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When your cherry is popped that means that the hymen has torn in which case, yes, it will most likely bleed. However the hymen may just get stretched, so it may still hurt, however it will not bleed. Often times certain activities such as horseback riding, inserting tampons, or masturbation may cause the hymen to stretch or even tear without any bleeding or pain, so you may have not even noticed if this has happened.
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