Has he tried to be more stereotypically "feminine" in small ways? If atm he has no notion of what he wants or how he really feels, other than he wants to present as more feminine, could he give it a go, without having to go all the way? A more androgynous style, to test the waters?
Eg growing his hair, wearing some black nail varnish and a bit of black eyeliner, having his eyebrows styled. A bit of fake tan. Waxing his arms/armpits/chest.
Also, would he consider getting some stereotypically feminine piercings done, both ears, nose, belly button? Or a feminine tattoo?
I actually personally find this sort of aesthetic very sexy, and have dated/slept a fair few androgynous types over the years (male and female).
How does your dh normally present? What's his style like? What's his personality like?
You said you carry the mental load/do the wifework, and I think you could use that as a way to broach the idea that actually being a woman, is much much more than just looking like a woman (which doesn't require one to actually be a woman). Does he have sisters, neices etc? I think many men don't understand how differently boys and girls are often raised, and the social conditioning females undergo, from we're ridiculously young. The ones who didn't enjoy male conditioning, wouldn't have nesseccarily been any happier with the reality of the female version.
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