Timid, Chapter One

Timid

Chapter One

By Shorngirl

Venturing Out

I suppose it was curiosity more than anything else that took me to that club. I’d never been the adventurous sort, but being fed up with my mundane lifestyle, I was determined to spice it up.

I worked from home as a systems analyst and made fairly decent money doing it. The benefits were good, and it afforded me the time to delve into my various interests.

The fact that I never had to drive to work but once a month for meetings was a huge plus. It saved wear and tear on the car, and saved me time as well. I guessed this was the way the tech industry was going. Companies learned during the pandemic that it was more cost-effective to keep everyone at home.

It was after one of our meeting days at the office that I ventured out, determined to visit this niche venue. You see, and I’m ashamed to admit it, all the free time I had at home had turned me into a bit of an autosexual.

I was a single woman, lived alone and so the opportunity to masturbate was a constant temptation. Admittedly, there were days when I never dressed at all, staying naked the entire day.

I wasn’t particularly narcissistic but found playing with my own body, and experimenting with different toys and techniques to be a constant distraction. Mind you, I never allowed my dalliances to interfere with work. The two were distinctly separate. I had a work computer and a personal one.

The internet was my closest companion, and I know how strange that sounds, but as a singular person, it was an invaluable outlet. I had no interest in porn as it was labeled in the mainstream. Instead, I found particular fetishistic sites to be of more interest to me.

I had my favorites; bondage and humiliation being at the top of the list, but lately, I had delved into a new and strangely erotic fetish. I first stumbled into erotic haircutting entirely by accident. I was watching a bondage video, a particularly strict one, where a young woman was severely bound and suspended, eventually upside-down.

It was while she was inverted like that, that her tormentor took a pair of scissors to her hair. It was long, black, and very nearly grazed the floor from where she was hanging. The haphazard way the man chopped into her luscious mane sent shivers down my spine, settling in my sex furiously.

Masturbating, I watched as her hair got shorter and shorter, her sobs and pleas for him to stop ignored. When at last, he had taken it to within a few inches of her scalp, he finally stopped.

Still in tears, the woman was flipped over, her long hair littering the floor of the ‘dungeon’ set. She had been a beautiful woman, but with her hair sticking out in random tufts all over her head, she was anything but attractive. I came long and hard with that realization.

A bit taken aback, I shut down my computer and hopped in the shower, trying to wash the cobwebs out of my head. That final scene really knocked me for a loop.

The next day, I watched the same video again, and found myself fast-forwarding to the haircut scene. Again, I was aroused beyond measure. Noticing some different links at the bottom of the page, I was soon scanning the web for similar forced haircutting scenes. There were many, the theme as varied as you might imagine.

I had no idea that I could be so overcome by a fetish, but this seemed to be something I was not going to be able to leave alone. Slowly, the bondage scene fell off the menu, but humiliation scenes remained a strong second to the haircutting. The two just seemed to run hand in hand.

Anyway, back to the present and my adventure to explore this particular spot on the outskirts of the city. I was dressed in my conservative work suit and worried that I was going to be out of place. I needn’t have worried. There were as many suits as there were people dressed in fetish attire. Secretly, I wished I was one of those, wearing something leather with a good deal more flesh exposed than not.

There wasn’t a main show or anything, but little scenes seemed to be happening all around the club in various corners and rooms. Disappointed that no alcohol was served, I was sipping at a diet Coke as I wandered. It was what most people did; wander. I felt like a voyeur, watching such private interactions, some involving some fairly intense BDSM.

That was when I spotted her. She was dressed in latex, skintight and formfitting to the point that I could plainly see the bars pierced through her nipples. The only thing missing was the hood, but to my delight, her head had been shaved to the skin. She wasn’t taking part in any scenes per se, but was wandering just as I was.

Finally able to pull up next to her at a particularly involved scene, I surprised myself by speaking to her. “I love your look,” I said, loud enough to be heard over the obtuse scene.

“Why, thank you.” She smiled, her lovely face only accentuated by the absence of hair. Even her eyebrows were missing, and I swore that her lashes had been plucked out as well. Utterly hairless, I thought. How wonderful. “I’d say you should try it, but with such lovely hair, I think you would miss it too much.”

Her words ignited a fire in my loins, and I had to reply. “I think you might be surprised…” and then to my shock, admitted, “…I have a bit of a haircutting fetish.” I couldn’t believe I had been so bold. What was I thinking?

She was a good six inches taller than me and smiled as she retrieved something from a small pouch secured to her waistline. It was a business card. “You should call me.” She suggested. “You really are quite lovely.” And with that, she bent down and gave me the lightest kiss on my lips, completely taking me by surprise.

By the time I had regained my composure, she had wandered into the crowd, lost in the bodies that milled about in the darkened atmosphere. Without looking, I slipped the card into my bag and quickly made my way to the exit. I had had enough for the evening, that was for sure.

Once I was safely ensconced in my apartment, I ripped off my clothes and masturbated furiously. Imagining the encounter with the strange bald woman had progressed much further, I came in rapid-fire bursts, leaving me utterly spent.

I’d never in my life imagined sex with a woman until that moment. I’d only ever had one encounter with a man, and that had been distasteful, which was, perhaps, why I had chosen my singular sexual preference.

Still moist with sex and sweat, I slipped my hand into my bag and pulled out the card, surprised by what I read.

Samantha Owens

Individual Styles

for the Modern Lifestyle.

Hair, Nails, and Ephemera

Certified Electrologist

         I flipped the card over, finding a printed phone number as well as an email address. Curiously, below all of that, there was a number neatly scrawled in ink, which looked suspiciously like a cell.

Almost frightened by my sudden enthusiasm, I placed the card carefully along the inner frame of the bulletin board, hanging over my workspace. And…there it sat for what must have been weeks, taunting me. Each time I would see her name, my senses roiled with an unexplained ferocity. Several times I had gone as far as allowing the number to connect, only to hang up before anyone answered.

An Invitation

I thought I’d finally worked up the courage to talk to her when a text appeared on my cell. I was working, so I only had a moment, but the words were plain, and it was an invitation.

Unknown: I know who you are blondie. I know what you want. Meet me tonight at 34365 Pullman Avenue. I’ll expect you at 9 pm.

There was no way around the blunt nature of the text. She was fully expecting me to comply with her request, giving no information on what the place was or what was expected of me, how to dress, nothing. Of course, my heart was racing the rest of the day, knowing that there was no way I could not go.

I wasn’t all that surprised to find the address was a tavern. I had hoped secretly that it might be her salon, but not disappointed, as I was certainly ready for a drink. It wasn’t much of a place; one of those neighborhood joints where everyone turns when you walk through the door. They did, and it gave me that ‘what the hell am I doing here’ feeling, in spades.

I didn’t figure I’d have much trouble spotting the woman from the club but was surprised when a tall brunette walked up to me from the far end of the bar. “I was hoping you wouldn’t chicken out.” She smiled, from under what was obviously a very expensive wig.

“Hi.” Was about all my feeble mind could manage at that moment.

“Come on, let me get you a drink.” She signaled to the barmaid who poured something from the top shelf. “This will calm your nerves, which I’m sure must be a little on edge right now.”

I took a sip of the amber liquid, the strong burning sensation giving way to the pleasant finish of a fine single malt. “You have no idea.”

“Oh, I think I do.” She took a sip from her own drink and smiled. “So, you know who I am. What’s your name?”

“Penelope,” I mewled. “… Penny Warnock. Nobody calls me Penelope.”

“Do you mind terribly if I do?” Samantha eased. “I much prefer Penelope to Penny. Has a certain… bohemian quality to it, don’t you agree?”

I laughed under my breath. “If you say so. It was my grandmother’s name, to be honest, but you’re more than welcome to use it.”

“So, Penelope Warnock, do tell me about your little fetish.” Samantha encouraged, looking down the bar to see who had just entered. It was just that kind of place.

I quietly began explaining how it all began, not leaving out the fact that I was a bit of a recluse. When I reached the part with the bondage haircut, she smiled.

“I love that video.” Samantha cooed. “It’s so… raw, so unscripted.”

“Whatever do you mean?” I asked.

“Have you ever read the comments?” She questioned. “The haircut was totally avant-garde. Those tears were quite real, my dear Penelope.” Samantha grinned, waiting for my response. Suddenly, my entire interpretation of the scene changed, and I squeezed my thighs together as if to hide my arousal. “You find that titillating, don’t you?”

“Yes.” I managed, opening my thighs slightly, and catching her looking down as if she could see the heat radiating from my sex.

“You’ve imagined yourself there, haven’t you?” The woman asked. “Hanging upside down with those luscious blonde locks being hacked off a bit at a time; …It really bothers you, doesn’t it?”

I tried not to imagine it, but the scene had played over so many times in my mind that I was helpless to stop it. The only difference being it was Samantha as the tormentor. “I…”

“It’s alright you know.” She leaned into my ear. “Look at me. No one would be the wiser.” She raised her drawn-on brows, her eyes glancing upward toward the hairline of the superbly coiffed wig.

“I don’t think I could pull that off,” I admitted, finishing the scotch in my glass.

“I guess there’s only one way you’ll ever find out.” Samantha mimicked me, setting her glass on the bar with a flourish. “Let’s take a ride.”

Nervously, very nervously, I followed her out of the tavern and into a small lot at the side. With my car nestled safely into a spot on the street, I climbed into the passenger side of her Ferrari. “This is nice,” I said, looking around the lavish interior of the supercar.

“Just wait.” She smirked, firing up the racy engine perched directly behind the seats. I was pressed, rather violently into the seat, as Samantha rocketed away from the lot, and I swore we were way in excess of the speed limit. When I glanced at the speedometer, my suspicions were confirmed, the needle passing the one hundred miles per hour mark with no indication of slowing.

“Um…I…” The streetlights and trees were a blur at the sides of the road as we quickly left the city edge behind. In what seemed like seconds, Samantha pulled into a large Victorian mansion, the car seeming to find its designated spot on its own. “That was impressive.” My breath still caught in my throat.

She laughed. “I barely opened her up.” She walked around, opened the door, and assisted me out of the low-slung coupe. “Someday, I’ll show you what an Enzo can really do.”

“Aren’t you worried about the cops?” I asked.

“Not anymore.” She chortled. “They have their hands so full as it is, I doubt they’d even waste their time.” She was right of course. Things had deteriorated in the city, and the first thing that was cut was the police budget. “Come on.” She indicated a well-lit side entrance.

Once inside, I was surprised by how different the place was. I was expecting high ceilings and marble floors. What met my eyes was far more contemporary. White Berber carpets lined the floors, and the walls, equally as white, blended into the ceilings seamlessly. It was all rather homogenous.

I was led down a long corridor, having shed my boots in the back hall, as she had done. I realized that I wore nothing underneath, so I was barefoot, the rough carpet tickling my soles.

She looked down at my naked toes, her attention prompting me to wiggle them self-consciously. “I suppose you’re ‘commando’ as well?” Smiling, curtly. To be honest, I couldn’t even remember.

Samantha opened a door, inviting me into a very nicely appointed office. An oak desk dominated the space, and she was quick to assume a spot behind it, indicating a club chair that faced her. “Before you sit, may I ask that you strip?” As if nothing could be more normal.

Once again, my heart was racing. There was nothing to be done but comply with her request. As efficiently as my shaking fingers could manage, I removed my clothing, folding things neatly and setting each item at the center of her spacious desk. Utterly naked, and turning what must have been a dozen shades of red, I was once again offered the chair.

I watched, concerned, as my clothes and purse were quickly scuttled, the clicking of a lock confirming that they were well and truly taken from me. I worried that I might leak onto the rather expensive-looking upholstery, but on closer inspection, realized that a cotton doily was centered directly beneath my buttocks.

Noticing my concern, Samantha smiled. “Mustn’t be leaving tracks on my furniture, Penelope. I trust I was prudent in protecting it?”

“I’m so embarrassed.” I spluttered, realizing that we were talking about the fruit of my arousal, leaking from my sex.

“Don’t be. Why, I’d be disappointed if it was not needed.” She grinned. “So!” I jumped at the increased volume of her voice, the tone suddenly sharper and just a little icy. “I’m going to need a promise from you, Penelope.”

Still stunned, I nodded, but eventually managed a subdued, “Okay.”

“Whatever we do, here; it stays here. Understood?” She demanded, the authority in her voice undeniable.

“Not a problem,” I assured her.

“Good. Then where to begin, my little blonde nudie?” She giggled, looking over the edge of the desk. “Tell, you what. Why don’t you leave that up to me?”

Samantha took me by the hand, leading me out of her office, farther and farther away from where she had locked up my purse and clothing. The hallway wrapped through the house, ending very abruptly at a heavily framed door.

Etched into the header were the words: ‘Lasciate ogne speranza, voi ch’intrate’, and although I didn’t recognize the phrase, the words themselves sounded ominous. As she opened the door, Samantha noticed me staring at them.

“Just a little joke.” She chuckled, flipping a switch that illuminated a long descending staircase. I suppose I should have asked what the words meant, but at the time I was too nervous and too excited.

Naked and Nakeder

Samantha’s basement, and I use that term very loosely, was ornate. Unlike the bland almost sterile atmosphere upstairs, this was over the top. The walls were laced with gold, and the ceilings high and vaulted. Sconce lighting gave the place an almost frightening ambiance.

I fully expected Samantha to escort me to a dungeon, complete with every instrument of torture ever devised. To my surprise, we ended up in a very clinical room, with several complex pieces of equipment lining the walls.

“Why don’t you lie down on the table there and make yourself comfortable, Penelope,” Samantha instructed, while she flipped on one of the machines, a series of lights cycling along its front. Doing as she said, I felt very much like I was at the gynecologist’s office, without the benefit of a gown. “I was going to start with these,” She mewled, tugging gently at my manicured bush. “…but we just don’t have the time, tonight. I think we need to make a statement, what do you say?”

She rubbed some gel over my brows, the ones that I had just spent fifty dollars threading. I loved my brows, as blonde as they were. I watched as she carefully adjusted a wand that looked very much like a pen, inserting something from a sealed package into its tip. If it was what I thought it was, I certainly didn’t want it anywhere near my eyebrows.

“Are you… is that…” I tried, but as she shed her wig for the first time that evening, I was enthralled. Her scalp glowed in the overhead light, the perspiration from being encased in hair having heated it. All I wanted to do was reach out and touch it; to run my fingers over its glistening surface.

A few minutes later, she wiped away the gel, and I was relieved to feel that my eyebrows were still quite intact. That, however, was about to change. “The numbing gel will take away a bit of the sting, Penelope, but I’m afraid there’s no way for me to eliminate the discomfort entirely.”

And with that, she began. I could feel the needle as it slid beneath my skin, the slight twinge of heat at the outer edge of my left brow. Every so often she would reach in with tweezers to lift away the hairs that had been separated. I knew what was happening and was utterly powerless to stop it. Instead, I found myself reaching between my legs, desperately wanting to masturbate.

“You have my permission to play…” Samantha smirked. “…but don’t you dare come.”

So, as I stroked my clitoris ever so lightly, edging to the brink of coming countless times, I tried to imagine what I would look like browless. She was very efficient, and I knew she had switched sides at that point. I think it had only been an hour when she sighed, reached over and switched off the machine, and declared me done.

“Can I see?” I asked, mutely.

Smiling, Samantha brought a handheld mirror up to my face, revealing my reddened but utterly hairless brow. “We’ll need to do that a few more times as the hair cycles, but your well on your way to being a browless girl.”

I ran my fingers over the naked skin, feeling the smooth ridge where hair had always grown. “I’m going to have to get very good with an eyebrow pencil,” I admitted.

“You’re so light, I wonder if anyone will really notice. Once the redness fades, you’ll see.” She sat me up and had me sit on the edge of the table, worried that I might keel over. “How are you feeling?”

“A little woozy, but fine,” I said. Not having had an orgasm, and come so close so many times, I was still very hot. “Samantha, I really need to…”

“Oh, you will, don’t you worry.” She assured me. I was almost positive I knew where we were heading then, and my instincts didn’t let me down. I wasn’t far off on my estimate. She had a lot of interesting-looking toys.

I tried not to shake as she fastened some elaborate wrist and ankle cuffs, desperately trying to keep my fingers away from my clit. Of course, I knew she would blindfold me, but knowing it didn’t make it any less traumatic.

Now, I was only listening, trying to decipher what she was doing as chains clanked and clips were fastened and rope was cinched. Then there was that sound. The same sound I knew so well from the video. The rapid clicking of chain through metal as tension mounted in my restraints. Soon I was struggling to maintain contact with the floor, until suddenly, it was gone.

I had always tried to imagine what it would feel like to be suspended, but nothing prepared me for the actual sensation of hanging by my arms, breasts, and legs. Now, it was Samantha who toyed with my clitoris, flicking my nipples with her fingers, her tongue, and finally with a crop.

Things were moving now, and I almost knew what was happening. I could feel the blood rush to my head as I was slowly inverted and I felt my hair fall away from my shoulders, pulling on my scalp in the most peculiar way. As long as my hair was, it surely matched the girl’s in the video. I tried to imagine my blonde tresses hanging down from my head, grazing the floor with their impressive length.

Samantha was very good at sensing when I was about to come, and toyed with me that way a few times more before I heard that sickening sound. There was no mistaking that sound. Metal on metal, sliding precisely until they closed with a click.

Opening and closing, fast and then slow, until I felt them capture my hair. “Oh, God!” I shouted.

Samantha silenced me with a deliberate kiss, her tongue invading my mouth, but just as she did, I felt the shattering crunch as the blades did their worst. I think she had a bit of a sadistic streak, because just at that moment she uncovered my eyes.

Disoriented, I took in the room, inverted and utterly unfamiliar. I looked up and saw a lengthy strand of my hair laying on the stone floor, curled against itself. “Oh, fuck!” I managed as she dipped her tongue into my folds, the blades again sending a torrent of my hair to the floor beneath me. As hard as I tried not to look, the sight was electrifying.

I was that girl; the girl in the video. Over and over, Samantha sliced into my luscious blonde hair, and each time, the pile beneath me grew larger. As hard as I tried, and as excited as she kept me with her tongue, the tears came. I never sobbed, but Samantha hesitated as she saw a few shimmering drops join my hair on the floor.

She walked around and looked me in the eye, her face upside down. We watched one another for a second until I finally broke contact. This time I swore I would come. Her attention was intense, and her teeth nibbled, encasing my clit and swirling her tongue deftly around it.

The scissors were working non-stop now, as if there had been some unspoken permission, and perhaps there had. I knew that there would be very little remaining at the end. How could there be, with a veritable sea of blonde covering the floor beneath me?

It crept up on me slowly, at the edges of my vision, and then burst into light as I came long and hard, screaming, thrusting in my bonds and rattling the chains that held me airborne. In the periphery, I could hear the scissors still working, as if on automatic, independent of what had just occurred.

“There,” Samantha said, tossing the scissors atop the voluminous pile of hair, so thick they barely made a sound. Working quickly, she brought me upright again, and just in time, because I very nearly blacked out. “You okay?” She asked.

“My hair.” With tears still flowing and strands of my detached mane stuck to my cheeks, I finally sobbed.

“Penelope. You knew it had to go.” She comforted, running her fingers through what must have remained of my hair. The lack of any resistance was surely indicative of how short it actually was. Was I like the girl in the video; with haphazard tufts of hair sticking out at odd angles from my scalp?

“I must look a fright.” I managed, gathering myself finally.

“Actually… it’s pretty frightening.” She chuckled. I tried not to, but I couldn’t help but laugh along with her. “That’s my girl.” As she slowly undid all my fastenings, I managed to get a hand up to feel what was left, and it was more drastic than I imagined it would be. “Hang on there. I’m not all that convinced I should let you see it before I straighten you out.” Samantha sighed.

Finally, back on my feet and able to move around, I stuck both hands to my head, rubbing the twisted shocks of hair with my fingers. “Maybe you better not.”

Leaving the playroom and the pile of my once glorious mane behind, she led me down to another room. This one looked much like any salon might, except for the single chair. “Have a seat, and we’ll get you ship shape in no time at all.”

At that point, she spun the chair, but I couldn’t help but catch a glimpse of my tattered head in the mirror. Whatever she was about to do, it had to look better than that. I knew they were coming, but hearing the clippers switch on was still a bit of a shock, and I was startled, the shiver continuing for a few seconds.

I felt the bare metal against my forehead, the humming blades vibrating through my skull as they ran over the top. I had no idea how short Samantha was clipping it, but it had to be very short indeed. Seeing clumps of blonde scrap fall over my bare shoulders, past my naked breasts, and onto my legs seemed a bit anticlimactic after my experience in the playroom. Still, I was unable to keep my fingers away from my pussy as I felt the cool air hit my scalp for the first time in my life.

I could feel Samantha’s breath blow errant tufts of stubble away as she worked, and the sensation was wonderful. I loved the way the clippers felt as they skimmed over my emerging scalp. I knew that when I finally saw myself, I would be shocked and delighted all at once. Of course, nothing could have prepared me for that moment.

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