I would certainly consider it if my wife would agree to fuck other guys. Only I still want my turn even though she might find a bigger cock. Mine is very average (maybe below) and can't last very long. Medication helps but after I cum I'm soft in minutes. It's my feeling that she has more in the tank. She enjoys sex and seems to be ok with my cock but has nothing to compare it to.
I wouldn't adopt a sissy lifestyle, but I've let or asked my GF to fem me out for a night.
So far, it's just been me wearing her lingerie, but we do have plans for full make-up, likely painted up like a *****.
We've also enjoyed the fantasy of her femming me like that, then turning me over to her lover or another man, like a prize.