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Do you mean play together on the same Xbox, or play online together from different locations? If you're trying to play on the same Xbox online, you can't because he can't login because he doesn't have an Xbox LIVE account on your machine, he's just a guest. It's also possible that the 48 hr card might have expired.
Make sure that you have an Xbox Live Gold subscription first,
Second You won't both be able to play at the same time enless it is a game that provides guest support(and in some games WITH) guest support you cannot play anything ranked online. To sign in a game with Guest support hit the guide button on the second controller select choose profile and scroll down, if u see "Guest" as a profile and you did not create it, then that game has guest support, and you can both play.
If u are just trying to let him play alone then you have to sign him in how you would normally