The Prettiest Girl in School

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The Prettiest Girl in School


By Dreadlocks



Leslie Mayfair, sighed as she read the front page of the school newsletter, knowing she would have to manage the fawning closeness of her faux friends, and the scorn of just about every other girl at Kennedy High.

She was seventeen, a senior, and set to head off to the Ivy League school of her dreams, and yet she was disappointed. She was disappointed because once again, she would only be recognized for her beauty, rather than her intelligence.

Oh, her teachers knew how smart she was, but the other students, her peers, only saw the long blonde hair, the angelic face, and the figure of a goddess. Was she doomed to be cursed with this stigma all her life?

“Isn’t it exciting!” Maureen Wilkes hovered around her. “The prettiest girl in school, two years in a row. I don’t think that’s ever happened.”

Leslie painted on a smile and thanked her ‘friend’ whose only reason for being such, was the accolades she received for even being close to her. It was the same with every one of them, with one exception. Madeline Cray.

Madeline, or Del as she loved to be called, as much as it irked her parents, was Leslie’s best friend. Del was always there for her, not for her genes.

When Leslie made her way to lunch in the B cafeteria, she looked for Del and found her at her usual table by the window.

“You’re not going to sit with her again, are you?” Brenda Stiles asked, tugging at her shirtsleeve. “She’s such a loser.”

“That’s enough, Brenda. She’s my friend, and I really don’t care what you think.” She’d said it a hundred times, defending Del against the glam gang that seemed to congregate everywhere she went. Leslie did her best to avoid them, but she had been appointed their leader, in spite of her hatred for their shallowness.

“Hey, you.” Del mused, kicking a chair out from under the table with her foot.

“I suppose you’ve heard.” Leslie moaned, opening the packed lunch that her mother always made for her.

“Kind of hard not to. You’re the ‘talk of the town’ Les.” Del was everything that Leslie wasn’t, physically that is. Oh, she was her match on the IQ scale, and had her own plans for college. Del was tall, lanky, with more of a boy’s figure than curvy. Her hair was cropped short, her chestnut curls flopping onto her forehead and barely covering the top of her ears.

Leslie envied her ability to simply not care about her looks. She was cute, again, in a boyish sort of way, with a scattering of freckles on the bridge of her nose, and a gracefully pointed chin, the only feminine attribute she could boast.

Del never wore makeup, and still, her skin looked healthy and fresh. Leslie often wondered what would happen if she showed up in school sans her makeup and coifed hairstyle. Maybe she might lose some of her unwanted entourage?

“I hate this.” Leslie moped, taking a bite out of her swiss cheese and lettuce sandwich.

“I don’t know why you don’t just do something about it,” Del said, as she had done on numerous occasions. “A quick trip to the barber, a good wash of that face, and voila!” Del thought about her statement for a second. “Nah, you’d still be gorgeous.”

“I know, I know!” Leslie cringed. “I just can’t work up the courage to do it.”

“You want to do something right now?” Del smirked. Leslie always worried when her friend had one of her ideas. It invariably landed them both in trouble. “Lose the push-up bra, Les,” Del suggested. “I know what you’ve got under that jumper, and it’s not what’s on display to the rest of the school.”

“So, just walk into the restroom, rip off my bra and go around au-naturel the rest of the day?” Leslie grumped.

“I dare you.” Del grinned.

“Damn!” Leslie simmered. She was serious, and a dare was a dare. “Fine, I’ll do it.”

“If it’s any consolation, I never wear a bra.” Del reminded her.

“That’s because you’ve got no tits, girlfriend.” Leslie kidded.

“Neither do you, smartass.” Del bit back. “I double dare you.”

“Shit. Fine.” Leslie stood and walked across the cafeteria, heading for the closest girls’ room. Closing herself in the stall, she slipped out of her pullover, regretting the fact that she’d worn something so form-fitting. Sighing, she unsnapped the front closing underwire bra and allowed it to slip down over her shoulder and off.

Looking down, she cringed over the small points that represented her actual endowment. The bra was everything. It was the extra full, padded variety that added two cup sizes to anyone who wore it. Without it, she looked like a pre-pubescent kid.

“Fuck.” Leslie regarded herself in the mirror, hoping that no one would walk in. Her breasts were practically non-existent under the woven top. It wasn’t so tight that her nipples poked out, but there was no doubt that she was pretty damned flat.

She heard the squeak of the hinges on the outer door and knew her time was up. Pushing through, she passed the girl as she walked by, and she couldn’t help but notice that her eyes were glued to what was missing about her.

And, there was no missing the subdued chatter and giggles as she walked back to her table, and a waiting Del.

“See, that wasn’t so difficult, was it?” Del didn’t even bother to see how Leslie looked. “That’ll give ‘em all something to gossip about.”

“Del! Look at me,” Leslie said, emphatically.

“Wow. Well, you probably could have picked a looser top.” Del managed, suppressing a laugh.

“I didn’t know I’d be baring my underdeveloped chest, now, did I?” Leslie grimaced.

By the end of the school day, all anyone was talking about was Leslie Mayfair’s boobs, or lack of them. Even her regular troupe of groupies had deserted her, reverting to gathering some distance away, tittering amongst themselves.

Leslie walked out of school, a bit overwhelmed but somewhat thankful that her action had resulted in the annoying glams giving her some space. What she didn’t expect was a talk from Mrs. Goodwin, saying that there was some discussion over her title, and whether it was awarded on false pretenses.

Leslie felt like scolding her for being so shallow, but then again, she was the queen of the Glam squad, and Leslie had even seen her gossiping amongst her old ‘friends’. All that would do was get her in trouble, and that was something she just couldn’t do. With her acceptance to Cornell on the line, she didn’t need any drama.

As Leslie walked by the school dumpster on her way home, she pulled the push-up bra from her purse and tossed it in, vowing never to wear anything like that again. She’d just have to revert to the camisoles she used to wear when she was younger.

She wasn’t depressed, she was angry. Angry that something so trivial could turn so many people against her. “Screw them.” Leslie barked at no one in particular as she walked down Main Street.

Just as she was about to cross the street to Walnut Avenue and home, she spied something that had been a topic of conversation that day. She remembered Del saying ‘…a quick trip to the barber, a wash of that face, and voila…’.

Leslie stared at the spinning pole for a few minutes, finding herself almost hypnotized by the rotating helix illusion, the red, white, and blue stripes appearing to move up the pole. In her scientific mind, Leslie knew the explanation for the illusion, but still seemed caught in its grasp.

Snapping out of her trance, she eyed the door to the ominous place; a place where she had never been. She knew her father frequented this shop, and she worried they might know who she was by way of his patronage.

Setting all that aside, she walked, almost straight-legged to the small step-up and before she knew what was happening, she had pushed open the door. A small bell jingled over her head, and suddenly all eyes were on her.

There were two barbers, standing beside two of three overly large chrome and leather chairs. The men occupying those chairs had turned their heads as well. All were undoubtedly wondering what on earth a girl such as herself was doing in their domain.

“Can I help you, young lady?” The one barber asked.

Without answering, Leslie simply walked over to a row of wooden chairs and took a seat beside a boy slightly younger than herself.

“We cut men’s hair here, honey. Maybe you’re in the wrong place.” The other barber said, continuing to run a buzzing machine up the back of the man’s head. They cut the hair quite close, and Leslie had to pry her eyes away.

“No, this is the place. I want a haircut.” She asserted.

“Alright, young lady. Why don’t you go and get a number from the rack over by the door, then.” He insisted.

The boy next to her showed her his number, and as if instructing her in barbershop etiquette, pointed to a hanger that held plastic cards. She rose, embarrassed, and took the next number from the rack.

“You’re Leslie Mayfair, aren’t you?” The boy asked, quietly.

Almost afraid to answer him, she simply nodded, turning the plastic number card in her hand. She swore the number 27 would be indelibly ingrained in her mind for the rest of her life.

“You shouldn’t be in here. They’re gonna scalp you like they do all the kids.” He warned.

“Why are you in here, then?” She asked, finally looking at him.

He hesitated for a moment, and then smiled. “Because I like getting scalped.”

She couldn’t help but notice the small bulge in the boy’s jeans grow larger as he talked about it. She imagined him running home after his head was peeled, and jerking off in the bathroom, or something.

“Maybe I want to be scalped too.” Leslie sighed, running her fingers through her waist-length mane.

“Wow. Really?” The kid said, and there was no mistaking the bulge now. Self-consciously, he turned and adjusted something, and the bulge disappeared.

A snap of a cape brought the two of them to attention, the one gentleman rising from the large chair. His hair had been shaved all around with only enough to stand up on the top. She’d seen her grandfather with a haircut like that, but he was a marine.

“Twenty-Six!” The barber called out.

The boy fidgeted in his chair, and then stood, walking over to the empty chair which had been spun around in his direction. He turned and slipped into the chair, looking at Leslie as he did. A strip of stretchy paper was wrapped around his neck, followed by a red and white striped cape. All the while, his eyes never left hers, nor did hers stray from his. It was as though he wanted her to see this, to watch this, to see.

“Been a while, Billie.” The barber chortled, running a comb through the unruly red curls that adorned the kid’s head. He had been spun around to face the mirror, but in that mirror, their eyes met again.

The barber didn’t ask what he wanted done. Instead, he simply reached for the clippers from under the counter and slipped off the plastic guard. For a second, a concerned look swept over the boy’s face, his eyes wide as the whirring machine was placed at the center of his forehead.

Leslie watched as the ginger hair succumbed to the blare blades, leaving a barren strip of pale white scalp in their wake. Their eyes met again, only now the look had changed. His lids were half-closed, his face flushed with embarrassment, and a satisfied smile replaced the thin nervous line of his lips.

It was as though he was in a trance, yet at the same time saying to her, ‘you see, look at me, see what he’s doing to me.’

Leslie looked away for a moment, aware that she was the source of the boy’s embarrassment. Yet she was drawn back to them a moment later. By now the entire top of his head was devoid of hair, his look one of quiet submission, as if he had absolutely no power to stop what was happening to him. Her eyes wandered from his eyes to the jet white skin of his scalp and back again. This, in itself, caused him to blush even more acutely.

Leslie decided at that moment to give the boy her undivided attention, giving him the fantasy he so desired, she knew. To be so severely tonsured while the ‘prettiest girl in school’ looked on. Leslie was certain that this moment would be fodder for masturbation for months. She would give that to him.

The other barber had finished with his cut, and had disappeared into the back of the shop, and Leslie thought she heard something about lunch. So, it was just her, the boy, the barber, and the number 27, which she so nervously held in her sweaty fingers.

The barber seemed almost cruel in the way he tossed the boy’s head around, working the whirring machines in front of and behind his ears, into the small indentation at the base of his skull, so that he was universally shorn. If there was one hair on his head longer than an eighth of an inch, she was a monkey’s uncle, Leslie thought.

As he rose from the chair, the bulge was back, and he made no effort to hide it from her as he walked to the register. In the light that shone through the large front window, just the slightest hint of auburn could be seen, like a halo around an otherwise bald head. As he had warned, scalped.

“Twenty-Seven, the barber called, looking straight at Leslie, the number superfluous, as there was only the three of them there. Finding the will from somewhere, she rose from her chair and walked to the waiting chair.

“Hold your hair up.” The barber demanded, almost angrily. Without thinking, Leslie did as he asked. The paper strip felt odd against her neck and seemed to stick to itself, like crepe paper. A few red hairs stuck to the cape as it was fastened around her neck, as if he had forgotten to snap it clean.

Leslie let go of her hair, allowing it to cascade over the cape which enveloped her small frame. The boy was lingering in the front of the shop, as if to see what was going to happen to her. He ran his hand over his stubbled scalp, met Leslie’s eyes with his own one last time, and slipped through the door, the bell ringing as he left.

“We do short, men’s haircuts here, young lady, so I hope that’s what you want.” Again, his voice was terse with what seemed like frustration.

“The boy said you scalp all the kids that come in here. Is that true?” Leslie asked, her voice audibly trembling.

“The boys know what they want when they come in here.” The barber insisted. “If they want something girly, they go down to Supercuts.” A note of offense in his tone.

“So, I guess I’m a kid.” She couldn’t believe she was capitulating to this man’s rigid standards. “A kid who knows what she wants.” There. It was out. She had said the words that would doom her luscious platinum mane.

“As long as you’re sure. I don’t want some angry father storming in here, accusing me of ruining his daughter!” The barber didn’t seem to be hesitating, as he grabbed the same clippers he had used on the boy; the boy that left without a single hair on his head. He cleaned any remains of the poor boy’s hair out of the blades with a small brush.

“I’m seventeen, and graduate in a month. I think I can make my own decisions, if that’s okay with you.” She scowled, but tempering her outburst, knowing it wouldn’t do to piss him off.

The barber leaned into her, lifting a long lock of hair over her ear, and whispered. “You ain’t gonna be no pretty girl when you walk out of here, honey.”

Leslie swallowed hard as the clippers whirred to life, winding up to a high-pitched whine that seemed eager to have at her crowning glory. She swore she could hear the individual blades gnashing against one another as they came close to her face.

Out of the corner of her eye, she thought she saw someone, but quickly brought her attention back to the mirror and the long-haired girl that stared back at her, with the curtain bangs and sheets of platinum blonde surrounding her as they danced over the cape.

“Let’s give the boy a show, shall we?” The barber chortled, as he spun the chair away from the large plate glass mirror and towards the front of the shop, where the same boy looked in, his hands shielding his eyes as he looked through the window. The sun reflected off his naked scalp, but she met his eyes through the glass, wide and fascinated by what was about to occur.

Unable to see anymore, she only felt the sensation as the blades of the clipper slowly bit into her long bangs. Rivulets of silvery blonde silk rolled off her shoulders and onto the black and white tile floor, quickly covering the red curls that had been so stark a moment before.

“No changing your mind now, girly. I bet he’s as stiff as a flagpole under those jeans of his. What do you think?” The barber prodded obscenely, seemingly aware of the strange, fleeting relationship she and the boy had shared only a few moments before.

A second pass with the clippers, and it was evident, even without seeing, that something was drastically different. Leslie could feel the cool breeze from the ceiling fan caressing her scalp, which she knew was as naked as the boy’s had been.

Another pass, and then another, and the breeze against her scalp was palpable, almost cold, its virgin surface never before having been so rudely exposed. Leslie struggled to look to the side, only to catch a glimpse of what was happening to her gorgeous hair. He denied her of that, angling the chair ever so slightly away from the mirror.

The boy was still glued to the window, only now he wasn’t alone. Three more boys had joined him, and it had turned into some sort of perverted peep show.

“Look at them, girly girl. You know they’ll never forget the time they watched the prettiest girl in school get her head shaved bald.” He teased.

Leslie wondered how he knew, yet she couldn’t stop absorbing the sensation of the clippers as they worked their way up the back of her head. She felt his breath, the barber’s breath, as he exhaled against her freshly exposed scalp. ‘Was this really happening?’ Questioning herself. She was being shaved. She was being shaved bald! “Oh my God!” She suddenly blurted.

“Oh, yes, young lady. Are you just now realizing what’s happening?” He boasted, stripping another swath of long silvery hair from her head. The metal of the clippers was getting hot, the blades struggling, but only slightly, as they severed her luscious blonde locks.

Then, suddenly, she was the boy, the barber tossing her head back and forth, just as he had with him, nibbling behind her ears, in front of them, and then in that most intimate place where her skull met her neck. She felt the blades as they found that small valley, making certain that she was as bald as the boy.

Yes, she remembered how he had looked then, when the barber was searching for any errant hairs, knowing that she was no different. He was bald then, just as she was bald now. She looked down at the sea of hair that littered the floor, the black and white tile hidden by what had been shorn from her head.

Finally, the clippers fell silent, finding their place on the hook under the counter. The boys in the window cajoled with one another as they went their separate ways, having witnessed her humiliation. They would never forget her, but for reasons that she was too embarrassed to even consider.

Leslie felt the chair being turned, and she instinctively closed her eyes, not wanting to witness the devastation that was sure to be revealed to her.

“Open your eyes. It’s all gone, girly.” The barber chuckled.

So, she did. She opened them slowly, but the image could not be denied. The familiar face she knew so well was gone, replaced by a white, hairless, bulb. Leslie tried desperately to see it any other way, but her small pretty face was eclipsed by the expanse of naked scalp that overpowered it. There wasn’t a trace of hair, unlike the boy. He at least had a slight tinge of red, where she had nothing at all.

“I’m bald.” She said under her breath. “I’m really bald.”

“Not so pretty now, are you.” The barber laughed. “Billie told me, you know; ‘she’s the prettiest girl in school’ he whispered.” The barber slipped the cape from around her shoulders, and snapped it, sending a rain of long blonde silk flying into the air. “Nope.” He exclaimed. “Pretty just doesn’t come to mind. Not anymore.”

Leslie reached up and ran her fingertips over her head, the sandpaper stubble shocking to the touch. That was all that remained of her hair, she knew. She folded her ears back with her hands, but they insistently popped back, the only distraction from the round bald knob, as they protruded from the sides.

She stood, in a daze, and handed over whatever fee the barber demanded, she hardly remembered. Leslie knew she had to leave, to walk out of that shop and onto the Main Street of her town. By tomorrow, those boys would surely have spread the news of her humiliation far and wide.

As she walked toward the door, she felt the unmistakable clinging of moisture in her panties. ‘Had she peed herself?’ No that wasn’t it. The friction of the damp material against her clitoris left no doubt in her mind, what the moisture actually was.

With the tension of the barbershop behind her, she suddenly felt embarrassed. The humiliation of walking down Main Street totally bald, of walking into school the next day, should have been overwhelming. In fact, she should have been terrified. The reality of it was, the only thing Leslie felt was intense sexual arousal.

She had thought less of the boy in the barbershop for having been aroused by his haircut, but there she was, experiencing exactly the same thing. ‘So, it wouldn’t just be the boy that was running home to masturbate, would it?’ Leslie chuckled, inwardly.


8 responses to “The Prettiest Girl in School

  1. I really like your willingly-downgraded stories (though, in stories like this, it’s clear that it’s only a downgrade in the mind of some folks). I loved the imagery you created here of her beautiful hair slinking down the cape as every last bit was taken from her… And given her beautiful features, it’s fun to think that she became even more popular than she ever expected among a certain crowd.

  2. Hi Claire,

    Wow that was an awesome story! I loved the focus of Leslie having her long hair shaved in front of witnesses like Billie. I think it’s always more exciting (and sometimes more embarrassing) to get a dramatic haircut in front of witnesses.

    1. Hi Sam! Glad to see you reading my humble offerings once again. I missed you. Yes, I thought the added humiliation of being shorn before her classmate was instrumental in achieving the utmost in Leslie’s fall from grace. Glad you liked it. Already hard at work with my next piece, so hopefully you’ll enjoy that as well.

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