Wow, this is a long time ago. Hope you found your solution.
First off, I'm a guy.
Scientifically speaking, with the benefit of my past partners' experience:
First time is likely to be painful. Unless you're one of the lucky ones (tore your hymen during sports, etc.)
Second time is not painful, just tight. Fear may scare you away, though. But then that means no more intimacy for you.
The first time is the most painful. It's good after. Unless you have a lousy partner.
Some girls like it rough - a little bit of fear of pain causes a rush of adrenaline; increases the heart rate and breathing, reduces pain.
Sex before you're properly lubricated is a little bit painful, and exciting.
That's what I'm told, anyway.
Then again, some girls are forever lubricated just thinking. Personally, I think I have way less interest in sex than any of my past / present partner(s. My definition of fulfillment is reading Newton or Einstein's works at the library.)