Freelancer Pt. 01-02

Freelancer

John really hadnt expected anyone to notice his advertisement or take it seriously. He had no skills to speak of and after dropping out of high school it had been really hard to find a job. He got the occasional job serving fries at some chain restaurant or the other, but soon got fired because there were others who were much more punctual and willing. After all it was hard to put in the effort when it was a mindless service job. Or so he thought. Turned out he just needed the right mindless service job.

When his parents had finally kicked him out he had to find a place to stay and the rent and food sucked up most of the minimum wage he managed to scrape from his occasional jobs. The end of the month was approaching and he had no idea how he was going to come up with the money to make rent this time around. So as a last ditch effort he had went online and posted an ad on Cragslist, offering his services. He was honest about his skills and capabilities, however he did add a line which said that he was willing to do any job as long as it paid enough.

"19 year old with little work experience, and no qualifications. Willing to put in any amount of effort required at any job, as long as it pays. I'm really desperate." His was one among many others' last ditch efforts to make some easy money.

So he was naturally surprised when he got a call regarding his advertisement. He was watching TV on a Tuesday afternoon when he got the call from an unknown number. He picked it up with the intention of telling whoever was on the line that they had the wrong number.

"Hello, am I speaking to John Reynolds?" a female voice asked from the other end of the line. "Y-Yes this is him" John replied, taken aback that the call was indeed for him. "I'm calling regarding your advertisement on Craigslist. I might have a job for you if you're interested." John didnt have to think twice. He was desperate after all. "Yes I'm interested!" he said, trying not to sound too eager.

"But dont you want to know what you'll be doing?" she asked. "Well I suppose. What would I be doing?" he replied.

"Mm I'd rather tell you in person if that's all right. My name is Dr. Rachel Westwood and I run a clinic out of my home. I'll text you the address. Meet me here at 5 Pm. Oh and dont be late."

John agreed and hung up the phone. He wondered what kind of a job would a doctor have at a clinic for someone so useless as him. It would certainly not be anything related to medicine. He concluded that she probably wants him to clean the place up everyday or something of the sort. Either way he had no other option but to go check it out.

Despite Dr. Westwood's strict reminder that he had to be on time, John managed to reach 15 minutes late. He was already messing up. He rang the door bell at the address not knowing what to expect. The door opened and he was surprised by who greeted him.

Dr. Rachel Westwood was a lot younger than he pictured. It looked like she had freshly graduated Med School. She might have been 24 but that was it. She was also lot hotter than he had expected. She had a thin sexy body with curves in all the right places. She was wearing a sleeveless t shirt with a doctor's coat over it. The t shirt did her gorgeous boobs justice. They were not huge breasts, however they were the perfect shape and in his opinion, the perfect size as well. He had to struggle to keep eye contact. She was wearing black tights that reached almost up to her ankles. If he could see it, he was sure her butt would be so sexy that it would make him cry. It was hard being 19. Literally.

Her cute oval face sported a frown as she told him "I told you to not be late". Without waiting for a response, she ushered him into the house and straight to her clinic. "Take a seat" she said and gestured to where the patients usually sit. She herself proceeded to sit on her king size chair which seemed a bit too big for her.

"So Mr. Reynolds, before anything else I need you to sign a non-disclosure agreement. In case you dont know what that means, you should never disclose what I ask you to do to anyone. There will be legal consequences which I know you cant afford."

John was taken aback by this, but he agreed and signed it nonetheless, without even reading it. Now he was driven as much by curiosity as by his need to make rent. Dr. Westwood took the papers and filed them into her drawer. She looked at him and smiled for the first time.

"So, here's the deal. I'm going to completely frank here. If you don't like what you hear, you can walk out and never come back. If you dont however, I have a job for you." John nodded silently and she continued.

"I... need to be comfortable while I'm in my office. As you can see I have a very nice clinic to make this possible. However, I cant seem to be very comfortable in my chair. My job tends to get boring and the very least I can ask in return is that I have a comfortable chair. That is where you come in. I... " she hesitated, and her confident demeanor cracked for a second. But she cleared her throat and continued. "I need you to be my seat." She paused to observe John's response before proceeding. John tried to keep a straight face but he wasnt sure what she meant by that.

"More specifically, I need you to sit on the ground, put your head on the seat of my chair, facing up - and this is important, you need to face UP at ALL times - and let me sit on it. There I said it." she finished with a sigh. This was the fourth guy she was offering the job to and so far none had taken it.

John however was different. His mouth hung slightly open as he heard her offer. It was a demeaning thing she was asking him. There was no way he could have expected that this was what she would ask of him. He sat there thinking what he should do. It was humiliating and probably painful as well. Dr. Westwood was thin but she was still an adult human. If she sat on his face with her full weight it would definitely hurt. And this was not for a small duration like five or ten minutes. He would have to be her seat as long as she ran the clinic which could go on for hours.

It was so weird for him to picture it. Right now she and him were two adults having a conversation, but if he agreed he would be revoking his status as a human and just be a seat. She was looking at his face and talking now, but if got the job, she'd be sitting on it.

However, if he could tolerate the pain and the shame, he couldnt deny that it was an easy job. He just had to lie there after all and he would get paid. There was no way he could mess this up. And he really needed the money.

He gulped as he realized he was actually considering the doctor's unorthodox proposal. She didnt offer any words to make his decision easier, but stared blankly (and in his opinion unabashedly) at him, waiting for him to respond. He wanted to ask many questions, but at this point curiosity won - he wanted to see how it would feel like to be in the position that Dr. Westwood had proposed. He could always quit if it was too painful or too weird.

"Al-Alright I'll.. I'll take the job. What are the details? How much will-" Dr. Westwood cut him off at this point. She seemed excited and relieved that John had agreed. "You'll be paid by the day, which means you have to do a whole days worth to get paid at all for that day. I can't have you running off in the middle with half pay. I'll pay you eight hours worth of minimum wage although I will run the clinic only for five hours. I also wont tolerate any sick days. You can have the weekends off unless you want to make some extra cash."

John had to admit, being paid above the minimum wage itself was a new accomplishment for him. He agreed to her conditions and sealed the deal by signing another document that she produced. And just like that he had a job.

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A couple of weeks into the job John had mixed feelings about it. It was pretty much what he had expected in the beginning. Rachel (as he called her in his mind. She was adamant that he address her only as Dr. Westwood) was pretty strict as bosses come. The first day of the job was tough. She didnt give him any pointers on how to deal with the pain, posture, breathing or anything really. As far as she was concerned, that was his job. He was being paid for it after all.

The only thing that made it easier was just how sexy she was. The first day of the job after he had gotten into position, she approached him matter-of-factly and straddled his body. She looked back and down at him and caught him staring shamelessly at her perfect buns. She was again wearing tights although this time they were white. The thin material stretched over her shapely butt dipping in to the valleys and rounding her cheeks. He could see the frilly borders of her underwear below her pants. She really was a bombshell.

And then without warning, she sat down, taking care to make sure the centers of his face and her butt were aligned. His nose slid smoothly in between her butt cheeks and was soon mushed down as her weight started to descend completely on his face. He hastily closed his eyes before they came in contact with her butt. Her butt was so soft that it permeated all the crevices in his face. He could feel his eyeballs being pushed down into their sockets as she sat down completely. She felt a lot heavier than he would have thought and he began to panic out of instinct.

But she shushed him and continued sitting. He knew that if he opened his mouth wide enough he might be able to breathe. But that would expose his teeth to her soft butt and he knew Rachel wouldnt like that too much. It was unlikely that she expected him to hold his breath for hours. It was impossible. She was a doctor, she would know.

He only had seconds to figure out how to breathe before he would push her off in his panic. He knew that might just get him fired without any pay. Suddenly he had an idea. Maybe he could breathe through the sides of his mouth. With some effort he slowly widened his mouth sideways as if he was smiling. It was hard because her entire weight was still perched firmly on his face and the friction made it hard to move. When he did move it hurt quite a bit, as if he was rubbing his face on a rug. Finally after smiling like an idiot under her ass, he managed to sneak in air through the sides of his mouth. It wasnt enough to satisfy his suffocated lungs, but he still kept at it, trying to be calm. He breathed in hurriedly, making a slight hiss sound and breathed out the same way.

He heard her make a disapproving clicking sound with her mouth from on top of him. She didnt like the noise. She reached down and gently smacked him on the side of the head, and berated him. "Be quiet. I have to work."

He figured out that he would have to breathe a lot slower if he needed to be quiet. After a while he thought he had the hang of it. But soon another problem surfaced. The pain. She had been sitting on his face for a while now and it was really starting to hurt. Plus, he was really uncomfortable, with his head bent all the way back. He really wished he could take a break, and just stretch himself before resuming. Dr. Westwood however did not seem to care. She did not relent.

There was another problem that she kept adjusting her position (without getting up) that completely messed up his plans to breathe. She would cross her legs suddenly and lean a little towards one side in the process. This cut off half his air supply and he would have to make do somehow. There were even moments when he couldnt breathe at all. She didnt appreciate his attempts to let her know when this happened, so all he could do was lie still hoping she would move a fraction of an inch so he could breathe again. The small hole that opened up when this happened really was not enough to satisfy a minutes worth of suffocation, but he managed to make do.

After what seemed like an eternity, Rachel got up. Blood and relief rushed to his face and pulled his face up, cupping it in between his hands. His cheekbones and forehead was reeling with a numbing pain and his eyes were showing funny images here and there from being sat on for so long.

But when he looked at the clock he realized to his surprise that it had only been an hour! Four more of this?? He couldnt believe it. Dr. Westwood told him to get up and sit on the patient's chair. He obeyed wordlessly, too ashamed to even look at her. The woman had used his face as a seat for an hour after all.

He sat on the chair, gently massaging his face, making sure to make a show of it. She might take it easier on him if she saw that she was hurting him too much. "Look at me", she commanded. Hesitantly John obeyed and was greeted by the bright glare of a flashlight. His already pained eyes shut themselves on impulse. She clicked disapprovingly again and told him to keep his eyes open. She shined the light into his eyes, examining them and then proceeded to do the same with his mouth and ears.

"OK you're fine. Come back under" she said and got up. As she waited expectantly, John got up reluctantly and resumed his position. There was no mercy for him today. She plopped back down on his face unceremoniously. He winced as the all-too-familiar weight of the doctor engulfed his senses again. This was going to be a long day, he realized.

Four more hours passed by, painfully and slowly. She had seven clients in this duration. She was especially strict that he make no noise whatsoever when the clients were there. John felt that she was getting off on the fact that her clients did not know that she was sitting on a face.

At the end of the session, she did another medical checkup on him and was pleased to find that there was no 'lasting' damage. His face had gotten a little bruised, but there was nothing that would leave a mark. He was clearly tired and ready to drop and she gained some pleasure by knowing this. Being a doctor she could quantify just how much she had hurt him. This also meant there was no point in John's embellished actions of being in pain. She knew and didnt care.

She handed him a duty sheet and told him to fill out the start time, end time and duration of the 'session'. This had to be done everyday. Afterwards, she would sign against it. He had to submit his duty sheet at the end of every week and she would pay him what was due.

A week passed by in this manner and John finally got his first pay check. He set aside what was required for his rent and was pleasantly surprised that there was some surplus. He went straight to a bar and had a beer since a very long time.

One of the other patrons of the bar decided to strike up a conversation with him. "Tough week at work huh?", he asked. "Oh you have no idea...", John muttered.

As he sat there drinking his beer and gently nursing the lasing pain on his nose, he couldnt help but think that he had it pretty good. But little did he know that Dr. Westwood was only getting started.

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Freelancer - Chapter 2

"Uuuughh..." John grunted and started to breathe freely again, his chest heaving with effort. It always took a toll on his lungs to breathe through the small cracks that appeared when she moved on top of him. He needed to put a lot of effort to push the air out and even more to breathe it in.

It wasnt the end of another session. It hadnt nearly been long enough, although it seemed like an eternity. John could tell the time a bit better now thanks to his 'work' experience. No, she wasnt done with him yet. She was probably taking a bathroom break or even just stretching her legs out. She often complained that it was too painful for her to keep sitting on his face. That he wasnt the comfortable seat that he was paid to be. She would get up and look at him, as if demanding a resolution or at least a reason.

John would hesitantly look up at her face and apologize. Not like there was anything else he could ever do. He was still ashamed to look at her after she had objectified him in this way. Maybe a few hours would let him gain his composure, but right off the butt? No. His head would be flooded with short term memories of how - just moments ago - she was denying him his precious breath and refusing to get up even when it was apparent he really needed a break.

It had been over two months since he had started working under Dr. Westwood. Literally. It was the longest he had ever held on to a single job. All things considered, he was now pretty well off. He had more than enough money for all the basic amenities such as rent, food, alcohol and even some money in the way of savings. He just had to put up with the part where his job was sucking the life out of him. But then again, who really liked their job? Isn't everyone complaining about how their soul is fading away at some cubicle job?

John would have no complaints if things had remained the same as it had during the first couple of weeks. Human beings were resilient creatures after all. He developed the discipline required to stay still under her even when his primal instincts said otherwise. He finally perfected the way to breathe under her without disturbing her too much. Save for the unavoidable saliva stains that he left on her sexy butt cheeks, he would say he was getting pretty good at his job.

There was no saying when it became as hard as it was these days, but if John had to guess, it would be that day. It was a particularly less crowded afternoon. She had almost no clients that day and spent most of the time typing away at her computer. John never knew what she was typing. It was not his business. His business was to lie still. And so he did, listening to the "click-clack-click" sounds coming from above him as the good doctor typed away.

That day it was particularly hard for him to breathe. It seemed like an accident. Just a problem with the way she way sitting. Her butt was too far down his face. His eyes were still submerged under her velvet-soft butt. However his mouth was now somewhere in the middle, where his nose used to be. And his nose no longer had its privileged position of nesting right in the middle. Instead of the soft pressure her anus used to give, it was harder and insanely more painful now. Her tail bone was resting too close to his nose bone.

He still managed to survive without pushing her off, but the pain was too much to keep on bearing. What was worse was that more pain meant that time moved slower relatively. He all but held his breath in anticipation of her getting up again. But she didn't! It was then he realized that she liked this new position. It couldn't be comfortable for her at all, but it was enough that it was hurting him.

Half an hour or so into it John really couldn't take it anymore. He tried struggling gently, try to appeal to her kind side. She must have one! But no such luck. John didn't know what to do. On one hand he felt like throwing her off his face and quitting his job right there. So what if he didn't get paid? This was unbearable. As a human being he should have the freedom to stop doing this. On the other hand, he had made it this far. This was just one bad day. In the end he decided to keep at it.

But the decision did not come easy. John felt himself overcome by emotions. He was ashamed at himself for letting this woman use him this way. Humiliated that she was hurting him so much and so easily! Then out of nowhere, the tears started coming. It was all just too much. His tears had nowhere to go. They spread out from his eyes and into her pants-clad butt cheeks. It was as if a dam had finally broke.

He started weeping openly (or as openly as one can with his face shut off perfectly by a butt). His breathing lost its slow steady pace and he heaved in air forcefully making loud hissing noises. He was forcefully sucking air even though there were no openings to provide him with air. Saliva started oozing out of his mouth and this together with his tears made her pants considerably wet. John knew he had let Dr. Westwood down. This realization only made him cry harder.