One of the biggest thing that helped me get comfortable was having a large group of trans friends and we go out very regularly as a group, there are girls in all stages of their transition but all very presentable.
It allows you to see how people react to trans people when they know the group is trans and it allowed me to laugh and have a great time even when I knew I was being clocked, it also showed me that even when people know I'm trans they can still be attracted to me and they don't see me as some freak.
We pretty much go anywhere we want, being in a group of 6-10 girls removes any worries about personal security and having friends by your side helps in my experience.
Perhaps the two of you could explore some local trans groups and see if that makes here more comfortable?