Crossdresser Clothing

From a Crossdresser …


“I shall attempt to describe myself , my feelings, and my view of life in this great big World.

First of all…..I am a transgendered crossdresser. That is to say, that I feel both femine and masculine at different times. For example, while I`m working I`m definitely masculine and do a masculine job, when I`m in a typical everyday social situation I`m in a masculine role. However, when I`m at home my femine side emerges and usually I`m dressed in femine clothing and feel very femine. I love to have my makeup on as well as jewelry and a classy outfit. I think, act, and speak in a totally femine manner. I am very comfortable and feel very open this way. This crisscrossing of roles has at times caused a few minor problems.

For example, I`ve been at work, or social occasions, and some of the women that I`m around a lot and comfortable with have been having conversations about normal everyday femine topics. I find myself starting to assume my femine role, wishing very much to join in the conversation or activity. So far I have been able to catch myself before anyone has noticed, thus avoiding any problem. Keeping this guard up has not been a problem so far, however I`m a little concerned that someday I`ll be tired and forget where I`m at and slip completely into my femine side before I realize what I`m doing. This could cause some real problems. Hopefully this will never happen, but the possibility exists. I would love to be completely open and honest with the world, however I realize that this is not possible in the everyday world I live in. So for now, until social attitudes change for the LGBT community, I shall have to remain this way and try to maintain a delicate balance between both sides of my persona.”

BRA – the Passion of a Crossdresser


“Do you love bras? I do. I have a whole drawer-full of them. Lacy cups, stretchy straps – irresistible! My love affair with bras goes back a long way.

When I first tried on my sister’s clothes as a teenager, perhaps the most interesting – and pleasurable – garment was the bra.

Flat chested, I had no real need to wear it, but didn’t consider omitting it as I dressed. The web of straps was completely alien to the clothes in my own drawers. That, in itself, was exciting.

Crossdressing Outfit

Slipping the straps over my shoulders was no problem. Then, I tried to fasten it behind my back. The hook and eye seemed to occupy that area of the back where one can never scratch an itch – I tried reaching from below, I tried reaching down from above. Neither did the least little bit of good.

I struggled with the bra for ages and, eventually, I gave in. Unlooping my arms from the shoulder straps, I turned the bra back-to-front and fastened it around my chest. Then, I swivelled it back and wriggled my arms back through the shoulder straps. Admitting defeat on fastening the bra behind my back was the most disappointing part of trying on my sister’s clothes. I had a sense of cheating, of not doing the thing properly.

On subsequent occasions – and there were, of course, many of them – I tried repeatedly to engage the elusive hook and eye behind my back. The struggle became a regular feature of my LGBT dressing.

That was over half a lifetime ago. many things have changed since then, and – not least – I have changed. No longer do I struggle to fix the bra behind my back. Without thinking about it, I fasten my bra in a similar way to that first attempt. I do it rapidly, with more assurance and usually without geting the straps tangled – but the method remains much the same.

Over the years, I must have seen a number of women putting on their bras, but, oddly, cannot recall how any of them managed it. They include a wife to whom I was married for ten years. Perhaps my teenage feeling of putting the bra on wrongly placed some psychological block in the way of taking note of the methods real women used?

Bras do not have to fasten at the back, although that remains the standard way of fixing them. Front fastening bras exist – indeed, I have one in my collection. I haven’t seen one, but I know side fastening bras have also been made.

Apart from front, side and back fastening, the fourth possibility is not to fasten at all. I also have a bra with no breaks in the straps, which I put over my head, as though it was a camisole. It’s made from a stretchy fabric but – in spite of that – of all the many bras I own, it is the most difficult to put on.

I suppose my teenage self would have liked that, but would have regretted its lack of hooks and eyes – so different from the ways in which male clothes were allowed to fasten. The bra without hooks and eyes hugs me delightfully – and it is very pretty – but I don’t wear it very often.



I think that the difficulty in fastening the bra was one of its attractions in my early cross dressing days. For the same reason I then enjoyed struggling into dresses with back zips.

One element may have had to do with enjoying the process of dressing in girls’ clothes. There were so many experiences to be savoured. If it took a while to struggle into a garment, that prolonged the process, gave me longer to savour it. Now – it seems – I enjoy being dressed rather than enjoy the process of dressing. I still take pleasure in wearing a bra – but very little in putting it on.

There may also be a link between difference and difficulty. If it was difficult to put clothes on, it was at least partially because they were different from my male garments. There would have been no point in taking the risk of wearing my sister’s things if they were no different from mine.

The reasons I no longer feel that way are probably complex. For one thing, difference is second cousin to novelty. Once something is familar it is no longer different – and wearing women’s clothes has certainly become familiar.

More – over the years I have become increasingly comfortable with my cross dressing. The clothes help me to feel the way I am. They are an extension of an inner, feminine, me. The familiarity of the bra, not it’s difference, is something I now enjoy – an expression of the me with whom I’ve struggled to come to terms, and whom I now treasure.

Finally, perhaps, there were considerations around adventure and danger. Exploring my sister’s clothes from the inside – and making the first steps to explore my feminine self – was an adventure. Nor was it an adventure without danger. I cross dressed when alone in the house – but I was not in control of my family’s movements. People could return unexpectedly (and, on at least one occasion, did so). I didn’t know exactly how they would react to discovering me in my sister’s clothes, but preferred not to find out.

There is a sense that an adventure is not an adventure unless there are difficulties and dangers on the way. The difficulties increase the dangers. If something was difficult to put on, it would also be – to some extent – difficult to take off. The scene is easy to picture. The sound of a key in the lock. Me struggling with a zip at my back, and then with the bra fastenings. The sweetness of that danger of discovery!

Now, I share a house with a fellow transvestite – and all of that teenage danger is far in the past. In recent years, however, I have once more known the sweetness of danger – by stepping out publicly in woman’s clothes. Before I reached this stage in development, there was another sense of danger connected with the bra.

This surfaced when I ventured out in feminine undies beneath my male clothes. It must be a step which many transvestites take. There didn’t seem much danger in wearing women’s knickers. They were unlikely to come to light unless I had an accident, in which case being exposed as a transvestite would not be my most pressing problem.

On the other hand, I was a good deal less confident that the bra could not be seen through my shirt than that the knickers could not be seen through my jeans. This piled on a whole lot of fresh dangerous glamour to wearing my bras. After all, women’s bra straps are often visible through the fabric of their blouses – especially from the back. I sometimes wonder whether women are unaware of this, or do it deliberately.

Either way, the bra is the most frequently displayed item of women’s underwear. I find that very attractive. On many occasions, dressing at home, I have craned my neck to see in the mirror whether I could glimpse my bra straps through the back of my blouse. There was always a pleasure in being able to trace them, and a disappointment in failing to do so.

Pleasure in wearing a bra beneath my male shirt led me on to a further piece of boldness. I started to take delight in hanging my freshly washed bras on the line in the back garden. There are few, if any, garments more instantly visible as non-male. Pegging out my bras, I had a feeling of displaying my transvestism to any neighbours who cared to look. That I enjoyed.

The difficulty in struggling into it is not the aspect of wearing a bra to which my attitude has changed over the years. Trying one on for the first time, it felt – to my delight – quite different from anything I had worn before. It was uncomfortable – but an enjoyable discomfort. Today, I find my bras a lot more comfortable – and that now pleases me.

These days, I look for three things in my bras – support, comfort and prettiness. I think that a lot of women would list the same things, and often in that order. Of these, the desire for support stems from my using correct weight breast prostheses – which are quite heavy and do need supporting. Comfort has to do with not liking my bra straps to cut in. The prettiness is the icing on the cake, but attractive trims and fabrics – such as lace – continue to delight me. They represent a lot of the point in cross dressing.

The question of support brings us to the function of the bra. Essentially, it is a device for supporting the breasts. When I first tried on my sister’s clothes, I don’t think this had occurred to me. The bra was simply something girls wore. If I was to dress as a girl – and I was determined to do so – that meant wearing a bra.

One day on the beach, the inter-relelationship of bra and breasts were brought to my attention. My sister had changed into her swimming costume, leaving her clothes in a neat pile with the bra at the top. It was a new one which I hadn’t yet worn.
While my sister went off for a swim, one of her school friends picked up the bra and said “I didn’t realise that she needed falsies.”

The friend certainly had much larger breasts than my sister – and there was an element of bitchiness to the remark. ‘Falsies’ was overstating the case but, unlike any of the bras I had tried on, it was padded. In each cup was a fairly stiff sponge rubber cone.

For the first time, the bra presented itself to me as something to hold breasts – rather than just something girls wore.

I know, too, that there would be no peace for me until I’d worn the padded bra. I had no breasts, and those ‘falsies’ were the nearest thing available to me. A desire had been awakened within me which would lead, many years later, to my prosthetic breasts.

When I finally I had the chance to wear the padded bra, it came as a disappointment. Without small breasts inside the cups, they simply didn’t work. They may have the power to make a real girl look as though she cups a size larger than reality, they didn’t have the power to make my flat chest look as though I had breasts.

The idea of a padded bra had been placed in my mind. What I used were things from my sister’s undies drawer – usually knickers. I rather over-did it. Not content with filling the bra cups, I inserterd several more pairs than they could hold. My reasoning was ‘the bigger the better’ – common enough thinking amongst transvestites, but not a view I still hold.

In some ways, I was pleased with the effect of the knicker padded bra. In other ways, I remained doubtful about it. My doubts centred around taking measures which, I felt, a real girl would not. In a sense, it made me feel less girlish. On the other hand, it had a gratifying effect on my reflection in the mirror – especially when I wore something with a bit of stretch.

During the years as a closet transvestite, the stretchiness of my sister’s – and then my own – tops was probably the decisive factor in whether or not I chose to pad the bra. if it was stretchy I used padding, if it wasn’t I didn’t bother. As a variant on using undies to fill my bra, I also tried cotton wool. Eventually my choice fell on camisoles – I found that a neatly folded camisole was about the right size for filling a bra cup, without over-filling it. Moreover, two camisoles formed two equal sized breasts – collections of knickers proved difficult to keep even sized.

I recall, long after my teens, cross-dressing for my future wife. “You’re wearing a bra!” she said with obvious surprise in her voice. I was surprised by her surprise. Of course I was wearing a bra – it was an inevitable part of dressing as a woman. I hadn’t attempted to pad it partly because the dress I was wearing wasn’t of a stretch fabric. It was also partly because having the padding fall out as she undressed me would only emphasise my flat chesteness, and detract from the experience.

It was only when I started to expose my feminine side to the public gaze – in clubs – that padding my bra became a matter of course. Belatedly, I became aware that, without my padding, my clothes didn’t hang properly. With this awareness, my bras took on a fresh significance. I was still using two camisoles as breasts, and there was no way to hold them in position without a bra. Increasingly, I became aware of the shortcomings of the camisole in that role.

Not before time, I bought a pair of cheap boobs. I suppose I could have glued these into place, but I never did so. One advantage of using a bra, rather than glue, was that it ensured that the boobs were correctly placed. It’s unexpectedly difficult to figure precisely where the breasts should be. Another reason is that, from the start, I’ve liked bras, enjoyed wearing them – and still don’t feel properly dressed without one.

At last I gave up on the boobs and invested in a proper pair of prosthetic breasts. It was a step I’ve never regretted – except to regret that I didn’t buy a pair years before.

The prosthetic breasts have changed the sensation of wearing a bra. They are the correct weight – which means that they weigh heavily in the cups. The heavy cups tug on the bra straps in a way in which the boobs – and lighter forms of padding – never did. It’s a wonderful feeling.

Over the years my love affair with the bra has seen many changes. The older I grow, the more I love my bras. This is no mere infatuation, it’s the real thing. I am a proud member of the LGBT community!”

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