What makes a Cross dresser?

Unlike most of the members here, I came late to crossdressing. As is well documented elsewhere on the site and many times in the chat room, I only started crossdressing in my early fifties. So what happened? Why did this happen “out of the blue”? The whole experience has caused me to ponder these and similar questions on numerous occasions and, whilst I have no definitive answers, I realize that perhaps this late onset was not as sudden or unexpected as it seemed. When I think back on my life so far, there are several subtle hints that individually mean nothing, but collectively perhaps suggest that there was more to me than met the eye.

I vaguely recall that when I was very young, (pre-school age) when getting ready to go somewhere, my grandmother would always lick her middle and index fingers before scrunching my hair into a “wave”. Almost without fail she would comment to my mother “With hair like this, he should have been a girl.” I never thought anything of it except that I had nice hair.

During my primary school years, I did all the usual boy things: played footy and cricket (neither all that well), marbles, cowboys & indians, Robin Hood, William Tell etc. I had a collection of Matchbox cars, the usual boy comics and a good collection of Biggles books. At the same time, I had no difficulty playing tea parties with my sisters and cousins (most of whom were girls). I never played dress ups and I’m sure I didn’t play with dolls by myself but occasionally joined them when that’s what they were doing. I also read The Magic Faraway Tree and many Secret Seven and Famous Five books.

Apart from being one of only a few boy cousins in a sea of girls, I was also the oldest of the kids in our neighborhood. I used to take the younger kids under my wing so to speak and when we were playing organized games, I always made sure that no one was left out. At one stage the adults of the area used to refer to me as The Pied Piper. Whilst it would be incorrect to say that this empathy & nurturing behavior is absent in the masculine, they are characteristics more usually associated with the feminine. I never thought anything of it, it just seemed natural and the right thing to do.

I was never jealous of my sisters although, from my perspective at least, they had it easier than me. At the time I attributed this to expectations for the eldest son that was so common in the ’60s and the usual economic situation that exists in most families where life becomes less arduous as time goes on and the mortgage shrinks. However, I do now believe that overall, girls have it easier in the early years, at least from the point of view of more freedom to express themselves and often less expectation. Not that this is necessarily right, it’s just the way it is in most cases.

Into adolescence, I had long hair (didn’t everyone?), wore V-knee jeans, flairs or baggies & platform shoes with pastel colored or paisley body shirts. Hey, it was the 70s and I didn’t stand out at all. However, thinking back on it, I did pay probably more attention to my appearance than many of my mates.

Fast forward 40 years and I sit now fully waxed, with painted toenails, earrings, anklet & toe rings, wondering whether these early tendencies were perhaps indicators of something more that was successfully suppressed by prevailing social norms.


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  1. Olivia Livin 2 months ago

    Maxine, I too can remember things in my younger life that may or may not have been indicators. I don’t dwell on it. Being femme makes us happy and at piece, lets be that.

  2. Gemma Moore 2 months ago

    I recognise the person in your story so well.

  3. Kay Jameson 3 months ago

    Great Googly Moogly I feel like you just described my whole life. So many parallels.

  4. antoniorl2 6 months ago

    Fresh lodgings stage for throw:

  5. Author
    Maxine Doos 7 months ago

    I have been absent from the site and the sisterhood for WAAAAYY too long. Real life has a habit of getting in the way 🙁
    Thanks so much for all your kind comments.
    It really is gratifying to know that this article was so well received and that so many of you found it familiar or helpful.
    Just a minor update… I now have pale pink SNS on my finger nails with glitter highlights on my right ring finger and left index finger. Tanya thought it was strange as she has highlights on both ring fingers. But to me (male brain) it was an obvious choice as these are the toes that have the toe-rings.

    Hugs to all,

  6. Cristy Springfield 7 months ago


    Your story sounds so much like mine it is scary! I guess a lot of us have this in common. Thanks for sharing!


    • Author
      Maxine Doos 7 months ago

      Hi Cristy,
      Thanks for the kind comments.
      I’m glad you enjoyed my musings.


  7. Bill Johnson 8 months ago

    I totally agree with the feeling I get when wearing womans clothes.

  8. Frances Flip 9 months ago

    Well I’am truely inspired I’am going to take a bath and dress up nice with my wig and makeup nails and all then take a drive and see where i end up thanx love francis

  9. Bianca Leerouge 9 months ago

    Lilly I could not agree with u more. I see no desire in myself to fall into what people generally associate cross-dressing with being bi or gay.
    I’ve only ever chased the company of other females but nothing makes me feel more beautiful in myself than being dressed up in my prettiest clothes to make the best impression I can on my lovely girlfriend.

    • Stef Smith 9 months ago

      Me too
      I m not gay
      And I have no issues with the gay community
      I like what I like when it comes to clothes
      I like being the peacock so to speak
      I m sensuous so I love soft fabrics
      I love high heels and pretty toe nail polish
      Tight jeans
      Form fitting dresses
      Thats my right if it makes me happy

  10. Rozalyne Richards 9 months ago

    Hi girls I’m new to this site I’ve been a cross-dresser most of my married life I have been dressing up in secret when ever i get the chance it always makes me feel a better person after a dressing up session I’m not sure why.

  11. Arman 9 months ago

    Bravo Paula. You have some guts. Do it all the time and don’t feel shy for a second.

    • Lilly 9 months ago

      I try to dress them as much as possible but I have a 15 year old kid in the house so it makes it a little difficult I can’t wait to have the house to myself when I can be what I want when I want how I want. I feel real confused because I’m not attracted to men but I love dressing like a woman I love women. It really confuses me because I don’t really know how to I think of myself for a label for it. In my own words and thoughts I would consider myself a male to female lesbian I guess

      • JackieOhNo Raples 3 months ago

        I’m trying to think how George Carlin would think of
        what I am thinking.
        I am a red blooded American male who loves to see beautiful
        ladies and often kidded I must be lesbian because I love women…
        Recently I was looking at pictures of beautiful crossdressers,in pretty outfits and make up. I enjoyed looking at these pics as much as real females,I was getting turned on some what…..whether I was dressed as male or female I was fantasizing about kissing or making out or more …. I love thinking about this,maybe I’m bi
        Luv JackieOhNo

  12. Charee' or Char (Shar) 9 months ago

    I am 56 this year; i am dressing now almost every where, public, on the job sites (construction), I am getting better n better every day at; “Living independently of the good opinion of others…” The more we show up girls, the less we will be different and the more we will be as “normal” on the street as anyone else not in a suit…That’s my vision…freedom to be…
    Char xox

    • Arman 9 months ago

      Char, namaste to you too. Great for you. You are doing what is good for you and feel for you. Nice work and I am pretty sure you must be feeling extremely good inside.
      Many namaste to you with my hands together.

      • Charee' or Char (Shar) 9 months ago

        Awe, Thank you Arman. I believe and teach, that we are only really responsible for one persons happiness and life; our own. The trick is creating our own joy with out violating the basic rights of others in the process.
        Every day my soul and confidence expands a little further and I Am free to be me…without judgment, but rather with deep love and appreciation for my-Self 🙂

        Namaste’ Dear Arman
        there is only one of us. . .

        Char xox

  13. Kendra Carter 9 months ago

    Hi Maxine and thanks for sharing your story! For myself it simply started as something of a curiosity. You know, how it would feel wearing women’s lingerie, what it would feel like next to my skin and all the other thoughts that go through our minds. Wow. I had no idea it would feel so good! My philosophy of life is to ‘live and let live’ and as long as no one is being hurt then why not. So let’s enjoy ourselves!

  14. Serena Sorenson 10 months ago

    I am almost envious of all of you ( as terrible as it sounds) that the only dressing and expressing I can do has to hide under my male clothes. I can’t garner enough time or privacy to go full out. I do enjoy the feel of a see through bralette under my t shirt and how a thong feels pressed tight on my skin. You ladies are lucky

  15. Harietta 10 months ago

    Hear ye, hear ye!
    I submit that the current social fashion construct assigned to men is actually in conflict with our true natural tendencies.
    I feel joy in either mode, but my happiness in a pretty floral sun dress with my hair french braided and my makeup upbeat and current…happy, happier…happiest
    Talk amongst yourselves…

  16. Harietta 10 months ago

    Sorry, but the tone of your post makes it sound like a femme part of ones’ identities is odd or exceptional. I don’t think so.
    If we are talking about pure crossdressing, meaning enjoying clothes socially assigned to the opposite sex then it absolutely is not.
    Fashion is a social construct. The advertising industry has made billions for companies building a giant, almost unassailable wall between what is male style and fashion and that of womens’.
    So men, currently at least, do not wear floral scents like rose. They don’t have long hair cascading in lush curls down their backs. High heels and stockings are for women…of course.
    But just flash back three hundred years to the french court and men did all of that. They wore makeup. They had elaborate colours to wear and stockings. Beautiful shoes.
    The look at the other animals….It’s the male with the better feathers, the male lion with the mane….the peacock?
    Now the current boring Mr. Dressup box may be a holdover from pioneer, log cabin, sod house times and twentieth century military attire…and that is fine.
    But to say to me that rubbing Givencey all over my torso and setting my blonded hair in ringlets is somehow verboten?
    Not at all. It is perfectly fine and probably naturally more in line with nature, for men to be pretty too.
    I wore blue tinted lashes yesterday….yum!

    • Arman 9 months ago

      I fully agree with you Harietta. There is no doubt about what you mentioned re – advertising industry. Lets take an example of women, these days wearing clothes or dress up that are traditionally mens’ – like pants, shirts, hair styles etc. From the other side of the coin, why men should feel bad or society should make a mockery if men wants to wear or wear girls clothes and dress up like a girl/women. We all men need to get to gather and revolutionize the for liberty of freedom to wear what pleases them. Not only that but, the wives have to get into their head that it is fine and they should work as a team.
      If the husband likes to wear girls/womens’ clothes, wives should encourage and help to make him feel good and confident.
      I like to see that happen soon. Bravo all you wonderful people.

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