I have Diva cup, the smaller size. I can't seem to fit the cup all the way in, lengthwise. It is simply too long. The stem as well as the bottommost part of the cup sticks out of my vaginal opening no matter what I try. I have a shorter vagina, so that may be the reason.
But the thing is, I really, really want to get my money's worth out of the cup. I can't afford another cup right now, and I don't like tampons very much.