A Lesson in Humility

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A former assistant teaches her old boss a lesson.
4.2k words
4.16
27.9k
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Part 1 of the 2 part series

Updated 06/13/2023
Created 04/27/2017
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Jaxon16
Jaxon16
29 Followers

"There is no way I am settling any agreement with that bitch."

"Lisa, we discussed this a hundred times. If you don't comply, their discovery will go through all of our books and that could lead to lots tax trouble for us." Jack conveyed. "Let's see what she wants."

"Mr. Fox, Sarah is here with her lawyer. Should I show them to the conference room?" asked Andrea, the receptionist.

"Sure. Get them some coffee or water. We will be right in."

Andrea brought two bottles of Poland Spring for Sarah and her lawyer, Virginia.

Jack and Lisa walked into the room along with their attorney, Michael.

After a few curt greetings Virginia started the conversation. "We have some incontrovertible proof that Lisa had abused Sarah for years, right up until the time Sarah left Fox Holdings. We have affidavits from numerous employees who witnessed her mistreatment." She paused for a moment then continued, "Jack, are you ready to commit perjury, when I call you the stand."

Michael interjected, "no need for that. Aside from spousal privilege, we agree to the harassment. Maybe not to the degree you say, but we are here to make a settlement. How about two years salary?"

Virginia answered, "that is a start at least monetarily, but Sarah has a few stipulations to add."

Sarah pulled out her tablet and collected herself. "Lisa in the three years I worked for you I gave you all my time and effort. You never complained about my loyalty or my capabilities, but for some reason you used me as your punching bag. You made comments about my weight, my clothes, my sexual activity, and my hair on so many occasions I wore a hat every day for the last year."

Lisa tried to respond. "Sarah I love you. You were the best, and we are lost without you. Take the money and come back to work. I promise I won't make another comment about that bird's nest. Oh sorry, that was the last one."

"Lisa, we tried this twice already. Obviously, you can't help yourself. You really need to be taught a lesson about humiliating people. So, to start I will take the money upfront." Sarah walked over to the window. "I am going to add a few other terms that will make you pretty uncomfortable."

"And those are?" asked Lisa with a touch of venom.

"I was thinking about having you add 30 pounds onto that frame of yours. Maybe going from a size 2 to a size 12 would give you some perspective? But that may give you some health issues. Not sure why I care about that, but I do. And it will just take too long. I need something more immediate."

Lisa spoke with bravado, "I would have to eat like the cow you are and not exercise at all for months, so you are correct about that. What else do you have?"

Following another insult from Lisa, Sarah now raised her voice, "how about I make you look like Mike Tyson? You surely gave me no slack, when I got a little flower on my shoulder."

Jack grabbed Lisa's leg and spoke to Sarah, "Sarah, Lisa is nervous. Please excuse her. I get you want to inflict the same humiliation on her, but you can't have something permanent like a face tattoo."

"Of course I would not demand that. It would be cruel even by Lisa's standards, and it would break this deal." Sarah looked back at her tablet. "She also told me the nose stud I got was demeaning. Maybe a big hoop right through her septum would be shameful enough." Lisa touched her nose subconsciously. Sarah paused for a moment reviewing her notes, then she continued. "Lisa made fun of my clothes, so I get to pick her clothes for a year."

"Every day?" asked Lisa with exasperation.

"No, just on Monday. You usually take off on Mondays, so now you work for me. I will control you on Monday. You called me a slut many times, when I wore a short skirt or low cut blouse. The fact that you wore clothes even more racy on the same day seemed to be lost on you. If I send you an email on Sunday night to wear a miniskirt and a white blouse, you better show up wearing that outfit. And if I say to go commando, you better not have even a thong on under that skirt."

Lisa pondered for a moment, "I can live with that. What else?"

Sarah motioned for Lisa to come the window. "Look outside."

"Sarah, what am I looking for?"

"Do you see the bank on the corner of 14th St.? Now look just before that."

Lisa spotted the Wells Fargo then spoke, "There is a barber pole. That is a barber shop." It took her a moment to register Sarah's intention. "I am not getting my hair cut. No one touches my blond locks except who I choose. And right now that is Javier on Madison Ave."

"You will have your hair cut or we go to discovery right away. I will not budge on this. You joked about every haircut I ever got. One made me look fat another like a clown. You were relentless. Now you will be the one that people will stare at."

Suddenly, a little more remorseful Lisa asked nervously, "what do you have in mind? A bob? I could manage something at my shoulders."

Sarah interrupted, "not that easy. I was thinking something quite drastic or in stages for each Monday. Let's start with a sculpted pixie, and we can go from there each week."

Lisa's temper rose again. "Maybe a pixie at my salon with my hair dresser. But there is no way I am going to a barbershop full of men to get a drastic haircut."

Virginia had been sitting quietly taking notes but now she spoke, "Sarah has made this haircut the priority, non-negotiable part of the deal. You will comply with all her stipulations or we go to discovery. And she knows where all the secrets are."

Michael asked for a break. Virginia and Sarah excused themselves for the ladies room leaving Lisa and Jack with their lawyer. Michael spoke, "Lisa, I don't think we have much of a play here. Anything found in discovery and eventually at trial could mean significant fines and penalties and maybe some jail time, if the authorities start to poke around. I strongly advise you comply with her provisions."

Lisa remained silent until Sarah and Virginia came back into the room. She then spoke, "I am ready to accede to your demands. I have been a bitch to you and a few others over the years. Poor Jack over here has borne more than anyone else. I am really sorry for all that I have said and done. I assume the pixie is just the start," she stated with a little hope she would have some hair by the time this was done.

Sarah replied, "Finally, some contrition. I accept your apology, but I still have my year with you. As far as the haircut, I was going to start with the pixie and gradually have it cut shorter each week."

"Until I am bald, I gather." interrupted Lisa.

Sarah nodded. "However, in lieu of your new found humility, let's start with a complete razor shave, and you remain bald for three months. After that you can start to grow out your hair, and we will see."

Lisa did not argue. "I wonder what I will say to everyone. A fund raiser, a lost bet, an allergy?"

Jack answered for her, "Maybe try the truth. I humiliated several people on a regular basis, and I am now making amends in my own humiliation."

"I am sure you will figure out something because you won't be able to hide it," Sarah added. "No hats, no scarves, and definitely no wigs. If you need protection from the sun or rain, then wear a hat. But whenever you are inside you must show your head. Also, on Monday after your shave you will go sit in the chair and have your make up done at a place of my choosing. You will have lots of skin to makeover, so it will take a while."

"Anything else," asked a humbled Lisa.

"There will be penalties, if you don't comply. Mondays are sacred. From 9AM until 6PM you will do what I say. You must wear the outfit of my choice, you must be on time for your shave, you must go for your make up, you will run a few errands for me, and you must walk or use public transit. No Ubering around." Lisa just nodded yes. Sarah continued, "Also, I will have someone randomly follow you all week to make sure you comply with keeping your head bare. Right now, I believe you will comply, but after a month or two of having your head shaved you may have other ideas."

"What are the punishments for any failure? What if it's not my fault like the subway gets stuck?"

Virginia answered, "First, Sarah has full discretion over the actual occurrence. If you don't agree, this deal terminates and we start the law suit. You have one freebie a month, as long as you call Sarah with a credible explanation. Also, the same applies if you forget to remove your covering indoors. The second mistake in the month you lose those perfect eye brows. "

"More work for the make-up lady," Lisa said glumly.

Virginia continued, "A third one in the month adds another month of shaving."

Sarah interrupted, "No, I think the hoop through the septum for a month for a third infraction. Anything more than that we will assume you don't care anymore, and we go to the lawsuit."

Touching her nose again Lisa asked, "When does this start?"

Virginia spoke, "Michael and I can have the contract written up by this afternoon. You and Sarah can sign it around five o'clock."

Sarah continued, "You have the weekend to get ready. On Monday wear your leather mini with a white button down blouse and a pair of knee high boots. Make sure to show your boobs, and you can choose your underwear. See, I am already being nice. Oh, always have big earrings on Monday. They will offset the lack of hair. "

Lisa signed the contract later that day with little fanfare. She went about her business on Saturday not giving much thought to Monday. On Sunday night she and Jack went to Diamani, one of their restaurants, for dinner. The thought of coming here to work the front of the house with a bald head terrified her. Her only consolation was the restaurant was closed on Monday, and she would not have to work in some slutty outfit that Sarah chose.

When they got home Lisa opened her laptop to check on an email she could not read on her phone. Her mind wondered a little and she googled "bald women." She could not believe how many pictures, videos, and articles came up on her computer. At first, she thought the women looked terrible and raw. But the more she inspected the pictures, the more she could see how their features popped out. They had no hair to distract from beautiful eyes or lips, cute ears, or a lovely neck. Conversely, she could see that not all heads were round and smooth. Lumps from various bones or discolorations on the scalp made for a very ugly bald head.

"Jack, come in here. I never found out how this is going down on Monday." she called out.

Lisa was at her vanity trying to inspect her scalp. "What are you doing? Did you try to call Sarah?" he asked putting his hands on her shoulders.

"Looking for moles and bumps on my head. And she just sent me back a text with the answer "Surprising you." Were you able to cancel your meeting for tomorrow? I could use the support."

"Sorry, I have to drive to Boston first thing to meet with the contractor for the new location. He won't be able to meet again for two weeks, and we have to get started."

"OK, I will manage." She brushed out her hair then pulled it back into a tight ponytail.

"Lisa, you are so pretty. Barring some really ugly scalp condition you can pull off being bald for a year. I even think it might turn me on."

"I am glad you think I will still be beautiful. Even having to explain a hair donation and "the new me" to everyone should be fine. But Sarah has the power to make me miserable starting with having the whole ordeal done in a barbershop in front of strangers."

"Like you just said, you will manage," was all he could say rubbing her shoulders more intensely.

Lisa tossed all night. Her restlessness kept Jack awake, too. "Lisa, it's 2AM. I have to leave in a few hours. I know what will calm you down." He rubbed his hand up her thigh and stuck two fingers into her vagina. Jack used his thumb to rub her clit, and Lisa began to moan softly. She put her hands on his head and shoved him down the bed. Jack immediately started to lick and bite her clit as his fingers probed her G-spot. Lisa came much quicker than usual. She needed this release, and now he did as well.

"In my mouth or in my pussy?" she asked him.

"On all fours," he commanded. He grabbed her ponytail and used it for leverage to slam up into her vagina.

"Did you give Sarah this head shave idea? You realize you won't be pulling on my hair for a long time."

"No, but the idea of a bald headed blow job when I get back will likely distract me during my meeting today."

"I'll send you pictures. Good luck getting any work done." Imagining Lisa's head being shaved was enough at this point, and he came hard deep inside of her. Lisa followed him with another orgasm of her own. The energy they released from the sex exhausted them, and they crashed right away in a spoon.

Jack woke at 6, got ready, gave Lisa a kiss and words of encouragement, and left in dire need of a cup of coffee. Lisa fell back to sleep, until her alarm went off at 7:15. While washing her hair she relished in its silkiness and weight for the last time. Lisa also realized she would no longer need to dry her hair and blow it out; a quick pat with a towel would now do the trick. She went for maximum coverage wearing a pair of boy shorts under her skirt. She did not need any additional embarrassment as the skirt barely covered her ass.

Lisa took the subway up to Union Square wanting to start her day in compliance with Sarah's demand for public transportation. The train was packed, and she had to stand. She observed many men and women staring at her in her provocative clothes. She did not even want to think about how many would be staring at her every day, even when she wore old jeans.

From the top of the stairs of the subway Lisa walked east down 14th street. She located the barber shop next to the bank. Gathering all her confidence she opened the door to the shop expecting Sarah to come rushing toward her. However, Sarah was not there, and Lisa could not find a familiar face.

"Are you in the right place, young lady?" asked one of the barbers.

"I thought I was supposed to meet someone here. Sarah Goodman said she made an arrangement, I think."

"You must be Lisa. Sarah said a pretty blond woman would be in here at 9. I am Dan. Take a seat, and I will be with you soon."

Lisa sat down in the chair at the end of the row to wait for her turn. The place was pretty crowded. Five men waited ahead of her, but with three barbers working she figured it should not be more than twenty minutes. She had never been in a real men's barber shop before. The starkness of the red leather chairs, the white painted walls, and tiled floor felt intimidating enough, but it was the masculine smell of aftershave that made her nervous. Would the barber use that on her head after he finished? The butterflies in her stomach morphed into termites eating away at her insides. And she had to pee desperately.

"Where is the bathroom?" she asked Dan. He pointed to the back room and she quickly walked over there. Of course the seat was up. "Men!" she thought to herself.

As she returned to the main room Dan had finished with his customer, so he waved Lisa to his chair. Before she sat down he uncovered a camera strategically positioned to film her. "Sarah wants to make sure you have something to remember this day."

"That's very nice of her, but I think it is more for her own enjoyment or to post online for more embarrassment for me. Dan, how did you get chosen as the lucky guy to shave my head?"

"I own the place, and I told Sarah if you showed up I would shave you for free. Are you ready?"

Lisa nodded with little conviction. Dan snapped a cape around her neck. It was not very long and her legs stuck out from about mid thigh. He brushed her hair for about five minutes removing every knot and tangle. Lisa loved having Javier brush out her hair, but this time her fate awaited and her bladder became uncomfortable again. Dan started to gather a few sections of hair. He saw Lisa look at him in the mirror with a quizzical expression.

"Sarah said you have lovely unprocessed hair and to donate as much as possible. This makes it easier."

Without a word Dan snipped off eight bundles of twenty inches of blond hair. By this time another five men had entered the shop, and all of them were staring at Lisa in the barber chair. Dan continued to snip Lisa's hair until only an inch remained all around. She tried to avoid looking in the mirror without much success. After further inspection she actually thought she looked pretty good with a crop. However, that was short lived as Dan fixed an attachment to a clipper. He started by her right ear removing the inch of hair leaving only blond fuzz. He worked the clippers around the back of her head and finished by her left ear. Dan switched the guard and used a comb to reduce the top to about a half inch. After another few minutes of sculpting Lisa was left with a very short flat top. Dan used some sort of sticky gel to get the hair on top to stand up straight.

Finally, Dan spoke to her, "When I finished this part of your haircut, Sarah asked me to give you this note."

"Hello Lisa. You must look like a marine right now. Wish I was there, but I wanted you to feel alone. And I will have the video. I want you to run a few errands before Dan finishes your haircut. Go to the bank and withdraw $50 for Dan's tip. No ATM, go to a cashier. Then go to Skechers on Union Sq. West and try on a few pairs of running shoes. Walk around the store a little bit each time. Finally, go to pizza place around the corner and order two pies for lunch to be delivered to the barber shop. Have fun! Sarah"

"Damn coffee," Lisa thought to herself as she rose from the chair to use the bathroom.

Again, all the stares as she walked to the back room. However, rather than ridicule from all the men in the shop she received multiple compliments. "You rock that buzz cut, you look great, and I wish my wife would get a cut like that," were among those she heard.

The same scenario played out on the streets of Union Square. This was New York and anything goes, but Lisa gave a striking image of a non-conforming woman. Hence, almost everyone stared and many gave the same complements she heard in the barber shop. The bank teller was embarrassed to look at her, but he did say she looked great as he handed her the fifty dollars. At Skechers her confidence grew, she even bent over a little to tie the running shoes not worrying about the salesman catching a peak of her butt. When ordering the pizza two men asked her for a date, and rather than rebuke them like she normally would, she joked, "I already have a lucky guy at home."

On the walk back the stares from people now excited her. She knew many women envied her courage, and all the men wanted to sleep with this hot babe. She rounded the corner of 14th street and looked up at the sign above the barber shop, "Dan's haircuts." She smiled. "Hey Dan, the pizza should be here at noon. Too bad this fade, flat top has to go. I got so many compliments."

"Really, let's see if the chrome dome elicits the same response," blurted out Sarah.

A startled Lisa spun around to see Sarah sitting on one of the waiting chairs. "When did you get here?"

"I followed you around just now. You seem to have been a hit with most people. Maybe in three months when I let your hair grow back, you can be again. Think about that, if you feel like committing a violation of our agreement. Sit down! Dan is waiting for you."

Lisa thought for a moment that Sarah might deliver her remaining hair a pardon, but she sat down resigned to being an egg head for three months. Dan drew the cape around her again. This time a bare clipper made quick work of the flat top and light fuzz on the lower part of her head. Lisa sat staring at her head in the mirror, while Dan excused himself to the back room. Although her scalp was excessively pale, she saw no weird knobs or bumps. And her skin did not have any discolorations.

Jaxon16
Jaxon16
29 Followers
12