A little help with wife’s confidence level

So I’m hoping to maybe get a little advice here. I’ve been lurking on the site for some time now reading, learning, or at least trying to. To some degree is kind of information overload.

First, where my wife and I are at. Well over the years I have let her in on a lot of my kinky desires. We started out with some strapon play. Later we started playing dom/sub role, eventually we added in chastity, more recently doing orgasm denial more. And she’s becoming slowly but surely a little more comfortable as the Female Centered Role.

In general though, I see she still isn’t really confident. She doesn’t see herself as beautiful as I see her. Part of that I believe is her weight, which she brings up a lot. I think she’s beautiful regardless but she doesn’t agree with me when society says she needs to weigh less. I try to show and tell her how much I love her body.

What tends to happen is that she only kind of takes control. She’ll put me in chastity and tease me for a little bit but then feels bad. I wrote up a contract completely giving her control which she loved. It requires me to go down on her or pleasure her how she wants at least once per day, but as often as required. Limits my orgasms to no more than twice per month, but under the requirement of being earned through a system which improves my odds based on how well I pleasure her.

Over the last month, she had me released from chastity on the basis of self managing my chastity. Well in a weak moment I ended up masturbating without permission. Yesterday she must have recognized that the attention I was giving her was a little off from where it should have been if I was properly denied so she asked me if I cheated. I was honest and said I had, so she put me in chastity for cheating (never thought I would be held accountable for cheating with my own hand). 

Well even just last night she had already let me out of chastity to allow me 15 minutes to have a ruined orgasm because of my pleading. Even though I had cheated it was quite awhile ago. So she made me edge and denied me several times from being allowed to reach the ruined orgasm until she said so. And then finally when I was giving permission I had trouble getting there. Time was running out, and it was difficult but I decided to go ahead and fail to reach my ruined orgasm allowance in time. So she did deny me any orgasm at all. And then for the rest of the evening and this morning I showered her with affections. Foot rubs, massages, coffee in bed. Trying not to “Top from the Bottom” as they say, I wanted to try and show her how being more confident and taking more control can be better for her. I think it worked to some degree. It’s really hard for me to not have an orgasm when she’s allowing it though but I’m hoping in the long run it will be worth it.

I’ve brought up cuckolding a little bit once before. I didn’t just really come out to discuss it, I just tested the waters a little. I immediately got a response that shows she has all the most common issues immediately in her head. “It’s just an excuse to cheat” I think that one was directed at the men allowing it, which means she doesn’t really know what cuckolding is. There was also a couple comments that followed about how women sleeping around, so she has the standard monogamous programming in her head as well.

So I know I need to bring this up to her directly and have a real conversation about it with her. I have some ideas with how I can do that from the forums and such. But I’m also interested in how I might bring up her confidence and empower her to be more in control of our relationship in the mean time. I’m making some headway, I hope I’m doing it the right way by just letting her experience what having that control is like without “topping from the bottom” by telling her she needs to do this or that or the other. But I’m open to any and all ideas.

I also thought that it could be beneficial to kind of start planting some seeds of my fantasy. When I pleasure her with my mouth every day I have started trying to ask her what her fantasies are. I keep asking if she’ll tell them to me while I’m pleasuring her. She always shies away from that idea. Another clue to me that she just doesn’t have the confidence to really open up. She says she doesn’t have any fantasies. I’ve thought about asking her to tell me about a romantic encounter she’s had in the past or wanted to have while I pleasure her? Some way to kind of start broaching the subject and show her how turned on I am by the thought of it? Maybe this is wrong also but I don’t think she’s ready for that discussion yet and not trying to really avoid the conversation but instead lay the groundwork for it.

Anyway, any advice would be helpful (even the advice I don’t want to hear because maybe I need to hear it, LOL)