Im pretty sure I go right through
I pierced China's ears so many times when we first started that I thought I should just buy her some diamond stud earrings!! It's totally normal and they'll heal up! Try poking at a 45 degree angle, not straight in at a 90 degree angle
Here's something I wrote up for others that needed help with testing...maybe it'll help you too! (substitute "her" for "him"...LOL)
It can be really helpful to establish a routine with testing. Pick one spot that you want your "testing spot" to be (I like the kitchen counter because it's got good light and it's at a good height....it also already blocked 2 escape routes due to the wall and the backsplash) It can be anywhere though...a rug on the floor, a table, a particular spot on the couch...wherever is good for you.
Take him there as many times a day as you can and just give his ears a quick rub and then he gets a yummy (low carb) treat. Most cats aren't objecting so much with the poking..it's the fooling with their ears they don't like, but once they're desensitized to it and learn to associate a certain place with the treats, they usually start to come when they're called! Or even when they hear us opening the test kit!
You also have to remember...you're not poking him to hurt him...you're testing him to keep him safe and understand what's going on inside his body. There's just nothing better than truly understanding what's going on inside your kitty's body and with this disease, the more knowledge you have, the more power you have against it. The edges of the ears have very few pain receptors, so it really doesn't hurt them.
Also, if you're nervous and tense, it's going to make your kitty nervous and tense too. As silly as it might seem, try singing! It forces you to use a different part of your brain!
It's also important to make sure his ear is warm. A small sock filled with a little rice and microwaved or a small pill bottle filled with warm water (check temp against your wrist like you would a baby bottle) works well.
When you're first starting, it's also important to use a lower gauge lancet, like 25-28 gauge. Most of the "lancet devices" come with 33 gauge lancets and they are just too tiny to start with. The bigger lancets (that are lower numbers) make a bigger "hole". As you poke more and more, the ears will grow new capillaries and will be easier and easier to get blood from...we call it "learning to bleed"
Finding the right "treat" will be a great help too! Freeze dried chicken, bonito flakes, little pieces of baked chicken...whatever low carb treat you can find that he really enjoys will help him to associate the testing with the treat! China's Achilles heel was baked chicken, so I'd bake a piece, chop it into bite sized pieces, put some in the refrigerator and freeze the rest to use as needed. It didn't take long for her to come any time I picked up the meter!
I feel so bad. Im pretty sure I go right through
. If you need help setting up a 
