Why do I crossdress? Pondering the imponderable

I have literally been inundated by requests; wait no, that is not really true, but one or two people may have asked me why I crossdress so I thought I would devote some time to answering the question as best I can. This is a very difficult question to answer simply because I do not truly know the answer. There are all sorts of reasons ranging from the superficial, to the very deep and it is quite hard to determine what is really going on in my mind.

Thinking hard about life’s important questions

For the purposes of this article I will confine myself to the conscious reasons for crossdressing and I will try to avoid any sub-conscious, hidden or whatever reasons. I will also not delve into sexuality and associated topics. Not because I am afraid to do so, but because I am trying to write a 800 word article, rather than a 800 page book!

It is true that many crossdressers confidently declare that women’s clothing is more comfortable. This is often patently not true. Not only is women’s clothing made for women and thus necessitates squishing and squashing various bits of the male anatomy into frankly unpleasant shapes, thus creating some discomfort, but it is often uncomfortable for women too (yes I am looking at you corsetry). However, I have found myself saying that I feel more comfortable dressed. What is going on here? How can an otherwise (mostly) intelligent and (generally) sane person say that wearing stilettos, a bra, a g-string, stockings and a tight dress that barely covers your bum is ‘comfortable’? Well, because it is comfortable (corsetry notwithstanding).

The fact is that I feel better when I am dressed in this way than I feel dressed in male clothing. This seems insane. So why is this? All that I can say is that I feel more congruent when dressed in women’s clothing. The clothing seems to match my self-image better, I am somehow more comfortable, more me. I am able to access my innate femininity better, I am better able to express my femininity and this juts feels, somehow, right. I am able to express myself better, I can be sexy, attractive, pretty and playful. I do not feel this way if I am in men’s clothes. In men’s clothes, I am serious, boring, unattractive and somber. This is not to say that I cannot be these things when in women’s clothes, but I feel more complete and more completely able to express more of myself in women’s clothes.

Women’s clothes are also usually more sensual than men’s clothes. There is a wider range fo fabrics and fabric designs that result in a far wider sensory experience. Men’s clothes tend to be cotton or wool. They are generally ‘harder’ fabrics that whilst providing warmth and coverage do little else (except maybe scratch). Women’s clothes come in a variety of materials (cotton, wool, nylon, viscose, lycra, silk, satin, velvet etc) and are made differently they are thinner, softer and include lace, stretch fabrics etc. This means wearing women’s clothes is a sensual experience. Add to this the heightened sensation your skin has when shaved and I am surprised there aren’t more crossdressers. Just walking down the street can be a multi-sensory experience (with different tactile senses, sounds, sights and even smells coming your way from the clothes) depending on the way you are dressed (note I am explicitly excluding the additional impact that some crossdressers may feel as a result of fetishising the sensation of women’s clothing).

I also think that my body actually looks better in women’s clothing than men’s. I have quite refined features, my ankles and wrists are small (even for a woman) and as a result I sometimes look silly in men’s clothes. A large man’s watch dwarfs my wrist. Clumpy work shoes look ridiculous on a delicate well turned out ankle. On top of that I think my legs are my best feature and it is practically impossible to ‘showcase’ legs in men’s clothes other than running shorts or a Speedo. I think I would get some strange looks if I arrived at work in a Speedo. (Would I get stranger looks arriving at work in a pencil skirt? Moot point, perhaps.)

The feeling of congruency is important to me. It feels good to sense that your outward expression fits the inner you. I am simply not able to achieve this when dressed in men’s clothes. This I think drives some of the enjoyment I feel when dressed. So, why do I dress? Because it is fun, I enjoy it and it fits who I am.

Why do you dress the way you do?


Add yours →

  1. I wear high heels and on some occasion skirts, thigh highs, tights and capris cause I like them; I like them all and enjoy the way they feel and fit. Heels are the biggest part of it and it is basically as I explained; I like them. 😉

    Liked by 1 person

  2. I hate to be unimaginative here, but you sum it up nicely with “Because it is fun, I enjoy it and it fits who I am”. The same applies to me. I wear what I enjoy and reflects me (well most of the time). The rest is just details.

    I would agree with you, shaved skin really really does heightened the sensation especially on my legs. For me it is worth the trouble of shaving my body every day to have that sensation. 🙂

    Liked by 2 people

  3. The only possible answer for me is: because I do. I don’t like boy’s clothes, and I’ve recently learned that I don’t *have* to wear them. So I don’t anymore. I like the person in the mirror more. My ego appreciates getting compliments on my sense of style. There is a certain joy just knowing I’m signaling something important about myself to the world. My self esteem has improved.

    Liked by 1 person

  4. Interesting blog 🙂 I’m actually the wife of a CDer and know many other CD wives and it’s funny how different we see all this to our partners. I believe my H and many others would say the same as you: It’s fun. It feels right. I look better in women’s clothes. Thing is, you don’t really look better in our clothes. I mean no offence with this either, but there’s few people alive who would say that a man looks better squeezed into heels and skirts with his face covered in make up and his head in a wig. Even those men with more feminine features will still appear more attractive if they’re wearing a men’s shirt and pants made to fit the male body. So these explanations only explain why you feel a need to continue dressing, not why you started in the first place.

    Again, most of the wives I know, including myself, figured out this answer with just a few conversations with our partners. Remember, we remain objective because we don’t have the CD feelings clouding our perspective, so we can hear the reason beyond the words. In my H’s case, his father rejected him. This had a huge effect on my H’s overall development and he very much latched onto his mother and sister for comfort and as role models. Sexualizing these feelings in puberty made the behavior permanent. This isn’t rocket science (counselling revealed much of the same) and its been unbelievably proven as a behavioural pathway with many human habits, but so many people can’t even remember that moment when their world view shifted as they were too young or it wasn’t a particularly traumatic or memorable moment. I mean, some little boys just think women rock 🙂

    Anyway, that’s my H’s story. My friends H’s have many others (excitement, curiosity, acceptance, fear, fantasy) but all have an individual story that becomes lost in the CD feelings. All I can suggest is if you really want to understand why you started all this, you must fight beyond the murk and the collective explanations, and delve back to that very first thought. YOUR thought, as the path to CDing is as individual as the man wearing the dress. You might be surprised what you find there, and how simple it all is. After all, there’s really nothing wrong with men modelling women as we are strong, clever, beautiful and powerful in our own right. Perhaps CDing will become obsolete when it finally becomes acceptable for men to emulate women in everyday life.

    Imagine a more feminine world. I think we’d all be happier living there 🙂

    Liked by 2 people

    • Thanks so much for such a comprehensive response. It is great to have a female point if view. I think the nuanced point here is that whilst we may not actually look better, we feel better and therefore think we look better… After all, self perception is inherently subjective. If we dress the way we do it is for selfish reasons. We do it not to attract sexual partners (we often already have one or realise the partner we want, a heterosexual woman, will not be attracted to us en femme), so we do it simply because of how we feel about ourselves dressed. I fully acknowledge that this is not a simple or easily understood activity, by the participant ir anyone else.
      I would also posit that our partners are not always all that objective. You see us as men first, presumably find us attractive as men and then we drop this on you (sooner or later). Of course your emotions will affect how you perceive us in both ‘states’. We may actually be better looking men than we are women (this is unlikely but I present it as a hypothesis), but the crossdressers partner will be unlikely to recognise this fact because of the fact that s/he prefers the male presentation for their own reasons.
      Having said that, thank you (again) for your valuable contribution and I value your input and agree that often we see ourselves as being much better looking women than we in fact are. This is why so many of us take lots of pictures and then discard so many of them in disappointment. Reality can be harsh.
      Finally thank you for accepting your crossdressing partner, you are an amazing person for being open minded and supportive, no matter what form this support and acceptance takes (yes even don’t ask don’t tell is a form if acceptance). I hope your husband appreciates you.


  5. Power to ya!

    I cross dressed for 30 years before i realized I didn’t need to, that my interest in it was only superficially addressing the actual issue. Then over the next ten years I stopped wearing breast forms, I stopped getting women’s clothes until I only had a few pieces: I focused on my body, not what covered it. In contrast to that trend my identity as female grew more and more.

    At age 50 I decided to come out. I now wear women’s clothes because, well, I’m a woman.

    Liked by 1 person

  6. I have spent amazing amount of time trying to understand this most basic question. I don’t have it all figured out but my most logical answer is I am emulating the image I love and admire so much. There is nothing beautiful or classy about men or men’s clothes. LadyMuck sort of hit on the issue… “Perhaps CDing will become obsolete when it finally becomes acceptable for men to emulate women in everyday life.”

    Liked by 1 person

  7. You look beautiful. I always say, it doesn’t matter what anyone else thinks, as long as you like your outfit. Excited to have found your blog. Great that your are so willing to be open and honest.

    Liked by 1 person

    • Thank you, you are very sweet to say that. I have been reading your blog and I will say that you are a beautiful person. Your love for your family, community and God shine through the pages. You are so accepting of people which is amazing. Thank you. After reading a blog filled with hatred the other day you have single handedly restored my faith in people again. Thank you!

      Liked by 1 person

      • Wow. No, thank you. It makes me happy to know I make others happy. If my blog can help people see that not all Christians are judgemental and unaceppting, I will feel like I’ve done something right. I’ve been told many times that I’m naive, but I truly believe that there is good in every person.

        Liked by 1 person

  8. Great blog!!
    Having given the quesiton much thought over the years, I have come to the conclusion that I cross-dress to become that which I desire the most, namely a gorgeous blond woman in highly stylized, highly feminine clothing. Instead of dating a real woman (which I have done….and even married twice), I have a deeply-rooted desire to become as opposed to simply enjoy another person. It’s like when one is a Young boy and one sees a race-car driver for the first time and wants to become one. Or a pilot, or a policeman.
    I have no desire to become a woman on a permanent basis, just on occasion. I realize that this affects my desire for real women. But so be it!
    Another line of thinking led me to the conclusion that this owed to the fact that I was a very sexualized, dominant male who needed to control both my desire and the object being desired. I love the company of strippers and escorts…but only when they are in costume.
    Anyhow, that’s me for what it’s worth!!

    Liked by 1 person

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