When I first started trying to use a cup I had problems with it not sealing, I saw a gynaecologist for something else and they found a polyp (a lump like a mole) in my vagina. After it was removed my cup now seals properly. Look at putacupinit.com (put a cup in it .com), they explain how to find your cervix and lots of other helpful things.
I just used mine for the first time last week. I love the cup, but I also experienced the same issues as you. I couldn't tell where my cervix was (ha!), and had leaks. I tried inserting high and also tried putting it low- still had leaks. when i would put it low, when I would come back to check on it, it had worked itself higher in the vagina. I am also searching for answers.
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Good luck.
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