My dry run was a bit disheartening. I used the Punch-Down method, because it seemed to be the most popular. But the DivaCup kept popping open too early, and I was kind of unaware that insertion and checking for a seal involved sticking fingers all the way up in there.
But I persisted and finally found a folding method that worked for me -- the good ol' C-fold. For me, the C-fold allows me to grip closer to the end of the Cup while maintaining the fold and not have to put 4 fingers plus the cup inside my vagina at once. Checking for a seal was tricky because there wasn't much space for my finger to slide around the edge, and maybe my fingers are short.
My concern is with the cup riding too high. I woke up this morning after my first night with the cup and found that it had ridden a little further up. Instead of feeling the stem about a centimeter up (normal usage), it was a about 2cm up. Keep in mind that it's the stem that's at that point, not the actual cup. While I could grip the stem with my thumb and pointer, it was hard to to keep it low enough so that I could break the seal. If a finger slipped and I let go, it would go right back up there.
I'm not asking if the cup can get lost in you, but rather, can it go so high that it would be near impossible to get it down (and thus have to seek out a helpful third party)? I finally worked the sucker down far enough so that I could manage to break the seal after 10 minutes.
Also, is it possible for the suction to actually hurt you, as you're pulling out? I mean, pretend you just tore the cup out without breaking the seal - could that cause any potential problems?