Kitten, I think Gary's suggestion of talking together is your next step.

In your first post you said something that sent up a caution flag for me.
He also says that he feels very sorry for what he used to do. He was almost in tears when he thought about past experiences he has had. I don't know the details but he was very much into it for a while. I'm not sure what to make of all of this. And I don't want to do anything that could bring up bad memories for him.
The question I have is is what does he feel sorry for? Is it sorry for opportunities missed, relationships ended or is it sorry for actions that caused harm. If it is the later the question could be important for your safety. While I can understand you not wanting to bring back bad memories, but you need to know this and what is the root cause for the sorrow. Your boyfriend too will need to come to terms with the feeling that are causing him sorrow and holding him back. BDSM has a habit of bring these memories out and its better to get them out in the open outside of a scene.

Also in your reply you describe an experience with you in a dominant role, and your enjoyment of it. Then you express a desire to take a submissive role. At some point you need to ask yourself which role you wish to explore and very importantly the reasons why. The same is true for your boyfriend.

In your reply you also say:
But the more I think about it the more I'd like to try my hand at subing. I don't know if he would be willing to thou. Like I said he really had a bad experience with this in the past, he was a dom.
Again you mention "a bad experience" and the fact that previously he took a dominant role in the relationship. Could he have made a bad choice and learned that the dominant role is not for him. This could be why he responded positively to you when you exerted a dominant position. Again you need to talk and find out what the cause is.

As you explore the various roles in this lifestyle this forum, and others, can offer you a large array of knowledge and occasional wisdom from those who have gone before.

I think you may benefit from meeting in person with others in the lifestyle and discussing your situation. A quick google search lists two munches in Mississippi. And a forum search on munch will give you some good advise on how to participate. Talking with others in the lifestyle could be of great help to you and your boyfriend.

I agree with Gary that this is a challenge. Given some time and talk you two may be able to take your relationship to the next level.

I hope this makes some sense. So continue posting and we may be able to help you make some sense of it.