Giving him the guitar sounds like a great idea. Bring it over, with your guitar, and keep it simple and light, and just say, "I thought it might be kinda cool for us to learn to play a song, together". Suggest one that you've been thinking of playing with him. Keep it open to where he can ask you questions concerning chords etc...If he doesn't know the words to the song, then use that oppurtunity for the two of you to sit down, and write out two copies of the lyrics. One for you, and one for him.
When he complains that the strings hurt his fingers, just say something like, "Oh yea. I remember how that bothered me too, when I first started out playing, but look what happened when I didn't give into the pain", at which point you show him that your fingers grew little calouses on each finger, and it doesn't bother you, anymore.
You can elaborate more about your first encounters with your guitar. How bulky, and awkward it felt trying to hold this big thing in the comfortable position, and how at first, you felt like such a spaz when you were first trying to master playing a chord, and getting cramps in your hand, and while working over the strings to get a good clear sound to come across.
You don't have to give the guitar directly to him, and state that your GIVING it to him, with the expectation that he will fullfill some requirement.
After spending the evening with him, and laughing, joking, and foolin around on the guitar, when your ready to go home, just tell, "I'm gonna leave this here with you, so we can do this some more when I come next time."
This way, you'll be intrusting the guitar to him. (unspoken, of course). In this way, you'll be planting a seed within him. An unspoken bond of trust.
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