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It will get easier you just need to take a little more time maybe with foreplay before you try intercourse then go slow and don't rush things :-)
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I also have a couple of questions about the connection between tight vagina and painful sex. Whatever we try, it doesn't work. He just can't insert his penis inside of my vagina. And we did use that water-based lubricant. I don't know what is the problem. I know that I was reading that this can be a sign of some infection, especially if you had some other boy beside your boyfriend. Well, I haven't. For the last two years, I am sleeping only with one guy, We tried the stimulation, lubricant, and alcohol as well (to make me relaxed), but in the last 10 days, nothing can happen. We just can't have sex and I am becoming desperate.
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