How to feel confident and start to accept crossdressing

Confidence—it’s just a ten letter word!

Feeling Confident as a Crossdresser

As we all know, us girls in the T-community tend to be quite generous, some would say lavish, when it comes to ourselves. We quite happily buy that new dress, that new pair of shoes, breast forms, corsets, even make-up, on a “wants” not necessarily a “needs” basis!

That’s all fine as, naturally, we do have to try and look our best for every occasion.

Yet there are some things none of us can purchase, no matter how much available money or resources we have. And, perhaps, one of the most important of all things is tantalisingly out of reach for many of us… yes, that’s right, c-o-n-f-i-d-e-n-c-e.

As many of us do, we can spend hours getting ready to go out to a function, an event or just to meet friends in a restaurant. We spend a long time making sure our En Femme Fashions look just right, our hair perfect; spend an hour in front of the mirror checking and rechecking our foundation, blusher, eyeliner and our overall appearance. But think about going out and still the butterflies in our stomach twitch and tingle. Still our nerves jangle and send shivers of fear, trepidation, maybe nervous anticipation, across our shoulders and deep down the small of our backs.

With a lot of practice, many of us have been able to attain an appearance of almost physical perfection, attain a level of excellence in our dressing so that, on the face of it, to any outsider we look like a “typical” woman, look like the epitome of femininity; yet still the missing ingredient, confidence, isn’t there.

Overcoming Your Fears

How many times before leaving home dressed have we all fretted for half an hour or more about stepping out into the big, wide world? How many times have we all sat in our cars for 5 minutes, 10 minutes, 30 minutes trying to get the courage to open the car door and stride purposefully and confidently into the shopping centre (or any other destination). How many times have we taken a deep, deep breath…, puffed out our cheeks and let the air accumulated in our mouths exhale slowly, very slowly as we fight to conquer the nerves which seem to be consuming us?

I don’t know about you but, in the early days when I first started going and about, I used to be almost a nervous wreck before leaving the safety of my home or wherever else I was. The tension, the self-induced stress was immense—but I knew I had to go, knew I had to leave my safety zone (simply because deep down I wanted to or, should I say, felt compelled to do so). I felt I looked good, looked seriously passable—and all I lacked was confidence.

Then, almost overnight I found what I was looking for; don’t ask me how but I did. Confidence flooded through me, touched every part of my body—almost as if I had had an awakening!

So, whilst some of these next few comments may seem pretty obvious, amongst other things, I realised that if I dressed appropriately for my age (including wearing the right wig) and my build; plus adopted the mannerisms of a female in terms of walking, sitting and general body language, then no-one would pay any attention to me.

The Reality

I finally accepted that most people are too engrossed in themselves, their partners, their friends (or more so, these days, their smartphones) to pay other people that much attention. I also finally understood that, whilst many women will give you a cursory glance, they are simply checking you out, looking at your nails, your hair, your clothes—to see if, subconsciously, you present any competitive threat to them and/or their man!

I learned to revel being in crowds, the more people the better—quite simply, in such situations most people don’t look directly at you (unless, of course you are teetering on 6” heels in a micro mini skirt and caked in heavy make-up in the middle of the town centre at noon on a very hot day!) and their expectation levels of actually coming across a T person in a typical public setting are very low.

So, just like the ingredients of different types of cakes will vary, what makes up the magical confidence for each and every one of us will vary. But always remember, once you have “it”, your T life will suddenly have another dimension or two—and, after all, it’s only a ten letter word!


  • john v

    thank you for the confidence, of going out.. I am over sixty, still have nice lags and body to wear short skirts and dresses and over six inch spikey heels.

    do you think I am dressing the worn way for my age. thank you for spike heels

  • Sylvia

    Thanks for a good, inspiring article, which goes a long way towards helping us gain that ever-so elusive confidence.

  • Patricia Kay

    Despite how much I try, I usually come up short on c-o-n-f-I -d-e-n-c-e.

    Despite my years of cross-dressing I have only had a couple of dozen times that I actually have gone out in public and the vast majority of those times I was out with someone else. So it’s no surprise that I have been out by myself even fewer times. Because of this, despite how nice I think I’ve done my makeup or how appropriate my attire is for my outing I have a tendency of delaying leaving the safety of my room as long as I can and worry about being ‘read’ and possibly embarrassed. Once out I realize most people don’t pay any attention to you and businesses are more than happy to talk with you and help you in order to obtain your business and they do so in a manner that should make you comfortable. As a consequence I am gaining c-o-n-f-I -d-e-n-c-e on going out alone to more places and willing to try new destinations.

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