Fantasy Football by Heyyyy13

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He knew it wasn’t a good idea. He had really believed he had a shot when he agreed but in the end Jack realized he royally messed up. Agreeing to the fantasy football punishment of getting whatever haircut the group agreed on seemed fine when he figured John would be the one in the barber’s chair. But when his top picks ended up hurt and his scores plummeted his fate was sealed. He was still waiting on his friends to come together on a punishment style. He did know one thing for certain. They wouldn’t take pity on him - whatever it was, they would choose short.

Lately his blond locks had gotten a bit overgrown. He’d been sporting the same medium length side part for years and in the last few months hadn’t gotten much beyond a trim. Neglecting even that the last 3 months, his hair was well covering his ears and touching his collar.

He figured telling his girlfriend before it happened and before they chose would be a good idea. She really loved his blond hair and it would really hurt her to see him without it if his friends chose the worst possible punishment. He looked over at her on the other side of their shared living room where she working on her graduate thesis.

"Hey babe" he said looking up from his phone. The same phone that would soon tell him the style he’d be sporting for a while. She simply mumbled out a "yeah?" Without looking up from her work. She had known the punishment for the loser of fantasy, but hadn’t thought to ask in a while. Like him, she figured someone else would lose.

"I lost" he said.

"Lost what? Your phone?"

"No. The fantasy league." As soon as the words left his mouth he heard her stop typing. She continued staring down ahead saying anything. He tried to find the words to say but then his phone buzzed. When he saw the screen showed a notification from the group chat he figured there was no sense in dragging things out. Maybe his friends would take some pity on him.

He couldn’t help but be a bit surprised when he saw the haircut he had in store. Jack hadn’t realized his girlfriend moved across the living room until she sat down next to him. "That’s what you’re getting?"

"That’s what they chose. Could be worse I suppose. They could’ve had me shave it all of" he told her trying to find a positive angle.

"Still not much left" she said looking at his phone at the image of the flat top they had sent.

"You’re not wrong" he told her.

He had expected her to sulk but he was surprised when she moved away towards the bar. He was even more surprised when he heard the sound of her keys. She really did have too many things on her keyring.

"Where are you going?" He asked her.

"Don’t you have to get that haircut?" She asked him.

"Well yeah, but we don’t have to go right now" he said a bit apprehensive. She wasn’t the only one dreading it.

"I wouldn’t push it with your friends. Wait too long they will tell you to shave it all off." She was right. He felt almost robotic as he moved. He didn’t really remember much of getting into the car or the drive. He didn’t really snap out of his trance until they stopped in front of one of those old style barbershops that still had the spinning pole. He hadn’t been to one in years and he was surprised she didn’t just go to a great clips which was where he usually went. Sensing his confusion she said to him "if you’re getting one of those old fashion clipper cuts you can at least make sure its done by someone who does them regularly".

She had a valid point. He walked inside behind her. He felt like a bit of a coward standing behind her as she spoke to the barber sitting at the front desk.

"My boyfriend here lost a bet and now his friends are insisting he gets one of those old time style flat tops. I wanted to make sure he gets a nice haircut not some hack job like he’d get at great clips. Can you make sure it looks sharp and he avoids looking tacky."

Tee barber, who had to be easily late 40s, looked away from his girlfriend and at him. He then turned back to Jack’s girlfriend and told her "he actually has the face shape to pull one off quite well I think. He is a bit on the thinner side so I may need to buzz the sides down quite a bit to make it look good on him".

"That’s fine, I just want him to feel at least a tiny bit good with it. I know it’s not his first choice, but it could end up being a good thing. He hasn’t changed his hair for years ya know? Plus he’s gotten quite shaggy lately if you couldn’t tell. Honestly -" She paused and smirked at him before saying "I will be glad to see it gone. He needs a nice cleaning up. He’s never gotten the sides shorter than an inch since I’ve known him, or the top for that matter. Seeing him with it buzzed down will be great."

Jack was stunned to say the least. He had never heard her mention anything about his hair being too long in the past, or else he’d have considered getting it shorter. But here she was, was talking about his hair like he wasn’t even there.

The barber fired back at her with a laugh by saying "He could definitely use a good clipping. Is it okay if I end up needing to go white walls at least for part of it?"

"I trust your judgement there. This is probably the shortest I will ever get to see him so I want to enjoy it while it lasts. I just want to make sure he looks good." She told the barber.

The Barber reassured her by saying "I will make sure he walks out with something that genuinely looks good on him."

"Good" his girlfriend said before lightly gesturing towards Jack to go sit down in the chair.

Jack, with his fate sealed, sat down in the barbers chair. He looked at his girlfriend who had taken a seat directly in front of his chair. She excited to watch him get shorn like a sheep. With the cape on and his girlfriend for an audience he waited for the drastic haircut to start.

The barber combed out his overgrown side part and sectioned off the top, clipping it out of the way.

"Head down" the barber said somewhat coldly. Jack just did as he said. That’s when he heard the clippers roar to life. He hadn’t seen what guard had been put on, but he knew it would be shorter than the one’s he had gotten the last decade of his life. He felt the clippers at the base of his neck work their way up all the way to the crown of his head. Blond hair fell in large tufts onto his lap. With the clippers back at the base of his neck again, he felt them rise and more hair fall. This continued until the clippers reached up around his right sideburn. Before long he felt cool air on the back of his neck and the pile of blond locks on his lap made it look as if he would have not a hair left on his head.

Jack felt fingers forcing his head back up and he locked eyes with his girlfriend. She was watching with a smile on her face. She was enjoying seeing all his blond hair come off. The barber asked "Is that short enough?" and before Jack could answer his girlfriend said "I’m not sure".

"How about I finish the top and if its still too long I can take it down more." The barber replied. Jack watched his girlfriend nod her head in agreement.

Jack felt the clip come out of the top section of his hair and what was left of any length he had fell into his face. The barber collected it in his hand and cut a solid inch of all the hair off throwing it in Jack’s lap.

The barber then grabbed one of those spray bottles and continued to spray until it was soaking wet. Grabbing a blow dryer he held Jack’s hair straight up and dried it all until every strand was standing completely upright.

Picking up the clippers and removing the guard on them, he positioned his comb and began to take off the length in strokes. Jack continue to watch his girlfriend as he sat with his hair raining down around him. It seemed with each pass of the clipper and clump of hair that fell her smirk grew more.

Quickly all the hair on the top of his head was reduced and the piles of hair no longer on his head grew. Jack expected it to be over, but without warning the Barber took the clipper that still had no guard attached, and ran it from the base of Jack’s neck up to the middle of his head and stopping at the occipital bone before flicking away. Jack watched in horror as the less than 1/4 inch strands rained down and joined the cape. The barber didn’t notice this diss comfort and continued to peel off the stubble in very rhythmic fashion. Buzz from neck halfway up his head. Flick the small clump of blond fuzz away. Pause. Position the clips at the base of Jack’s head. Repeat. All the while Jack watched his girlfriend grinning ear to ear at the amount of hair coming off.

Once he had removed all the hair on the bottom half of Jack’s head, he snapped another guard on and ran it up to the crown, blending the sides close to the top. After spending an eternity taking off more blond hair by blending the short sides Jack was really starting to relax. The vibrations against his head finally were calming and he knew his fate had been sealed.

The barber removed the guard again and with the comb he pressed against the side of Jack’s head vertically, revealing some pesky blond locks that were still long, the using the clipper to send them to the floor. He continued to remove hair all the way around Jack’s head from where the flat top met the sides. Jack watched as what he imagined was his normal cowlick that gave him trouble fell to the floor. "Well, if it’s not there, it can’t cause issues" he thought.

"I’ve already given him a bald fade, is it okay if I use a straight razor to make it smooth?" the barber asked his girlfriend.

"That would be great, thank you."

"Should I take that line higher before I do?" The barber asked, referring to the fade line. Jack looked at his girlfriend worried she would say yes but surprisingly she told the barber "no I think for now his hair is short enough". While Jack didn’t like the way she emphasized "for now", he was relieved that no more length was going to be taken off.

Taking lather and a straight razor, the barber removed every hair from the ears down on Jack’s head. He imagined with the blond color, that the sides looked almost bare.

"Can you actually shave his sideburns a bit more?" Jack heard his girlfriend ask the barber who simply took the straight razor and pulled the skin shaving them off just below being level with the tops of Jack’s ear. He felt the barber running some product through the top of his head before unsnapping the cape and sending all the blond hair that had been sitting in his lap to the floor.

He was almost afraid to see what he looked like. His girlfriend was still staring at his head and at the massacre he saw on the floor he almost wondered if he didn’t have a hair left to look at.

"You were right, he does have the face to pull it off" his girlfriend told the barber.

"You know, I do those cuts for a lot of older guys, and former military, but rarely get the chance to do one that actually looks good. I personally hate those horseshoe ones or doing anything that involves a landing strip."

Upon hearing this Jack whipped around. He finally got a good look in the mirror and he was surprised to find it actually looked… good. He was so distracted he almost didn’t hear his girlfriend respond "I am going to pretend I know what that means." Yes his hair was much shorter than he usually had it and the sides looked really bare, but it brought out his jaw. The face so often mistaken for being boyish now looked more masculine and adult. He still had about an inch of hair left on top.

"If you don’t want to look like that every day I’d recommend using some product to push it in some. It makes it look a bit softer and not as harsh." The barber told him. He just nodded.

"What do I owe ya for making a man out of him" his girlfriend joked.

"On the house if he promises to come back and get it cleaned up in a few weeks" the barber said.

"Deal." Jack said shaking his hand.

"If you don’t mind me asking, what would you have chosen for him if you could’ve picked the style ma’am?" the barber asked.

"Honestly a crew cut with just enough to style is something I’d like to see on him. I’ve always really liked short hair on men. I think if the sides are more than a number four, then you need to walk through the barber’s door." She replied. The Barber just laughed as they left.

When they got back to the car he looked at his phone, realizing he had left it in the car. Apparently his girlfriend had sent them proof and his friends were already responding. They were a bit upset he actually looked good with the cut meant to be a punishment. And with the look his girlfriend was giving him, he knew that later it might actually have been a good thing all a long.

"So a crew cut?" He asked her. She blushed red.

"I mean he asked. I didn’t think in a million years I’d have seen you with it this short, let alone shorter." She responded now having lost all the confidence she had while in the shop. He hadn’t realized till now, but her making the decisions for him and demanding hair be cut was a huge turn on for him.

"I might consider it actually. Especially if I know my girl likes me with short hair this much. Maybe next time I can figure something out without having your instructions." He told her with a wink as they pulled out of the parking lot.

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