My daughter (15 yrs) has had her period for about a year and a half, which happened to coincide when she wasn't on swim team. Recently she joined again, and she did the swim part of the triathlon with us today. Last night was a crisis because her period started and she has never successfully used a tampon.
She had tried early on and gave up. She had tried with an entire box of the smallest size. A friend advised us to try Tampax Pearl as having the easiest applicators so I got the smallest of those--still no luck. She was sobbing because she'd have to miss the triathlon. Since it was in a lake, I told her to put a pad in her swimsuit until right before the start, then take it out for the swim. That worked this time but it won't work for swim meets!
Last month her solution was to skip a week of swim practice, and she's been worrying about it ever since. I wish I'd been less oblivious and realized the problem sooner.
She doesn't think the problem is an overgrown hymen because she did manage to get one tampon in once (but not sufficiently far in, I think, it hurt and she took it out). I'm going to take her to a doctor to make sure everything is ok.
Any thoughts or suggestions? She's interested in the DivaCup, which I've heard great things about, and besides with that we'd know how much which is an issue (I think she, like me, has unusually heavy periods, but I've never been able to prove it). But if she can't insert a tampon I don't see how she'd be able to insert the DivaCup.

