Why Do I Crossdress?

Why Do I Crossdress

Why, why, why?

I imagine most of us have, sometime during the course our lives, sat down and pondered why we cross dress. Why we have that burning desire, no…, let me rephrase that: why we have that essential, irresistible, unforgiving urge need to now and then don women’s clothes and, for however long we are able, portray ourselves as female.

I guess a simple, yet somewhat flippant, answer would be: Well, I don’t know, I guess I just like to be like a woman now and then. However, if you spend some time contemplating this aspect of your character, you may find that there is more to it than that.

So, furrow your brow, takes a few moments to reflect and think:
Why do we do it?

Clearly, as with almost all T-people, it is something we were born with—so is it to do with whatever happened to us in our mother’s womb? The oft mentioned “Oestrogen wash” for example?

Or was it something in our social development, our upbringing where, say, we were the only male in a household of females? Or did we get cajoled into playing girls parts in school plays at school—and secretly enjoyed it?

Do we have a feminine looking body—in all or part? Maybe long slim legs below a male torso, or slender fingers, nice skin, long eyelashes and/or a girly lips/mouth?

What about our characters? Don’t like the rough and tumble of boys or men’s games, don’t like getting our hands dirty, but rather enjoy more passive activities such as reading, painting, even knitting (many men do!)? Don’t like the typical coarseness of men?

Do we simply admire the textures and feel of women’s clothes compared with the drab, coarse fabrics men usually have to wear; suit and tie, trousers and shirts, compared with skirts and tops, and dresses in silk and lace, nylon and satin, cotton and, oh, so many other fabrics and styles (long, short, mini, tight, flowing, loose…).

Let’s not dwell on shoes and boots and sandals, we’ll be here forever, but just think: high heels, low heels, flat shoes, thigh length boots, calf length boots, ankle boots; and hair adornments, earring, bracelets, rings, necklaces; scarves, shawls, cardigans… in colours sometimes we have never dreamt of.

Or is that we are simply, fundamentally women?

Women hidden inside a male shell; hidden because general society is hypocritical towards people who are just that little bit different. Fearful of something out of the ordinary, fearful of diversity, the majority suppress the minority (as always...).

Do we dress because we are rebels? Dress because women can wear men’s clothes and no-one makes any comments but, put a man in a dress, and the world might as well end?

Do we dress because it is our sanctuary, our shelter from the tough, tough world of being a man; from being the hunter and provider, being the figurehead?

Frankly, whilst I have my own opinions and thoughts about why we do what we do, if I’m truly honest, I’d have to say, despite all of my questions, a resounding: I don’t really know!

Still, this article this might give you something to think about the next time you slip in to a nice pair of panties and bra, breast forms, tights and a dress, and get ready to show the world the real you! Mightn’t it?


29 comments


  • Veronica

    I cross dress because I love women’s clothing. My tastes run to the most feminine items I can find. Garter belts and seamed stockings are a favorite. I love petticoats – I think it is the sexiest item of clothing for a woman. And when I dress, I feel like a woman. I love going to clubs wearing a tight miniskirt and a crop top and watching the guys watch me. I don’t just dop it in public, I wear a sexy peignoir or frilly baby doll to bed every night. Even when I go out as a man, I havee panties on underneath my pants. I guess the real reason is it just makes me feel good.


  • Emily

    I cross dress because of self esteem. As a man, I have had a life of mostly rejection and failures. I carry a lot of baggage. Dressing as a woman allows me to become a totally different person, a new person that loves herself. I will admit that I started as a child and had a few episodes through the years, but it manifested into something that I have shared with my loving wife, who is in total support and loves me for who I am. We have fun filled weekends together. So happy now!


  • rachel

    I cross-dress because I prefer being dressed as a woman as I know deep down from been a young boy, I was different to the other boys & that I should be a woman. I began purely out of curiosity trying on mother’s bra & knickers when I was about 16, I was soon buying my own miniskirts & high heels as I realized being dressed as a woman really made me feel happier as it released all my feminine thoughts that were been repressed, it’s just so different been a woman but I really enjoy putting my makeup on, doing my hair which I’ve now grown shoulder length as it’s far better than wearing a wig & choosing which outfit to wear, & I’ve always loved the smell of women’s perfume & now I’m the one wearing it, having my ears pierced was a euphoric moment as love wearing dangly earrings, going out as a woman was rather nerve wracking at first as I had to drive to another town at first, but the thrill of hearing the sexy clatter of my high heels puts me at ease, realising men were actually taking note of me as we passed in the street put a smile on my face & as for men I was fortunate enough to be caught dressed by my older brother who insisted on taking me out clubbing & introducing me to the world as Rachel & now I feel more than happy to let men have their wicked way with me, it just feels so exciting & natural for me to end up in my sexy lingerie & CF me 4" stilettos whilst been seduced by a well-endowed man as I’m just so happy I found the real me :- A Woman


  • Adrienne

    I think I cross dress for purely sexual reasons. I started in about 6th grade and tried on my mother’s stockings out of curiosity. I was skinny with hardly any body hair so as I added lingerie, the image I saw in the mirror was very erotic. Having a stockings & high heels fetish also played a part.
    As an adult, I really enjoy the feel of a new pair of sheer pantyhose, bra, panties, and outfit. The last thing that I put on are (ideally) a pair of 4 inch pumps. The feel of high heels on my stocking feet just can’t be beat!I love the career woman look – and I really get aroused at seeing myself in a mirror.
    I am hetero but curiously, dressed as a woman, I very much fantasize about being with another cross dresser and or another caring man. The thought of orally pleasing a man would make me feel like a real girl! My ultimate fantasy would simply involve another dresser like myself.
    I did have one opportunity many years ago – I met a cross dresser at a club and we decided to go to her motel room afterwards. She politely asked if she could kiss my nylon clad legs and I agreed – this was all so new to me and I was very nervous. She kissed a trail from my ankles to my upper thighs. We touched each other through our stockings, and that was it. I got scared and shortly left for the safety of my car.
    So I guess this “hobby” of mine is for sexual gratification, ultimately. I always end my nights/days dressed up with masturbation in front of a mirror, etc. I guess I’m hopeless, but wanted to get my two cents in. I also love everyone’s input here! Thank you for the opportunity for our community to communicate!


  • Annaleigh

    I cross dress because it makes me feel pretty, sexy, and helps me leave behind my daily srresses. Only recently did Annaleigh come into being, but she just spent a day treating herself with new panty hose, a slip, and her new black dress. Annaleigh felt like a queen


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