My first experience on it was kind of 3 or more years ago.
I know your feelings about sharing this experience with your wife but you must understand that your wife, for perfect and passable you can be, your wife still seeing you as a dressed man.
It takes so long so she can perceive you as a woman and feel comfortable with you going out.
About passing, this is something interesting about cds, you think you're passable, nice people ere (I disagree with that dishonest attitude) compliment you based in a pic and tell you are amazing and passable but you are not. So for your wife going out can be an embarrassing situation.
Today I can see pics of that first time and now, I the one that feel embarrased and feel sorry for her.
One year later I fulfilled my dream on traveling with her. I haven't improves my presentation but it was helpful for her to see people's reaction that wasn't so negative.
That was the point to star full.time as a woman.
After all this years if learned more about the simplicity of make up (of course now, after 2 years on electrolysis, I don't have yo wear beard concealer and.tons of make up) and I learn about different situations for dressing.
Now we are just two women in anybsiyuation and people sees us like that and all the time they call us "ladies"
For that first time I recommend you ask your wife about make up and dressing so you involve her in your plan and she will feel more confident with you ok for the situation.