OTJ = Off The Juice, it's a term used for kitties that no longer need insulin
With pokes, first take a few minutes to breathe. If you are nervous, anxious, upset, etc. it will transfer to Oreo. It is definitely normal in the beginning to feel that way, but you really need to make it a pleasant experience for Oreo. Give some loving, pats, scratches etc. make sure you are both relaxed and not stressed, talk to him in a soothing voice. I know, sounds silly, but it really does help.
Next, how are you poking? Free hand? Do you use a lacing device? What gauge lancet are you using? In the beginning, the ears don't bleed easily so a bigger gauge really helps (the smaller the number means a bigger gauge. I think try for 26-28). Make sure you really heat the ear until it is warm, it helps to bring the blood into the ear. Also, are you using an antibiotic ointment with pain relief? Many use neosporin, it helps to make the blood drop bead up rather than getting lost in the fur. Are you using a tissue or something on the inner ear as well when you are poking? it helps to give you some stability, and you won't accidentally poke your finger. After you poke, sometimes you do need to sort of press on the ear and kind of push the blood to the poke spot. If Oreo is upset when you get the bead of blood, you can transfer it to the back of your fingernail and then from there transfer it to the test strip. Don't forget to hold a tissue to the ear to stop the bleeding and reduce the bruising.
Also the rule is.... Three pokes, and then take a break even if you don't get blood. And treats for Oreo, do you have freeze dried meat treats? My cat loved them in the beginning. Some people even let their cat nibble on the treats while their doing the poke, it's a good distraction.