Meeting Her Expectations

Story Categories:

Story Tags:

Views: 9,055 | Likes: +72

Meeting Her Expectations


By Shorngirl


         I had always prided myself on my ability to weasel out of responsibilities and sticky situations. It’s not that I didn’t excel at what I enjoyed doing, it was that I supremely hated doing things that I disliked.

         So, I was at a loss as to why I found myself in the most awkward of situations, unable to bargain out of or explain away the actions that led to where I sat now. But I digress; I suppose an explanation is in order.

Three Weeks Earlier

         I was so excited to be starting this new position. It had been a long time coming, and through a good amount of hard work and corporate finagling, I was about to step into a position that I was totally unqualified to fill. I suppose it was a risky bargain, but then, nothing ventured, nothing gained.

         The marketing division of the company had been grooming another person, a man, for the position, and I was determined to step in and steal the spot out from under him and the team that was so determined to see the guy succeed.

         Even though I lacked the required education that was a prerequisite for the job, I had proved to both my manager and their direct superiors that I was more than capable of filling the rather large shoes I was about to step into.

         So, when the announcement came, it was a shock and a disappointment to the other team. To make matters worse, the woman who would be my direct superior was not impressed by the board’s decision. She seemed upset, and I was worried that this might influence how she treated me. Come to find out, the man that was my direct competition for the position had been involved with her at one point, and they had remained close.

         “I’m not quite sure who you bribed, or how you managed to convince the powers that be, but apparently, I’m stuck with you, Madeline.” Those had been the first words from her, after a round of congratulations from my colleagues in my department. I suppose I should not have been surprised, but I couldn’t deny that her

 words hurt a bit.

         Fast forward to my first day on the marketing management team, I was immediately singled out and pulled into Ms. Shire’s office for a ‘chat’.

         “I’m not aware of the dress code in your old department, Ms. Kenyan, but here, we pride ourselves, not only on the work we do, but our professional appearance.” She immediately eyed my hair, which I had gone to great lengths to fasten into a somewhat messy updo. “I’d like you to at least meet the standards that the other members of the team uphold.”

         “This is a brand new suit, Ms. Shire. I hope that…”

         “It’s not the suit, it’s the hair.” She stated, shortly. “You’re going to have to get it cut.”

         I wasn’t sure if this was some kind of punishment that she was meting out because she didn’t like me being there, or if she was actually serious about this unannounced policy. I looked at her, her salt and pepper hair styled into a rather masculine pixie that was neither flattering nor attractive. “You want me to cut my hair?”

         “Is that too much of an ask, Ms. Kenyan, because if it is, we are certainly getting off on the wrong foot.” She frowned, expectantly.

         I gathered all my fortitude and looked at her directly. “No, it’s fine.” I managed. I was very attached to my hair and prided myself on how it looked. Now, I was being asked to cut it, quite certain it was merely to satisfy a vengeful whim. “How short?” There was a tremble in my tone, and I was sure she caught it.

         “Off the shoulders, for now, Madeline.” She smirked, as she sat behind her desk. “We’ll see how you do with that.” She motioned to the door, and I obliged her; retreating to my desk. My hand went to my hair immediately after sitting down, and I couldn’t help but mourn over its impending fate.

         To my surprise, Ms. Shire slipped a card onto my desk that afternoon, informing me that she had taken the liberty of making an appointment for me. If her haircut was any indication of the sort of salon she frequented, I was not inclined to keep it. “If it’s alright, I’ll go to my own salon, Ms. Shire.”

         She pulled up short, looking down at me from the door of my small office. “You’ll keep the appointment, Madeline.” It wasn’t a request. With that, she walked away, leaving my door open.

         Looking down at the card I was more than a little dismayed to see that it wasn’t a salon at all.

Sal’s Barbershop

Unisex Haircutting

For the

Discerning Adult.


         At the bottom of the card, I noticed that a time was written and my jaw dropped at the immediacy of the situation. ‘Six O’clock, TODAY! Do not be late.’

         “Fuck.” I seethed under my breath. I couldn’t believe she was going to get away with this, but I just didn’t see any way around her demand. If I ignored her, things would only get worse for me, regardless of my performance.

         At the end of the day, Ms. Shire swung by my office, acknowledging my work so far, but falling short of being complimentary. “Don’t be late for your appointment, Ms. Kenyan.” She smiled, deviously. “I look forward to seeing the ‘new you’ in the morning.”

         I painted on a smile and nodded, watching as she slipped away from my door, leaving it open once again. Closing out the advanced gradient tables I was examining, I tossed my things into my briefcase. A bit wobbly in the knees, I stood from my desk but refused to give in to my nervous anticipation. “It’s just a haircut, Maddie. Relax.” I told myself, even though I knew it was so much more than that.

         Deep down, I knew this was more symbolic of my bowing to her demands. The haircut would be a constant reminder of her dominance, and that really irked me. So, as I pulled up in front of the modest little shop, I was determined to keep as much of my hair as I could, and still meet her exacting instructions.

         The small plaza was crowded with cars, and I wondered what else was happening to garner such a full lot. Half of the storefronts were boarded up, and I struggled to figure it out. Maybe the lot was being used by adjacent businesses. ‘Yes, that was it’, I decided.

         Of course, my theory was smashed to bits as I pushed inside the barbershop, only to find it full. Not just full, but filled with men from my office, save for one. Ms. Shire sat in one of the large swivel chairs, angled towards me as I entered. “A full five minutes early.” She exclaimed. “One would think Ms. Kenyan is excited to lose those precious locks of hers.”

         There was some general snickering at my expense as I set my purse and coat in the only available chair. A man, whom I assumed to be the barber, was dressed in a white mid-length smock. He smiled, curtly, turning the open swivel chair toward me, inviting me to sit.

         I looked around the room, not a charitable face to be found; the prescribed audience only there to further embarrass me. This would be humiliating enough were I to do it alone, much less before an audience of my peers. I sighed, audibly, and resigned to the barber’s invitation. My legs felt like sticks of wood as I slowly turned and lowered myself into the polished leather seat.

         The murmurs amongst the men continued as the cape was wrapped tightly around my neck, but rose to include some laughter as the barber unfastened the clasps holding my hair in place. Watching in the large mirror, my hair tumbled over my shoulders, the blonde strands curled from being restrained all day.

         “Entirely too much hair, wouldn’t you say, Sal?” Ms. Shire pointed out, reaching forward to tug on the locks closest to her.

         “It is long. I don’t think I’ve ever cut hair this long before.” He announced, running a comb through my beloved mane. “How are you wanting it, Miss?” He asked me.

         Just as I was about to direct him, Ms. Shire intervened. “I think something short; a style a bit more fitting of her new position. Yes. Something a bit more masculine.” She insisted.

         “But you said…”

         “You’re starting at the beginning, so let’s do something fresh.” She cut me off, and I was silenced that easily.

         And so, there I was, my vulnerability obvious to everyone, and my hair at the mercy of a vengeful boss. I looked at the barber and tried to keep a straight face as Ms. Shire barked out her instructions. My heart was sinking as her description resembled something more akin to what a marine boot might expect upon their induction.

         I heard clippers, numbers, and razors, all in the same sentence, and I really was ready to abandon the chair and bolt for the door. But as I looked up, any chance of escape was cut off by the men who had surrounded the chair. “Shit.” I heard myself say, as the chair was turned back toward the mirror.

         “Yes, shit indeed, Madeline, and you are definitely in it.” Ms. Shire chuckled.

         “She has to agree.” The barber insisted. “I could lose my license.” The loud jeers of anticipation settled with that sobering statement, and for a moment I thought a reprieve was at hand.

         I looked at Ms. Shire, who seemed disappointed, but not thwarted, by any means. “Well, Ms. Kenyan?”

         I so desperately wanted to spite her, to tell the barber to give me a nice lob, or something. A lob would be easy to grow out, should my apparent misadventure into upper management fail. It would also meet the initial requirements laid out in her office that morning.

         The thing was, I knew what she wanted, and anything short of that was going to cause friction; friction I didn’t need as I started my new job. As humiliating as it was going to be, I had to bend to her will. “Just do it.” I managed, staring back into her deep blue eyes.

         The smile returned to her face, as the barber prepared. The chairs were so close that our toes were almost touching as she leaned forward, relishing what was about to happen. I groaned as I felt and heard the scissors begin to lop off my hair.

         One glorious strand after the next fell to the floor as the barber traced a line around my head level with my eyebrows. Each scrunch of the blades sent shivers down my spine, and was more fuel added to the raucous behavior of the men who surrounded me.

         I looked ridiculous, really. What was left behind was a micro-bowl cut with the remnants of my mane still falling from beneath. A few quick slashes of the scissors made quick work of what remained, however, and I knew all too well what came next.

         The barber didn’t give me a lot of time to worry about it, and I think I was grateful for that. Whatever blades he was using as he slipped the whirring clippers underneath my newly formed bangs, left very little behind.

         The stubbly path that he carved could not have been more than a quarter of an inch long, and I could plainly see my snow-white scalp through the light blonde bristles. “Jesus.” I panted, as a second path widened the gap. It was beyond humiliating.

         “Yes, I love it!” Ms. Shire exclaimed, rubbing her hands together greedily. She was certainly enjoying the spectacle. The barber was at least skilled, and made quick work of the rest, and in under a minute, all that remained of my precious hair was a barely perceptible sheen of stubble, made almost invisible by my light coloring.

         The thing was, I was far from the end of my ordeal. The only relief I was offered was when Ms. Shire excused her brood from the shop, leaving just the barber, herself, and me.

“You see, Ms. Kenyan, I was so disappointed when William failed to get the position you so undeservedly stole, that I made it my mission to make your life a misery.” She stood and walked around behind me, so I was forced to look at her in the mirror, my reflection so decidedly altered, that I nearly looked away.

“I didn’t steal it, I earned it, Ms. Shire.” I returned, but not in a hostile manner.

“So you did, just as you have earned this.” She cocked an eyebrow as her fingers ran over the top of my head, stroking the course stubble back and forth. “Dye it black, as we discussed.” She barked.

The barber was quick to help me out of the chair and over to a sink, where he loosened the cape and whet what remained of my hair. I couldn’t see what he was doing, but the smell of the dye was filling my nostrils as he worked it into my stubble.

“I couldn’t very well leave you blonde as you might actually look stylish with your new cut. No, I think this will be better.” She chortled, as she took her seat once again, awaiting my return to the chair.

Twenty minutes later, I was back. The whitish-blonde buzz was now a stark black, making me realize just how much hair still remained on my head. I had never dyed my hair, having always been the stunning blonde that boys and men would lust after. I shuddered, wondering what my boyfriend’s reaction would be.

“You may finish.” Ms. Shire blurted.

Whatever clippers the barber used on the sides and back of my head, were very different from those he had used before. They left nothing behind, save for a ruddy black shadow, something akin to that on a man’s chin near the end of the day.

The sensation was different as well, and it would have almost been pleasant were he not shaving me to the skin. The buzzing vibrated against my skull, as he worked the blades close. He shaved up to a line that left a tuft of hair on my crown resembling a worn-down eraser.

My ears, which had always been hidden beneath my hair, stood out, but not so proudly as to be large. They seemed odd, stranded, and barren, their attachment to my head revealed in vivid detail. The diamond studs that I wore now seemed pretentious and out of place, which bothered me more, perhaps than it should have.

“Now, you must hold perfectly still.” The barber warned as he ran a strange-looking comb through the top. He restarted the clippers and ran them over the comb, the sound sending a shiver down my spine, like fingernails on a blackboard. “Please, Miss, you must be still.”

“Do as he says, Madeline, for Christ’s sake!” Ms. Shire scolded, slapping my hand which had worked its way out from beneath the cape.

I resisted the temptation to shiver as each pass was made over the teeth of the comb. It was a struggle, but I did the best I could. I couldn’t see in the mirror as the barber stood in the way, but as he moved to work from the back, my mouth dropped open.

The crown of my head looked as though it had a horseshoe stamped onto it in black, with the shaved opening in the back. The black stubble in the center was short enough to reveal my scalp, but maintained a shadowy tinge. Now I saw the reason for the dye.

“Shave the landing strip, but not with a blade. Let’s leave a little shadow, shall we?” Ms. Shire demanded, chuckling under her breath as the barber complied. I watched, almost mesmerized, as the clippers carved out the center of the horseshoe.

I sighed breathily as the cape was finally removed and I was allowed to gather my things. Looking in the mirror one last time, the image was not one of the sexy young blonde that had awakened that morning. No, all that remained was a very masculine looking…man. I couldn’t even see myself as female, nor would anyone else for that matter were it not for my clothes.

“Oh, Ms. Kenyan. I had my shopper pick this up for you. Do wear these to work tomorrow.” She handed me what appeared to be a clothing bag, the clear plastic revealing what could only be a man’s suit and a pair of wing-tip shoes bagged neatly over the top.

My face dropped, knowing that she had me exactly where she wanted me. Nodding, I walked out of the shop and hurried to my car, tossing everything in the back seat before escaping with a chirp of my tires.

It had been the most humiliating experience of my life, and I wanted nothing more than to forget it. So, I was puzzled by the fact that I was unable to keep my fingers from exploring my new nakedness. The air from the vents felt cool against my exposed scalp, and I knew that I couldn’t possibly be feeling what I thought I was.

Pulling into my driveway, I looked up and down the street, thankful for the cover of darkness. I would have pulled into my garage, were it not for Steven’s car parked in front of me. “Steven!”

I had completely forgotten that my boyfriend insisted on celebrating my new position, even though I had adamantly asked that we not. “Oh, for fuck’s sake.” I chided, pushing open my door and striding up the steps. “This is going to be so much fun.” I sang, as I fumbled with my keys.

Just as I was inserting the key in the lock, the front door swung open. “Maddie?” I heard him, but I couldn’t face him as I pushed inside and ran to the closest bathroom, slamming the door behind me. “What did you do?” He laughed, and for a moment I was annoyed with the idea that he found this the least bit funny.

I heard him try the door, but I had locked it. “Madeline, unlock the door.”

“I didn’t do this, it was done… to me,” I explained, reaching for the handle and twisting the lock. The strange feeling of arousal that I was experiencing during my ride home was long gone, replaced by the dread of impending rejection.

The door opened, and I managed to look up, his smile seeming to lift my spirits just slightly. “I’ll have to admit, it certainly is a different look for you.” He mused, stepping in and running a hand over my denuded head.

“You hate it, I know you do.” I bawled, the tears forcing their way belligerently through my lids.

“Hey, I’m just surprised is all, Maddie. Is this some kind of initiation?” He asked.

“Something like that.” I mewled, swiping at my tears and then allowing my hand to run front-to-back over my head, the bristles tickling my fingertips.

“Then, what do you say we do them one better? Let’s finish the job.” He suggested.

“What, you want to shave me bald?” I asked, the idea almost attractive to me to be honest.

“I’ve always thought it would be wild to date a bald woman. I do… did, love your hair, but they’ve forced our hand a bit, haven’t they?” Steven reasoned, picking up a safety razor from the back of the toilet and wielding it menacingly.

“Let’s do it.”

I was exhausted the next morning, and admittedly a bit sore. Steven had been a crazy man once my embarrassing recon was gone, and I was back to loving the way it felt, even more so now, without the stubble. I’d managed one last orgasm by my own hand before readying myself for work.

Without the hair, I was back to looking feminine again, but I donned the man’s suit as requested, wingtips and all. I felt a bit like Daryl Hannah but without the hair, enjoying the way the tailored suit hung from my frame. I’d opted for some conservative hoop earrings, not over the top, but decidedly feminine.

I’d raised a few eyebrows on my way to the seventh floor, but my new look was hardly a surprise to anyone in my department. They’d been there, and it would take a bit before that inequity was leveled.

When Ms. Shire caught a glimpse of my shiny bald head, she seemed a little annoyed. “You shaved.” The scowl suddenly evaporated into a smirk. “Well, plan on keeping it that way.”

I ran a hand slowly over my scalp, the smooth skin exciting my senses, and a bit too inappropriately for the workplace. I’d need to be careful. I tightened the tie that I had struggled with but succeeded in tying that morning. “I plan to.” My smile was genuine, and it seemed to irk her even more.

“You look ridiculous, but it will have to do.” She muttered.

“My boyfriend would disagree with you.” I sighed, contentedly.

“Have those reports on my desk by ten o’clock, Ms. Kenyan.” She turned and left my door open, again.

“You’ll have them, Ms. Shire.”

9 responses to “Meeting Her Expectations

  1. Well….

    I suppose I could change my character’s name since I wasn’t quite ready to publish it yet anyway. I wanted to let it sit for a few days, and then revisit since I think I may have let it get too dark, plus, it’s always easier to find typos with fresh eyes.

    Interesting dynamic between Madeline and Ms Shire

  2. Hi Ginger, Sometimes dark is good, if it conveys the idea you trying to express. Sorry if I inadvertently penned a name you are using in one of your stories. I was doing the usual random name search where I run the alphabet and settle on a choice. Anyway, I’m looking forward to yours soon.

    1. Hi, I realize I was just being hyperaware and over thinking things. Thanks for being patient with me.

      I just left my Madeline as Madeline. I didn’t name her randomly, and I’m having trouble thinking of her as anyone else.

Leave a Reply