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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.
s 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, and 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 is 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.
I like the look, I like the idea, I agree, it shouldn't be a fashion show. I'd love to have the guts...
It is a commitment to your femininity. To dress or not to dress - what a silly question.....
Polly, you've got me thinking 🙂
My family took a trip once, and I stayed home for a number of good reasons. It was only 4 days being alone and it was wonderful.
Day 1 was a fashion show of everything feminine that I own. Fun, but that's not the real life. So, I got dressed and went out for dinner. That was exhilarating. Then back home, changed into lingerie and slept that way. Woke up feeling like Lea. That was new.
Day 2 was dressed as Lea, shopping, running errands, felt normal.
Day 3, being Lea started to sink in more. But so did tiredness of dressing. More girly activities at home and out.
Day 4, sadness as Lea time was coming to an end.
It was fun being immersed, without hiding, just being me, Lea.
I don't get it. Except for an experience by Lea (1) staying home to cross dress is just exploring the tip of the ice berg so to speak.There are gay bars all around where you can 1st test the waters and build confidence.Nothing beats getting dolled up and going out in to the civilian world as a woman. You don't know what you are missing
Totally agree about keeping the same outfit and enjoy the day
I dress up at some point every day and even sleep in nightgowns, but doing things in my fenced in backyard is about as far from my house as I’ve ventured within the last 10 years. I used to be more adventurous but got pulled over in a routine driver’s license check once. Pretty embarrassing!
Thank you for sharing your thoughts with us. For me. crossdressing ceased to be just a dress up activity when I started going out in the world.
Once a month I get the opportunity to spend a weekend en femme with my wife and friends from our CD group. I get dressed up on Friday and go out for lunch and then dinner later followed by an activity such as a concert, play, or something similar. On Saturday I get dressed up again and go out for the whole day. We don't focus only on going to places that would be considered "safe" for CD's but rather into the world at large. We do what the general public would do -dining, shopping, entertainment, etc. Sometimes if we're going to a really nice restaurant or evening event I may change into something more formal. If not, I may wear a single outfit for the entire day.
Once you step out the door en femme it all becomes completely real, just like for any other woman. I find myself sometimes even forgetting that I'm en femme as the experience becomes so natural.
@polly "Dropping the trousers and reaching for tights is always a lovely feeling." That sums me up precisely! lol
I enjoyed your article very much and what you say is very true. I found that after coming out to my partner that I do tend to choose an outfit and keep that on for the whole day. Sometimes I might change into something different if I have been working from home or doing the chores, or if we are having a special girly night in. I think that once you have embraced and accepted that 'this is what I do', by dressing for extended periods you lose that need to try and wear everything you own in those precious, secretive, stolen moments.
I don't do 'full-femme' outdoors, but do wear feminine underwear, trousers or jeans, tops and so forth with only a hint of makeup. My hair is long so I wear it in a high ponytail or bun. I usually do any shopping first thing in the morning and on my return, do my makeup and change into a much more feminine outfit.
"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."
That is so true! The excitement of dressing hasn't gone, but it has been managed and channelled in a different direction. The thrill of being an immaculately dressed secretary whilst WFH for example, is controlled I find, experiencing a continuing feeling of pleasure in being who and what I am... if that makes sense.
Polly I loved your article and the cute picture of you accompanying it.🥰
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 her bra after she is through going out, so she questions why I would enjoy doing that. When we have gone out she will help me with makeup and the look but she only does light makeup usually.