If it hurts when you put a tampon in, you may not putting it in right. Using a tampon shouldn't hurt. When you insert a tampon in correctly, it should feel almost non-existent – that's the incentive for using them. Putting tampons in the right way can be tricky. I went through at least half of a box of them before I got it right. Here are some steps you can follow. First, buy two boxes – give yourself a trial and error buffer. If it turns out you get it right on the second or third try, well, you'll have a box of unused tampons that you will come in handy in a month. Second, it helps to put one of your feet up on something. This will help with the angle at which the tampon will go in. Third, you don't necessarily want to insert it straight up. Instead, you'll want to go in at an angle. As you're inserting it, you'll be able to feel if it's in comfortably and correctly because as it's going in, you'll, basically, start to feel it less. Don't give up or feel discouraged if you don't get in the first ten or even twenty tries. As for your thoughts around your hymen, Dr. Molly is better suited to address that with you.