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The thought of going out dressed as a sissy that first time can be terrifying and daunting, even if you have been cross dressing privately for years. However, you want to show the world that inner girl. Furthermore, you want to dress the way you would like to dress out in public.
How can you ease into going out cross dressed?
First of all, you can start very small and simple. Start by wearing feminine clothes underneath your male clothes. You can wear a pair of frilly, satiny panties and get comfortable with that for a couple of weeks. After that, proceed to wearing women’s slacks, or a nice pair of women’s designer jeans. You can slowly start adding one article of clothing at a time. This could take a few months to do, but well worth the transition.
Once you feel completely ready, go out cross dressed en femme. Perhaps you are ready to wear that dress out, or slip into that flirty skirt. The best place to do it in is at a nightclub where crossdressers and transgenders are welcome. Also, you can shop during the day at a mall where you can freely be yourself and do it in a public, safe place.
Dress tastefully, and don’t overdo it, such as applying too much make-up, or too much gaudy jewelry. Unless, of course, you plan on doing a stage performance! Just the right amount of sissy make up or a few pieces of jewelry is enough to express your femininity. And you will still be quite stylish.
Wear high heels that are not too tall, especially if you are tall, unless you are looking to be taller to help your feminine look.
Remember to have fun, and to relax! When you are confident and relaxed, it will exude from you. Everyone will be able to feel that just by being in your presence.
If you have any questions about going out dressed as a sissy, or need guidance, call the Sissy School Mistresses. If you are looking for information on crossdressing men, and how this issue affects relationships, see also: Crossdressing Men: Is the Crossdresser Really Powerless to Stop?