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First, do not have sex with him until you are sure that you are ready. You can help him get off in other ways without having sexual intercourse.
Porn should be a problem only if he's choosing the porn over you. If he's using it only when he's not with you, and he doesn't avoid contact with you to use the porn, it shouldn't be a problem.
Have you considered looking at the porn with him? I don't know if it's your cup of tea, and if it's not, that's ok, but you did say you found some for him. It might be a way for you to bridge the gap. If it is, maybe you could find some that appeals to you, and enjoy it together.
As for the first time question, yes, it's going to hurt. Minimize this by making sure that he takes his time and that you are well lubricated; it'll minimize the discomfort. If you don't lubricate well enough on your own, there's no shame in using something to help out.
The amount of pain will vary. I'm sure someone will be along soon to share her experiences with this.
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