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Going out Dressed as A Sissy: How to Take that First Step


If you have been cross dressing privately for years, the thought of going out that first time completely dressed can be terrifying and daunting. However, you want to show the world that inner girl, and you want to dress the way you would like to dress out in public.

How can you ease into going out cross dressed?


Sissies Going Out: Getting Started


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, start by 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 to go out cross dressed en femme , and 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 night club 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.


Sissy Style – Less Is More


Dress tastefully, and don’t overdo it such as too much make-up, or too much gaudy jewelry – unless 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 still makes you 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! If you are a confident and you relax, it will exude everyone will be able to feel that from 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?


For sissy training sessions, call 800-356-6169