Honestly, i suspect that questioning oneself is a normal and persistent aspect of being transgender. Having a supportive wife and being able to find opportunities to go out together has to be very gratifying. Wish I had been so fortunate in my own life. It speaks well of you and your wife.
During my marriages, I too largely confined myself to under dressing, but eventually I realized I wanted more. I quite mistakenly assumed that I could slowly turn up the level...and that my wife would acclimate like a frog in a pot of water. That was a horribly mistaken assumption and it eventually cost me my marriage.
