I have an iPhone 4S and my friend has two ipods with two Apple ID's.  Why can't he receive messages on "Message" on one and he uses a free text app on the other which receives messages from my phone just fine.

My friend has two ipods.  Two Apple ID's and on one ipod he has a free text app on it and only Message on the other.  He cannot receive a message from my iphone 4S on the one with Message, but receives it fine on the one with the free text app.
He can also receive a message from my iPad on the one with Message.
My question is how can he recieve a text from my iPhone to the ipod which has a different Apple ID than the other but does not have a free text app?
Also on the ipod he has the free text app he has not upgraded to ios7 and won't.

Are the use the correct email address for the contact? Those are listed in Settings>Messages>Send and Receive. When Messaging somene the iOS devices used the email address (or phone number if applicable) listed in the Contact app for that person.
Thus, it appears the you Contact apps only has that one email address listed for the person you are trying to Message.
If he can send you a Messages can you reply to it? If so save the sender to your Contact app.

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