I have to say, that for the most part, I am a fair employer. I have ten people working for me in my office and it has thrived for nearly five years. Four of the employees are men, and six are women. There is no real preference, everything is based on skill and experience.
So, it was upsetting when one of my most valued employees decided to move on to another position. I gave her a good reference, of course, but was sad to see her go. Most importantly, it left a gaping hole in my schedule.
I had interviewed at least twelve prospective hires, but was so disappointed in the turnout that I decided to hire a headhunter. That was precisely when Sherry Youngs walked through my door. Lucky thirteen, I guess.
Sherry interviewed well, displaying an advanced intellect, and was frankly overqualified for the job. Having an MBA from NYU would normally open plenty of doors. Despite this fact, when I offered her the job, she took, no questions asked. Something was fishy with this situation, but I was not about to talk a gift horse in the mouth, as it were.
To be honest, Sherry was quite stunning. At nearly six feet tall, she towered over just about everyone else in the office, including most of the men. I guess one might refer to her as statuesque. I imagine she would even be considered beautiful under the right circumstances.
I could tell her hair was quite long, but she wore it up, in a twisted blonde bun. After she had been with us a few weeks, I noticed that she never changed that style and I often wondered just how long her hair really was.
Rachel, one of my struggling but reasonably competent employees confided that she saw Sherry with it down in the ladies’ room. Apparently, it was well past her waist.
Do I have a hair fetish? Not as such, but rather a penchant for the lack of it. It wasn’t something that I was proud of, but there it is. Everyone has some little quirk, and as innocent as it was, this was mine.
Sherry was an outstanding worker, and quickly became one of my star employees, all that in a matter of a couple of months. So, it was quite a surprise when she came to me with a problem.
“Come in, Sherry. What can I do for you?” I asked, seeing the concerned look on her face. She and I were the only ones left in the office, the only ones with that sort of drive to excel.
“I have a slight problem, Mr. Williot. I seem to be rather short, financially this month. I was hoping that you might be willing to give me an advance to make ends meet?” She had taken a seat in the chair opposite, and I could see that she was sincere.
“Sherry. I have to tell you that I do not, as a rule, offer advances to any of my employees. It sets an unsustainable precedent. I hope you understand.”
“Look, Charles.” She leaned forward over my desk. “I’m in a bit of hot water.”
“How do you mean?” I asked, not insulted by her admission. I could see that she was reticent to discuss whatever it was, but I had a feeling it was going to come out.
“I have a bit of a… gambling problem, Mr. Williot.” The pain in her expression that accompanied that admission was nearly palpable.
“There are organizations that specialize in that problem, Sherry. Gamblers Anonymous, for instance.” I suggested.
“I know, and I’ve tried. I just keep falling off the wagon.” Sherry sat back, slumping into the chair.
It was starting to become apparent why she was working so far below her credentials. I wondered if she had burned one too many bridges with her habit.
“How much?” I asked, knowing I was crazy for even entertaining the idea.
“Two thousand?” She mewled, ashamed of it.
“Two thousand dollars?” I asked, matter-of-factly
“That would pay off my debt.” She sighed.
“And what of your debt to me, should I grant you this advance? It would take you quite some time to pay off a debt of this size, on your salary.”
“I’ll do anything you say,” Sherry whispered.
I wasn’t certain, but I thought she had just told me that she would do anything, so I repeated it back to her, to be sure. “You’d do anything?”
She simply nodded. I’ll be candid and say that my cock twitched just a little with her admission. I think to be safe, anything blatantly sexual was off the table. That would simply open me up for all sorts of problems. No, this had to be done in a way that I would enjoy, but not in so forward a manner.
“Take out your bun, Ms. Youngs,” I said, haltingly.
I think my request took her by surprise. She indicated the two tortoiseshell prongs that held it in place, and I simply nodded. Upon their removal, her hair tumbled over her shoulders in a waterfall of golden strands that nearly took my breath away.
She smiled, wryly, and worked her way around my desk, dropping to her knees in front of me. She was about to reach for my zipper, when I interrupted her plans.
“Turn around, Sherry,” I suggested, sternly.
“I thought you…
“Stay on your knees, just turn around so that you are facing away from me.” My request puzzled her, and I could tell she had no idea where this was going. “How much money did you say you needed?”
“Two thousand dollars.” She uttered.
“I cannot advance you any money, Sherry.” I saw her head drop in disappointment. “But I can give you the money, in exchange for something else.” I opened my desk drawer, pulling out a rather substantial set of sheers. “Are you willing to make that exchange?”
“Yes, anything. I really need the money. I’m afraid they’re going to come after me.” She warbled, desperately.
“A thousand a foot.” It was all I said, but as I ran my hand through her fantastic tresses, she got the message. A small whimper, and then she regained her composure.
“You want to cut my hair?” She asked, horrified.
Again, I repeated. “A thousand a foot.” I could almost see the wheels spinning in her head, computing her losses. Finally, she nodded. “Say it, Sherry. You have to say it.”
“Fine.” She muttered. “A thousand a foot.”
I could tell she was sweating bullets as I wrote out the check. She jumped ever so slightly when I tore it from the ledger.
“There you go.” I handed her the check over her shoulder, and she took it greedily, examining it. I could see from the tension in her shoulders that she was considering bolting for the door. “If you run, I’ll stop it before you ever reach the bank.”
Then came the resignation that I had been waiting for, when I knew she would willingly submit to the sheering without argument or threat of retaliation.
Measuring it out, I used a sheet of copy paper, adding a couple of inches for the shortage. Holding my fingers at the mark, I secured the hair with a rubber band one inch below.
“Are you ready to make the payment?” I asked, scissors at the ready.
There was a moment of resolve, where she knelt taller, but as I did not make the cut right away, that resolve faded one again into resignation.
“I asked you a question, Ms. Youngs.” I said, firmly.
“Ready for what?” I pushed.
“I’m ready to make the payment.” Raising her voice ever so slightly.
I wished I could have seen the look on her face as the scissors gnawed into her hair. There was no mistaking the slight scent of what could only be arousal that emanated from her during those few seconds. If it had taken ten seconds it was a lot, but those ten seconds were some of the most erotic that I had ever experienced. I doubted that I would ever enjoy that sensation again, ever, so I savored the afterglow of the damage I had wrought.
The hair that once covered the top of Sherry’s buttocks now just grazed her shoulders. The cut wasn’t half bad, to be fair, only a few errant hairs that escaped my cut, remaining below the line. I offered to straighten it up for her, but she had had enough for that night, and stood, backing away from me.
“If it’s any consolation, Sherry, it actually looks good on you.” I offered.
“I can’t believe I let you do that.” She accused.
“You needed the money, I needed the hair,” I smirked, laying the severed ponytail on my desk reverently.
She disappeared, most likely to pay whatever loan shark she owed the money to. I doubted she would be back.
The hair itself held little for me, other than as a reminder of the act. I lifted it to my nose, smelling whatever conditioner she must have used that morning. Make no mistake, I would cherish the hair and I began to think of creative ways to display it. In the end, I simply deposited it in my drawer with the scissors.
Much to my surprise, Sherry did return to work the following week. She had called in that Friday, no doubt to visit her hairdresser. I would have loved to have been a fly on the wall for that conversation.
Gone, was the bun, replaced a blunt bob that was only a tiny bit shorter than I had left it the previous Thursday night. She looked damned good, and everyone in the office complimented her on how brave she had been, and how well the new cut suited her. If they only knew.
There were no looks or private conversations concerning what had happened between Sherry and myself, nor did I expect there to be. It was a business transaction as far as I was concerned, and it appeared that Sherry was being a good sport about it.
I fully expected what happened next. It had only taken a little over two months for Sherry to return to my office one evening, begging to be bailed out again. I had sincerely hoped that she had mended her ways, after the ‘haircut’. Part of me was excited that she hadn’t, but another part of me was disappointed; a very small part.
“How much is it this time, Ms. Youngs?” I asked as she stood uncomfortably at the foot of my desk.
“Twenty-five hundred.” She moped, knowing how little she had left to bargain with.
“Well, that’s thirty inches of hair, and I doubt you’ve got half of that.” I mused.
“I know. I was hoping we could make, other arrangements.” She suggested.
I knew full well that she was referring to sexual favors, something that seemed enticing but dangerous. “That’s out of the question.” I thought for a moment about just how I could best take advantage of this situation.
“Then I don’t know what else I can do, Charles. I’m desperate here. They said they would make it hurt this time.”
Hearing the almost frantic tone of her voice, I knew that I could request almost anything and she would probably comply. “I tell you what we’re going to do. I’m going to take as much payment as you can afford right now, and then take payment once a month until the debt is paid. Hair grows at half an inch a month, meaning we should be square in two and a half years.
“Whatever. Do what you must. I just need the money.” She said without thinking.
“Very well. Follow me.” I led Sherry out through the offices and, shutting off the lights, locked the place up.
“Where are we going?” She asked nervously, as I opened the door to my car.
“To see a friend.” I returned, making my way down through the older part of town. I glanced over to watch her every now and again, and I could see that same resignation that I recognized from her first ‘advance’.
I hadn’t been down to Burns Barbershop for quite a few years, but I remembered going there as a young man. Famous for cuts that were always a little shorter than you asked for, it had been a regular haunt for me before I started the business. There was one barber in particular that I was looking for, and sure enough, he was sitting in his chair, the newspaper open and a cigarette burning in the built-in ashtray that resided in the arm of the oversized barber chair.
Pushing through the door, Sherry in tow, I was thrust back into my youth and it made me wonder why I had ever stopped going there.
“Well, look who the wind blew in.” The old man bristled, folding his newspaper and snubbing out his cigarette
“How are you, Cliff.” I returned.
“Charlie. Never figured on seeing you again.” The last time I had been there, Cliff had relieved me of my hair after I had requested something a bit shorter. I ended up with a crew-cut, and a short one at that; the sides shaved smooth with a razor. It was a way to nurture my burgeoning fetish for short hair.
Now I was about to watch my ultimate fantasy come to fruition. When I sat in those chairs, waiting for my cut, I would often dream of a beautiful woman with long flowing hair, walking in and having her hair cut short, by one of the Burn’s barbers.
“I’m not here for me.” I corrected.
“Not her. You can’t be serious.” Cliff chuckled.
“Sherry, this is Cliff Marcus. He owns this shop.” As their eyes met, Sherry immediately forced hers to the floor. “She owes something, and you could help me collect.”
Cliff suddenly stiffened, but then a knowing grin spread across his face. “I see.” Was all he said, snapping the cape that been folded behind him over the back of the chair. “Why don’t you have a seat, Sherry.” Cliff turned his chair so that it faced Sherry, who was nervously fidgeting beside me.
“Climb in, Ms. Youngs,” I ordered.
Slowly, she walked over to the chair, and spun to sit. Her tall stature fit the old-fashioned barber chair, all but the blunt bob, which seemed conspicuously out of place.
“How much are we…collecting?” Cliff asked, looking back and forth between Sherry and me.
In the first words she had uttered since leaving the office, Sherry finally spoke. “All of it.” Resolutely, she shook her head, causing the blonde bob to bounce and swing about her shoulders.
Cliff snapped the cape around Sherry’s neck and I took my place in the chair opposite, as I had so many times before.
“All of it, huh?” Cliff mumbled, as he lifted the old Oster Classic 76 off the hook and changed the blades with a snap. The clap of the motor firing up, caused Sherry to jump a little, which in turn caused my already stiffening cock to twitch. This was my fantasy.
“To the bone,” I suggested, garnering a smile from Cliff as he examined the superbly coifed young woman in his chair.
Without any warning or fanfare, Cliff ran the Osters right down the middle of Sherry’s head, revealing her jet white scalp. Mercilessly, she sheered her, like a sheep. It was the only analogy that came to mind. With his practiced knowledge of the skull beneath the hair, Cliff had reduced Sherry’s bob to absolutely nothing in a matter of a single minute.
The floor around the chair, which had seen its fair share of hair, was covered in discarded blonde strands, lifeless and somehow less significant separated from their roots.
I could see Sherry, her shocked expression in the large plate glass mirror locked in place. Her mouth was open in a little O, and it was just as I had imagined it. Breaking my reverie, Cliff laid a hot towel over Sherry’s head, wrapping it expertly as he had so many times in his life.
I could see the tenting of Cliff’s trousers, and I knew he was enjoying this every bit as much as I was. I wondered if he was partaking of that slight scent of arousal from Sherry that I had smelt in my office that fateful night.
Without the hair, Sherry’s stark angular features were exaggerated and almost made her appear a bit masculine. Her long ears, which matched her tall stature seemed a bit out of place now. How wonderful, I thought.
Removing the towel, the whine of the lather dispenser indicated the final stage of this spectacle. The chairs around me had filled in, not with customers expecting a cut, but rather observers, that had been passing by outside as the main event was unfolding.
One of the other barbers could be seen leaning against the jamb of the rear door, smirking lustily at the violent de-tressing.
“Oh, my god.” Was all Sherry could manage as the straight razor began to make short and deliberate strokes over her scalp. It was an artform, shaving a head as Cliff did. The eyes of the men on either side of me widened as the glassy smooth surface of Sherry’s scalp appeared. Her naturally blonde hair made for a very clean white appearance, with no sign of stubble under the skin. It was glorious.
Of course, Sherry didn’t think it was glorious at all. For a moment I even thought I saw a tear form on her cheek, one which she swiftly brushed away with a caped hand.
Cliff, ceremoniously removed the cape in a flourish, eliciting a subdued clapping for the assembled men, who one by one escaped into the night. One would even suspect that the entire thing had been staged, were it not so spontaneously done.
The only person who did not leave was the other barber, who was quick to point out the flaws in Sherry’s otherwise pasty-white pate. The commentary must have been devastating to Sherry, who had not only undergone an appearance-changing event, but was now being picked apart for the flaws in her scalp and skull structure; a scalp which they themselves had denuded.
“Don’t listen to the man, Sherry. You have a lovely head, one which I am looking forward to enjoying for many, many, months to come.” I thought that perhaps my comments really didn’t help her come to terms with her new stark appearance.
Sherry was, for all intents and purposes, still a handsome woman, and I would probably be hard-pressed to find another so well-appointed. I helped her from the chair and could feel that she was physically shaken from the experience.
Cliff had grabbed a broom and was about to sweep up the mounds of blonde hair that circled his chair like a moat.
“Are you going to allow my friend to clean up your mess, Ms. Youngs” The look she gave me was priceless. As dutiful a recipient of my generosity as she was, she took the broom from Cliff’s hands, sweeping up her own hair from the well-worn linoleum tiles. When at last Sherry had cleaned up her sheddings, we bid goodbye to Cliff and his rude employee, who had made me look good in comparison, and for that I was grateful.
“How will I explain this to my boyfriend?” She muttered under her breath, thinking I had not heard her over the road noise, as we drove.
“Well, Ms. Youngs, how would you have explained an illicit affair with your boss? I don’t know which would be more harmful.” I chided.
“This,” She indicted her head, which reflected the lights from outside nicely, “I can’t lie about.”
The following day, I fully expected to receive a call from Sherry concerning her absence from work. She did surprise me on that front. Much to the shock and horror of the other staff, she did show up, and in all her gleaming glory.
I paid her debt, of course, but with the strictest instructions concerning her gambling. If I so much as caught her near a bingo hall, the consequences would have been even more severe than the one she was already paying.
Her boyfriend left her, of course, especially after she told him the truth. And so, I wasn’t all that surprised when she showed up at my door, a few weeks later, suitcase in hand. It was going to be a wonderful couple of years.
One response to “The Advance”
Great story! Interesting scenario.