Sarahjanus's Blog

May 10, 2010

Crossdressing is complex

Filed under: crossdresser, travel, Uncategorized — Tags: , , — Sarah Michelle @ 6:17 pm

Now I understand why my wife packs three suitcases to my one.

I have three skirts, five tops, three dresses and three pairs of shoes. They are all in the black/blue/grey family. Even “en femme” I still dress drab. My business suits in my working life were all the same, black/blue/grey. I am not yet flamboyant en femme, although given the opportunity I probably would be. I do have one very bright multi-colored summer dress with a flounce to the skirt. It makes me feel pretty when I wear it, but that’s another line of thought for another day

Since I’m a closet dresser and don’t go out, I don’t have coats, hats or sweaters. I can dress in the house in one of the basic outfits and be comfortable all day. Any item goes with any other item so decisions are easy. While I was on my journey, I bought a casual skirt. It’s a stretchy but not tight khaki coloured knee-length skirt. Great for driving in which is where I wore it. A lot of my male clothes are also khaki, so I could match t-shirts to the skirt and not feel that it was a glaring mis-match. Where I ran into problems was with everything-else, shoes, socks, tights, purse.

And that was my epiphany; no wonder she has to pack so much. As a male I pack white underwear, a couple of pairs of pants, one black or dark, one beige or khaki, or perhaps brown, two belts, one black one brown and a selection of t-shirts, golf shirts and socks.  This can easily be a weeks clothing, two weeks if it needs to be because there is always a laundromat or a laundry service available somewhere along the road.

The addition of a khaki casual skirt [which by the way is the most comfortable thing I have ever worn, I would live in these if I could], focused attention on the fact that I had nothing at all to go with it. I needed some casual tops in the same color family. My other blouses and tops are dressier, suitable for an office environment which is what I have always dressed to before, so none of them would work or match. Even if the colors worked, the business look over casual didn’t.  My nylons and tights are all dark-colored, usually as dark as I can get them because I can’t shave my legs. My wife would notice and there is no reasonable explanation for that. Besides, casual skirts call for bare legs, preferably tanned legs.  My shoes are all black, varying styles and heels but clearly black and clearly business or party style. I could dress for an evening out but not for the day.

My man shoes are too clearly man shoes to combine properly. I needed something less bulky, finer, lighter. So there I am, in my new skirt, bare legs one day and dark tights the next, wearing my gender neutral black and white runners and a gender neutral golf-shirt. I had decided to brave the public in a series of towns far from home, and I did. I got some disapproving looks but no one said anything directly to me. I mused after each foray; were the disapproving looks because I was out in public in a skirt [probably] or because I was so poorly dressed. Weird is weird, whether well-dressed or not, so it was probably seeing a middle-aged man in a skirt that triggered the glares.

I need a new purse as well, and I haven’t even considered jewellery yet.  Now I also know that given the opportunity I would dress to the hilt. I know exactly how the progression would unfold. In the two days that I wore a skirt, I became braver and more comfortable getting in and out of the truck and travelling short distances on foot. I would add a top the next time, and shoes after that, until I was clearly and unambiguously dressed like a woman. In that progression, cosmetics would be added, touches at first, bit by bit until my face was fully done. I watch the exercise every morning and I am amazed at the difference. I’ve played around with it at home and could master it fairly easily I think.

Given the opportunity; I would travel with a make-up bag, a suitcase full of shoes and belts, and a suitcase full of clothes that could be combined in a variety of ways to allow for casual dress on warm days, casual dress on cool days, and a classier level of clothing for events, places, restaurants. Yes, as a man I travel light but that is because I don’t care what I look like as a man. Dressed as a woman, I want to look like a competent, well-dressed individual, clean, neat and tidy, well-presented. This is also how I know that my male side is not the same as my female persona. One couldn’t put clothes together to save his life and the other is quite good at it. Given the chance to shop with my wife for my wife, I can find what looks good on her and find all the pieces that need to go together. I can do the same when I shop as Sarah.

Now I face the greatest problem known to modern man [versus women]; I need to do my “en femme” laundry.

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