Just adding my tuppence worth, since perhaps there are other women who've joined since this discussion was started and haven't seen it yet. I actually wrote a blog post on this a year or so ago (
here, in case anyone wants to read the whole thing), so I'm just going to paste some of that text here. Short version: love, love, love my mooncup and am soooo glad I did persevere until I got the hang of it.
"That day convinced me, however, that I should consider at least trying the mooncup, as it would be ideal for a day when you don't want to be carrying supplies with you. So I bought one. And then did nothing but take it out of the packaging for a look and think to myself, "Must try that sometime". Eventually I did try it once or twice but really didn't click with it at all. I waited until I got my period at a weekend, and luckily it was a weekend when my housemate was away, too, so no-one to notice if I was spending longer than usual in the bathroom or wonder what the hell this silicon thing was boiling away on the cooker. I didn't heed the advice I'd heard over and over again to cut as much as possible off the stem and, well, ouch! I eventually did get it down to something I feel comfortable with, probably a little bit over half a centimetre. But I also really struggled to just contort my body in such a way as to be able to get the bloody thing (pun intended) in or out. Once the contortions had finished, I really did like it, but it just all seemed like too much hard work somehow and since I loved my washables so much I just left it in the cupboard.
A while after moving to Germany I decided I really should give it a proper go again. Same thing, I used it once and then felt like it was too much like hard work and gave up. But at the beginning of last year I really, finally, actually made a proper effort. I re-read through the thread I've mentioned above, I read through all the FAQs on the mooncup website and anything else I found that I thought might help and I gave it a proper go, telling myself that I was going to use it every month for at least six months, even if I only used it for one day each month, and that if after that I still didn't like it, I'd just leave it be. It took about three months for me to get it figured out and by the end of six, I couldn't imagine ever being without it.
I had blamed a lot of it on being overweight and therefore not as agile as I felt I needed to be but really, it turns out that I just needed to find the way that really worked for me. For what it's worth, for me that means a slight squat and then going up on tiptoe. I discovered this completely by accident but this position seems to tilt my pelvis at just exactly the right angle to allow me to really easily insert the mooncup. The body is a funny old thing. Before I figured that out I had had some success with making sure that my back was against a wall (otherwise I sort of kept pushing myself backwards and could never get a grip on the ruddy thing). Lots of people say that using the mooncup really made them feel more in touch with their bodies and I must say, I have to agree. "