Gwen’s Degradation 

Gwen’s Degradation 

Gwen Wilson tapped her foot against the tiled floor as she listened to the principal of her son’s school lecture her on her son’s appearance. The 11-year-old lad sat beside her, all innocent and lost. 

“Well Ms. Gwen, I am afraid I will not be able to allow your son to attend the classes until the matter of his tidiness is sorted out. Here, at St. Augustine’s Academy, we take these matters very seriously.” 

She did her best to explain to him that it was entirely her fault as she forgot to make an appointment at the hair salon, but the orthodox principal would not take it. As the youngest senior partner of a law firm and a single parent, she was always juggling between things. A high-profile case has taken up all her time and energy this past week and as a result, she has forgotten to take Leo for his trim.

“That is certainly not an excuse we entertain I am afraid,” the principal said with a pinched expression.  

And even though Gwen wanted to roll her eyes at him, she chose to put on a smile. “I understand. But I am sure you can do something about it.”

And he did have a solution. You can take him to our in-house barbershop and Mr. Cain will take care of the problem.”

She detested the idea of taking her son to a barbershop as she would never grace her presence in a place like that. But she could not let Leo miss a week at school. Much against her better judgment, she acquiesced. “Alright if that’s what it takes.”  

The principal pulled out two cards from a drawer and thrust out his hand. “Here, take these. You are going to give him these red cards and he will do the needful.” 

She finally found the in-house barbershop of St. Augustine’s Academy and pushed through the door. The sight that welcomed her was completely stranger than what she was used to. It was like a one-chair establishment and a waiting bench. On the opposite, there was a countertop that held an assortment of combs, scissors, clippers, spray bottles, shaving equipment and other items. The rest of the place was borderline dingy.  

A man came through the back door, donning a white uniform and black pants. His hair resembled those of military guys and so does his physique.

“I am looking for Mr. Cain,” said Gwen. 

“And you have found him.” He wore a stern expression and stood with his arms crossed over his broad chest. “And you are…?”

“Ms. Gwen. And this is my son, Leo,” she introduced and then outstretched her hand holding the red card. “The principal sent us here. My son has run into a little trouble with his hair and we were hoping you’d be able to help us.” 

He stepped closer, inspecting the young lad’s head with much disdain. “I see that. How many trips to the barbershop did he skip?”

Gwen did not like his condescending tone. If she hated the principal earlier, she despised this draconian barber even more. “Well, it’s not his fault. It’s mine. I could not find the time for an appointment.”

Mr Cain turned the chair around and ordered the young lad to climb up. “C’mon boy, let’s take that mop off your head.” 

Leo did what he was told while Gwen chose to sit on the waiting bench. She watched her boy being caped and the barber quickly combed down his head full of golden curls. “The school rules say off the collar, over the ears and no fringes. The shorter the better,” he narrated, fingering the curls and the length at the back. “But it looks like we have to take it tighter and shorter than required.”

Gwen did not feel very good about this. And the pit in her stomach dipped further down when she watched him pick up a clipper instead of a pair of scissors. With his big hand, he firmly guided Leo’s head down and ploughed the machine right up the back of his head through the cow lick. Before the curls could roll down to the floor, he made another pass and then another, until the entire back of the young lad was mowed down to a stubble. 

Gwen could not believe the massacre of such beautiful curls of his sweet boy. The barber was practically butchering his head. But for some reason, she felt powerless to stop him. For a wild moment, she wondered how the clipper felt against the scalp. But then again, the thought was as dangerous as intriguing. 

The barber briefly glanced at Gwen and then attacked the sides, shearing them to the same length. He moved on to the top and decided to exchange the clippers with the spray bottle and comb. Once the tresses were drenched to his satisfaction, he picked up the scissors and started chopping off good five inches of length. Eventually, Gwen realised that even though the top was spared from the clippers, the fate of her boy’s hair was still doomed. Oddly, she could not stop looking. 

Apparently, Mr. Cain was as devious with the scissors as he wielded the clippers.

Within minutes, he reduced the top to the shortest length, leaving a small bump in the front and then tapered out the look. Finally, he dispensed a pump of oil in his hand, liberally massaging over Leo’s head and then creating a sharp parting. 

“What do you think?” Mr Cain asked Gwen as he released the newly shorn boy from his chair. 

Gwen felt her son’s head and almost grimaced. The sides and the back were like velvet and the top was savagely short for her liking. “I think it’s enough for the principal to let my son attend the classes. I don’t want him to miss the school for…something as silly as a haircut.”  

Mr. Cain patted the boy’s back, instructing, “Off you go, son. Back to classes.” 

When the door closed behind the young lad, the barber turned to her. “You didn’t like the haircut.”

“It’s shorter than the required length,” Gwen said tersely. 

“It is,” he admitted with an air of authority. “That’s what the red card is. Kids who are sent here with a red card get scalped because that’s the punishment for slacking on their haircut.” 

“It’s just hair, for God’s sake!” Gwen huffed. She has failed to understand the fixation with the hair of St. Augustine’s Academy and its teachers.

“We will see about that,” the barber said as he turned the chair towards her. “Come, it’s your turn now.” 

Gwen froze. “Excuse me?”

He pointed at her hand. “You are holding a red card, aren’t you?”

She looked down and momentarily lost her words. “Yes…but that’s because I was mistakenly given two cards.”  

The barber shook his head with a dead cold expression. “It wasn’t a mistake; I assure you.” 

“You got to be kidding me!”

“Ms Gwen, didn’t you just admit that Leo’s untidy appearance was your fault?” 

“Yes, but…” 

“So why should the boy alone be penalised for your mistake? The parent responsible for the child is equally answerable as far as my logic dictates, don’t you think?” 

Gwen sat tongue-tied. Never in her glorious legal career has she been challenged and left speechless. People knew her as a shark; one who left others dumbstruck. But sitting there, watching him brandishing the clippers with absolute authority and muscle made her feel malleable. 

“Young lady, let’s not waste my time. Sit down, right now!” He snapped, almost making her jump. 

Dread started to fill her. “What kind of…a haircut?” 

“That is my decision to make.” His voice dropped dangerously low. “Sit. Down.” 

She shook her head in a feeble protest. “There’s no fucking way I am getting my hair done in a barbershop! Absolutely not!” 

The barber calmly strode to the door and locked it. 

Gwen was quickly up on her feet. “What are you doing?”

“As much as I despise unruly appearances, I detest the usage of such profanities within the school campus. Perhaps, I need to teach you some manners before I will have you in my chair, tightly caped and secured.” 

His demeanour was too composed and controlled. But before she could snap out a snarky comeback, he crossed the distance between them in three long strides and firmly grabbed her by the nape. In a flash, Gwen was pressed against the nearest wall beside the counter as he picked up a paddle brush and smacked it against her pencil skirt-clad ass. 

“What the…you can’t!” She yelped. But the next two smacks drowned her voice. “Ouch. Stop. It hurts, it hurts!”

“Apologize.”

“What?” She tried to turn her head despite the firm hold. “No way—” ‘Smack’ “Ow! Okay, okay. I am sorry!” 

The spanking stopped and the hold against her nape slackened a bit. She took this moment to turn around, facing his stern profile. “This half-baked apology is not good enough so I will give you another opportunity.” He tapped the paddle brush against her skirt. “Take this down and bend over the counter.”

Gwen froze. “I am not a student. You can’t…I mean…” One hard look from the barber cut her off.

She hopelessly looked between the locked door and the man and finally gave in. Stepping up to the counter, she gingerly reached for the zip of her skirt and dropped it. The fabric pooled around her legs as she shamefully bent over like an errant student. 

Mr. Cain watched as the sophisticated woman was being reduced to a meek lady with just a few spanks. And the knowledge that he held some power over her made him act quite forceful. He exchanged the paddle with the leather strop that was often used for sharpening the straight razors. 

“With the students, I generally use the paddle brush or my hand.” He traced the curve of her panty-clad ass, making her wince. “That does that job for me. But with stubborn, ill-tempered and arrogant parents, I like to use this.” The leather strop cracked against his palm making Gwen flinched. 

“And spankings are best given on the bare.” Unceremoniously, he pulled down her panties letting them snag around her knees and ordered, “Keep them here.” Though her parted thighs kept the panties in place it also allowed the shameful visual of her privates exposed to him. Oddly enough, mortification dampened her lips.

Thwack. “No cursing at St. Augustine’s Academy! Is that understood, young lady?” 

“Yes,” came a strangled, little voice. 

Thwack. “Yes, what?” 

She closed her eyes as if to hide the embarrassment. “Yes, Sir.” 

Thwack. “You will sit on the chair without throwing a tantrum. Is that clear?”

“Yes, Sir.”

Thwack. “And you will have the haircut I give you, without so much a peep.”

“Yes…Sir.” 

Thwack. “Stand up.” 

As soon as she obeyed, her panties joined the skirt pooled at her feet. The barber decided to actually make her comply but physically taking her forearm and putting her on the barber chair. Gwen hissed when her sore and naked red bottom came in contact with the leather seat.

“Perhaps that sting will keep your mouth shut and make you behave. If not, I do have a cane in the back,” he threatened. 

He tied the cape a little tighter and proceeded to take off the eloquent French bun she had done in the morning. Little did she know that her hair would taken down by a barber with little to no care. 

“That’s quite an amount of hairspray,” he muttered, struggling to run the comb through the chestnut locks. And after a while, he gave up. “No, this won’t do.”

The comb was swapped with his trusty, pointed scissors and Gwen felt the steel against her nape. He grasped a section and lopped it off at her neck and decidedly dropped in her lap. A good 7-inch of chestnut locks lay lifeless now. And when she forlornly tried to look down upon it, her head was jerked up for the next cut. Heaps of shorn hairs filled the white cape as a lone tear slid down her eyes. 

When the barber finally paused the assault, she realised that her hair only grazed the delicate neck.

He gave her a comb over now, moving on to snipping the length at the back.  

“I have never had short hair,” she sniffled over the incessant sound of the crunching blades. 

“Perhaps you will like it then.” 

More hairs rained around her as she endured every lift and chopping motion. She thought for a moment as to how she would explain to her colleagues and contemporaries about the shorn state of affairs, how the entire event was wrongful but what she has failed to explain to herself was the growing moisture between her legs. 

She hated the haircut, undoubtedly, and yet she could do little to prevent it. Gwen had never felt so submissive and powerless at the hands of another, the gasping arousal as the barber reduced her precious locks to a degrading length of a man’s head.

The barber, having chopped her previously jagged bob into a pixie, went on to grab the clippers from the counter. As he oiled the machine, he spoke, “I could have stopped at short back and sides, just to give you an idea so you won’t make the mistake with your son. But I believe you will like this even more.”

Terror and thrill filled her in equal measure when she heard the menacing buzz. The firm hand held her by the nape and the clippers ploughed right through the middle of her head. Gwen jolted slightly at the feeling, with a raging vibration against her scalp. Her closed eyes took in every pulsating pass over her head, and her pussy throbbed even more. 

She could not help but reach for her clit. “Oh! Oh…” she moaned as the barber reduced the top to half an inch. Pass after pass lined until the hair was shortened to his whim. 

He noticed her and purposely drove the clippers slower and tighter, making her feel the vibration more acutely than ever. It ran around her ears, baring them and when her head was pushed down to her chest, her nape to crown received the same fate as the top. 

Gwen was close, so close to exploding when the clippers halted. A frustrating whimper made past her lips as the barber smiled.    

“So, I was right. You do like the clippers. Don’t you?” He teased, rubbing his long, calloused fingers over her shorn head. Gwen felt the heat from his skin and bit her lips.

“It’s alright, I get it,” he said, going over the counter. “This was just number 4 and allows some length. Now this…” He removed the guard and waved the device in front of her eyes, “…will feel even better.” 

Gwen dejectedly looked at it and bowed her head. 

“That a good girl,” she heard him say before the droning buzz filled the space. 

He ran it over her nape, higher and higher until it touched her crown. He folded down her ears as he would do it with those little school boys and bared the perimeter. Shredded hair filled her neck and shoulders as the previously cut half an inch gave away to her white scalp. 

Gwen felt the hot steel teeth more intently as her scalping continued. Her fingers worked desperately, fearing the vibration would stop as she chased the orgasm steaming from the throes of her humiliating haircut in a barbershop. Within minutes, her climax was denoted followed by the halt of the clippers. 

“We still have a lot more to do,” the barber said, picking up a different clipper. 

The half-inch length was tapered and faded with the whitewalls as the clippers went back and forth against her skin. When it all ended and the barber spun the chair towards the mirror, Gwen’s jaw dropped. 

She was unrecognisable. Her head sprouted less hair than her son with the longest being on top that could hardly be pinched between her fingers while the rest of her head was shaved to the bone. If it wasn’t for her diamond studs, she’d look like a man.

The barber removed the cape, exposing her nakedness. 

He took the liberty of stroking her clit, then trailing a finger along her swollen, wet lips as she whimpered and watched herself getting defiled in the mirror.

“I will see your son every fortnight. But you will come to see me every week and without fail.” 

His free hand reached out for her head, fingertips scraping against her shaved nape and higher.  

“This haircut will remain constant until I decide otherwise,” he whispered against her ear. “And if dare to skip the appointment, remember there’s always a parent-teacher conference. Unless you want to end up bald, you will keep the appointment. Is that clear?”

“Yes…sir,” came her strangled reply.