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There should never be pain from squirting. Regarding the fisting: have you tried multiple times and gradually worked up to it; or did you try once and force it? Fisting is a tad dangerous if not built up to, well lubed, and if you aren't relaxed.
BTW: Definitely go to a doctor. You could have a urinary tract infection, an injury, or both (or something else).
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Numbing your bum before anal is like putting makeup on skin cancer.
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