Crossdresser Heaven

Why do men cross dress – A follow up

Two weeks ago I wrote an article entitled why do men cross dress? and I asked you to write and tell me – why do you cross dress?

Thank you to all who responded, both on my blog and to my question in other forums. The responses fell into a few different categories:

  1. I cross dress because it feels natural, “right”. When I crossdress I’m less cranky and feel stress relief. I feel complete, liberated, content.
  2. I cross dress because I enjoy wearing woman’s clothes, with no particular desire to look or present myself as a woman. It’s fun.
  3. Woman’s clothes are more exciting, prettier, more colorful.
  4. I cross dress because I enjoy feeling feminine – presenting myself as a woman, behaving like a woman.
  5. When I cross dress it’s sexually exciting – I get a thrill out of wearing woman’s clothes
  6. When I cross dress I’m sexually excited by what I look like wearing woman’s clothes
  7. I dress because I feel I really am a woman inside, and I’m just dressing in the clothes appropriate to my gender.

In writing this post, I felt compelled to express how different we all are – we each cross dress for different reasons, enjoy different types of clothing, and have different ‘end goals’ in mind. Imagine my surprise at a recent comment on my last crossdressing how to post, which said something to the effect of ‘Not everyone who cross dresses wants to pass as a woman’ and ‘it’s too bad your outlook on cross dressing is so narrowly focused’. Yikes!

As my regular readers know, I try hard to avoid being narrowly focused on any particular denomination of cross dressing. I apologize to my dear reader A if I came across otherwise.

I wonder if there is more behind this though. I recently received an email from a transsexual who said that there are regular flame wars on a forum she frequents between transsexuals and cross dressers. Yikes! again! Has the transgendered community become so diverse that we spend more time focusing on our differences than our similarities? I hope not. It’s only together that we will be able to change the hearts and minds of the world. Only united that we will usher in an age of tolerance and acceptance.

Tags: , , ,

About the Author

Vanessa Law is a women enjoying the freedom to be who she is every moment of her life! She blogs about the transgender journey at Please comment below and tell me what you think!

44 Enlightened Replies

Trackback  •  Comments RSS

  1. gail says:

    Crossdressing for me remains a mystery.
    It’s erotic, exotic, sexy, somewhat taboo, with an element of risk, dare I say danger thrown in and all tossed together in such a fashion as to make it irresistible.
    Yet that doesn’t explain why I was drawn to it before I had any idea of the above.
    The elements so mixed in me so all the world could say this was a Woman. In the end it’s all poetry.

    • Stevie says:

      “It’s erotic, exotic, sexy, somewhat taboo, with an element of risk, dare I say danger thrown in and all tossed together in such a fashion as to make it irresistible.”

      Boy, does that sum it up for me. Even now, in my 50s, it’s still irresistible to me. I have been cross dressing off and on since my early 20s. I might go years without and then something prompts me to start up again. I’m never quite sure what exactly it is, although it does correspond somewhat to periods in my life when I’m not in a relationship (except when married to my ex-wife who enjoyed my hobby as much as I did). So maybe I’m trying to be both halves of a relationship, male and female, by myself. Or is that too weird?

      • gail says:


        I know just what you mean!!!
        I have often thought one of the reasons I cross dress, among many, is to make up for the lack of regular female companionship.

        And yes it is weird and sometimes downright confusing.
        I’m never sure whether to cry or snicker during chick flics.


  2. AngelaMarie says:

    Crossdressing for me came naturally ! For me,it was more of a way to eliminate depression. Dressed as a female, changed me in ways that are too hard to explain !I never had any sexual pleasure from doing it . My sex drive as a male was very low,almost non-existing !While I was completely dressed ,I would feel like a totally different person,with a different set of likes and dislikes.

  3. Brianne says:

    I have a feeling there could be hormones involved, my feeling started as far back as a 5year old wishing to have a pair of those pretty patent leather shoes with a strap and bobby sox with lace at the top to start school in. Now I am 63 and have constantly be a crossdresser whenever the chance arose.
    I have felt the changes getting stronger as I have aged. It is like a swing going from male to female with every swing getting stronger.
    There have been years at times when I have been a contented male, then slowly my female side is upon me and out comes my pretty clothes, with soft textures and lovely colours. That seem to fit so well and make me feel at ease and happy.
    Most of my wardrobe now is feminine and I have an aversion to buying male clothing If I have to appear male there is always some fem clothing there, if only underneath.
    So getting back to hormones, could there be endorphin’s which are responsible for our feelings?
    Has anyone else found the Watson scale, which tells you from 1-5 how strong your feelings are. At the moment I am 4.
    Just love your site, as it is nice to react to others like me.

  4. Cross-dressing is normal , why ? Females ,which are more than fifty percent of the population of the world, cross-dress so often in Western society the last 45 years, that this term never applies to them anymore for the the last 40 years; how absurd ! An analogy would be that ” murder ” can never be applied to males since they commit more homicides than females by far. Males are ,therefore, excempt from criminal prosecution but females aren’t.What is good for the goose is good for the gander.

  5. Jay says:

    It can still be confising at times. But for me it is kind of clear i should be female and why i am not is still puzzling i just kind of have alwasy felt that i should be a girl when i was very young i always felt gilrs were magic and i wnated to be one of them and dress like them in pretty cloths dresses skirts there clothing was so much better then male clothing this continured until i was in grade schooll when somehow i began to lose that somewhat but it never did go away and now i still find i wish i were a women women are msostly better then males so there are many reason why i still want to be a female!

  6. allen says:

    hello crossdressing well i am 51 now been crossdressing since i was 9 or so remember finding my first garterbelt and nylons at a friends house it was his mothers of course i took them went into my basement tried them on and never looked back the only bad thing about it i am alone you see most women i meet even my x wife never got into me dressing in womens cloths so since then i was 21 at the time after she left i have been alone i have grown more fond of dressing now i usually only wear womens underthings under my male cloths out at home well i dress fully and i mastubate alot in my sexy lingerie in the past 2 years i been on pills to help my breast grow u know hormones and things like breast pumps nipple pumps things like that it seems to work my breast are getting bigger my bras fit now and i am injoying looking at my cleavage and feeling my breast honestly if i could i would turn myself into a women but because of my job (I AM A STEEL WORKER) i cannot do this i have a mortgage and bills i need to pay like the rest of you i just wish i could find away to meet a women or even a full time cd who would except what i do and injoy it with me but here in wisconsin i find no place club etc. who i can go to and find the help i need so if anyone from wisconsin can help me i would appreciate it i dont want to grow old alone i really dont but i cannot give up my dressing its to late i tried many times so if you are interested in helping me my e mail address is oh by the way when i am dressed i call myself ALICE thanks for listening LONELY CROSSDRESSER BY ALICE (allen)

  7. Lynn Jones says:

    > regular flame wars on a forum she frequents

    An old phrase springs to mind: “never the twain shall meet”. CDs and TS folk are – if I can generalise – on different paths. Outwardly to the public the two may seem similar – to put it brutally – men dressed as women. However, that’s vastly over simplified and (IMO) just plain incorrect.

    I’m not the first to say this and it’s something that does the rounds on most TG forums and/or blogs. Transgenderism is a sliding scale – indeed I think it was Helen Boyd who suggested it may have two scales: frequency and intensity.

    Frequency is how often you want to “dress up”. where as intensity is the old sliding scale ranging from ‘no interest at all’ (most blokes) through to ‘Inside I am female’ at the other. We all fit somewhere on that graph.

    For what it’s worth, I think it’s true that not everyone wants (or can) pass. Some CD folk are happy to wear a skirt and heels and go no further. Others ‘go all the way’ with make-up, wig and aim to ‘fit in’ when they go out.

    There’s room for us all I feel as we all started somewhere. Has anyone burst out of the closet looking totally fabulous at their first attempt? :)

  8. glyn says:

    I crossdress because I love to feel feminine,My wife tells me I am less cranky and get very sexy when dressed.I now have more bras,pantie and girdles than my wife and my wardrobe if getting almost as large as hers.We often buy matching clothes.Unfortunately I am in the closet just my wife knows.

  9. Marti says:

    Crossdressing from my perspective is more than just a question of why I am a CD. It revolves around why did circumstances dictate how I began. Why did I continue when the circumstances changed. And why do I continue to do it today after 28 years? Is it normal? By society standards – probably not. But for me – it came down to one important facet of my life – Dealing with stress. By dressing up I got a chance to look at my problems from a unique perspective and for some strange reason come up with answers calmly.

  10. Vanessa Law says:

    Marti – an interesting observation. I’ve heard many crossdressers say they feel a relief from stress when dressed. I hadn’t associated that with better problem solving, and the unique perspective that calm and femininity brings.

  11. Jade says:

    I’m going to ressurect this interesting discussion.

    Like all crossdressers trannys whatever the world  calls us I too started thinking about this side of my life as a child. In my Teenage years I experimented with mums clothes, pinched some Lingerie from the store I worked in as a saturday boy and generaly played with the whole feminine side.  As an adult I occasionaly dressed, all in secret, nobody as far as I know had any inkling that there was this other aspect of me. I did grow my hair lon and braided it etc but more as a Steve Tyler wannabe lol lol.

    The problem wasn’t mine it was the world I live in. A world that has created clear boundaeries and divisions that are actualy very artificial and in fact change throughout the ages. Cross dressing in men is still quite Taboo (though thank god its slowly becoming more discussed if not yet more acceptable unless its a parody or a means of making fun of people sadly) Yet Women happily wear trousers, jeans, suits even. They are able to cross boundaries in dress and even behaviour far more freely than men at present. Who says its a mans world lol?

    As a child I loved dressing upl. Not as a girl particularly. Just in General. One day I would play as a guardsman, a Nasa astronaught, a commando, a cowboy, a knight or a Roman soldier. In secret I was a princess too lol. As a young man I loved performing in dramatic productions. that whole thing of taking time out of the day to be someone else. To live a different life just for a few hours realy exited me and continues to do so. I no longer perform. work and other pleasures curtailed that a bit. But I still enjoy the sense of being someone else. I can do it in my male life too. I’m one person at work, another with certain freinds, another with my loved ones. I’m comfortable with several skins. And they all give me pleasure to inhabit.

    I thought about specifically why I dress as a female an awful lot I enjoy being a man as much as I
    enjoy being a girl and have no real sexual interest in men. I’m as
    happy in Jeans and a Tshirt fixing an old engine as I am in stockings
    and suspenders (see I’m such a man Lol) Its femininty and duality that realy turns
    me on sexualy and women do that very very well 😉 I finally realised I’m not
    gay or transexual but I do have a wonderfull other side, alter ego that I
    love to explore once in a while. Its exiting, sexy, and totally fun to
    become this person.

    I think that is why I have this aspect to me. In girl mode I’m someone else. I look completely different and can explore completely different ways of being. Its fun. Sometimes a little erotic and I think,  very healthy.


Leave a Reply