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!


  • Steven aka Veronica

    Reading the above, hits me right where it hurts. Confidence. It may be a ten letter word, but having it is so hard. When I get away from my area, when going out, I do fine. Sort of. I'm 77 and I know at that age, it's hard for me to look good, but when I'm downtown, or in a nightclub, I could care less, what people think of me. I may be old, but I'm beautiful. But, when I'm ready to go out, leaving the house, walking to the car, is the hardest thing in the world for my to do. If I could just have the confidence then, that I have when I'm away from the area where I live, I'd be out everyday.

  • Sheri

    I started crossdressing at a very early age. I would play dressup with my female cousin when i was 5 years old, and even then i felt i should be a girl. My aunts and moms friends would always say how pretty i was, and want to sit me on thier laps. I was always so tiny, and always mistaken as a girl. I always loved dressing up, and in my early 20's, i started buying lingerie and little minidresses. I hung around with girls, and they fell in love with me, but i just dated them so i could try on thier clothes. I almost was caught, dressed in my girlfriends sexy black babydoll, panties and full make- up. Luckily i was in the bathroom, so i locked the door, took off the nightie, and had a long bath, scrubbing off the make-up! I have been blessed with very little body hair, a very feminine figure, and i am only 5 ft 5. I have purged so many times, never lasting long, then regretting what i did. I only feel comfortable when dressed, whether i am in a sexy lingerie set, shaved legs, stockings and garterbelt, bra, panties, stiletto heels, breast forms, make-up, or a sexy minidress, showing off my curvy bum and sexy legs. I love posting my pictures on different sites, and love the comments i get from a lot of men. I have tried c.d. dating sites, but there are too many men who are more interested in getting at my unwanted male part. I have been with only one man, and he thought i was a super sexy girl. I wanted to pleasure him, and when he came in my mouth, i had the best female orgasm ever! We lost contact when i moved, and have never met a nice top man since. I love to go out on halloween, dressed in my french maid outfit. I wear stockings, garterbelt, panties, stilettos that i am very proficiant in strutting in, beautiful pinafore under my dress, breast forms, wig and full make-up. I have made many women angry at thier men, who can't help, but to stare, or at least look twice at my sexy legs with my garters showing where they attach to my stockings. I want to live as a woman so much! I call myself a crossdresser, but i am sure i am transgender, as i have never felt like a man; i am a sexy woman and always willbe

  • Willbe

    Try using your own experience when out as a male. Do you check out women with in-depth inspections? Probably not. That is what I have come to realize. No one is paying more than a cursory glance at you as you walk down the street looking your best as the woman you are. Get over it girls just be you.

  • Ashli

    I am a mature crossdresser. I go grocery shopping every Sunday morning dressed – Usually jeans and a top. I make rounds to three stores I see practically the same checkout people each week. they now recognize me and make small talk. Same when I shop at Macy's and Nordstrms. Once you engage with the same people every time, go our gets easier.

  • Don

    Thank you Kathy, How true you are ,I panic soon as I am ready to go and I don,t know how many times I have sat In my safety zone and just could not get up enough nerve to leave. To this day I am very shy and nervous to to venture out of that zone. Unless I am somewhere new that I haven,t been before I am always frightened in areas that I live .The risk is just to high if I go out where I live I don,t think I will never go out when it comes to my home area. I very much enjoy and learn from your advise and comments that you talk to us about . Thank you very much hugs Kathy :)

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