The two most important things:
-- establish a routine. Set up a "testing area" of the house where it all happens, and get him used to it gradually. Start by just calling him over and petting him, letting him go. Then call him over and play with his ears a little, once he is used to that, then try poking. Try to stay calm-- if you are stressed, he will be too! Some people find that singing (even if, or especially if, you can't sing!) helps calm everybody down.
-- treats treats treats! Give him a treat he really loves, every time. Even if you didn't get a successful test, or even try. Soon he will associate the testing spot and the materials with the treat, and come running! I don't think they ever love the pokes, but they are very quick to learn that, if they sit still for a poke, they get something good!
When you do the poke itself, try to go in at an angle, so you don't just poke straight through. You are aiming for the edge of the ear,
not on a vein. Here's a picture of the "sweet spot" you want to aim for:
Lots more information here:
http://www.felinediabetes.com/FDMB/threads/hometesting-links-and-tips.287/