My first time using a cup (Evacopa size 2, it’s a local brand) has been a bit of a disaster. It took me 2 days of attempts to insert and another 2 days to remove, so it was up there for a full day, which is obviously way longer than any brand allows but I just didn’t have the strength to deal with it with my cramped hands sooner.
Evacopa does carry a smaller size (1), but it’s recommended for people under 20. I’m in my 20’s and haven’t had a childbirth or penetrative sex, but I do have a high cervix and heavy flow.
Once the cup was inside, I couldn’t feel it and it was perfectly sealed, with the stem safely within the canal. I went to the bathroom several times with no discomfort.
The problem is getting it in and out. I’m an anxious person – still, I tried my best to relax, bear down and take deep breaths while in every possible position. It was fairly easy to get in one finger but it took a lot more time and effort to get in a second finger, which is necessary for both insertion and removal.
During insertion, my fingers were cold and shaking from keeping the cup in an origami fold. During removal, I had to grip the folded body with both hands to keep the seal broken, with the worst pain coming from the rim. The pain was burning, not sharp, and faded quickly, with no signs of tearing or injury hours later.
I’m going to get a water-based lubricant in the future anyway, but if there’s anything else I can do to make insertion and removal more practical, I’m all ears.

Red Herring Answered question August 3, 2021