Skirt Day Ch. 01: How It Began

Lisa wondered why it was that despite her successful career in middle management and a plethora of dating options consequent to her tall, blonde good looks, she still felt empty and unhappy. In fact she didn't much like dating--all too often she would find the guy's shallow attempts to impress, to make her laugh, and to get into her jeans to be frustratingly unsatisfying. She usually delivered a forceful rejection to each guy, and even went on to instruct him on how to improve his life.

Her career was taking off--she felt a promotion coming--and with a recent raise and no children, a paid-off house and car, and fully paid student loans, she had all the money she needed and more; not bad, she thought, for twenty-six, especially with how hard she'd worked at this job since she started. Why not more happiness from such early stability and success? This she asked her recently hired therapist, Joan.

After several weeks, Joan found it a major breakthrough when she realized that Lisa's dating disappointments--and perhaps business disappointments as well--came from her displeasure at docile partners. Joan explained her theory to Lisa: you find forceful men attractive, but you are so self-confident that you are too forceful with them to allow them to assert themselves.

Joan thought of a potential therapy for Lisa. She began asking Lisa questions about how she could tone down her aggressive stature. One session, Joan had an idea:

"Lisa--I notice that at every session, you are always dressed quite similarly. Baggy jeans, a dark-colored blouse or sweater. You never dress in a particularly... feminine way," Joan observed, looking for something.

"I prefer to dress this way. It's comfortable."

"And fairly gender neutral..."

"So?"

"So, why don't you ever wear a dress? Maybe a low-cut top? High heels?"

"I don't think I would be taken seriously if I wore those things. People would think I was, you know, just a girl."

"Do you even own any dresses?"

"I have one floor-length evening gown that I bought for a Christmas party some years back, and another that I've had since high school."

"Floor length? I'll bet it was more conservative than the other dresses at the party."

"Of course. Many of the wives of the employees wore short little cocktail dresses. You could just see the men looking at their legs and breasts the whole time. I would never wear something like that to an office party. What if my colleagues saw up my skirt? They should be talking to me, not my breasts."

"Maybe so. But Lisa--I think this might be a route to explore ways to enrich your life. I think you box yourself in too much. You are always so concerned about earning respect and being the leader. It even cuts into your wardrobe. But your wardrobe is one of the easiest things we can augment. So, doctor's orders, I want you to try this: after today's session, I want you to go shopping. I want you to find something feminine--a dress or a skirt--to wear to our next session."

"That shouldn't be hard."

"Actually, it should be, so I'm going to make it a little harder on you. I want it to be short. Well above the knee. I want you to buy a skirt that seems just long enough to you, but absolutely no longer, and wear it here with bare legs. The weather is plenty warm for it."

"You're not wearing a skirt, Joan. Why should I?"

"I almost always wear a skirt on a date. Do you?"

"No."

"Well, there you go."

That afternoon, Lisa went shopping, figuring she must be paying her therapist for something. She had not worn a skirt above the knee since childhood--and then she never liked the threat of being exposed and teased by the boys. But she was an adult now and she could handle it.

She tried on about 5 skirts and ultimately ended up buying a dark green, loose a-line skirt that fell to just above her knees. She put it in her closet and forgot about it until her session a week later. As she shaved her legs that morning, it occurred to her that although she shaved her legs almost every morning, there was never really any point until today.

The feeling of going outside with her legs no longer safely wrapped by denim or cotton pants, or at least knee-length shorts, was one she had not felt in a while. She could feel the slightly cool air on her knees and thighs as she took the subway to her session, and she knew that she looked more feminine, more exposed, more weak than her usual self. But there was something else.

"What else?" asked Joan.

"I guess I do feel more attractive. That's the point of this, right?"

"That's part of it. It is very nice looking, although you still look quite conservative. What I want for you, Lisa, is to feel vulnerable. I think that's what you're missing."

"Feeling vulnerable doesn't sound like a good thing."

"I think for you, it will be. Do you have a date next week?"

"No."

"An important business meeting?"

"Just one departmental meeting. Why?"

"This is what I want you to do: tomorrow, take your new skirt to a tailor. Ask her to shorten it by 4 inches. Don't try it on for her, just ask her to do it. Ask her to call you when it's done. Then, the day she calls you, whatever day it is, you pick it up. And then the next day will be important. On that day you will wear the skirt, again with bare legs. You will wear it even though it will feel too short for you. You will do this because I told you. And whenever you wear that skirt, I want you to try to be passive. I want you to do whatever anyone tells you, whether it be a coworker, a friend, or even a stranger. So that as you wear that skirt, you are labeling yourself as a humble servant, at the mercy of the world. Of course, it's really our secret that you will do what anyone asks, but that won't change the feeling of it. Do you think you can do that?"

Lisa was shocked. She did not know if she could do it. But it sounded like a challenge. She thought about it, and Joan added

"I dare you to do it, Lisa."

So it was a challenge! Lisa believed nothing was too difficult for her, so this shouldn't be, either.

"Remember, when you wear that skirt, you will do whatever anyone asks, starting with putting on the skirt in the morning and wearing it all day."

The tailor gave Lisa a slightly funny look when she asked her to shorten her perfectly nice skirt, but Lisa told her she only wanted to know how short it would be--not see it. Lisa felt a little embarrassed, but she did not let it bother her since it wasn't her idea.

For the beginning of the week, Lisa felt a great anticipation for her "skirt day." She resolved that she would indeed do what anyone told her (not that anyone would, since no one would know that they could) and the thought somehow excited her. She rationalized that it was the danger of it. It's highly unlikely that a stranger on the street could stop her and ask her to strip naked and have sex with him, but if he did, she would have to. The more Lisa thought about it, the more simultaneous dread and excitement filled her. On Tuesday she picked up the skirt, which looked noticeably smaller in her hands although she did not try it on. On Tuesday night she had a little trouble sleeping, wondering what would happen the next day.

Wednesday morning. Lisa wakes up, showers, shaves her legs, brushes her teeth, takes her birth control pill, and returns to the bedroom. Wrapped in plastic is her fate for the day, hanging next to the white blouse she plans to wear with it. She picks out her favorite set of underwear--somewhat high cut white panties and a bra with just a little push to it. She buttons up the blouse (all but the collar button), and then removes the skirt from the plastic. She slides it up her legs, and when the hem reaches her knees she realizes that the waistband is still half a foot from her waist. She slides it higher and when finally she fastens the button at the waist she feels that her legs are almost entirely exposed. She wonders after all if she can go through with this!

She looks in the mirror. The skirt only covers half of her thighs. She feels exposed, vulnerable, and anxious. She turns around and bends over. It's hard to tell in the mirror, but she's confident her panties are still covered, even though the backs of her thighs are in plain view. She tries sitting down, exposing more thigh as the skirt rides up. "This is how it will be all day," she says. She knows she has to go through with it now.

Then she feels it: with the vulnerability comes excitement. What will happen to her? What adventures will befall her now that so much of her is exposed? It seems very different, slightly scary, and above all, alive. As she puts on a pair of flat sandals she purchased yesterday, grabs her purse, and walks out the door, locking her house behind her, and--for the first time since Joan's little speech about jeans and sweaters--her pants too, she pulls down her skirt as far as it goes, swallows her fear, and realizes why she has been paying Joan all this time. For the first time in years, she is looking forward to her day.