Going out in public is one of the hardest obstacles for transgenders to overcome. Many will find a local group and attend events en mass. These events are usually in LGBT friendly areas, and provide a sense of security and of being out in the real world.
But when you get down to it, it's really not, the general public rarely inhabit these areas. At some point you will either resolve yourself to this life in the security blanket, or make the plunge into the real, everyday mundane world of the general public.
From time to time, I have large amounts of outside work to do that involves a truck, some tractors etc. I always wear overalls for this, I like to match apparel to the task. My dog loves to be involved with this outside work, loves riding in the truck etc. So for several years now, whenever I put on my overalls, she becomes very excited. She has associated the overalls with a fun day.
There is a restaurant in my local town where we like to dine. I decided that it was time to be myself and went as Jess. The first time they seated us with curtesy, but I did get some looks of uncertainty from our waitress. She was pleasant, and polite, and somewhere during the meal I made a small joke that she found funny. The uncertainty seemed to disappear. We tipped well and that was that. A week later I returned, this time I was greeted with a smile and seated. The third time, I brought my sidekick along, and was greeted with a 'you look very pretty tonight', and we were all treated like gold.
My point here is that humans can sometimes be trained just like my dog. She(my dog) came to associate my overalls with fun. The restaurant staff came to associate my attire with pleasantries and nice tips.
If you ease into life, and show everyone that you are not something strange and unpleasant, they will become acclimated to you. And by way of association, all of us.