For reference, I'm a 17-year-old virgin, and a rather small person.
Daunted by my first try as well as a bit sore, I hopped on the computer and came across this community. Since then, I have tried the 7-fold and punch-down (modified so it's as small as I can make it), and diamond fold. I practiced the origami but can't hold onto it without it popping open. I've tried sitting, standing, squatting, and laying down, and also tried in the shower; laying down was the most successful but I still can't get it very far without it hurting so much that I stop.
After that I got sore and discouraged, so I threw on a pad and went for Sunday exercise (physically taxing foam-padded sword fighting), but coming home to the stupid mess of the pad after all my physical exertions just made me want to try harder. I explained my frustrations to my mother and she actually gave me some lube [o.o], but I haven't tried that yet.
I'm sore from fighting, cramps, and trying my cup... I think I'll go swallow some painkillers and maybe try again in the shower.
*Side question: I'm excited that you can get away with active stuff while using a cup--I always use pads and it's horribly messy; at least, the Divacup website had a testimonial from a rugby player who used one. I get bowled over by big shield-bearing men, rolled on the ground, hit with padded weapons, and have to run all over the field. What experiences have you had with using a cup while being very physically active?