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my girlfriend's hymen broke when I fingered her, and she bled then. she may have fingered herself before and broke her hymen, who knows...
personally, I wouldnt worry too much about it...as long as she's STD free.
as for anal sex, most girls would say not having it would be the most pleasurable method. its likely going to hurt her alot.
they make lube with a numbing agent to reduce the pain for her, and if you're bent on trying anal sex, I would try using a finger/toy first to get her used to having something in there.
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