I suggest that you get her to consult her doctor next time she goes about this problem.
I would take future intercourse with caution making sure she is not feeling pain by this. It may have just been the final tear of the hymen but I don't understand why it would take 5 times. Just use caution next time you have sex and take things slower.
The cause of bleeding also leads me to believe she may have started her period. My friend has had this before while having sex, he pulled out at the end and found blood and his girlfriend started her period. Ask your girlfriend if she did start her period a few days after having sex with you. That also can be the cause of bleeding.
If not next time take it slow and have her consult her doctor next time she goes to see him/her.
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Just trying to help as much as I can.
Please understand that I am trying to give you the best opinion that I can think of.
You can take my advice or leave it as you please.
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