4 steps for learning how to crossdress

Written by Elise Wren

As i like to say, cross-dressing is an art. It’s much more than just wearing clothes that makes you comfortable, it’s about all the feelings you get in the process. Cross-dressing is expressing yourself in the way that you're meant to be. Although, as any type of art, cross dressing requires a little bit of skill and there is no better way to become skilled other than practicing. First, you will need to build a little bit of confidence, and in no time you shall be feeling that nothing can stop you, so let’s start with the basics.

1-Find a safe place

If you are still building confidence and have some insecurities, the very first thing you will need, is a safe place where you can practice and master your skills, and be able to store your cross-dressing materials as well. In this case, a small bedroom or even a closet shall be enough, as long as you can fit a mirror on it. Also, if you can use travel bags and backpacks to hide your stuff if you don't want people to find it, or you can even consider storing it on the trunk of your car. Once you feel comfortable with your space, you are ready to go.

2-What do you need

Every artist needs its own art supply, and it’s not different with cross-dressers. You may start by getting some makeup essentials, such as a foundation and some powders, and making sure that everything matches your skin tone, as well as something a little darker than it for the contouring. An eyeliner and a red lipstick will do wonders to highlight your feminine features, and you might also want to shape your eyebrows with an eyebrow pencil, but that is it and we are done with the face.

Shaping your body can be a little tricky, but as always, we can find a solution. A simple waist trainer is actually a big deal in terms of reducing your waistline and achieving an hourglass figure, but you might also consider a corset to finish the job. Hip pads can help, depending on your shape, but it’s not always essential. And of course, you probably want breasts, and for that we have a lot of options. From the classic stuffed bras to more sophisticated silicone breastplates filled with cotton or gel, your choice depends only on you (and maybe on your budget). A stuffed bra with socks or padding can look quite convincing while covered by your clothes, but if you want some sort of cleavage, i would recommend an underwired bra combined with push-ups and makeup, or the silicone breastplates, and a bodysuit can also help you hide whatever you’re using to shape your waist.

Last but not least, you still need the clothes, and you will be a lot more convincing if you choose something accordingly to your age. Keep an eye on the current fashion, and observe what people around you dress like. Pick something that fits you and shows only as much skin as you would like in public, but that does not hide you so much. With all of that in mind, you’re all set to start, and will be soon looking stunning!

3-How to become Skilled

That’s where the fun begins! The most important part here, is to get to know yourself, and what do you want do look like. Practice with makeup, try contouring your face with it until you are happy with the shape of it. Shading and lighting are very important here, and a mirror will surely help you. You can create a really cool light effect by using an illuminator on the parts of your face that you want to highlight, and a powder or foundation a little darker than your skin tone on the parts that you want to conceal. Getting your face to look feminine is about 50% of the work, because that’s the first thing people will notice about you, so you might be prepared to expend an extra time on it when getting ready.

The other 50% is all about your silhouette and your overall look. Trying to get an hourglass shape? The very first step is understanding your body. Do you have an even shape and need a smaller waist? Then go for it, using the wait trainers that i mentioned earlier. Do you have a slim figure and need to buff some parts? Then you shall invest on butt and hip pads in addition with a breastplate, creating the curves you want. Want to hide your belly? Then a corset might help you. It all really depends on your natural body and the shape you want to achieve, and you must always remember that people come in every shape and size, so it would be nice to understand what kind of woman you want to resemble, and which one is the ideal for your own natural body type.

The clothes you pick will also play a major role in completing your look. You must reflect on how much of your body you are willing to show, and pay attention on every inch of it. Shaving will help you a lot if you want to show your natural legs without using a black pantyhose, or if you´re using anything without long sleeves. You might also want to hide your torso if you are only using a stuffed bra with socks or something like that, so pay attention on the collar of your shirt. Crop tops might work, but they go better with silicone breastplates and bodysuits underneath.

Dresses and skirts will surely feminize you, but they are also a little tricky. Be sure to tuck when using one of these, and pick an underwear that makes you comfortable. Speaking of tucking, i must say that it’s not as hard as it seems. Most of us want to get rid of our “stuff” when cross-dressing, and tucking can help a lot. You can use gaffs or even a padded underwear to make things easier, but if you need to, you can improvise with tape or socks. One thing to remember about tucking: If it hurts, you are doing it wrong. You have to be very careful, and with enough training and practice your “stuff” won’t be noticed.

4 - Final considerations

After all these tips, the most important thing i have to say is that beauty has no bounds, and there is no limit of what you can achieve if you practice enough. We must always remember that everyone has its own beauty, and nobody is perfect, but we can always improve ourselves if we want to. Never give up on your dreams, always remember to be yourself, no matter what other people might say about you, and you shall live a happy and wholesome life.