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First off, you should be asking this question to a gynocologist to be sure.
Now that we have the legal disclaimer out of the way, I'll give you my input. More than likely your later guesses would be correct. It is more than likely a yeast infection. It could also be a latex allergy or sensetivity to the lubrication from the condoms. If its something to do with the condoms though, the symptoms usually occur during or immediately after sex. My wife and I are both sensative to the N-9 and very shortly after sex it burns like all hell.
It is also possible there is a physical complication. When a virgins hymen tears it can on rare occasion cause issues. But unless your boyfriend is in med school to become an gyno, see a doctor.
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