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Not so long ago, my boyfriend and I tried having sex, but could not go through it 'cause it hurt too much (on my behalf). We have tried several more times, and it still hurts too much to keep doing it. I know it might sound dumb, but my boyfriend was saying that maybe his penis was too small for him to "break&enter". Does that make sense? I tried talking him out of it, but failed.
On my honeymoon was the first time I had sex with penetration. We had always messed around in other ways prior to getting married. It is very normal for a virgin to experience pain the first time she has sex. The first night of our honeymoon we couldn't get his penis all the way in because it hurt too much. I actually went to a doctor to find out if something was wrong. He said I was normal and that since I'd never had sex, it was going to hurt for awhile until I was 'stretched' enough. So that night I told my husband not to stop no matter how much it hurt. I CRIED throughout the entire time that it took him to finish the act. There was blood on the sheets also. It just takes time and a lot of 'practice'!
Then I doubt its anything to do with him, youre supposed to be able to use a tampon w/o any pain...even when you are a virgin. So Im guessing you might be over sensitive & there is also a medical condition...Vulvadinea (sp) I think its called. Google it. You should go to a gyno & tell the them about it. They will be able to give you ideas about easing the pain...etc. & figure out whats going on.