Hey there,
Though none of us should be read as gospel - we've all had our own experiences, and you're the only one who knows your own circumstances - in my opinion the answer is simple. Stop feeling like you're hiding it. Just don't go out of your way to let everyone know.
There are a few important things you need to know the/an answer to before you decide what your next best step is. These are important pertinent questions to who will accept you, and how well.
1 - Does anyone know? How do they feel about it? Can you open up to them more, ask them how people you know would react?
2 - How would your family, particularly your parents or siblings, feel about this? Most people associate it with homosexuality, so just take their feelings on that and extrapolate from there. It's how I went about it in the beginning.
3 - Is there a nearby town or area where you're unlikely to know anyone, but is LGBT friendly? My advice is to practice with some makeup at home, get a girl to help you, watch YouTube videos on tips for colors and application techniques, etc, get a cheap decent looking wig, unless your hair is long, and then pack that stuff in a bag, and go have an evening on the town. Starbucks and anywhere with a private bathroom is a good place to change and put on your makeup.
Trust me, telling your first person is the most nerve wracking. I told my best friend first, and even though she's a very open-minded lesbian, I had NO idea how she'd take it. I had the same questions: Would she think I was less of a man? Would she think I was too strange for her to know? Turns out she loves me all the more to know that I'd share something like that with her.
As to going out, well, that's up to you and only you. If you're confident and carry yourself well, most people won't pay you a second thought.
Ok, I know I took this to the whole next level here, but I had to go a bit in depth to answer your questions fully. Hopefully it helps.
