Tampon troubles?

That's pretty normal. I've had my period for 20 years and always hated them.

Firstly, I suggest you get better tampons.

At your age tampons aren't recommended due to higher risk of TSS, so if you are going to use tampons instead of safer options like menstrual cups or sanitary pads then you should do all you can to reduce your risks - that includes not using rayon tampons like Tampax. Opt for cotton tampons like Cottons or Natracare which are not only safer but less likely to cause you any discomfort as they're not as rough, drying, and they're hypoallergenic.

Make sure you're using correct absorbency - do not use tampons with light flow like spotting, only use during full flow (if the tampon isn't saturated after 4-6 hours your flow is too light for that tampon) - this isn't just about safety but also blow provides lubrication too, you can also use lubrication like KY Jelly or natural oils like olive oil to help.

Make sure you're relaxed - the vagina is a muscular tube so if you're tense vaginal muscles tense causing the vaginal walls to clench together, thus making it more difficult or painful to insert anything. Practice tensing/relaxing vaginal muscles so you can relax when needed and take a nice deep breath before inserting, also don't get frustrated if you don't get it first time. You can also try masturbating prior to inserting a tampon as when aroused the vagina naturally relaxes, opens, increases in size, and lubricates to allow things to be inserted.