I'll start by saying COUNSELING IS GREAT! For your own sake, and also for the sake of your relationship, please look into it... and feel no shame because of it. I respect people more if they tell me they go to counseling, since I truly believe EVERYONE needs to go, but few admit to it. (And yep, I'm a counseling regular.)
Damn, my bf and I get excited to tell each other that we masturbated (living 3 hours apart). "Guess what I did last night, honey?"... I think we are just glad that the other person is having a good time. Hearing about his masturbation turns me on, and vice versa.
However, even that attitude has taken a LONG time to develop. Having spent my former life in a Christian setting, I can tell you that it took quite a while for me to loosen up... to sex, porn, and everything else. I will echo everyone else and say DO NOT HAVE SEX until you can imagine looking in the mirror the next morning and thinking, "Yes, that was for ME, that was my decision and I am very glad that I waited and did it with this person." Believe me, I screwed that one up pretty bad myself my first time... don't do that to yourself.
And for when you finally do it, whether with this guy or someone else... whether it hurts, I think depends on the person. Do you use tampons? Do you masturbate a lot (putting your fingers way up there)? Maybe you have a vibrator or dildo (I recommend trying a small one)? If you do any of the above, your hymen may already be stretched a bit and it might not hurt. However, I know some girls for whom it hurt a lot, and they bled... and really, a lot of that had to do with the guy. If the girl wasn't totally convinced of her decision, and if the guy wasn't absolutely careful and gentle and took everything as slowly as possible, then that can increase the pain factor much more (due to not knowing how to relax, which comes with time... heh, pun intended). I actually didn't hurt that much the first few times, but my brain started freaking out, I think, and it woud hurt a little every time (right when he slid in) for several months... until I could finally let go. And I definitely recommend lube... absolutely no shame there, everyone needs it at some time or another and it certainly can't hurt to try, even if you don't end up needing it.
And porn? Hell I don't know what to say there. I completely understand the feelings you have when he watches it... I used to feel that way too, insecure and inadequate and jealous. However I had quite a few discussions with my bf about this and over time came to realize that porn is NOT reality, and that for the most part, most guys don't expect porn and reality to match up (I say most: if you are dating one who does think that way, then find out fast and get out). My bf works pretty hard to make sure I know that I'm sexy, all the time... and I know he means it. So I've learned to separate the porn from the real thing... heck, I've become an advocate for us to watch porn together to get turned on... who would have thought!
Anyway sorry this is so long, hope it was helpful... this is a good place to talk about this stuff. Btw how old are you, and how old is he?... you don't have to say, but it gives me a better idea of where you're at.