A thought that can arise in the cross-dresser’s mind is the idea, or even temptation, that one could wear women’s clothes on a permanent basis.
Having cross-dressed for over twenty years, I had experienced the usual highs and lows of the practice. To cross-dress can be an occasional delight; assembling an outfit in front of the mirror, putting on make-up and maybe doing a little more. Perhaps photographs can be taken, unless one does not wish there to be any permanent record of one’s activity. One might risk a brief outing, perhaps a walk round the block, or a slightly longer, if riskier excursion. But returning home, one removes the make-up, clothes and lingerie and, perhaps, regards the whole episode with a kind of irony or even humour. One has recharged one’s feminine ‘batteries’, as it were. Being or presenting oneself as male the rest of the time should be easier, having found a brief release.
Other times, the cross-dresser might find time to spend a whole day in feminine attire. However much one might love wearing women’s clothes, it can sometimes be hard to do this. One can become aroused at the experience, counteracting attempts to feel feminine. Males are also hyper-conditioned to wear trousers at all times, so switching to a skirt or dress can seem strange if worn for a long time, even if one enjoys it. A full day’s cross-dressing might just be a lengthy dressing-up session, trying on lots of outfits in turn and enjoying the novelty of each. Delightful though this can be, it distracts from a bigger challenge – the prolonged wearing of women’s clothing in any situation.
I certainly enjoy all the modes of cross-dressing outlined above. There are several looks that I particularly adore, such as the smart secretary, Goth girl, hippy girl and, I admit, even schoolgirl – although the latter is purely a fancy dress option! I also love modes evoking the 1920s or Victorian times, although I can only improvise the looks with similar items. I have often worn such outfits for a while, switching between them at home for a rush of girly fun.
There is however a deeper, subtler pleasure, that comes from calming down and taking a slower, longer approach. Cross-dressing all day is a good first step, and it feels great to achieve such a day. But one can try almost anything only once. So a second day is not only an extra achievement, but actually enhances the memory of the first day. Even more can be said of a third day, when the second day is sandwiched between the first and third. Regarding the second day, one neither dressed as a male the day before, nor did so the day after.
If one can cross-dress for a fourth day, then one has a substantial history of continuous girly time. The three-day span is an entire period in itself, yet the future stretches out. Those three days will have brought, inevitably, many feelings and sensations that one would normally look back on in male mode after a briefer cross-dressing spell. Now one is still in girl mode, yet looking back on feminine moments from a continuing feminine perspective.
So what is the best way to try a run of continual cross-dressing? The novelty technique of trying on outfits is not a good approach. One cannot spend all day, every day, just dressing up in front of a mirror, taking photographs and getting changed. There may be chores to do, shopping to get, exercise to take. One is still a human being, however dressed, and needs a bit of fresh air!
My approach to continual cross-dressing involves a certain routine that becomes almost a discipline. It’s no good lying in bed late wondering whether to do it or not. If I have decided I will cross-dress for days on end, then I treat it as a serious business.
As I wake, usually quite early, I put the radio on. I slip back into bed and consider my thoughts. Day one is slightly different from other days. One might only cross-dress for a day, of course, and the day before was male. Sometimes, I have made the decision the night before. I am already in a nightdress, so it is easy to get up and don women’s clothes. But one still has to actually do so.
There is usually a buzz of conflict in the mind. The pragmatic male side telling me to shake it off, get up, put those trousers on. I have got up, had my trousers half on and then frozen with a feeling, almost of horror, at the sense of denial. I might freeze for some minutes, lower the trousers, pull them up again and then come to a decision. At times, I have decided to put women’s clothes on anyway and see how it goes. I can always take them off, after all.
Dropping the trousers and reaching for tights is always a lovely feeling. Then an outfit is selected, perhaps with a glance at the weather. Even then, there is the thought that I might, just might, go out. Once one shaves and puts on make-up, one is seriously in girl mode.
For continual cross-dressing, it is important to quell excessive excitement and channel it into commitment. It means having a high standard of make-up, knowing one will wear it all day. A look achieved at eight in the morning will have to last a long while, under potentially critical eyes.
It is also good, I feel, to wear the same clothes all day. It takes away the sense of this being a dressing-up activity that, although highly enjoyable, stops one really living in the outfits. If a female secretary gets dressed in a business suit, she wears it all day – perhaps through a long commute, time in an office, walking through a city and a train back. She might do this five days a week, whereas many a cross-dresser will don an outfit for just a few hours. Maybe a line can be drawn around six o’clock, when something else can be chosen for the evening, but swapping clothes too much diminishes the sense of fuller satisfaction.
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I am very fortunate that I often get to spend the whole day in the same clothes I started with. I work part time from home. Usually all day Tuesday. My wife is home a lot but doesn’t disapprove of me getting comfortable in a sun dress, some leggings, or a skirt and a top or whatever. I have an extensive wardrobe. I like One World dresses. If I really try to up my game with the makeup, or I wear larger breast forms she will sometimes give me some complaint. She doesn’t wear much makeup and usually takes off… Read more »
Hi Samantha – that sounds a great scenario! I guess what is a pleasurable novelty to us can seem a hassle to actual women who do it all the time? Best wishes, Polly
This is so affirming and excellent advice
Thanks so much Erica!