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The "Boys Wearing Skirts to School" Challenge
Whatever Blows Your Skirt Up

by St. George

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Copyright on this story text belongs at all times to the original author only, whether stated explicitly in the text or not. The original date of posting to the MMSA was: 20 May 2011

At first glance there was nothing unusual about the small, slight figure in a skirt walking towards the door of the school. The person appeared to be in the neighbourhood of twelve years old, with a mop of short blond hair and a piquant little face... a rather cute, if tomboyish girl... no, wait a second...

Alex Blackwell was well aware of the eyes that were suddenly focused on him and couldn't resist meeting some of those flabbergasted stares with a cheeky grin. Alex was certainly no girl, and there was something in the shape of his legs and the way he walked that dispelled the illusion of femininity. Sartorial expectations, after all, are merely conventions; and the flouting of those conventions does not alter the wearer's essentially masculine or feminine nature. The modern world is accustomed to seeing girls and women in trousers, but men and boys in skirts are still uncommon enough to cause a bit of consternation; and this was most certainly a skirt and not a kilt. Young Alex had borrowed his sister Alice's extra uniform skirt.

A member of the staff hurried off and a few moments later reappeared with the head teacher, Mr. Rogers. Rogers' mouth tightened into a grim line and he placed a hand on Alex's shoulder, saying,

“I think you and I had better have a little talk, young man.”

Once Rogers had Alex safely in his office, he exploded,

“Just what are you playing at, eh? Is this meant to be some sort of joke?”

Alex treated Rogers to an infuriating little grin and replied,

“No, sir, it's not a joke. You gave me detention and made me go home and change clothes when I came to school last week in shorts. It's still just as hot this week as it was last week, innit? Well, if I can't wear shorts, then I'll wear a skirt; skirts are allowed in the uniform policy, innit?”

Rogers sighed deeply, counted to ten mentally and then forced himself to speak in a calm tone.

“Skirts are allowed in hot weather, yes – for girls, Blackwell. You are not a girl, and, therefore, you are not allowed to wear a skirt.”

Alex's chin tilted to a defiant angle.

“It don't say in the uniform policy that only girls can wear skirts, sir. I read it through three times and it just says that skirts can be worn in hot weather. If you let the girls wear skirts but not the boys, that's like discrimination, innit?”

Rogers fumed in silence for several long seconds as he lamented the passing of the day when he would have caned the youngster for impertinence. Now it seemed that every rule had a loophole, common sense counted for naught and every pupil had a well-cultivated talent for argument. At last he spoke.

“Very well, Blackwell. Wear your skirt. I'll bet that by the end of the day you'll find it anything but cool. In fact, I'm guessing that your classmates will make it pretty hot for you.”

Alex merely shrugged, and the grin never left his lips.

As for Rogers, he was by no means as confident as he had sounded. At one time he could have predicted the sort of outraged reception a boy in a skirt would have found among his peers, but now... It was clear that Alex Blackwell had the sort of strong, confident personality that made him a leader. Rogers closed his eyes and rubbed his temples as he envisioned a school filled with boys in skirts. The story would get out. He would be made a laughing-stock on television and in the newspapers and on the internet. There was just one thing to do: the uniform policy must change. Better he have a school filled with boys and girls in short trousers than boys and girls in skirts.

Alex rather enjoyed his day in a skirt. He and his mates enjoyed the consternation he caused the staff as he sprawled at his desk, legs indecently splayed with a total disregard for the fact he was wearing a skirt. There was the added satisfaction that very little work got done, as Alex's skirt distracted both staff and pupils from lessons.

Truly, there were some disadvantages to the skirt. Hoisting up his skirt complicated the process of peeing. The skirt was a nuisance when running about kicking a football, as it tended to fly up in the breeze and give everyone a glimpse of Alex's boxer shorts, which were patterned with bright yellow 'smiley' faces. The breeze that played around Alex's thighs made him feel almost naked; and though it wasn't unpleasant, it took some getting used to.

It wasn't until Alex came home that afternoon that he discovered the true disadvantage of a skirt. His father, Albert Blackwell, was waiting for him, and not in a terribly happy frame of mind. A telephone call from his son's head teacher had led to his unwontedly early arrival. Blackwell père greeted Blackwell fils with a sour expression.

“My son in a skirt... well, I must say this is a proud moment, and congratulations are in order. Mr. Rogers asked me to tell you that he is changing the uniform policy to allow pupils to wear short trousers – proper short trousers that are appropriate to the school uniform, mind you. He also asked me to dissuade you from returning to school in a skirt, lest it start a trend among the other boys.”

Alex's cheeks flushed with triumph and his eyes sparkled. He said,

“Well... I dunno, Dad... the skirt's very comfortable, innit? ...So until the uniform policy is actually changed and I get the right kind of shorts, I think I might as well wear Alice's skirt.”

Alex's father put a heavy arm around his son's shoulder and walked him up the stairs and into Alex's room. By the time the penny dropped and Alex realised his father's intentions, he was lying face down over the man's lap. The skirt forestalled the usual struggle to bare Alex's bottom. There were neither belts nor buttons nor zips nor hooks to deal with. It was a simple matter of flipping the skirt up and then dragging the boxer shorts down.

The spanking that followed was a very thorough affair, as for once Alex's father had not wasted most of his energy in the bottom-baring battle. He smacked happily away, ignoring Alex's outraged howls of protest as his bottom turned a deep rosy hue. Never had Alex experienced such a spanking in his life!

When at last the man released the indignant boy, Alex tried to rub his well-stung cheeks, but that nuisance of a skirt fell down and covered the hot sore mounds. Never had rubbing a sore bottom after a spanking presented such a challenge!

Alex glared at his father and demanded,

“What was that for, eh?”

His father smiled a dark smile and replied,

“I thought that as the skirt makes your little bottom so accessible to spanking, I should take advantage of the opportunity. There's little doubt I'll take advantage of the opportunity every time you wear Alice's skirt.”

Alex came to school the following morning in conventional long trousers, but he was not too unhappy despite a lingering soreness from his spanking. It would only be a few days until he and the other boys could enjoy the comfort and freedom of shorts in warm weather. In the meantime, he would just have to endure the long trousers... which at least didn't leave his legs as hot as Alice's skirt had left his bottom!

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