I work as a teacher in a special school and worked in mainstream primary prior to that. My initial thought on reading your question was please make sure the first session is highly structured. You can certainly use it to get to know each other but if the structure is loose you are setting yourself up for problems. Sorry if you already know this - I don't want to be patronising. I know you want the sessions to be fun but the first thing you need to do is set some ground rules - you can do this in a friendly way but it needs to be done. For example, following instructions, completing activities, etc. I'd build in a rewards and sanctions system too. A simple consequences board could be good, eg when you complete the activity, you get 5 mins (?) free choice time, or time on the computer, or whatever would motivate him. If he doesn't complete the activity, he doesn't get the reward. Make visual boards as reminders and put pictures of cars/Dr Who on. From how you've described his behaviour, I would say this is essential if you are to get him to actually do anything. I do like the idea of getting him involved in cutting out or colouring in some of the resources as this will get him working without realising it, though I'd be selective about which resources so that the parents don't think you're taking liberties using teaching time as preparation time. Break the session down into small chunks. Do the parents want you to do his homework with him? I just wonder whether this will put him off working with you as it is too much like school? This will depend very much on his attitude to it I suppose. As to where to start, I'd try to come up with as many fun activiites/games as possible that will help him develop his skills. Look at letters and sounds for activities you could do with him to practise his reading and spelling. Find games on the computer that he can do to practice counting etc. Do lots of practical activities, eg counting his toys, playing a board game that involves him counting as he moves along, matching pairs of socks and counting these, etc. I hope some of this may help.