It sounds like when you are inserting the tampon you aren't going in all the way and then it will hurt. Needs to be pushed all the way.. good luck
I had the same problem really recently when I had to use one at the beach. The key is just relax and keep trying periodically though the day untill u get it don't poke yourself, just practice untill u get it. And don't forget to go in at an angle key part. As well as spread ur legs far apart help me a lot. Just be calm u got it:)
Tampons are not supposed to hurt when you are using them. I have always had issues with this and so I use pads most of the time and Tampons only when swimming. The more I use them, the more comfortable they are getting. Check and make sure you are inserting them correctly. That was originally my issue with Tampons