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?


  • 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

  • Annaleigh

    For me, it started when I was about 3 or 4. I remember putting on a costume dress at my babysitters almost daily, and I loved it! Later on, about 10-12, my cousin, brother, and I did a photo video for fun, and I was dressed as a woman. LOVED IT! Then it progressed to wearing my mom's bras and panties at night, typically from the dirty clothes (I know, eww, but it was all that was available to me), her swimwear, and a water bra that was given as a gag gift. I eventually took an ex's bra, and would borrow/wear another ex's lingerie (we were the same size, oddly enough) and a dress she wore at my command Christmas party. Now I only have panties, but am planning to expand that to an outfit to wear around the house when I'm alone.

  • Connie

    It started as a curiosity about lingerie. It became soooo much more over time….it became an actual need to look & feel feminine. I suppressed it most of my life but a few years ago, I finally got the courage to come out & open as Connie & it was amazing! I found an inner peace unknown to me until I went out as Connie for the first time in public. Now, it is my daily life to be Connie, open & out to the world & so very happy to be the REAL me….a girl!

  • REBA

    I am a Reba McEntire impersonator. I call myself. Reba Brooks. I have dressing as Reba since my 20's. And still love it. Almost 50 now.. I do feel feminine and feel like a woman when I dress.. Have had so Much fun performing as her. Love the wigs , make-up and costumes. It's something I really have enjoyed for years.. Love the complements

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