I'm 22, a virgin and have never used a tampon (TSS fears) or a menstrual cup in my life.. which is why I took ages to really decide to buy a cup in the first place.. the idea of the amount of.. intimacy.. that a cup requires, had me second guessing the whole idea.
When I received it in the mail, it just so happened that it was the 2nd day of my period.. so I was pretty excited about the timing.. but when I saw just how large it was, I was really scared.. and when I saw how large it remained in a C -Fold, I got even more worried.. but I gave it a shot anyway.. and boy did it hurt!
I tried and I tried and I tried.. first, I didn't expect the cup to be as stiff as it was.. every time I tried inserting the C-Fold (as I never considered that there may be other folds), I would lose my grip before I was in, so the cup would pop open right at the opening of my vag.. owwww.. and plus, everytime I tried to push it past the opening, it felt like I was hitting a wall of muscle.. and I just kept thinking "there's no where to go!"... after countless number of trials that day, one last really painful pop-open and I gave up.. and it was such a comfort to wear a pad after that!
Then I started googling.. and that's when I found out about other cup folds (why did Diva not mention them in the instructions?! arrrgh) , and how our muscles can tense so tightly that it can stop insertion / removal, how a lubricant may help etc etc etc.
So, I got a water based lube - Johnson & Johnson's KY Jelly - which was an embarassing purchase with a male cashier at the pharmacy *turns red* - and tried again the next day.. it took a origami / 7 fold, a few more tries, constant reminds to relax, and loads of lube for safety (note: fold the cup and then apply the lube.. I had mine flying all over the place bcos it became too slippery).. and it finally went in.. also I made a concerted effort to let my grip on the fold loose only after it would pop open inside my vag - so no more pain on insertion!
All in all, even though I've only managed to use my cup for the 3rd, 4th and 5th days, it's been great. Insertion is a cinch, I don't need the lube anymore, I forget I'm wearing it, and It generally pops open without hassle. Plus I didn't cut off the stem bcos I push it past my pelvic bone so that I don't feel it at all.
Removal on the other hand is another matter.. I can get it and grip it easily enough but having it come out at it's full size hurts.. I've been reading about everyone's removal tactics here and will make sure I release the suction and try punchdown fold...
I guess I'm now just waiting to test it on a full cycle.
A note though.. I never can spin my cup - not sure if it's because suction takes place the moment it pops open?