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For the past few weeks I've stuck to masturbating externally but one night I got curious and fingered myself with one finger rather deep. The next morning, I found a faint trace of blood on my underwear. Help?

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Chances are you've just started your period :)  I haven't heard of anyone ever breaking their hynemen with a finger before, usually because they don't go deep enough or because their fingers aren't thick enough :P  Breaking your hynemen is different from different women, but usually there's a sharp pain right after breaking it, which eventually becomes a dull throb and dies away after a lil' while.  You'll also bleed a lot for a short while, so no, I really don't think you broke your hyneman :)
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