If you really want to be serious about your husband being sissified and feminized, I suggest you go to a website like Fetlife. (
www.fetlife.com) It is a website for people with various fetishes, in my case, black men among other things. But there are people there who really are into their their pleasures, and know how to get things done.
I am also sure that you can buy tailor-made outfits for him, if regular sizing doesn't work. As someone else said, he'll need to clean up, massively, and that means below the eyebrows. I also like
www.aliexpress.com for shopping. They have all sorts of stuff we would never think of, and because there is no middle-man business in the way, prices are far cheaper.
Just a word of caution. Once his being a sissy gets out, he will BE out. There is no way to put the genie back in the bottle. There will be repercussions you can't foresee. I know when I was ***** by a co-worker years ago that the stigma that hung on me lasted for years, until I was separated from the company due to down-sizing. I can't imagine any of your friends keeping something juicy like that a secret. I don't think I could.