Since it was only 5:45 and the weather was perfect, Jennifer decided to take a stroll around the promenade in downtown Santa Monica. She kept catching reflections of herself in the store windows and could barely recognize herself. She loved the way the style looked, but there was something running through her thoughts…
She couldn’t get the thought of the clippers running up the back of her head and nape out of her mind. They felt so good when Jade did them, she wished that portion of the haircut could have lasted longer. ‘Maybe I should have asked her to go a little shorter on the sides’ She thought. ‘Should I go back?’ ‘No, that would be odd, and she’s probably done for the day’
As she was having this conversation in her head, she noticed that there was a small barbershop on the corner she had never noticed. “Ash Barbershop”, read the very basic sign above it. The barber pole was still spinning, which meant that the shop was still open.
‘No way. I can’t. A barbershop? I could never…’ She thought to herself.
Still, these thoughts didn’t stop her from giving into her curiosity and walking by to take a look. She looked through the window and saw a small, old-time looking barbershop with two large barber chairs. The place looked like it hadn’t been changed since the 1960’s and had a very vintage feel. Around the shop were various posters showing different hairstyles with numbers next to them, and a few miscellaneous posters that looked to be from the 70s. In addition it had some interesting Vegas-style décor around the two barber stations. The barber looked to be a very stern woman in her mid-50’s, she was about 5’8, slightly overweight, with blonde hair with white streaks put up on a bun, and was wearing a white barber’s coat.
The thought of getting another haircut after she had just gotten one was really starting to turn Jennifer on. ‘Even if I wanted to, how would I even do it, it would be so weird..’ she thought.
‘Well, my hair is already short, so maybe it wouldn’t be that weird…’ she continued on in her head. ‘But I don’t really want to choose the style… the surprise part was the most fun part…’ She went on. ‘Maybe if I said I lost a bet, then she could…’
“Excuse me miss, can I help you?” Said the barber, now standing outside of the shop.
Jennifer must have gotten carried and stood outside of the shop for a good amount of time, catching the barber’s attention.
“I noticed you just standing there in front of my shop for the last five minutes, I’m aboutot close up at six… I notice your hair is quite short, but we don’t really do women’s styles here, as you see by the posters on my wall.” She said.
Completely caught off guard Jennifer very awkwardly blurted out, “Oh that’s ok, I lost a haircut bet. I’m Jennifer”
‘What the hell did I just say’ she immediately thought to herself.
“A haircut bet? That’s a little odd. You millennials these days… is this one of those ‘TikTok’ things? Well, whatever it is, I close up in 10 so if you want I can take you now, and it’s cash only, $20….. I’m Ashley” Ashley said as she began to walk back into the shop, holding the door open for Jennifer.
“Ok” Said Jennifer, as she began walking through the door.
‘I cannot believe I am doing this. This cut looks great and it cost me $200 with tip, why am I even in here’ She continued to pontificate. ‘I can’t just leave now, it’ll be even weirder, and I work in the area, maybe she will see me or something’
The smell of the shop really caught Jennifer off guard. It was unlike anything she had smelled before. The shop smelled like a mixture of old leather, old spice classic deodorant, and stale cigarettes.
“Have a seat” Ashley said, as she patted the seat of the large barber chair.
The chair was also something Jennifer had never sat in. For one, compared to the salon chair she had just sat in an hour ago, it was massive. Moreover, it was a deep burgundy, with chrome accents all around, a neck rest, and a foot rest that extended forward.
She walked over to the chair and took a seat, her petite frame felt completely engulfed in the large chair.
Just then, Ashley pulled out a long tissue, and fastened it to her neck. ‘Strange’ she thought, I’ve never had anything like this put on me. She then took a large pinstripe cape, wrapped it around her, and pumped the chair up a few times to get her level so that she could begin.
“So, what’ll it be young lady? Which men’s cut does the bet require you to get?” Ashley asked.
“Oh. You have to choose.” She responded
“Oh no. I’m not doing that. It’s too late on a Friday for that kind of pressure, and I want to enjoy my weekend” Ashley Said. “If you really want a surprise, flip a coin, or roll some dice or something”
“Roll some dice?” Jennifer responded.
Slightly agitated, Ashley said “I was kidding, but, sure. There’s 30 cuts on this poster, roll that pair of dice until one of the numbers comes up, and whatever number comes up, that’ll be your surprise.”
There were some dice on the counter as part of the casino-like decoration, Ashley grabbed them and handed them to Jennifer.
“Go on then, I haven’t got all day” She said sternly.
‘I cannot believe what I am doing…Rolling dice in a barbershop to pick a haircut for a surprise? I’ve completely lost my mind… but this is giving me all sorts of butterflies and I can’t stop… plus I’m sure Andrew would love it’ She thought.
“Here goes….” Jennifer said as she rolled the dice onto the counter in front of her.
“Four the hard way! 22! Wow. Bold! Want to see what the dice chose or keep it a surprise?” Said Ashley.
‘Crap. What if it’s really short. What did I just get myself into’ Jennifer thought. ‘It’s not too late to back out….’ But the element of mystery gave Jennifer all sorts of butterflies in her stomach. ‘screw it. You only live once.’
“Keep it a surprise” Responded Jennifer
“Good choice” Retorted Ashely with a big grin on her face. “It won’t take that long to grow out, you have short hair anyways.”
‘Ok. That’s reassuring’ she thought. ‘Not too long to grow out.’
Without hesitation and in a matter of seconds Jennifer saw Ashley grab the guard-less big dark red clippers from her shelf that read “balding clippers”, place them at her forehead and plow them straight back revealing a large pale white completely bare strip directly down the top of her head.
The pretty pixie that Jade had just worked meticulously on was now being reduced to skin. Jennifer’s eyes grew huge but before she could even say a word, Ashley was plowing the clippers across the rest of the top of her head with breakneck speed. It almost felt like the clippers were right back in front of her forehead one second after they plowed through the top, dismembering any hair follicles that stood in their path. Within 10 seconds the entire top of Jennifer’s head was completely bald in a style that resembled male pattern baldness.
“Head down” Ashley commanded.
Feeling completely submissive and incredibly turned on, Jennifer obliged as Ashley continued to erase what was left of her once illustrious mane just a few hours earlier to bare scalp. She continued to run the clippers up the back and sides of Jennifer’s head with incredible speed and accuracy, firmly placing her strong grip on the top of Jennifer’s bare scalp as she finished up.
The feeling of Ashley’s strong grip on the top of her naked head sent welcomed shivers all throughout Jennifer’s body.
“head up” Ashley said again, and made a few more passes across the top of Jennifer’s head before finishing up.
“And time! I’ve still got it. Got you bald in 35 seconds. I was always the queen of induction cuts back when I worked in the army base.” She smirked as she clicked off the balding clippers.
“That’s some bet. I can’t believe you landed on 22, that’s completely bald. You had such pretty hair.” She continued in a slightly condescending tone. Almost as if she was mocking Jennifer.
Jennifer was completely speechless as she sat there in her pinstripe cape, just 10 minutes ago, she was walking through downtown Santa Monica with a very trendy pixie cut, and even got some compliments on her cut style, and now she was sitting in an old barbershop bald as hell.
“I….I can’t bel….my hair…gone so fast” She tried to mutter.
“Relax, we’re not done yet.” Responded Ashley.
‘Not done? What is she saying? There’s no hair on my head!’ Jennifer thought.
Just then Ashley placed a warm towel over Jennifer’s head.
“Feels good, right? This will make sure you have no irritation after I bic ya” Ashley responded.
‘Bic me?’ ‘What does that mean’ But she was too relaxed to think after the warm towel was placed on he rhead. Jennifer closed her eyes, soaking in the incredible feeling of the warm towel on her newly sensitive bald head. She had a million worries, but was also incredibly aroused by the entire situation.
Ashley removed the towel and went over to a little chrome dispenser, giving it a couple of pumps.
“This here is hot lather, bet you’ve never had this applied to your body!” She said with some enthusiasm.
Ashley then proceeded to rub the hot lather all over Jennifer’s head, making sure not to miss a single spot, until her entire scalp was covered in soft white fluff. The feeling was absolutely incredible.
“Normally I’d use a straight razor, but since we’re short on time, I’m going to just go for the Fusion 5” She said.
“Ok.” Jennifer Responded, pretending to know what that meant.
She then took out a brand new blue and orange razor from the packaging, and began to run it all over Jennifer’s head. With the first pass, it felt like the razor was going though sandpaper on her head as there was considerable resistance. To her dismay, her scalp was becoming even more visible as the razor glided across it, removing every last vestige of follicle, as if one had never existed.
“ah, that’s better, we’re gonna get ya smooth as glass” Ashley continued.
Jennifer was shocked at her precision as Ashley scraped the razor all throughout her scalp with incredible speed and accuracy leaving behind only the softest, palest skin – without cutting her. Jennifer was thinking it was all over when she saw Ashley go back to the shaving cream dispenser.
“One more time against the grain, I’m a perfectionist, I did say glass”
Jennifer just sat there in silence, barely even being able to swallow her own saliva after being so overwhelmed by the entire situation and the speed at which it was happening. She was thrilled that Ashley was going to lather her bald head up once more and glide the razor across it. This time however there was much less resistance, as the razor make made quick work of whatever faint stubble there was left.
“You look like you’re enjoying this….” Ashley commented with a smirk as she finished shaving the last bit of shaving cream off of Jennifer’s scalp before using a towel to clean it up.
“I normally don’t do this, but what the heck, let’s send you out of here with some flair” Ashley continued.
“Flair?” Responded Jennifer.
Jennifer noticed as Ashley grabbed a tiny bottle of clear liquid and a soft looking microfiber towel. She then proceeded to squirt the liquid onto Jennifer’s newly exposed scalp.
“This will sting a tiny bit, but it’s basically baby oil mixed with aftershave to keep your head bump free, and give it a nice shine” She said.
After this she unwrapped the towel, and placed it on Jennifer’s head, grabbed each end, and began to rub it across vigorously throughout Jennifer’s scalp, we extra attention to the top.
“There we go, just giving it a last minute polish, so you can leave here looking exactly like #22 – extra bald and extra shiny” Said Ashley.
‘Oh my Gosh. She’s literally polishing my head like a bowling ball. This is so degrading’ Jennifer thought. ‘But at the same time, so hot’
Once Ashley was done, she removed the towel and admired her work.
“There we go. Bald and shiny as a cue ball.” She said, once again in that condescending tone. “You had such a cute little pixie cut when you came in here, that was quite a brutal bet!” She carried on. “You’re going to need to give that noggin’ some sun!”
Jennifer couldn’t believe her reflection. Her face was literally a different color than her pale scalp because of the time she had spent in the southern California sun. Just two 2 hours ago she was admiring how lovely her long flowy hair was in a mirror, and now she was looking at overly shiny scalp that was at least 2 skin tones lighter than her forehead. For some reason thinking about it more and more turned her on, and she actually liked the way it looked because it made her eyes really pop. Moreover, she knew that this was Andrew’s ultimate fantasy.
“I love it!” Jennifer responded as she rubbed her freshly shaved head.
“Well, I wasn’t expecting that, I thought you’d be in tears. If I’m being honest, you looked better with hair, but you’re a pretty girl with a cute body, you can pull this off.” Ashley said, surprised as she undid Jennifer’s cape. “Anyways, it’s 6:05, off you go”
Jennifer hopped out of the chair, paid Ashely $40 and made her way out of the shop. “Thanks for taking me in!” she exclaimed on her way out.
Once she exited she felt the cool ocean breeze on her newly exposed scalp and smiled as it sent tingles down her spine. She immediately FaceTimed Andrew… and said “cancel the dinner reservations” …. Tonight’s going to be a REALLY good night.
Message from the Author: Thank you for reading my story! This is my first time writing so please feel free to offer any comments or suggestions. I would love the feedback.