Pretty in Pink

by Clark <Cclark@worldnetla.net>

The high school gym was packed with eager students, impatiently awaiting the arrival of Sheriff Applegate and Pete Dowden, former member of the recently disbanded Dragon youth gang that had terrorized the small community with vandalism and petty theft. The local police who had at last captured all the gang members were putting the boys through a rehabilitation process that involved not only punishment (physical, as an antidote to their violent activities) but embarrassment (various forms of humiliation to counteract their arrogant behaviour). The announcement summoning the students to the gym had been vague, referring to Pete's upcoming ordeal only as "appropriate punishment", but word of earlier discipline had already reached the school. Rumor, this time accurate, had it that the teenagers had been forced to wear feminine attire - petticoats, it was said, and even lace panties! - as they were exhibited to the city council. Before that, the boys had been severely paddled by the arresting police officers, and for further punishment, each "little missy" was spanked over the knee of a councilman. On his bare butt, too! No wonder the students laughed and squirmed in anticipation of what was in store for Pete this morning. There was little sympathy in the gym for the seventeen-year-old basketball player who had been one of the Dragons' ringleaders. In fact, unrestrained glee at the idea of seeing Pete in his frilly garments prevailed, and most of the students hoped to see a bare-butt spanking as well. Those who were doubtful that the school's administrators would allow a butt to be bare on the premises were heartened when the principal and vice-principal appeared, looking as eager as the student body.

Principal Walker tried in vain to supress a smile as he walked to the podium placed on a low platform on the gym floor and began the kind of boring speech one might expect. He cautioned that however harsh and unusual this morning's activity might seem, it was directed toward a worthy end, the curbing of juvenile delinquency. Yes, they the students were assembled to witness Mr. Dowden's punishment, but they should derive the proper benefit from the correction of this young vandal, as it was for his as well as their own good.

The students, devoting more attention than usual to this speech (they were in an indulgent mood, and besides, had already decided what benefit they were going to derive), were both relieved and excited when Mr Walker concluded,"All right, Sheriff, we're ready for Pete."

These words had hardly been spoken when cries of "No! No!" sounded from one side of the building. All eyes turned in that direction, just as Pete Dowden was thrust through one of the doors onto the gym floor. He was protestingly loudly, and when his classmates saw why, they burst into laughter.

Pete, just under six feet tall and husky, wore a pastel pink smock with short, puffy sleeves. As he struggled to retreat through the door which had slammed behind him, the smock, which barely reached below his waist anyway, billowed out, revealing lacy white panties. He also wore white knee socks and shiny black buckled shoes. To top off Pete's ensemble, a bright red bow had been pinned in his crew cut blond hair, and it was only a tad redder than Pete's blushing face.

The anguished teenager's attempts to flee were abruptly halted when the door he was pounding on opened, nearly knocking him down, and in walked Sheriff Applegate, followed by one of his deputies. The sheriff, holding a sturdy wooden hairbrush in one hand, grabbed Pete's left ear with the other and dragged him towards the platform.

Sheriff T. R. Applegate was in his late 30's or early 40's. His dark hair was only beginning to show a touch of gray. Of only moderate height and build, he nevertheless had more than enough strength to control with ease the unwilling teenager in his grip. The sheriff's normally genial disposition had been tried by the pranks of the Dragons, and while he usually took an indulgent attitude toward juvenile misdeeds, the gang's continued havoc had forced him into an uncompromising stance. His handsome face now wore a smile as he guided the young vandal through this procedure of attitude adjustment.

When the sheriff and Pete stepped onto the platform, the officer at last released the boy's ear to shake hands with Mr Walker. Pete looked about frantically, but realized the nearest way of escape was out of his reach. In addition, Sheriff Applegate now stood right in front of Pete, arms folded, the hairbrush prominently held in one hand. He pointed to the bleachers on the side of the gym facing him. "All right, son, you know what to do."

Pete begged, "No, Sheriff, please!"

Mr Applegate took a menacing step forward, and Pete realized he had no choice.

He turned to face the bleachers. Working up his courage, he began to step down from the platform when the deputy stopped him. "Don't forget this!" he said, and hung a cardboard sign on a cord around Pete's neck. In bold letters it read "I'm a little sissy!" Pete, knowing fully well what it said, wailed and tried once more to run off, but the deputy pushed him from the platform and toward the front row of seats.

The young man remembered what he was supposed to do - he had been instructed thoroughly and warned of the consequences of disobedience. Yet, here and now, facing the hundreds of students, he completely lost his nerve. He turned and cast a pleading look toward Sheriff Applegate. The Sheriff's only response was to tap the hairbrush against his palm. Pete gulped. Among the many spankings he had received in the past few days, an enthusiastic paddling from the sheriff stood out painfully. The hairbrush looked considerably less substantial than the paddle Applegate had used, but Pete knew his butt was in such a sensitive state that even the slightest touch... he turned to confront his classmates.

Sheriff Applegate had moved to the podium and spoke into the microphone. "I think all you boys and girls know Pete - but you may not recogzine him in his new little outfit. So show everyboday what a cute little missy you are, Pete!"

Blushing deeply, Pete clutched the skirt of his "petticoat" and performed a delicate curtsy.

The crowd roared, of course.

But Pete wasn't finished.

He turned and hesitated before proceeding. The sheriff motioned emphatically with his palm for Pete to continue.

The one-time gang member performed his curtsy again, this time pulling up the back of his smock.

The resulting sight produced an uproar in the bleachers.

Pete's panties, white silk trimmed with lace, had been intentionally chosen to be too small for his ample frame. As a result, they were not only tight in front, but in back they rode up into Pete's crack, revealing practically the entirety of the basketball player's butt!

All of the students in the audience who had been hoping to see Pete's bare butt had been expecting a pair of snow-white cheeks. But, of course, after repeated spanking, almost the whole of Pete's exposed butt glowed red. May shades of that color were represented, and the careful observer could guess the various implements used on Pete from the still visible marks - the rectangle of the strap, the oval of the hairbrush, the tiny circles produced by a paddle with holes.

Sheriff Applegate asked the students, "Do you recognize Pete, now? Why not give him a hand."

Lively applause followed.

When the sheriff decided the laughing audience had gotten their fill, he directed Pete to move over to the other side of the gym and repeat his "greeting". The basketball jock had to walk mincingly across the gym floor he had once trod so proudly. As he pranced over, Sheriff Applegate commented over the loudspeaker, "Look at that prissy little walk! Pete must like this much better than his old gang outfit! I'll bet he thinks he looks pretty in pink!"

While Pete began entertaining the other half of the student body, Sheriff Applegate discussed the hairbrush he had brought with the principal and vice-principal. Naturally, a paddle or belt would have been a more suitable instrument for disciplining a misbehaving boy of Pete's age. The hairbrush was a part of the humiliation, as were the feminine attire and the over the knee spanking position the sheriff planned to employ. Mr Walker voiced his whole-hearted consent.

Sheriff Applegate, seeing that Pete had complete his errand, stepped up to the microphone. "Okay, Miss Priss, get back up here. It's time for your spanking." He smiled and beckoned to Pete with a finger.

Mr Walker took over. "Now, remember what I told you, students. This - um, activity is for a social benefit. Sheriff Applegate has been forced to resort to - corporal - uh, punition, to..."

Applegate interrupted him. "What Mr Walker is trying to say, ladies and gentlemen, is that I'm going to blister little miss Pete's butt good!"

The ex-Dragon suffered another attack of cowardice and tried to scurry away. Two obliging seniors promptly took hold of him and marched him back toward the sheriff.

Meanwhile, Principal Walker and his assistant had moved the podium from the platform and set up chairs for themselves beside it where they would have a close up view. A chair had also been placed on the platform for Sheriff Applegate, where he and Pete would have center stage all to themselves.

The two seniors delivered Pete to the sheriff, now seated and expectantly brandishing the hairbrush. Sheriff Applegate remembered all too well the caustic criticism that had been heaped on him and his men during their search for the culprits responsible for the vandalism around town, and the sarcasm he had endured when the "criminal masterminds" were discovered to be mere pugnacious teenagers. He was determined to make Pete's butt pay here and now for all that trouble the gang had caused.

"Come here, Petey," he playfully ordered, then yanked the boy across his lap. Pete was suddenly overtaken with the full realization that he was about to be spanked in front of the entire school, and he began shouting, kicking his legs, and pounding the floor with his fists.

Sheriff Applegate quietly ignored him. "Now let's see. The skirt comes up!" And he raised the back of Pete's smock, revealing the panty-clad butt.

Pete cast a faintly hopeful look at Mr Walker, praying the principal wouldn't permit even partial nudity on school grounds, no matter how worthy the cause.

No such luck. Walker was beaming with approval.

Sheriff Applegate continued. "And the panties come down!"

"No, no!" Pete shouted, but the sheriff pulled the lacy silk halfway down the muscular thighs. This was entirely for added embarrrassment, because, as stated earlier, the sheriff already had more than enough of Pete's butt exposed for him to spank.

As the audience took in this exhibition, Sheriff Applegate decided to use on Pete a technique that had been effective on his own younger but less-deserving son. He raised the hairbrush and ...

Crack! ... attacked an area on the top half of Pete's right butt cheek.

"Ow!" Pete yelped, and grabbed a chair leg in agony.

He hardly had time to fully appreciate the oval of pain when...

Crack! The sheriff brought the hairbrush down on the very same spot.

Pete wailed and pounded the floor.

Crack! Crack! Crack! Sheriff Applegate directed the blows of the brush to one unfortunate area.

"Waah!" Pete cried, alternately grabbing the chair and beating on the floor. He kicked his legs wildly.

"Keep that butt still!" the sheriff yelled. He at last began working on the bottom half of the cheek. Crack! Crack! went the hairbrush.

Pete cried loudly, as the sting of his spanking seemed to be increased because it came from only one side of his butt.

The microphone was yards away, but Pete's yelps and the smack of wood against naked butt needed no amplification to reach even the highest bleachers.

The punishment went on as Sheriff Applegate gave the left cheek the same kind of treatment. He taunted Pete the whole time. "Yeah, everybody sees now what a little sissy you are, Pete!"

Crack! Crack! Crack! sounded relentlessly.

After that spanking pattern had been completed, the sheriff began applying the brush to the very center of Pete's now scarlet butt.

"Waah!" Pete could barely howl through his tears.

"Crybaby!" admonished the sheriff.

Crack! Crack! He spent a great deal of time on his current target area.

Pete's butt was burning so he didn't even realize when the Sheriff Applegate stopped spanking him. He suddenly heard the officer ask him, "Well, have your learned your lesson, missy?"

"Yes, sir!" Pete sobbed loudly.

"Then get up!" He pulled the crying teenager to his feet.

Pete hopped around uncontrollably. The back of his smock had dropped back into place, and he rubbed his fiery butt through it. The soft material was no comfort. Pete's panties had fallen to his ankles, and as he jumped about, they caught his legs and he fell flat on his sore butt! Not only that, the front of his petticoat flew up over his head, revealing his bouncing _c_o_c_k_ and balls!

Pete guessed from the laughter of his classmates that something horrible had happened. He quickly pulled the smock down and stood. After stooping down to raise his panties, he resumed he rubbing of his injured butt.

Sheriff Applegate again grabbed Pete's ear and dragged him over to one side of the gym. "Show everybody what that prissy little butt looks like now, son." He bent Pete over and pulled up the smock. Pete's panties, which had been only loosely in place, began to fall, and Pete clapped his knees together to catch them. Thus, the audience got a good long look at Pete's newly reddened butt. Calls of "Way to go, Sheriff!" sounded from the stands. Applegate acknowledged them with a wave. Then he made Pete repeat the display on the other side of the gym.

Principal Walker moved to the microphone and thanked Sheriff Applegate for his time and dedication, and hoped his students as well as Pete had learned a valuable lesson.

The sheriff and his deputy, flanking Pete, stood on the sidelines while the boys and girls left the gym. Sheriff Applegate said, "Well, it's time for you to go to class, too, son."

This remark silenced Pete's crying and he froze. "Whaaat?"

"You've missed way too much school already. So scoot!"

"But sheriff, I can't go to my classes like this!" Pete protested, indicating his sissy outfit.

Sheriff Applegate looked at him. "You're right, Pete, you can't."

Pete had a second of relief.

"Here." The sheriff reached over and straightened the lopsided bow in Pete's hair. "Now you can go." He gently patted the rear end he had treated so differently minutes before.

The deputy handed him something. "Don't forget this, sheriff."

Applegate smiled and gave it to Pete. It was a small pillow. "Compliments of the sheriff's department, son. Now go learn something." He was about to bestow another friendly slap on the boy's butt, but Pete had already scampered out of his reach, blushing at the thought of how he was going to have to spend the rest of the day.


More stories byClark