I have a lot of sissies ask me about how to pass as a woman.

I suppose that first, I should explain what ‘how to pass as a woman’ means. Passing is when you can convincingly dress and act in the manner of the entity you’re passing as. For example, when a person with male genitals can wear makeup and a dress, and act just like a woman, he can be said to be able to pass as a woman. Or when a drag king dresses in a suit and uses makeup techniques to create a five o’clock shadow, she is passing as a man.

Your first step, if you want to be able to pass for a woman, is to decide what kind of woman you want to be.

After all, as you well know, all women are not the same. We are not some monolithic bastion of sameness, here. There are stylish women, frumpy women, yoga chicks, hippies, soccer moms, professors, beach bunnies, sluts, whores, prudes and frigid bitches. We run the gamut and occupy the whole spectrum. So give it some thought. What ~type~ of woman do you want to emulate?

From here it’s everyone’s favorite step: Research!

If you groaned and sighed, you’re clearly not doing your research properly. Hit google’s image search, and look for pictures of the sort of femme you want to be. Then, search for the sort of clothing you see her wearing, the things you imagine you’d be wearing. I’m a huge fan of JCPenney, largely because of their GLBT inclusive advertising, but also because they have a surprisingly wide range of clothing styles. I can get yoga pants, a suit and a ballgown there, and not have to hock a kidney (and they offer shipping! Never leave your home, and returns are a breeze!). Check out their website, and look for things that make your little heart go pit a pat.

Don’t forget to also do some looking into makeup, hair, and nails. Some females don’t wear much, some of us love to play with eyeshadow. What sort of femme are you? Are you a mascara and pony tail lady, or do you glam it up with a full up-do and fake lashes? Cocksucker red lipstick, or do you go subtle with a nice dusty rose? There are tutorials on youtube that can help walk you through doing all sorts of styles of makeup.

While you’re researching, don’t forget to go native and observe.

Now, this is where I tell you not to be a total pervert. While I do want you to go observe actual real women, to see how we sit, how we hold a fork, how we open doors and smooth our hair… I don’t want you to be that guy in the coffee shop who stares and makes us uncomfortable. It’s a fine line, subtle, but one that you can learn to walk. Besides, if you do make your goal of passing, then it’ll be your turn to be made uncomfortable by some mouth breather staring at you lustily (or your shoes, sometimes shoes get stared at…)

With your behavioral research done, and your shopping spree finished, it’s time to put it all together.

This can be one of the most nerve-wracking parts of passing. The first time you get all dressed up, hair, makeup, outfit, shoes, underthings and all. Because you don’t know if you did it right! How do you know if you’re passing without revealing yourself to the world?! Simple. Set up your webcam, get on Skype or YahooIM, and contact any of the ladies of LDW. When you want a quick check, drop a line to your favorite Mistress and ask her to give you a once over. Or you can set up an entire session, and we can sit and critique, tweak and go full on girl over your new shoes. Any time you want to talk to a woman who understands, who accepts you and who will help you get better at passing, well. We’re here, darling.

One last bit of advice on how to pass as a woman:

Now, this comes from my staunchly feminist leanings, and from my refusal to let anyone tell me how to dress or act… How to pass as a woman: Put on clothes, feel fabulous, tell the world you’re a woman. Because I am no less a woman when I wear jeans and a T-shirt than I am when I paint my nails and wear a skirt. And neither, my sweetheart, are you (no matter what’s in your panties!)

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