I never got to two fingers in completely (did about halfway before I started going "oi, starting to hurt" and stopped), but I never tried while I was on my period (which should be when I'm the most stretchable, right...?). KY Jelly is my friend. I can get one finger in without any difficulty.
Since my period came yesterday, I was trying to get my divacup in yesterday evening (and this morning), spending about half an hour in the shower. I tried punchdown (and a weird sort of origami, because I thought origami was punchdown for some reason), and...I could get it in about halfway. Enough so that on the first time I got it semi-in (yesterday night, on third try), when I tried to pull it out I felt the infamous suction of doom...and if I could feel the suction (didn't feel it this morning, unfortunately), it must mean I'm doing something right, right?. Perhaps that should've been an indicator that I should've just shoved it the rest of the way in, but herein lies my problem:
When you fold it, you obviously have the tighter fold near the rim, so the entering bit is, well, small, and it gets wider as you go down the cup towards the stem. I can get my cup in about halfway, but when it hits its widest point (and it will have one, no matter which fold I use), I get kind of...stuck? It's not the length that's a problem; despite my small hands, if I can get a finger all the way in the cup is short enough. But whereas a finger (lubed) just slides up without a problem, I seem to have problems aiming my cup at the halfway mark so that it'd go the rest of the way in. (I suppose it doesn't help that I lube up the top of the cup to help matters, but I can't lube up the bottom 'cause that's where I grip it, so not only does the bottom half not slip in like I would like it to, the top is inclined to slip out if I keep waffling and try to figure out how to get this confounded thing in).
I mean, I guess I do know roughly where to aim because I've gotten an entire finger in and know roughly how my vagina is situated. But it's different when it's something bulkier like the cup, and despite slightly altering the angle and trying to push it's like I couldn't get it in any further. Whether it's because the widest point just refuses to get past the entrance or the entering bit's corner is digging into something, I dunno; it just feels...stuck.
Sorry if I sound bratty; I'm just pretty frustrated with the thing. (Although, I at least got it halfway in. That's...half the battle, right? ...I haven't even gotten to the fun parts about situating the cup and removing it...) Any tips?
For the record, I don't think it's my hymen that's the problem...unless I've really forgotten my high school biology, I don't think I have a hymen, because I don't see anything even partially blocking my vaginal entrance. (Then again, it's been a while since biology...)