Edidom25
“How the FUCK did I get into this?”
Sam had been asking herself the same question on repeat for the last half an hour. She was staring at her reflection in the mirror. A brush in one hand, Sam felt at this stage she was just delaying the inevitable. Her hair was not going to get much neater. It already shone in the dying light, red waves rippling down to her lower back, thick and healthy as it ever was.
It had started with a Reddit DM. SimonSays with an innocent question replying to her throwaway account’s post about ChatGPT and Haircuts. What was a fun conversation about her limited experiences indulging her secret little kink had turned into shared stories and secret fantasies. Slowly, she shared pictures of herself and her mane, teasing Simon in different styles, always hiding her face, and keeping anonymity. This was purely an online escape. But their friendship grew, and she started to anticipate their little chats. Talk of a meetup began. They lived relatively close by, so why not? And then he made her an offer. She had shared her dream of pegging a man for the first time and how much it excited her, so he offered a challenge. A simple game, online, with a chance to fulfill this dream if she won. And if she lost, well she had always wanted to be sheared anyway. Was it really losing? She just needed that push.
Of course, she had overestimated herself. And now she was styling her hair for what may be the last time. Simon had not given any specifics. He had teased her relentlessly, sometimes with a little trim, or taking her ponytail for a trophy. On the more indulgent nights, she would read and re-read his mini stories about shaving her to the skin as she was subdued to a hotel chair, gagged, and bound. Fuck that made her cum. She would take her husband to bed after those ones, and whilst Richard did not know why he was getting so lucky, he damn well appreciated it.
The plane landed 3 hours after she had left her house. It was a 15-minute taxi to the hotel, where Simon would be waiting in the hotel bar. Whatever happened tonight, she would remember this for the rest of her life. She had tied her hair back into a thick ponytail, deciding to at least have some fun for herself by teasing Simon with it. Whilst they had agreed no sex and nothing that would be considered cheating, she planned to take full advantage of this situation to have some fun.
As Sam entered the bar, her phone pinged.
“I’m here, back corner on the right…”
Her heart leapt. This was happening. He had even ordered a drink for her. At least it would calm her nerves.
She was met with the biggest smile as Simon spotted her. He was close enough to his pictures, so she let out an inner sigh of relief that this was not a catfish. He introduced himself and she felt the familiar casualness of their online conversations. Finding herself managing to slowly let go of some of the anxiety that had been building inside her, Sam let herself begin to relax. She noticed Simon stealing glances at the tail hanging over her shoulder and even managed to smile. They shared a laugh, and when he offered his hand to go up to the room, she was quick to take it. The lift ride was quick, and before she knew it, she was staring through an open doorway at an empty chair. Her chair.
Simon had laid out his “toys” already, brush, scissors, clippers…
“I’m hoping you’ve got more than overnight kit in that little bag?” he asked.
“A few things,” she replied with a smile.
Sam reached into her bag, bringing out her favorite vibrator. “This little guy has shared in every one of your stories, I couldn’t leave him at home.” Simon laughed at this as he gestured for her to enter the room. Closing the door behind them, Simon turned to see Sam already starting to undress. They had agreed that nudity was an acceptable choice of clothing, or lack thereof.
Simon took a moment to absorb the image of Sam’s body. He had noticed all her comments about her unhappiness with how she looked, but the woman in front of him was gorgeous to the point where he physically stuttered. The nerves were clear on Sam’s face, and Simon felt a need to break the heavy tension.
“Wow. You are… beautiful.”
Sam broke her stare on the carpet and looked up to him. Crossing the room in three strides, Simon brushed the bangs back from her face and held her chin.
“I mean it, you are absolutely incredible.”
This finally got a smile from Sam.
“Should I take a seat, Sir?” she asked, overdoing the seductiveness a tad but getting the ball rolling.
Simon pulled the cape from the back of the chair and ushered her down. Grabbing the comb, he slowly started to brush through the mane of hair in front of him. Her pictures did not do this justice. He remembered the photo of her pigtails, where each one had looked the size of a regular ponytail, but even still the volume of hair in front of him was immense. His free hand ran up the back of Sam’s neck, eliciting the smallest sigh as he felt her head push back into his hand. The gentle rubbing turned into a light pulling, teasing her head around, before he grabbed a fistful of her hair and pulled back with relative force. Sam’s eyes were closed, and her hand rested on her thigh. Simon reached under the blanket he had sat on and pulled out his little surprise. Releasing Sam’s hair, he took hold of Sam’s left hand and gently maneuvered it behind her. She felt a coldness before hearing a click, and Simon grabbed her right hand before she could react.
“Simon… What are you doing?”
He locked both her hands together with his cuffs, before standing in front of her.
“You’ve always told me how nervous you are to go the whole way. That you didn’t want to have to make that choice yourself. Well now, you don’t have to.”
Sam’s breathing started to get heavier as she tensed her arms. The cuffs wouldn’t budge, and she felt Simon draw her hair back from her face as he resumed his position. Simon tied off the two pigtails he had spent many evenings staring at on his phone.
“I’ll make sure we both have a memory to take home with us.”
Sam heard the all too familiar sound of scissors opening, as she felt Simon pick up one of her tails. She audibly gasped as the cold metal brushed against her cheek before the horrific sound of hair scrunching assaulted her ear. As thick as it was, it only took Simon a few seconds to force his way through the tail and the hair that was left curled against her ear. She could only watch in disbelief as a two-foot ponytail was dropped onto her lap, her insides twisting in pleasure contrary to the panic in her brain. The panic fought the pleasure, the hyperventilating beginning in earnest.
Simon took a pause, rummaging through the bag Sam had brought with her. Pulling out her vibrator, Simon flicked it on and carefully inserted it into the voluntary opening between Sam’s legs. Having been faced away from the mirror in the room, this offered a welcome distraction to Sam as she stared at the tail on her lap and half closed her eyes, praying that Simon would not take her down to the skin. The conflicting emotions of arousal, humiliation and panic made for an intense mental jumble that came close to shutting down her brain. Sam barely registered the awful noise of her second tail following the same fate, unresisting as Simon forcefully ran his hand over her shorn head, grabbing her hair and pulling her from side to side. This was her wildest fantasy, the dream she was terrified of living but had yearned for. Simon had gotten her to open her fetish-brain entirely and was now living out her most erotic, terrifying desire. The hair pulling pushed her over the edge. She was thankful Simon had had the foresight to put a towel over the seat of the hotel chair, save having to cough up on extra cleaning fees. Her juices flowed freely from her legs as the waves of pleasure took over her entire body, shaking against the restraints.
Simon laughed at the sight in front of him. This gorgeous redhead, naked, cuffed and now shorn, shuddering against the vibrations humming away from under her. He stroked her inner thigh with his finger, licking the cum off his finger. “This is only the halfway stage, my little pet. Make sure you don’t tire yourself out too quickly.”
With that, he picked up the clippers on the desk. Sam had been hoping they were there for mental torture, as Simon had written about in his many stories to her. He clicked them on, drawing her bangs back from her head. Frozen, Sam tried to speak. “Please. Please Simon, I can’t. I have work…” but her words were drowned out as the clippers met her hairline. Despite the pleasure, Sam couldn’t hold back the tears as her hair fell in front of her face. Simon was making sure that after every pass, he dropped the freshly mowed locks down her front. Clumps stuck to her body as the heat of her arousal made her sweat. Her breasts, magnificent to behold, took on a red felt as pass after pass they were covered with more of her once astounding mane. Sam could feel the clipper blades against her scalp as Simon carefully bent her ear down, pushing her head forward to clear her nape, making sure every single hair was clipped precisely. Despite the tears, the mix of the clippers on her head and the toy inside of her was too many vibrations for Sam to handle. Her body reacted on it’s own, the sick part of her brain that had yearned for this creating a magnificent crescendo of pleasure and she could only look to the ceiling as the orgasm, the most powerful one yet, consumed her. She was acutely aware of Simon making a second, a third, a fourth pass with the clippers. Clearly redundant to any actual haircutting, she was thankful for his efforts to maintain the crashing surges rolling through her body as long as he could.
Eventually though, she heard the clippers click off. Simon slowly ran his head over the velcro-like stubble left on her head.
“You are just as beautiful without hair as you are with,” he whispered into her ear.
“But I have one more job left.”
Simon walked to the bathroom as Sam sat in her own mess. Her breathing was hard, and her nipples were harder. Simon had been right, she thought. Whilst she would never have chosen this herself, it was the best evening of her life. She could only hope he was away for what she thought he was…
Simon returned with his hands behind his back. Whilst this wasn’t particularly part of his own fetish, he couldn’t let Sam end without a little reward for being so well behaved. He placed the contents on the bed behind Sam, before turning and laying the damp, warm towel he had soaked on her head.
“One final touch, before we finish,” he whispered in her ear.
He made sure to hold the can to her ear as he sprayed the shaving foam onto his hand. Just the noise was enough to make Sam jolt. The cold cream was a sharp feeling compared to the towel as Simon swapped them out, but the massage of the cream onto her head had Sam relaxing against the chair.
“Please don’t move now, I don’t want to cut you.”
The scraping of the razor accompanied by the unique sound was all it took for Sam’s third orgasm. She had long surrendered herself to her body, but this was the most intense one yet. She did her best to keep her head still, but her hands fought to touch herself as she squirmed and twisted her legs to push the vibrator against her most sensitive areas. Simon made sure to again take as much time as he could, double checking every stroke as he cleared her head of the rough stubble. He made sure to gently blow on the smooth skin left behind just to tease Sam, giving feelings she had never experienced as the chilly air brushed her scalp.
Eventually he was out of stubble. Simon opened the cuffs and Sam’s hands flew to her head. She nearly leapt out of the chair and ran to the bathroom, in search of a mirror. Her exclamations would surely be heard in the next five rooms over, Simon thought, but he could only pick up one of the tails discarded to the floor, laying it on the desk. What a perfect souvenir, he thought to himself, satisfied with his work for the night. God, he loved the internet.
©EdiDom25
