Cycle number three with the cup (Mooncup UK) and love, love, love it. This is my first cycle however with the stem completely gone. Initially, I tried trimming it but the smaller stem was stiffer and actually caused more discomfort than the original long stem (still more comfortable than a tampon though, and the after effects of disposable pads I was getting). Haven't had any problems with removal completely sans stem until this morning.
Woke up to do my usual removal and unlike the rest of my period so far, my cup had moved up much further into my vagina. Could still grab it/touch it, but just couldn't get enough of a grip to break the suction/pull it down. I was suddenly struck with an idea. Kegels are used to strengthen the vaginal wall, sure, but they're prescribed for women who are about to give/just given birth, if they can move a frickin baby maybe they'd move the cup back down to grip-able range?
Lo and behold, few strong kegels later and I reach up and it's back where it normally is and remove it no problem.
I'm very happy to have gotten this situation over with and see that I can handle it, but I didn't remember ever reading about a tip on doing this if you're having trouble getting the cup out/where you can grab it, so I thought I'd post and share. Keep up the fantastic, useful, and fun posts, ladies!