I was given estradiol pessaries after repeated kidney infections and found them really hard to use at first. Couldn't manage what was specified in the instructions properly. Felt dread of using them hanging over me every day.
Just wanted to assure others, they do get easier. Obviously using hard plastic applicator when things feel painful seems really harsh at first, especially if a hater of tampons...but the effects are worth it and after a month it became much easier for me. After two months, it's almost a normal part of bedtime routines and things are much more comfy.