The Master Disciplinarian: Session One

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My head was reeling with apprehension as I parked the car. I had considered turning around and leaving, but the choice wasn’t that easy. Not because I was coerced, but the alternative was criminal charges. 

I worked at a renowned investment agency, and for about six months now, I have been pinching a few hundred dollars, here and there. Initially, it was fun, but I found myself between the devil and the deep blue sea when the amount tantamount to five thousand dollars. 

So when my boss, Ethan Fischer, found out, he was kind enough to give me a get-out-of-jail-free card. That I’d have to attend a session with the ‘The Master Disciplinarian’ and submit to whatever punishment he deemed fit. And now, here I was, outside his door to do my penance. 

“Come in,” a masculine voice answered from the other side as I knocked and entered. And the sight that greeted me was a little unnerving. 

Sean Caldwell was sitting on the other side of his desk. He was in his late thirties, six feet three inches of perfection with an immaculate hairstyle, and donned a spectacular pin-striped black suit. 

“Good morning, Miss Collins,” he said and pointed to a chair. “Please take a seat.”

“Morning, Mr….”

“Sir,” he cut in sharply. “I prefer to maintain a high protocol during professional hours.”

” Sure…I mean…Sir.”

“You are an employee of Fischer Investment Inc. I believe,” he remarked, picking up a folder from the table with an engraved logo of the company I work for. And no doubt it was sent by my boss. “In all my dealings with them, I have found that they are very particular about their goodwill as well as the reputation of their employees. Which often leads to them to hire my services.” 

Often? I wondered who else was sent here before me. 

“Yes, Sir,” I mindlessly agreed. 

“Right.” He shut the file and looked directly at me. “I had a rather extended conversation with your boss, Ethan, last night, discussing the measure and severity of your discipline owing to the gravity of your crime. Embezzling company funds.”

“Look, I am really….”

He quickly held up his palm. “Hold on to your apology because I assure you that you will get plenty of chances for penance later. But, for now, please come and stand here,” he pointed at the spot beside him. “And while you are at it, let down your hair.”

I just wanted this ordeal to get over and leave. So, I stood up and stiffly complied, awkwardly pulling the pins out of my messy bun. A thick curtain of coppery locks cascaded down my back, and somehow I felt like my shields were taken down. I have often been complimented for the length and shiny of my hair, being naturally straight and voluminous. 

Sean Caldwell scanned me from head to toe in a manner that almost ran a slight chill down my spine and gave a small nod. “Good. As per my telephonic conversation with Ethan, your punishment will be dished out in two parts that fit your crime. One, you will receive a certain number of strokes with a cane. And two, you will be donating your hair for charity.”

I swear, the ground beneath my feet slipped. “What?” I gasped. “You can’t be serious….”

“I am as serious as the crime you have committed,” he shot back. “While the caning will serve as a quick rectification, one that will keep your backside sore for the next few days, the loss of your precious locks would make you truly penitent in the long run. Ethan has requested for a prolonged reminder, preferably something that you won’t soon forget.”

“I have never had short hair. I…”

“I don’t see how that’s a problem. Besides, you will be donating the hair for charity.” 

“Hair, right,” I was slowly registering the words. “And a caning?”

“Yes. Have you heard the saying, ‘six of the best’? Six strokes on the bare, and if you want to keep your clothes on, I believe the number would double up to twelve strokes. The choice is yours now. Six or twelve, Miss Collins?” 

My throat closed up. “Six,” I croaked. 

“Right. Please go and stand beside the couch and bare yourself from the waist down.” 

When I didn’t move an inch, wondering how did I land up in here, the rich baritone of the ‘Master Disciplinarian’ snapped me out of my reverie. “Miss Collins, my patience only extends so far as my professional commitment lies. You have a choice here — either go through this or walk right out, and no one will stop you. So make a quick choice, please.”  

Dejected, I wadded over to the couch and angrily yanked down my skirt. He merely looked at my way and raised a brow, prompting me to go on until I was well truly ‘bare.’ And only when my lacy panties joined the skirt on the floor, he coolly came forward with the dreaded cane in hand. 

My memory went blurry. One moment I was standing half-naked, and in the next, I was bent over the arm of the couch, and my legs widely spread. A firm hand was set on the back of my neck, holding me in place while his other hand swung back. Finally, a calculated flick landed on my ass, almost making me break the position if it wasn’t for the solid weight of his hand. By the third strike, I was cursing and sobbing. All six landed at different spots – from the swell of my asscheeks to the back of my thighs and sat spots. No wonder this man was professional. 

 “You can get up now and put on your clothes. Then, whenever you’re ready, let me know.” 

As badly I wanted to put on my clothes, even the merest touch of fabric throbbed my skin. Next, Mr. Caldwell led me to another room, one with a big chair placed in the center and made me sit on it. It was only then the reality dawned on me. 

His fingers gently ran through my long hair, reaching down to my lower back, and for a fleeting second, it felt exhilarating. “You have truly beautiful hair,” he murmured, too close to her ear. “Shame, we will have to chop it all off.” 

My heart was racing, and my stomach dropped. 

“I will call in the barber whenever you are ready.” 

Panicky, I shook my head. “Just get it over with. I don’t think I will ever be ready for this.” 

He fished out his phone, punching a few keys, and a man appeared in a white tunic. He was no hairdresser by any stretch of the imagination but one of those old geezers in male-centric barbershops. 

“Rowen, you know what to do,” he vaguely instructed the barber, taking a seat in a vantage point. The barber wasted no time in tightening the cape around me like a noose and brushed out my hair. It took some time to loosen the knots and secure the bunch with a hair tie at my nape. 

That’s it, I thought. My long hair days are over, and I have to live with a bob from now on.

I was expecting the awful sound of scissors, but instead, a dreadful hum of clippers filled my ears. Fuck. I quickly tried to turn around, but the barber prevented it. “Miss, sit still,” he chastised. The steel in his voice verified that I wasn’t the first unwilling victim in his chair. 

“Perhaps, I might help,” Mr. Caldwell offered as he smoothly walked over and clamped a hand on top of my head to restrict any further movements. 

The barber held my hair taut as the teeth of the clippers sank into the base. Closing my eyes, I could feel each and every strand getting severed. It went on and on until I could no longer feel the tension in my locks and switched off the machine. 

“Here.” The Master Disciplinarian took the bunch of approximately 20 inches of hair and draped it over my lap. “We will be donating this to the charity.” The sight of my hair…my beautiful, virgin coppery hair almost reduced me into broken sobs. The only consolation was that it wouldn’t be thrown or discarded away like garbage. But that didn’t lessen my grief.

“I want to go home,” I whispered, sniffing and tugged at the tight cape. “Can you please remove this?”

“Hang on. We are not done yet.” 

“What? But you said….”

Mr. Caldwell silenced me with a shake of his head. “Miss Collins, do you recall our earlier conversation of a ‘longer reminder’?” His fingers caressed the short hairs grazing my nape at the moment. “I am afraid a shaggy bob is not convincing enough for your employer. It needs to be shorter and sharper. But if you wish to rescind the agreement, all this will go in vain.”

And I realized that there was no turning point for me anymore. So, dejected, I just hung my head and nodded.

“Rowen, please begin.” 

Without a preamble, the barber grabbed a bulky clipper from the tray of accessories and fired it up. He pushed my chin further down, positioning the clippers at the base of my neck, and drove it upwards. I had no idea how short he was trimming the back, but the way he was wielding the device, terrified me. The metal touched my scalp, unnerving me with every swipe. And it wasn’t until he reached my sides that I gasped in terror. Large chunks of hair fell on my lap, on the floor, while he simply maneuvered my head from side to side until I could no longer feel the hair over my ears. I almost sobbed anew at the thought of a pixie cut. 

Next, he picked up a spray bottle, soaking the top, and commenced with a scissor and comb. I could distinctly feel the way he combed out a section, lifted a chunk of wet locks, and snipped them off. The incessant sound of scissors went on and on while I sat squirming in discomfort. In a way, I was glad that there was no mirror in the room, but at the same time, I was dying to look at the state of my hair.  

“Bangs?” the barber paused to ask Mr. Caldwell, who has been keenly watching me rather than the haircut. 

“No need,” he dismissed authoritatively. “And make sure the taper is tighter.”

Taper? I had no idea what words that meant, but when the barber combed down the hair over my eyes and hacked off the entire length ruthlessly, I knew that my ordeal was far from worse. And he didn’t just stop there; he lifted a section with a comb and snipped it shorter and shorter until he deemed fit. 

The barber went over the top and the sides way too many times, snipping here and there, as I watched the small tufts of hair raining down. And after a while, he cared to pause and look over to the other man for approval. Mr. Caldwell gave a brisk nod, and the barber finally put down his tools. 

And just when I thought that things couldn’t go any worse, I saw the barber walk back to me with a can of shaving foam and started to smear it around my head. Horrified, I turned to look at Mr. Caldwell, who simply leveled me with a ‘look.’ 

At the same time, he issued a chilling command. “Shave it a little higher, Rowen. Ethan was significantly insistent about whitewalls.”

“Sure,” the barber answered, promptly squirting another pump of foam in his hand. He repositioned my head once again, pushing it down, and brought the sharp razor against my scalp. And without a shred of doubt, I knew that I was getting an extreme haircut. The blade scraped against my skin in slow and deliberate swipes as I held my breath and tried not to wince in fear. Once the back was done, he folded down my ears and shaved along the perimeter and the sideburns. A small part of me was relieved that I was not completely bald, that even a short amount of hair was left on my head. 

At last, he wiped off the residual foam with a tissue and brought out the hairdryer. Which was completely useless if you’d ask me because he merely ran it for 10-15 seconds, making me realize how devastatingly short my hair was now.

“Is that okay, Sir?” 

“It will do, Rowen,” answered the Master Disciplinarian, and the barber quickly released me. 

It was the ultimate moment of my freedom, but somehow, I couldn’t find the strength to move. Mr. Caldwell came closer, offering his hand as he silently led me into the restroom. And the second my eyes fell on the mirror; I was shocked.

I was bald…not precisely, but there was nothing to speak of my once-glorious mane. I turned my head from side to side, gaping at the vast expanse of shaved skin at least two inches above my ears and more than half my back. Even the weight line of the hair was cut closer to the skin and only about an inch on top – which was the longest. The style was downright mannish with parted sides and slicked down like an obedient schoolboy who received one hell of a summer cut. 

Never in my life, I felt so vulnerable…that I sobbed, burying my face into my palms. A strong arm reached out and held me tight as I wailed like a little girl. Mr. Caldwell yanked a few tissues from the box, wiping the tears himself as I slowly started to regain my composure. It was a strange feeling – being subjected to his discipline and then his compassion. 

“Clean slate,” he murmured, wiping the embarrassing snot off my nose.

“Thank you, Sir,” I whispered softly. 

His long, masculine fingers reached out to touch my head and inspected gently. It was the first time I realized how sensitive I felt with his touch – stroking the exposed scalp, the shortest tuft of hair, and finally tousling the parted top. It was as if he was relishing the haircut…feeling with a kind of fervor that invoked his senses.

He walked me out of the room with the same care, and I grabbed the bag, preparing to leave. Then, silently, he plucked a card off the desk and dropped it in my bag as I gazed up quizzically.

“In case you need my services again.” 

And with that, I left.

By the time I returned home, my ass had throbbed like a glaring reminder while I mourned the feel of the wind in my hair. And yet…yet there was something pulsating about the whole experience. I didn’t know if it was the shame of being bared and caned like a bad girl or submitting to a humiliating haircut or both, but something awakened in me.

Suddenly, my phone pinged with a text: You look good with short hair, Miss Collins. Try shorter next time. And if you are brave enough, call me.

My nerves ricocheted, and I knew I’d be soon reaching out to him. Except, this time, on my own will.

And who knows what’s in store for the next time.



Thank you for reading. I have left a small window open for Part 2 in case you want the story to continue.

4 responses to “The Master Disciplinarian: Session One

  1. Roy,

    Obviously, there is a rather common tread running through a certain percentage of your stories. And, I will admit, both the fantasy (and the reality) of a forced head shave resonates with me on a few different levels. Particularly this story.
    Although the basic idea/concept of this story is not new, your version of a punishment cut with a twist at the end is perfect.

    That being said, as I was reading your latest story, I found myself wishing for a slightly different take on Miss Collins’ punishment. First, I was hoping that she would have been forced to take off all her clothes, and second … that her caning, while appropriately bound, would have been filmed (as well as her haircut) and sent back to her boss, Ethan.

    Regardless, the twist you presented at the end was priceless! I am so looking forward to reading Part 2, if you decide to write it!

    Final note … reading your story today has inspired me to finally finish two different ‘forced’ head shaving stories that I have been working on for quite some time now. Thanks for the inspiration!


  2. Hi Jenna,
    I can’t put it in words how much I appreciate this comment. And yes, I badly wanted to keep the entire ‘caning’ scene a bit more explicit, but I was afraid that the readers might not appreciate it because this site is for ‘haircut’ stories. Hence, I kept it short and restricted. However, for the Part 2, I am planning to explore more. Thank you so much for the feedback!
    All the very best for your stories and I am really looking forward to read them because ‘forced’ stories are so rare nowadays.

  3. I love your stories that have a disiplinarian theme. I also like the addition of other punishment methods. The Hawke Academy series and this one are my favorites. Really looking forward for a part two.

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