Actually, it depends.

If you purchased the songs using your Gamertag while logged in on his Xbox 360, then he'll be able to play the songs on his Xbox on all gamertags associated with that hardware. You, on the other hand, will ONLY be able to play the songs on your Xbox 360 at home ONLY WHEN SIGNED IN TO YOUR GAMERTAG AND ONLY WHILE ONLINE.

If you purchased the songs using your Gamertag while logged in on his Xbox 360 and then you go back home and transfer licenses onto your own Xbox 360, then YOUR COUSIN LOOSES THE ABILITY TO PLAY SAID SONGS. The license transfer DEAUTHORIZES the use of content on a system and enables it on another. Once this happens, you can use your Xbox and your content even if you are offline.

This measure was taken after the RRoD debacle, because many people sent their 360s in for repair to Microsoft, and they got a different system back. This made it so that they'd only be able to play the stuff they purchased while signed in and online on their gamertags. After years of complaints, Microsoft enabled license transfers, effectively killing the previous Xbox's ability to play the content, and in return you get the ability to re-authorize your new 360, which makes it so that Microsoft and your records show as if you had purchased all the content from that new Xbox, with all the benefits that entails.

Long story short: if you are trying to pay for 1 DLC and have 2 different people play simultaneously on different Xbox 360s, it will only work if one of you is signed in to the account/gamertag that actually purchased the DLC, while the other one is playing on the Xbox 360 where the purchases were made from, with the licenses still intact. If the gamertag that purchased the DLC transfers licenses onto another Xbox, the original 360 where the content was purchased from loses the right to play that content back.

I hope this helps.
Source(s):
Microsoft Tech Support (Phone), Previous experience.


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