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?


  • Cassandra Jade

    Hello girls, I'm Cassandra Jade (in the making). I am in the process of receiving my wig, butt & hip pads, corset and a few other items. I got 1 of my dresses, 2 pairs of high heel shoes, panties, my breast forms & it feels so natural to me. I wish I did this in my twenties when I was still young & prettier. Non the less, I can't wait to get out there. & strut my stuff. The world is my catwalk honey. I also wanna enroll in beauty school so I can both be myself & do what I love. It's difficult buying feminine products in brick & mortar stores because everyone see's this guy I'm trapped in. I desire to smell like a woman & have smooth feminine skin. Luckily I have the internet. I hope to post a pic of myself & my future man to reveal all that Sassy Cassie has to offer. Thank you ladies for helping me bring her out.

  • Oscar

    I cross-dress because deep down inside I always felt like a woman. When I was going through the lingerie department, specifically the panty section, I touched a panty to see how it felt, and I liked it so I purchased few panties and I enjoyed it. And then after a while, I added bras. And since I already had lingerie, I decided to add dresses, skirts, and shoes to my feminine wardrobe. After buying all these clothes plus my love for ballet, I knew I was a woman on the inside.

  • Danni

    I took my time….teenager 1980s with stacks of woman's magazines seeing the makeovers, the clothes…the Virginia Slim models and their wardrobe…and how it made me feel. Then I was trying to walk in heels…and that intoxicating sound on tile floor…

    Years later…I enjoy

  • Barbara

    I truly love the EN FEMME learning center. I have dressed for decades. For years I thought I was the only one….. I say that to say this; I love to dress and I really do not know why either. I wrote in comments of "Are you a Fetish Crossdresser" that I started (with mother's help) dressing at the age of 4. Totally innocent. But when I pulled on my first pair of full-fashion stockings and skipped around her bedroom, the magic of crossdressing took hold and never let go. But at the age of 8, my aunt stopped in to visit my Mother. She was a bit shocked to find her nephew wearing make-up and panties, and pulling on a old pair of mother's stockings. "OH My!… don't you know that little boys don't wear women's clothes! What is wrong with YOU!!! From that day on, "What is wrong with YOU! echoed in my head, every time I desired to dress. As an adult, I can't count all the times I purged all my lovely things. I finally went to a therapist.. She concluded, "There is nothing wrong with you dressing. Just don't try to explain it to your wife and others that don't dress. They will never understand, therefore they will judge you. Your wife and others don't need to know everything. As long as you do no harm to others or try to force them to accept something they don't want to understand, go enjoy your female side." I was free! I live a secret life as Barbara. I have studied and exercised to become a passable woman, going out ever chance I get, because as Patricia Kay wrote "it makes me feel so wonderful and complete.

  • Adeline

    I may be an outlier here. I dress for many of the same reasons. Early in marriage (early 20s) I wore my wife's panties, and told her because the material felt so good. Fast forward about 35 years, and the desire came back. She wasn't surprised, and was very supportive. She said that I have always had strong feminine characteristics, and do things like sewing (published author), cooking (fantastic soups), etc. She named my feminine persona. We are so connected over this, adding to the connection of more than 43 years of marriage.

    I'm still not out to friends or family (With some exceptions. Both adult daughters know.), but I underdress every day. I am wearing panties and a camisole as I type this, and a shirt/tie/slacks combo. And on the weekends, quite often, I am en femme for the whole time. We went on a week's vacation to the beach, and I was Adeline the whole week.

    But I still do traditionally male stuff. I have a crossbow, a traditional bow, multiple firearms, and a knife and hatchet target lane in the back yard. I love my wife, and enjoy heterosex with her.

    So why cross dress? Because it makes me calmer. One of the persons at work says she can tell when I am wearing man style undergarments. I'm more aggressive, in a job that doesn't need it, and I'm more likely to give solutions rather than have it be a team effort.

    Because it makes me feel more in tune with those around me.

    Because I like the feel of satin on my nether regions, and the feel of lace. I like the hug I am getting from the camisole. The feeling of nylons sliding up a shaved leg is very sensual.

    Because when I am Adeline and I look in the mirror, I can't help but smile. No, not attractive, but happy.

    I guess my question is why don't more men cross dress? Not looking to transition, just to feel the sensuality, the calming, and the joy of presenting as a woman for a while?

    I expect some blow back from this. I know that men have male privilege. I know that Trans persons have a tough row to hoe. I don't envy either group their issues. But there is a joy in putting on a skirt and blouse, adjusting the bra to just the perfect fit, getting the lipstick just right, that I can't keep from doing it.

    Happy life to all of you,


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