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well if it has only been a couple of times that you ever had sex that could be why, If you can't relax, or there could be something really wrong go to or call your gyno and tell them because it shouldn't hurt.
PS if your underage and your parents don't know your having sex there are places you can go that won't need your parent and when they call they will use an alias.
Good luck 
You're feeling this way because you're not ready. duh.
But, if you're going to be dumb and do it anyway then I suggest you be vocal. don't be afraid to speak up and tell him what feels good and what doesn't. Sex is not supposed to be painful. He's not psychic. Guys are not programmed with the knowledge of knowing exactly what a girl wants. Everyones different, so you have to teach him about what you like.
You might be allergic to the condoms he's using. The first thing you should do is change from latex to polyurethane condoms. People who have latex allergies (even slight) can experience pain during and after sex.
Is he the first person you've had sex with? Is this new for you? Is it only painful during intercourse or is it when he puts a finger inside too?
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Sex hurts?



Sex hurts?
Ok, weird question:
I don't qite enjoy sex the way my boyfriend imagines.
When I seep with him, it hurts me so badly that I wish he would stop.
And this hurt isn't a good hurt.
It's a very, very, VERY, bad hurt.
But I do enjoy sex.
In a...
way...
I like the thought of having him inside of me. (if that makes any sense)
And I like the closeness.
But I think that's pretty much it.
Any ideas as to why I'm feeling this way?