1000 freakin% you should do it.This may not be about dressing modestly which I do do outside our home. Rather, I have a question about dressing inside the home alone with my husband.. he has told me that you would like it if I would sometimes greet him at the door, when he comes in from work, with me wearing a short skirt and stockings! That feels out of my comfort zone, should I get past that and do it anyway?
Ask him to pick out what he wants to see on you, and do it with joy because HE says it's beautiful and amazing. To be blunt, your opinion on the matter means nothing if it matters to him. Just like your opinion on whether or not you are pretty enough to be called beautiful if HE says you are beautiful to him. What matters is not if I think I am acceptable to my Lord, what matters is what He calls me. I am to count myself according to His description of me.
It is exactly part of being submissive. Think of him as your king and lord. If you were the subject of a king, and the king said he wanted you to dress up in only green dresses made by a certain dress maker. What would that woman of old do in response to the King's wishes... You'd see her wearing green dresses.Is this part of being submissive, dressing like this?
I have tried many times but I just feel silly,
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You should ask him to tell you how you look when you do what he desires. And then tell yourself "*insert what he said* is what I am. I am not silly looking, I am *insert what he said*."if it means that much to him should I be finding a way to get beyond what feels comfortable to me?
Why? Because his opinion matters more than your self criticism.
Embrace the beauty and joy that he is trying to bring into your marriage. Enjoy that wonder and glory when you see the joy and happiness on his face.