Well I did my first trial run with my Diva Cup today. (They recommend practicing with it before your period.) It is quite easy to insert, and it really just pops into place – kind of amazing. The first time I inserted it, it didn’t open all the way though, I wasn’t expecting it to just pop into place so quickly and easily! So I took it out and inserted it again. This time, I was careful to go much slower, and kind of twisted it back and forth so it would insert. I could tell when it opened all the way (you kind of fold it up on itself to make it smaller to insert) and it created suction. I could tell it was open and had created the suction, because when I tried to push it out, it was much more difficult. So I just used a finger to push in on the side of the cup to break the suction seal, and then it came out very nicely.
I plan to definitely still wear at least a pantyliner when I use it during my period for the first time, just in case I don’t make a perfect seal, or if it isn’t in just the right spot. For now I can say it inserts VERY easily, and once it was in I couldn’t feel it at ALL. My period isn’t for a few more weeks, but I’ll let you know how it goes! I feel pretty good about it, and I expect to be really happy with it.