I got the Keeper size B this past February, and I REALLY want it to work, but I'm about to throw in the towel. I don't have any problem getting it in, it feels okay while it's in for the most part, but it takes me a minimum of 2 hours to remove. It takes a good hour of squatting for the stem to come down low enough for me to even reach it. Then it takes another hour to get it out because my fingers are too thick for me to get up the side of the cup or a grip on the bottom of the cup to break the seal. Every time I try it just pushes it back up. It rides up high no matter how low I insert it. And I keep pinching and stabbing myself with my nails, even when they're not long. The best I can do is to wait until it gets low enough for me to grab the stem, then stick a toothbrush handle up there to break the seal. And then it really hurts to pull out because I can't fold the cup. On top of that, it always spills. By the time I manage to get the stupid thing out, I've been poking myself for 2-3 hours and everything hurts and I just don't want to mess with it anymore.
Basically it's squat in the bathtub until my legs get too tired, take 10-15 minutes until they feel better, then try again. Squatting is the only way I have a shot at reaching it at all. I also usually try taking a warm/hot bath. Yes, I know how to "relax" and "bear down". If I didn't, it would take me 5-6 hours to get the cup out, the way it did the first time I used it. And sometimes it's been in so long that it starts overflowing and makes everything worse. I think I'm going to quit after this cycle. I've kept trying for the past 5 months because I believed it would get easier the way it does for everyone else but it hasn't. I really don't think the benefits are worth all this trouble and pain and I don't have 4-5 free hours each day to squat in a bathtub and torture myself. I'm just going to have to go back to changing a tampon and pad every 1-2 hours*, because even that's easier than using a menstrual cup.
* I've also tried those Instead cups, but they kept shifting and spilling, especially when I pee.