Virgin: No, but no sex deviant!
Cup: DivaCup Small
The awesome. I use the punch-down fold, and from the beginning, insertion was easy-peasy. It was tight, and hurt, but it worked fine. After a few minutes it positioned itself and.. woot! It has always worked this way, everyday of my periods, no issue with insertion.
Problem. Removal... Y'all must have some super long fingers and arms, but I really can hardly reach it EVERY time I try to remove it. I have the stem (how on earth y'all cut it off is beyond me), and all the ridges are there. But what kind of super grips are y'all getting??? As far as I know, blood and jellyness makes things super slippery (even ridges). I reach in, can get my middle finger and thumb (no, index and middle doesn't work but strain my hand worse) in to the first joint and my thumb nail. At that, i can barely grace the tip of the stem.
It usually takes about an hour, (literally, I have my period notes of insertion/removal time) of pushing and peeing and pushing and screaming. The first few times I cried. The actual first time, I had my husband tell me about his fishing trip and rub my knee to help relax me, but that still took 45 mins!
The second period was like that too, except one time, I'd overfilled it, and the pushing did nothing but push blood around it. More screaming and crying.
This is my third one, and it's slow starting... I wonder if there are really long stemmed cups? or cups with strings attached? That would be ideal...