One of the ways to make it easy--or, at least, easier--is to choose a place that is forgiving to the TG community. In my case, it was Hamburger Mary's in San Diego....I knew I could go in there, dressed and made up to the best of my abilites, and be OK with everyone there--a great confidence booster.
The following year was the big test: going for a walk on the beach in La Jolla in a one-piece suit, with and without a denim skirt...
To be accepted, or at least not openly mocked, in public as a woman was the opening to a whole new world, and it just kept getting better after that....
It can for you, too---and yes, being confident in the sexuality you are presenting yourself to be is more than half the battle.