Tease and denial
@hot-wifey I am not a lady, but I do have 2 cents to share. I sympathize with your situation. It sounds like you may have some things in common with my girlfriend who is very loving, would never intentionally hurt me, and finds that she does have to confront her inhibitions.
I would say that two things have allowed her to make a breakthrough to our mutual satisfaction and benefit. The first was a mindset change. Once she stopped thinking of herself as being a mean dick-tease, and started identifying as a loving person who cares to invest in really awesome foreplay, it became much easier for her to step up her teasing and start playing with denial. I encourage you to look at it as any kind of lovemaking that you have ever engaged in during your life. You will learn together and it is mutual love and intimacy and, frankly, your openness to explore T&D, not some elusive perfect technique that is most important and make everything alright.
The second thing has to do with the transfer of control that you are negotiating. I am sure that you are right that it is a buzz-kill for your lover if you are continuously asking him if he is OK and if you are doing it right. For me, it is the fact that my girlfriend is authentically taking control that does it for me (even if she doesn't fulfill my kinkiest fantasies) not that she is perfectly acting out some role for my benefit. Search your feelings and see if you can't find a part of you that really gets off, to some degree, on being in charge. If you can find that kernel, then embrace it and try to build from there.
If your lover is like me, he will say that he gets far more pleasure from you enthusiastically and authentically wielding control, even if it is poorly executed, than he gets from technically great teasing that is happening because he is making it happen. That is just topping from the bottom. That is nothing either of you wants.
One last suggestion that might help with both mindset and developing comfort with your control as you guys learn. Instead of asking for approval or inviting criticism when you feel insecure. Turn it around and demand that he confess things that you can use to your advantage and help learn his physical reactions. For example, instead of saying, "Am I doing it right?" or "Are you getting closer?" simply instruct him in a clear and direct way like, "You are not to cum without my express permission and I haven't decided if am going to allow you to cum. You are to tell me when you are getting close and in plenty of time to stop before you go over the edge," of "Which makes you hotter for me, this . . . or this. . . ," or, "Oh, that was close wasn't it? You almost came didn't you?"