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After my girlfriend and I hadn't seen each other for two months her pussy felt really tight around my dick, but she didn't complain of any pain though.
I would've understood if you had gone straight into sex without any foreplay or lubrication, but if you're in pain despite the fact that he uses lube then it may indicate a problem. Either you are allergic to the condom or the lube (or a combination thereof) or else you have a condition that needs immediate medical attention.
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Doncalypso... the one and only Haitian Sensation
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