I'm 30, a virgin (no, this is not the problem ;0) ), and got my small size mooncup a few years back.
I used it for a few months, getting used to it, but could never get it out without a degree of discomfort, ranging to pain on particular bad goes.
I have read so many posts about removal - they talk about rocking it back and forth, and slipping it out at an angle; or folding it over inside, and pulling it out from the bottom. I don't seem able to manage either of these properly.
Reaching it is no problem - the cup sits quite low (actually, uncomfortably low - see below). I have cut off the whole stem, but find it too tight to grip at the bottom with finger and thumb. I therefore have to slip my finger up inside to break the seal. I attempt to fold it and pull it out so that the whole rim is not coming out at once (happened a few times - VERY painful!!) but tend to end up with it still feeling too big anyway. The result tends to be my hand covered in gunk (which I don't mind so much, though not great for public toilets), the blood spilling everywhere, and worst of all, a lot of pain. Once or twice, I know I have torn skin/tissue at the bottom of my vaginal opening (?? would this have been my hymen??), as I have felt the sensation, and seen fresh blood on my fingers.
I do worry about removal each time, but remain calm and relaxed - nothing feels particularly tense, just very tight, like there's not much room down there. I can just about get two fingers in (without the moooncup in, and with lubricant), so wonder if size is the problem?
The other thing I've noticed - as opposed to many people whose cup seems to disappear off up inside, I find mine sits very low. I can feel it when I sit down. This is despite giving it a good poke once I've put it in. It just seems to slide back down. I'm pretty sure it's sealed, as it doesn't leak.
I would so much appreciate any advice on less painful ways to remove it. Having read some of the posts here, I'm now also thinking maybe I should try a smaller cup, like the colour Lady Cups. Could this be a solution?