete your Xbox LIVE profile.

•Need to find your Microsoft account? See Find your Microsoft account.

•Can't remember the password for your Microsoft account? See Recover your Microsoft account password.

2.Go to Settings and select Account.

3.Go to Your Billing Options and select License Transfer.

4.Follow the instructions to transfer the content licenses.

After the licenses are transferred, you need to download the content again to update the local licenses. Then the content can be used by other profiles on your console and
when you’re not connected to Xbox LIVE.

For information about how to download previously purchased content, see Buy and redownload content from Xbox LIVE

Recommend, just add your profile to the XBOX your son is using and download the games that you want him to have access to. Make sure his profile is set up on the new XBOX. Here is how the licenses work.

What is "Digital Rights Management"?

Digital Rights Management (DRM) technology is used by content providers such as Xbox LIVE Marketplace to control how game and video files are used and distributed. Xbox LIVE Marketplace sells and rents DRM-protected videos, games, and add-in content that
are covered by media usage rights that allow specific uses of that content.

When you purchase content, you receive a license to use that content. The license has two parts: the system license and the local license. The system license applies to the gamertag that purchases the content, and the local license applies to the console
where you first downloaded the content

Can I transfer a content license from one Xbox 360 console to another?

Yes, you can transfer content licenses from one console to another once every four months.

If your console was recently repaired or if you’ve purchased a new console, use the license transfer option on your console to transfer content licenses. Here’s how:

1.On your console, sign in to Xbox LIVE using the gamertag that you used to purchase the content.

•Don't know your gamertag? See Download, move, or delete your Xbox LIVE profile.

•Need to find your Microsoft account? See Find your Microsoft account.

•Can't remember the password for your Microsoft account? See Recover your Microsoft account password.

2.Go to Settings and select Account.

3.Go to Your Billing Options and select License Transfer.

4.Follow the instructions to transfer the content licenses.

After the licenses are transferred, you need to download the content again to update the local licenses. Then the content can be used by other profiles on your console and when you’re not connected to Xbox LIVE.

For information about how to download previously purchased content, see Buy and redownload content from Xbox LIVE

ok, you downloaded them to your xbox right? Then he played them, on your console, BECAUSE you downloaded them there originally. If you were to download your name onto his xbox and start playing a game there, he would NOT be able to play anything on that
console without your gamertag being housed there.

The gamertag and the console both have licenses for the content.

The console is the oringinal housing. The gamertag is the original owner.

If the oringial owner is playing in the original housing, all other players can play content housed there.

If the original owner moves his gamertag from the original housing, no one else will be able to play the content on the original housing until the original owner comes back.

If a gamertag that did NOT buy the content is on the original console, that tag can play content (so long as original owner has not moved his gamertag to another console housing.)

If the original gamertag wants to download in two spots, he has to be in each spot in order for the content to work. bottom line. no matter where it is, no matter if you license transfer to another console.

In short terms, this will not work. You can license transfer, but the original gamertag that downloaded the content will need to be active on the xbox AND NOT on another.