One of the most powerful ways you can ensure the best possible passing is by rehearsing your success in your mind. Visualisation is a very potent self-help technique used to assist people to achieve those things they really want, especially when they aren't sure how they are going to get them.
For you, this could really help to get outside the front door the first time, plus it is great for helping alleviate stress. Most of all, visualisation will help you to create a more powerful feminine presence.
The idea is to spend some time each day, at least ten minutes, imagining yourself out doing the thing that you most desire. If you want to go out dressed as a woman and be as accepted as such as you interact with other people, then this is what you need to focus on.
Rehearsing in your mind will bring your unconscious mind on board with your goal, and you'll find yourself doing things in a more feminine way without even trying.
Find a good time when you can be alone and relax, preferably at the same time and in the same place each day. Close your eyes. Take some deep breaths and relax the muscles throughout your entire body.
In your mind you need to see yourself dressed as a woman in the situation you want to master. Allow yourself to experience everything about it in your mind's eye.
You can try different techniques. Some people see themselves as if they were watching someone else. Some prefer to see the world through their own eyes. Some people find it helpful to hear the sounds associated with your success, the compliments from strangers or the greetings from regular acquaintances.
Also notice how things feel in your rehearsal. Sense the soft fabric of the clothes against your skin, you might feel the sun on your skin, or the cool evening breeze in your hair.
Notice how wonderfully feminine you feel throughout, and notice how much you enjoy the experience of passing every time it happens.
TIP:
Rehearse your first outing in your mind, over and over again, until it feels so natural to visualise your success.