Have you tried sponges (the latex ones)? I used to use them in my late teens and found them WAY easier to get in/out than tampons...and more comfortable...I am a shamless tampon hater :-D
I honestly can't remember the brand names, it's been years since I used one...but they're available at chemists, online and at sexual health organisations...made from PU, I think.
Nice and smooth and soft. No need for lube to insert or anything.
That's right, no drying out, no stickiness or getting stuck
Although it does take a bit of practice at first, I don't think it took any longer to learn to use than tampons
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