A crossdresser’s guide to stepping out (Male to Female Transgender / Crossdressing Tips)



I am going to start with an assumption. I will assume that you are a crossdresser who has come to the realization that hiding in your own personal closet is stifling your personal growth as a whole human being. You need to get out into the world! But you don’t go out because you are afraid of what the world will say. You are sure that you will be rejected by everyone with whom you have the most fleeting contact; that they will make fun of you. Further, you don’t think you will ever look good enough to go unnoticed in the outside world.

Well, there is hope. I have just described the early feelings of almost every crossdresser with whom I have discussed this subject. On the other hand, there are a large number of ETVC members who are perfectly willing to brave the outside world, and do it without incident. The purpose of this article is to help you notice some of the things you must address to make a successful transition.




Let’s start with the single most important step of your exodus from that little closet – self image. Quiz time! When you look in the mirror when crossdressed, what do you see?

A guy in a dress
A truly ugly woman who could derail a train with a passing glance
An average looking woman
A real knockout
Answer: a. A guy in a dress. At least this is the answer unless your self image is firm. Regardless of your physical appearance, be it anywhere from “b.” to “d.”, the transgender people with whom you interact are going to notice something not quite right, and will soon, if not instantly, see a guy in a dress. What do they usually notice? Well, it could be a flaw in appearance, or a display of masculine gestures (knees together, dear), but more likely than not, it will be a manifestation of abject fear. If you are truly afraid, you might as well wear a large sign, because your fear will show. When it shows, people are going to wonder what you have to be afraid of, or nervous about, and then they will pay close attention to you and figure it out.

So, how does one get over that abject fear? After all, we do something society scorns. Well, you could do it the hard way, like I did. I just started going out, late at night and never inside any place for a lot of years. Then I went where people were, got read, got laughed at, and ran. After a while I got used to it and I was not as afraid. I also did not get noticed as much. I’m no whiz at math, but I can add two and two, and usually end up with four as an answer.

Fortunately, that is not the only option. I had not heard of such a thing as E, and I did not know any other crossdressers. If you are reading this, you are probably a member of E. There is an easier way. Go to a meeting. Go in male clothes if you must. Just go! At the meetings, particularly the educational sessions, you will learn details of improving your appearance and deportment, and you will meet people who share your needs and will help you develop your self image. Also, it is non-threatening since you will be surrounded by other cross-dressers.

All right, now you know that you have a safe place to go, and that you don’t have to work on this alone. It is time to develop that self image. Shall we begin?


A healthy self image starts with the heartfelt knowledge that you are not sick, perverted, or strange. You are an individual with a need to experience, as much as possible, the full gamut of the human experience. That’s right, human. All you want to do, really, is to bring out the feminine side of your personality, and you choose to do it by assuming an externally female role. Society, as a whole, frowns on this because a man should not be feminine – that is weakness, and that is wrong. That attitude, however, ignores one very crucial and inescapable fact – women are human too. So, in actuality, all you are trying to do is to be fully yourself, and fully human. There is nothing wrong with that. Those who feel femininity is somehow inferior to masculinity are anachronisms. They should be fossilized bones, existing to be unearthed by archaeologists, instead of walking the streets, but they do still walk – male and female alike. And, unfortunately, crossdressers who brave outside world must deal with them. The first step, therefore, is to be at peace with yourself. If you can accept yourself, then fear will not give you away. Most people are not terribly observant, if you don’t give them anything to observe, and will accept what they see at face value. If you look like you have always been female, you will be accepted at face value. Even when you are read by someone, you will likely be accepted at face value because your self image is strong. People seldom confront others who are truly self- confident and comfortable with themselves.

Work on self image, but don’t expect it to bloom into full fruition overnight. Come to EC, RA, or such other meetings as there may be in your area, and let others help you. This is a difficult task, and there is no reason to go it alone.




No, this is not a make-up class. There are hundreds of sources for that information. I only have a couple of things to say on that subject. Make sure your beard does not show through your make-up. A beard is a uniquely male characteristic and a five-o’clock shadow will completely ruin an otherwise perfect presentation. The other is to make sure your make-up fits your age and the occasion. No amount of make-up which is acceptable for street wear will make a forty year old face look twenty. It only attracts attention, as does formal make-up in the mall. I would also recommend a stage make-up class at your local junior college. There you will learn about the variety of marvellous things you can do with make-up, and about the effects of highlight and shadow. Since you learn the theory, and not simply a mechanical application of one person’s method for applying make-up, you can effectively design a make-up plan to soften and compliment your individual face.


Body Hair:

Shave it, pluck it, bleach it, get electrolysis, or cover it. Those are the options. Ignoring it is not an option. Don’t let hairy arms or legs ruin your appearance. No matter what method you use, however, hair on the back of your hands, and particularly your fingers, is not acceptable. The lack of hair on a man’s hand is not really noticeable, but a pair of hairy hands is very noticeable on a transgender woman. Ditto on feet and ankles unless you wear opaque tights or boots.


Body and Clothes:

That’s right -body. You need to pass from the neck down as well as up. Your proportions need to be female as much as possible. A lot of women do have broad shoulders, thick waists, and narrow hips. Most of us, unfortunately, have broader shoulders, thicker waists, and narrower hips than these women. If you have any trace of a spare tire or “beer belly” it is time to invest in a corset or waist clincher. Unless you are blessed with very wide hips, then pad them. If you refuse to pad them, then wear clothes that make them look bigger. Broad shoulders can only be camouflaged with clothing. There are a number of good books to be found on dealing with various body types and clothing tricks to hide figure flaws.

Clothes should be appropriate to your size, weight, and age, and should fit. Blouses are not to be worn to show off your muscles. They should drape, not stretch, over your torso. And don’t forget that you will have breasts to contend with also. Unless you are young and willowy, you have no business in a tight, black, leather mini-skirt. If you are forty, dress for forty and forget those bygone years of youth and lost opportunity. You are trying to go unnoticed now. Finally, dress for the occasion. Look around you. How many women your age wear evening dresses and high heels in the mall? For that matter, how many wear a dress at all? Most of them will be in pants or a comfortable skirt, and comfortable shoes. You are sure to be noticed if you dress like a peacock while visiting the hen house.


As far as breasts are concerned, they should look natural. That means, unless you have managed to grow your own, that you will need artificial breasts. First, make sure they are large enough for your torso, without effecting the Dolly Parton look. They should be the right shape, meaning that several pairs of socks will probably be too lumpy. They must also have the proper weight to look natural. The weight gives them the proper movement and helps them attain a realistic contour. Foam rubber will not do unless crossdress you only need a little padding to add one cup size to your natural assets. Silicone is expensive, but probably the best. You can make do with well-sealed plastic bags filled with water. (Balloons won’t do, the shape is wrong.) Whatever your choice, be sure not to cinch up your bra straps too far. Breasts should go slightly below your armpits, not your collar bone.



Gestures/Body Language:


As I sure everyone has noticed, men and  cossdresser women have different ways of moving, standing, and gesturing. Your complete image requires that you learn move your body like a woman. The best way is to be coached by an expert. Failing that, watch the way women walk, sit, rise from a seated position, eat, stand, and gesture. You may be surprised, for example, to find that walking like a woman is not just a matter of moving your hips back and forth. Women have a lower center of gravity and walking is a matter of moving from the hips and letting the rest of the body come along. It is balanced. Men walk by starting to fall over and moving their feet underneath to give support before they finish falling.

Sitting should be accomplished with good posture, knees together, and arms close in – not taking up much room. If you sit with legs apart, shoulders hunched forward, and elbows on knees, you need some work.

Learn, and practice, the differences between the way men and women move. A video camera can be a valuable tool. If you need some outside help, enlist a friend or bug the E Education Co- Co-Chairpersons about some sessions in movement.



If you get everything else right and never have to speak, you will be fine. That is a little unrealistic, however, so let us cover a few key issues on voice. Contrary to what you may have heard, a high-pitched voice is not absolutely necessary. If done wrong, raising your pitch too much can damage your vocal cords. If you try a falsetto, you will only sound like Mickey Mouse. What to do? Well there are advocates of a number of methods for developing a passable voice. The following is simple and will get you off to a good start.

First, you should get your voice warmed up. This is easily accomplished by humming. Go up and down in a range that is comfortable. As you warm up you will be able to go a little higher. When you switch to speaking, stay in the higher part of your natural range. If you have to strain at all, you are too high and may hurt yourself. Drop down a little until you are comfortable.

Now, forget what you have heard about having to make your voice breathy. If you listen to women who have passed their teen years, you will find that very few of them have breathy voices. What you will find is that their voices are not loud and booming. Men shout at each other (listen at work – it’s true) in comparison to women, who speak with quieter, not breathier, voices. Support your voice from the diaphragm and let your voice resonate in your head, not your chest. These two things will not only eliminate breathiness, but will also make it easier to maintain a higher pitch. It will also eliminate that bass rumble that makes a voice undeniably male. In this one area I will go into detail as I learned this years ago while taking voice lessons (for singing) and don’t know of any particular outside reference.


Start by standing. Maintain good posture and stay relaxed. Place one hand on your chest and one on your abdomen. Take a deep breath. Did your chest move or your abdomen? You should feel your abdomen move first if you are breathing from the diaphragm. Your rib cage will follow. Practice this because you will need air to support your voice and your diaphragm provides it. It is also hard work, so you will need to get your breathing muscles into shape. Now place the fingertips of one hand on either side of your nose, and the other on your chest. Start humming, going up and down the scale? You should feel strong vibrations in the sinuses on each side of your nose, and none in your chest (or very little). If your chest is vibrating, work some more on breathing out with your diaphragm rather than your chest muscles. What you feel in your sinuses is resonance. The sound is vibrating in the sinuses, an effect forced by humming. You want to include more than your sinuses in this, however, or your voice will be intolerable nasal. You can easily hear the difference between full resonance and nasal resonance. Tighten your jaw, mash your lips together, and push your tongue up into your mouth, like you were trying to avoid taking foul tasting medicine. Now hum and listen. You should be making a very pinched, whining sound. Now, still humming, slowly relax your lips, jaw, and tongue. Go ahead and let your jaw drop (keeping your lips closed). You should feel the vibration spread to your tongue, lips, and even your teeth. Do you hear the difference? This tone should be full and pleasant, even though you are humming through your nose.

By using your diaphragm to breathe, you will be able to relax your throat and mouth when speaking. You will find that this not only allows your to maintain a higher pitch without hurting your vocal cords, but produces a clear tone which is pleasant to hear. You can also be more convincing by changing your speech habits. Don’t lecture (a tough one for me), but discuss. Make statements as questions rather than demands. For example, when calling the Lane Bryant catalog department, don’t say, “I would like to place an order.” Instead try, “Could I place an order, please.” That precise difference in phrasing was once given to me as an example, and it works, so I pass it to you. Finally, avoid speaking in a monotone. Speak with energy and enthusiasm and your voice will have a tendency to fluctuate in pitch, another common characteristic of the female voice.


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Even though I have only touched upon some highlights, clearly, there are a lot of things to consider when deciding to venture into the outside world. This should not, however, frighten anyone away from their goal. Simply remember that you will be learning different habits and give yourself adequate time to learn. If you are impatient, then attend meetings of the gender community organizations, because there you will be appreciated and accepted even if you have not yet learned to do everything, or anything, right. And no matter what, just remember the most important element of all – believe in yourself.