The Art of Cross Dressing – It’s all a matter of Illusion

Today I want to talk about something that I would have to say lies at the very core foundations of being a transgender person, and very much defines the spectrum that exists in our community. The important question that you have to ask yourself is, how much of the illusion do I want to create, and not only create it but in a way master the art of the illusion.

Male to Female Overlay

Male to Female Overlay

To get into what I want to discuss, which in a way is mostly a visual concept, I wanted to create an image that illustrates what we as transgender have to face in terms of what we both want to achieve, as well as how the general population addresses gender and the idea of conforming to the black and white gender categories. There are friends that I have talked to about the idea that gender should not have to fit into either male or female, but for the purposes of this article, and the main challenge I am constantly trying to master I want to talk about how we want to achieve the male to female transformation illusion.

The background image shows a muscular male, overlaid with the body shape of a female figure. Guys come in all different shapes and sizes, depending on how much you weigh, how tall you are, how fit you are, how much time you spend lifting weights, etc. So for the purposes of the article I wanted to discuss the challenge of going from an archetypal muscular male guy to transform into a woman. And the first biggest challenge we face is the size of our body parts.


I first became aware of this size comparison when I was traveling in Asia. At the time I was with my ex- girlfriend and we were shopping at one of the many department stores. Theres something about me that when ever I travel I like to try to find t=shirts that have images or statements that are totally bizarre. The t-shirt I bought that day I would say was slightly on the girlie side, as it was black with a lot of pink foil writing on it, and featured a cherub angle sitting on the toilet, but thats a story for another day. Anyway, after putting the t-shirt on I noticed how the size of it around the mid chest region was much tighter then any shirts I’ve bought in the West. And having a lot of Asian transgender friends on facebook, it started to make me aware that the reason they look so great as girls is because their whole chest region is a lot smaller then western males.

Chest size is one of the key issues when dressing as a woman, as its something you are unable to truly alter. A mans chest of always going to be more wider at the top and narrower at the bottom, where as a woman’s chest is going to be smaller, and the opposite. So the best way to overcome this is through the use of appropriate breast forms. If you read through the entire article which I hope you will. You’ll start to understand that the key to the illusion is not only size, but also proportions.


In taking a logical path, the size of our waists is the next item that has to be taken into consideration. This is not something that is important purely in size, but in proportion. All men know that the ideal shape of a woman is the hour glass figure. A narrow waist emphasises their wide child bearing hips, highlighting their potential for fertility, Balanced with narrow shoulders that show a weaker more submissive strength. Now women, who are producing all their female hormones are getting their fat placed in all the right places, in general that is. Some women love to complain about fat going to all the wrong places, but for us males the majority of our fat goes straight to our stomachs.

The great tool we have to alter this part of our body is of course the corset. Ill go over more information about corsets later in the series but the basics are quite simple. The key to getting a good waist line is buying a steel boned corset that can pull in your mid section very strongly. I have purchased both an expensive corset from Vollers, and another from eBay. Admittedly I had to buy the second after losing a lot of weight, but Id honestly say that it does a much better job then the more expensive one. Another important consideration when buying a corset is to measure the length its going to have A. from your sternum to the top of your pelvic bone and B. the circumference the bottom will have around your hips. These two measurements are VERY IMPORTANT! I often wear my corset out to clubs, and find that if length A is too long, the bottom of the metal plate on the corset where the clasps run will dig into your pelvic bone. The circumference at the bottom is important too because if its too much when done up, it can create too much ruffled fabric under your clothing.

Hips and Butt

In this section I want to first openly discuss the reasons and then direct you to some experts that can help you create your own custom solutions. I have so far brought some products that have had some relative success with, but it all depends very much on what you want to wear, and how realistic you want to look.

We all know that men have narrow hips, and women have wide ones. The simple answer to this is for making babies. On the other hand, not all women have butts, so its up to you whether thats something that you feel is important to your look. The hips work in relation to the waist, and the ideal feminine waist to hip ratio is 0.7. So if you managed to use a corset to pull your waist down to 28 inches, then 28 x 0.7 = 40 inches for your hips. Most women tend to have hip sizes around 36 inches, but they tend to be smaller in size so having the smaller waist if easier for them to achieve.

I was going to go into depth about how you can create the perfect hips but the following videos show a number of different techniques. The reason why I don’t recommend you buying hip and butt pads, or pants is purely because the majority of those products are aimed at helping women boost what they already have. When it comes to the art of creating them from scratch we actually have to build up a lot more volume, and at the same time make it look seamless to our bodies.

This is one of the first videos I watched, and great to show you the whole cutting process.


This is a video I watched more recently. Different method but a more customisable approach.


This is the one I love the most. He emphasizes on the size and placement of the pad that needs to be created.


The Face

Okay, now you are all thinking why did I leave the face to last? Well in my honest opinion, the face is the easiest part to camouflage as opposed to actual physicality’s of your body. You can check out my previous article on finding the right wig, and style. The only other area you need to work on is make up. Depending where you are on the pathway, if you are just starting out Id highly recommend seeing a make up artist or having a make over and seeing the skills they are able to employ.

One of the best techniques you can use to help achieve more feminine features is contouring, and if you type that into youtube the videos are endless. Contouring works on both the overall shape of your face, and the facial plains, as well as shaping individual features. So you can search for contouring, or contouring eyes, nose, lips etc. Just remember make up can work wonders, and another key element that again can spark the illusion to a whole new level is the use of fake eyelashes! They can be a tricky thing to master, but like all new skills, practise can only improve your skills.

Limbs and things

This is the final section thats more like a miscellaneous section that rounds up all the other areas that need some attention. Okay so heres something about dressing that women will always be jealous of, you may know it already. Men don’t get cellulite! So our legs are always going to look streamlined, toned, and well defined. So nothing for us to worry about there. Other then the fact that we may need to spend a little more time shaving them. šŸ˜‰

Our hands and feet tend to give away our gender at times, as they often are a little wider and less delicate. A way around this is again through camouflage, finger and toenails can be painted. Rings can be worn, and feet can be squeezed into shoes. When i first started dressing I rarely took any time to think about items like jewellery or the importance of accessories. Women have different mind sets to guys, and always focus on even the smallest of details. So always remember to think about both the picture as a whole, and the individual elements and how they all live together in harmony.

My only other thoughts I can add to this topic are skincare, and the scents that you wear. Obviously a woman has a lot less hair then a man, and whenever her skin is exposed she make sure its shaved and hairless. She also takes a lot of effort into keeping her skin soft and well cleansed. Plus most women you meet will have a typical scent that they love which either expresses their personality, or defines their favourite feelings.

Feel free to add any comments, and thoughts. I know I am constantly learning when it comes to the Art of Cross Dressing, and its only through practise, and talking to friends that I have come so far. Let this be a community that can help everyone grow on their pathway to finding their gender happiness.

Mwah x


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