Once you are feeling adventurous and finally decide to take the big plunge…towards crossdressing, wink*, you may feel you are not quite sure where to start or where to go from there or how exactly apply make up or… *insert a million questions here*. And that is ok; nobody was born with full knowledge about life, the universe and everything else. Keep in mind this is a process and a journey, so there’s no manual; you will need to experience a bunch of things to experience what works for you and elements of your cross dressing will probably change with time, those things are part of the experience.
Having said that, there are some things that can help you out a bit. The first I can tell you it’s: don’t ever hide, especially if you have a partner. Wearing her clothes, lingerie, heels or make up when you doesn’t know or suspect is a huge no-no (yes, I said that twice). The first thing you have to do is talk to her about your feelings and desires to cross dress, remember: honesty first. Let’s remember, being scared is normal, but once we do the thing that scares us the most, we look back on it with pride. Besides, you don’t know how they will react, so go and tell her! You two will figure it out, you crazy kids.
Once you two have figured things out, you will want to figure out exactly what woman you want to be. When they say, “imitation is the best compliment” that is kind of true. So go out to the world and observe women that you like. Obviously don’t do it in a creepy way that can make someone call the cops, but watch and analyze what is it about them that you like. Is how they dress? Their hair? The way the carry themselves? This will give you an idea what to imitate when you are your other self. And then, don’t forget to practice. Walking like a woman after years of walking like a man can take some time to figure out, so you will need to practice. Same goes with walking in heels, applying make up (watch online tutorials!) and body expression.
When you are ready, you can start to buy clothes and accessories. You can either go with your partner or alone. If you are alone and don’t want people to know, you can always chalk it off to buying things for your wife. If you have any doubts, sales associates are always eager to help you out look what you are looking for and to give a second opinion.
As for the breast and butt forms, my advice is to keep it proportionate with your weight and height unless you intend to look extremely voluptuous and exuberant. Do buy a corset because it will help you create the illusion of a defined waist and bigger hips. If you buy a pretty corset, it will not only make you look great with clothes on, but also without any clothes at all…wink*
Make up is a very big part of the cross dressing, so you want to invest in a good foundation. You will need a beard cover, a contour pallete and/or blush and highlighter, mascara, lipstick, eye and lip liner and eye shadows. If you are unsure about the wide variety of products, again, don’t be scared to ask for help to a department store cosmetologist because they do know best. When you are experimenting with make up, don’t go overboard, simple is better unless you want o look like a drag queen. And that goes for clothes as well if you are in public; dress for your age and your environment. This means if you are going grocery shopping, leave the short leather skirt and heels at home and wear something more demure. You can have that kind of fun later, wink*
Just take things slow and enjoy the process! If you are not ready for something in particular, just wait until you are, there’s no pressure. And also, like I said, there’s no manual so nobody can tell you what cross dressing entails and what doesn’t and what you should do or don’t do. You know what I always say, as long as people are willing and you are not hurting anybody, go out and have fun! Wink*