i have a few tips to people who were like me. i searched all over this community before buying a cup (small ladycup) and when i was having problems getting it and out the first few times. i must say, there wasn't a ton of info for my questions or tips that i found really helpful other than relax and keep trying (which can be daunting!)
for me, the cup sits really low, i cannot for the life of me get it to go up at all once inserted. this freaked me out because everyone seems to say it has to sit around your cervix and the stem can't sit outside the body. for me, that couldn't be further from the truth! so others like this, it's ok!! i'm 24, not a virgin and pretty petite, but i know there is more space in there.
easy tips from me that i didn't seem to find on the site (i'm sure they are there somewhere):
insertion - the first few times i tried, i made sure to have a mirror under me to see what i was doing. this sure does make a difference. not the most pleasant thing to look at... but it really helps and i highly recommend it. i use the punch down fold with the folded part facing upwards. i put water based lube ON the rim of the cup and smooth side after i have folded it. this is the easiest for me - lube is crucial for successful insertion! once i get the rim in, i let it open, then bring the whole cup down to the entrance to let air in since i cannot get fingers in there to do it. there's a whooshing noise to let me know it's ready and then i push the whole cup back in with the whole stem sticking out. after i walk around a bit, the stem goes just inside my body. i let it go where it wants to.
the first time i got it in, i was kind of freaking out because it felt like a flattened pancake and was sitting really low and i could not twirl it or move it up. but i've learned that is just where mine sits. i got this impression this was totally wrong. so if this is happening to you, don't worry! if it doesn't leak, you're fine. if the cup is open and forms a seal, it doesn't matter if it is high or low because there's no where for the fluid to go other than into the cup.
removal - one time, my stem did 'disappear' about an inch away from the opening, so i was confused and had a hard time 'bearing down' to get the stem. again, i used a mirror to help see what i was doing cause i don't have much space to get fingers in there. after a few times i realized that the easiest way to get it out is right after i pee! i drink a lot of water and pee a fair amount, so each time i peed, i noticed the cup comes down on it's own. then an 'ah-ha' moment occurred. if you pee like you have to do it as fast as you can, that constant 'bearing down' pressure makes the whole stem come out easily (for me). then using some TP i grab the stem and wiggle it back and forth and out it pops. if i don't want it out yet, i just pee slowly and no pressure. sorry if TMI but, it works really well. no scary 'i can't find it!' or 'it won't budge' moments for me anymore.
i love the size and the 'squishiness' of the lady cup. it doesn't hurt at all when i take it out. i haven't had any problems with it opening or leaking (yet..) and only the one time i had a problem with the 'slipperiness' of it, but since i got the hang of removing it, it hasn't been an issue.
it really does feel like you don't have your period and you can kind of forget about it! what a great invention. spread the word!!