Haircut Bingo

Haircut Bingo

Maddy was excited to finally be out on her own. She had graduated high school and was now apartment hunting near the university.

It’s not that she doesn’t love her parents, more that she craves the opportunity to spread her wings and experience the independence that comes with your own place. She had identified three apartments for rent and her and her dad were checking them out. The one she selected was within walking distance of her classes, the school’s gym,

and to other amenities she would need such as food and public transit.

She got all settled in and quickly was overwhelmed with schoolwork. It seemed the amount of homework increased as the daylight hours got shorter. She had developed a set routine—gym, classes, study, bed. She was a good student and did not socialize much. She wasn’t drop dead gorgeous, but wasn’t homely either. Most would describe  her as “girl next door” cute with a petite athletic body, perky C cups, large Disney-princess green eyes, and chestnut hair that fell in waves just enough to cover her ample bosom.

Her routine each night was to curl up on the couch and study until she got through all her homework, then unwind with a little television. From her couch she could look out her large front window and people watch when she needed a mental break from studying. As the daylight hours decreased and it got dark earlier, she realized that her window looked directly into the large front window of the barbershop across the narrow street. With the barbershop all lit up she could see what went on within.

She had never been in a barbershop before so she marveled at how large the two barber chairs were with the big footrest, worn red leather, and gleaming chrome. She’d also never seen the massive clippers before. They were ruthless and efficient. She shuttered just thinking about the damage they could do to her hair in short order.

Finally, there was the barber. Maddy had expected to see your stereotypical portly gentleman in a barbershop smock but that was not the case here. She was, in a word, stunning. Tall, slender, and shapely. Her typical attire consisted of tall black high heel boots, a short black skirt, white button down shirt with the sleeves rolled up and the buttons undone to give a peak at her ample cleavage, a beautiful face with high cheekbones, beautiful dark eyes with long lashes and seductive makeup, and a lip length bright red bob with just a hint of hair at her nape.

Maddy found herself taking longer and longer mental breaks to watch the barberette ruthlessly buzz her customers. She was amazed at how quickly the clippers sheared hair, some down to the skin.

Each day Maddy would race home from classes to take up her spot on her couch and peer over her text book into the shop. She googled men’s haircuts and learned to identify them as they were being cut—high and tight, flattop, induction cut, Caesar cut, etc. Because she was a visual learner, she even printed out a picture of an old barbershop poster showing men’s haircuts to help learn them all.

Maddy was extremely introverted so she didn’t date much and relied on self gratification to meet her needs. Since taking up watching the barbershop, she found her masterbation fodder migrating from boys to thoughts of those clippers and of that sexy barberette. More and more she found herself doing this while watching the action.

Of course there wasn’t always action. During the slow times the barberette would sit in her big barber chair facing towards Maddy and read a book. Maddy would sneak glances over her text book at her sitting in the chair with her legs crossed. She’d never seen a girl sit in the barber chair before and her imagination went wild. She’d pretend it was her in that chair getting all her hair chopped off into that lip length bob while she fingered herself furiously.

This continued for several months, now in December it was dark at 4:30, the shortest daylight of the year. This stalemate of watching haircuts, watching the barberette, and masterbating, while still exciting, needed more. Maddy looked over on her end table and saw the old haircut poster. Her mind created a new game to feed her lust—haircut bingo. There were 5 columns and 5 rows on the chart so she would cross off a haircut as she sees it cut, and whichever haircut gave her bingo she’d have to march across the street and ask for it.

This game added a whole new excitement to her watching as she carefully watched each cut to determine what it was then X it out. She’d stare at which haircuts remained and pleasure herself imagining herself getting one of those cuts.

By this time she had eliminated TV from her daily routine and now only watched the shop then studied after it closed for the day. She had even picked her courses for next semester so she’d be home earlier in the day so she could watch more.

Maddy’s parents had gone to Mexico leaving her alone for the holidays. School was on break and the barbershop was slow so she found herself sitting on her couch pretending to read while watching the barberette read her book most of the days.

It was the morning of New Years Eve and after an intense orgasm, Maddy had nodded off to sleep. She was startled awake by a knock on her door. She quickly sorted out her panties and sweat pants then made her way to the door.

“Hello, I’m Cassie and I run the barbershop across the street. It’s a slow week for me so I thought I’d offer the folks in the neighborhood a free haircut if they were interested. I’m licensed as both a barber and beautician. If you’d like I could brush your hair out and give you a trim or haircut.”

Maddy was stunned. The barberette was even more beautiful up close. And her perfume was intoxicating, lilacs. She was mesmerized by her beauty. Her folds were still slick from her earlier enjoyment, but she could feel the heat rapidly building again. Could she go sit in that chair? Could she behave herself in that chair? It was just a trim, right? And could she say no to the angel standing in her doorway?

“Ummm….hi Cassie, I’m Maddy. My mom usually trims my ends but it’s been a while and I’m not sure when I’ll go home again so I’d love to come over to your shop. Let me change first.  Please have a seat, I won’t be long”

Maddy scampered off to her bedroom to change. Now what does one wear to a barbershop? Or for a beautiful seductress? She opted for a low cut top and short skirt with ankle boots. She also opted for fresh frilly panties since her current ones were soaked.

She ran a quick brush through her hair and tussled it up a bit, then rejoined Cassie and they set off for the barbershop. Cassie unlocked the door and flipped on the lights.  “Please take a seat and I’ll put on some coffee” she instructed pointing to the big barber chair.

Maddy approached the chair. It looked even bigger in person compared to her small frame. She stepped up into it and sat back, her legs not long enough to reach the footrest. Oh my God, it is really happening! The fire between her legs continued to build.

She looked around the shop. Wood paneling on the walls, black and white checkered tiles, clippers, scissors, brushes, a blue jar of barbicide on the counter, and bright fluorescent lights overhead. The shop smelled of talc, clipper oil, and traces of Cassie’s perfume. From this vantage point she could see directly into her apartment, directly to her couch. Directly to where she’d sat fantasizing about sitting in this very chair. The heat bloom continued to intensify in her nipples and her pussy as she recalled scenarios that had played out in her mind.

“Here you go Maddy”. Maddy was snapped back to the present as Cassie handed her a cup of coffee.

“Uhh.. thank you Cassie”

Cassie set her cup on the counter and began running her fingers through Maddy’s hair massaging her scalp. Maddy was in heaven. She never wanted this to stop. Changing her panties had been a waste as these were now soaked too. How she wished she could just reach down and give her mound the attention it was soooo in need of.

Cassie was now stroking her fingers down the long locks as they hung down Maddy’s chest. Did she just intentionally brush against my nipple?

“I have a confession Maddy. I’m not offering free haircuts to all the neighbors, just you”

Maddy felt her cheeks flush. Did she just hear what she thought she’d heard? Was this woman she’d fantasized about hitting on her? She pushed the palm of her hand hard into her mound pretending to be straightening her skirt. A small moan escaped her lips. She hoped it wasn’t loud enough for Cassie to hear. Cassie took her coffee cup from her and set it on the counter.

“I see you watching me”. She continued stroking her hair, more intentionally now the ends on her breasts causing the nipples to be at full attention. Another moan, this one louder. “And as you can see from this vantage point, I can see where you pleasure yourself while looking at me. What you didn’t see was the little remote controlled vibrator I used to pleasure myself while dreaming of getting you in this chair. And now here you are.” That was the final straw. Wave after wave of pleasure erupted within and leaked out as her hands turned white squeezing the armrests, her toes curled, her back arched, and her pussy contracted again and again.  The moan this time was far from discreet.

“Oh my! And that was just from stroking your hair. I’m curious to see how you’d react if I started cutting it.” Now came an involuntary whimper.

“I’ll tell you what. Let’s have some fun. You hold this and I’ll hold the remote”. Cassie reached up Maddy’s skirt pushing her panties to the side and inserted the discreet little U shaped vibrator. Her hands lingered noting the lack of pubic hair on her mound as she stroked her folds. Another moan, but Maddy said nothing, too caught up in the overload of sensations.

“Let’s start with a slow pulse, how does that sound Maddy?”

A slight nod of her head was all Maddy could muster as the toy pulsed to life tickling her clit and vagina. What was happening? How was this going to play out? Should she run? Did she want this? It was hard to focus with this pulsing. She would need to invest in one of these toys when she got home.

“Let’s get you caped up shall we?” Maddy felt her hair gathered up and clipped up on her head then a red cape she’d seen hundreds of times on other people was now billowing around her and fastened over a tissue neck strip. Her hair was unclipped as Cassie began tenderly brushing it.

“You take very good care of your hair. It reminds me of mine before I cut it short and dyed it red. Do you like my hair Maddy?”  She leaned over so Maddy could touch her hair. Maddy shuttered as she ran her fingers up the short buzzed hair on her nape up into the silky soft hair that just brushed Cassie’s cheeks. Her own cheeks flushed red from the embarrassment and from the thrill of realizing her fantasy of running her fingers through this sexy red hair. Her breath hitched from the pleasure she was feeling. Now it was Cassie’s turn to moan as Maddy’s fingers lingered on her nape.  She pulled Maddy’s hair behind her ear, nibbled the lobe and whispered “you like that short hair don’t you? Maybe you’d like yours short like this.” She nibbled again and bumped the intensity up on the remote. Simultaneous moans.

The sensations between Maddy’s legs intensified. Cassie leaned in and kissed her passionately while caressing her breasts and pinching her nipples. Another moan.

“Let’s see what you’d look like with a lob, shall we?”

Cassie turned the chair away from the window and towards the mirror. Snip. The first cut was made. Chestnut locks 10” long slid into Maddy’s lap. Snip, snip, snip. Cassie continued around to the back lopping off Maddy’s wavy locks just above her shoulder. Maddy gasped feeling her clit thrum with excitement at the sight.  Her hand slid under her panties to help the toy working her sex.

Cassie continued around until all the long locks had been clipped. Maddy shook her head side to side watching the locks swing out from her head unlike she has ever seen her hair do. She fingered the locks in her lap noting how soft they felt.

“Look how sexy you look with a lob.  But I suspect you’d prefer shorter wouldn’t you Maddy. Maybe a short bob like mine.”  Another moan.

Snip, right at lip length. And on around  she went as six inch locks rained down.  Comb and scissors worked there way up Maddy’s nape shortening it to a fine pelt.

“Is this what you’d fantasized about? Having hair as short as me? Admit it, you came, maybe even squirted more than once fantasizing about having your hair cut like mine.”

Maddy knew she was right. Looking at herself in the mirror this was exactly what had brought her to many an orgasm and nearly another. She looked so fucking sexy now! One hand moved the vibrator to her g-spot and the other circled her clit till she came as hard as she could ever remember. Wave after wave of pleasure rippled through her body as she moaned through gritted teeth. This woman knew which buttons of hers to push and when. She would gladly submit to anything to keep this ride going.

When then orgasm subsided she looked back at her apartment thinking that nothing she could ever watch in the future would top the thrill of this day. How could she ever get a thrill from a routine haircut again after this?

Sensing the melancholy demeanor, Cassie leaned in and whispered, “Oh we aren’t done yet today poppet, and today is the first of many for us.”  Her tongue ran up Maddy’s nape followed by nape nibbles and kisses until Maddy closed her eyes and moaned in approval.

She walked around front and straddled Maddy’s legs while placing one of Maddy’s hands up her skirt inserting two fingers into her folds while she kissed Maddy, caressed her breasts and rolled her nipples between her thumbs and forefingers. Maddy was surprised by Cassie’s lack of panties.

A passerby paused at the sight of Cassie’s ass cheeks peeking out from her hiked up skirt as she made out with a customer who had lost a large quantity of brown hair.  They stared for a bit then moved on having some place to be.

Maddy undid Cassie’s shirt buttons then sucked hard on a nipple while driving her fingers deeper and working her clit with her thumb. Cassie’s pussy clenched tight on her fingers as she threw her head back and came hard with a yell of pure pleasure. She then collapsed on Maddy exposing her ass and south end of her glistening hoo-ha to anyone that might be walking by the window and leaving a slug trail of her excitement on the cape.

Regaining her composure, Cassie climbed off Maddy, rebuttoned her shirt, and pulled her skirt back down.

“Well Mini-me, as fucking hot as you are with a matching haircut, I suspect that you fantasize about going even shorter and you fantasize about having these big clippers chew through your hair don’t you?” A whimper and a nod is all Maddy could manage as she stared longingly into Cassie’s eyes.

“For starters let’s bump up the intensity of your pony ride.”

The sudden increased sensations caused Maddy’s butt cheeks and pussy to clench hard and her back to arch sending the hair in her lap flying down to the floor and her feet. Oh my God, I can’t take much more of this.

“Let’s try a nice bowl cut, shall we? I’ll use the big clippers for the whole haircut. Would you like that sweetie?” Another moan, this one with more oomph.

Oh my God, how does she know about the clippers? Can she read my mind? Is it that obvious? Am I going to have any hair left at the end of this? A fucking bowl cut? Finger harder! Finger harder! “Aayyyyy! ….Ohhh! Ohhhhh! …..Ohhhh! …..Mmmmmmm! ….Ahhhhhhhh! Fuck me that was incredible!”, Maddy yelled as she came again.

Cassie combed Maddy’s hair straight down over her forehead and around her head, then took the clippers and holding them with the tip of the blades towards Maddy’s bangs she plunged them in an inch above her eyebrows. She continued this line around her head creating the perfect cap of hair on top for the bowl cut. She then turned the clippers back over and ran them up the back and sides clipping all the remaining hair down to the skin. The sensation of the clippers on her nape was even more pleasurable than Maddy had ever imagined. She was in ecstasy as the clippers moved up and the hair rained down.

Cassie finished by running her thinning shears rapidly through the remaining hair on top to take the bulk out.

“There you go my little poppet, a perfect bowl cut. Now you look like an eight year-old school girl. Is it wrong that I want to fuck you looking like an eight year-old school girl?”

Maddy stared at herself in the mirror. She had a perfect cap of silky brown hair cut in a crisp straight line above her ears and eyebrows and bald skin below. She reached up and felt her bare scalp. She’d seen Cassie skin many a customer and wondered what it felt like. Now she knew. Cassie blew her warm breath on Maddy’s newly shorn nape knowing exactly how to push Maddy’s buttons. She reached from behind and caressed her breasts with one hand while running the other hand up her nape and through what was left of her hair. Another moan.

“As much as I love this look on you, I know this isn’t what you truly desire .” Cassie unlocked her phone and held it in front of Maddy. “This is what you really want isn’t it.”

On her phone was Maddy’s haircut poster with haircuts X’d out. “I found this in your apartment while I was waiting for you to change. It looks like you just need this one haircut to get a bingo in this column and this row. How about we give you this haircut so you can put an X here? And let’s up the intensity of your little joy buzzer too!”

Maddy was mortified. Had she really left her bingo game out where it could be seen? This was her ultimate fantasy and worst nightmare all rolled into one. She looked up to see the clippers approaching her head again. Oh fuck, she’s really going to do it! Do I want her to stop? And holy hell this vibrator is too much! I’m starting to go numb. She pulled it out and pulled Cassie close with one hand while sliding the other up her skirt to insert it into her sopping vagina. Cassie doubled over and clenched her thighs tight from the intensity.

“Aren’t you sassy and in control with your cute little bowl cut. And you are a naughty one too aren’t you.  Here sassy, you control the remote now.”

It took a moment for Cassie to gather herself after buzz nightgear was inserted. She moved gingerly back to the counter and picked up the big clippers again showing them to Maddy. Maddy jumped and her breath hitched when Cassie turned them back on.

Cassie ran the guardless clippers up the sides and back of Maddy’s head up to the crown spoiling the freshly cut bowl cut. She applied butch wax to her hands and worked it into the hair on top then vigorously brushed it until it all stood straight up at attention. Using a comb held horizontally Cassie cut the top front to back, side to side, and freehand until she had created a precise, crisp flattop which was no small task with a toy in overdrive between her legs. Maddy was in heaven with the sound, the smell and the feel of the clippers as they attacked what little hair she had left.

Cassie then lathered and shaved the back and sides with her straight razor. The feel of the blade scraping along Maddy’s scalp was divine, something she’d want to experience again.

“There you go love, Bingo! A sexy flattop haircut was all you needed.”

Maddy couldn’t believe the transformation. She had walked in here with hair women would die for and would be leaving here with hair women would die to avoid, yet somehow she liked it. Her hair on top all stood straight up and was flat as a board. The hair on the sides was shaved and starkly white compared to the surrounding tanned skin. Her cute little ears were fully exposed, her cheekbones and big eyes and lashes seemed far more prominent now.

She took Cassie’s hand and pulled her up into the barber’s chair straddling her. Her fingers attacked Cassie’s clit while her other hand and mouth worked her breasts until Cassie climaxed again.

Cassie gently ran her fingers over Maddy’s new haircut. “You are stunning!” She then cupped both cheeks with her hands and gave her a long passionate kiss.

“Maybe we should take this over to my apartment so we don’t cause an accident or have the cops called”

“I have a better idea. Let’s just close the blinds poppet and play with my other toys”

The end