All the comments above are great. Starting with therapy.
One piece more that is lost in a lot of people especially with their first outing.
Blend in.
Women do not go to the movies in dresses, jewelry and heels like that were going to a ball. Try this, go to a store a town or two away and go to a store that sells blue jeans. (I'm 25 miles from an outlet mall with a Levi's outlet.). Try on (men's and women's jeans look the same) a few that are high enough in the waist that you don't show crack when bending over.
A couple of things I noticed, first women's jeans are the best kept secret from men. They are very comfortable. Two, no one will notice. Wear them out to a store, to class, to... Wherever. You'll get comfortable as time goes on. Then start adding more and more.
This will help you decide if this is right. You can do other things too like let your hair grow, pierce your ears, wear female underwear (careful wearing bras, they can show and a part on the back will out you.
Again therapy is a great step I found it relaxing and helped me through the tough times.
Good luck and keep us up to date.
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