How to open up more?

Wow. This would be exactly what I was afraid of. Your boyfriend is, judging from what you've said so far, seriously emotionally abusive. A bunch of the things he's said to you are clearly demeaning and meant to put you on the defensive when you've done nothing wrong, etc.
I'd love to talk to you about this more in depth if you're willing. I don't want to just ramble into a vacuum, but I think talking to *someone* even if it isn't me, would be really good for you. You can PM me and we can talk that way, or I can give you my gmail chat info if you'd prefer. There's a way to tell it not to keep chat logs if you want to be sure he won't see it.

I agree with Mecalith. That does sound like emotional abuse. I've been there and I know how much you want to make it work, but sometimes it's better to just walk away. That's what I had to do and I've never regretted it. I'm here if you'd like to talk.

Well... how and why does he make you feel that way? What things are you having a hard time expressing or discussing with him? This sort of question is hard to answer without more information because the problem may not even be *you*, it could just as easily be his behavior or expectations.

Well, To be honest I am not exactly sure what he means when he says, "You could go so much deeper than that." I avoid one answer replies to his questions, and try to discuss my feelings about this in almost every situation. He makes me feel that way by telling me things like: "You are so simple." "I guess I will have to learn how to communicate on your level" or "Any girl would know how to communicate with her boyfriend to help him through things".... There are a few things that I refuse to communicate with him about without a counselor, which makes him very angry. Two years ago he accused me of cheating on him with his cousin while we all got into a huge dramatic fight (with alcohol involved) I left with his cousin, but dropped his cousin off at his house and went home directly after. I have tried having conversations with all three of us to prove that nothing happened. I have told him how terribly sorry I am for leaving him in that state. I have told him every detail down to every word we said to each other to what songs played on the radio in the car, and he still does not believe me. He treats me as if I have cheated on him when I didn't, and because he will not forgive me and still gets very angry and bitter about it I think it is best we seek out counseling for that discussion. Another thing he does is accuse me of having issues with liking girls. He even accused me of cheating on him with a girl we knew and bribed her into saying we kissed. (As in offered her $500 if she would admit we kissed one night). This NEVER happened. He will tell me he catches me staring at girls, and I have issues with my mom so he knows there is something amiss. I have told him where every insecurity comes from. Why I stare at girls, which is out of comparing myself, and how my relationship with my mom makes me seek out relationships with older women who can mentor me. He dismisses everything I say, and still accuses me of having problems. And because after 2 years of the accusations, arguments and conversations about both of these topics I refuse to discuss them anymore he blames me for every issue in our relationship. He says he knows that there is more to everything I just do not have any clue on how to communicate. I know I have issues in conversations that should be easy, but I always feel like I am on the defense with him. I want to be loving and our relationship to work, so I am working in every area to become better. I'm just not sure what to do..

From what you have said in the comments, I agree, these are signs of emotional abuse. I was emotionally abused for nearly 2 years by an ex. Feel free to message me. Be safe.