Gillian's Descent Ch. 04

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The slut meets her tormentors in a jail cell.
5.8k words
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Part 4 of the 6 part series

Updated 10/30/2022
Created 12/07/2005
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TheDarkCloud
TheDarkCloud
4,494 Followers

She felt like she was suffocating. The doors and the clear plastic partition of the police car seemed like they were closing in on her. Maybe it was just the after effects of the drugs she had taken, they certainly wouldn't have helped but she knew herself that a part of her conscious mind was very definitely still working. How could this have happened? How did she end up here, like this? And more importantly how the hell could she get out of it? That was the thing she had to get an answer to and quickly.

For a brief moment Police Commander Gillian Anderson allowed herself to think back over the events of the past 48 hours. It did not make for happy thinking. From the first moment that unmarked envelope had dropped onto her desk she had had grave misgivings and look where it had led her. Just look at what being willing to go to all lengths to preserve her career had done to her. She had become a call girl, worked in a seedy brothel and just tonight walked the sidewalks as a cheap hooker. And now this, arrested on charges of prostitution and drug dealing. Her career would be ruined. It had to be a further set up, what a fool she had been. She resisted the desire to shout at the two officers driving her to the station, 'Do you know who I am?' because undoubtedly they did and she could do no good through that so she sat in the back seat her wrists handcuffed behind her and considered what she would say to her lawyer.

Up front the two arresting officers smirked and took sneaky glances at their prisoner. Their sexy commander looked quite the whore in her outfit, her top ripped to expose most of her left tit and her fishnet stockings torn below the hem of her tiny mini skirt. Whereas Gillian was dreading being led into the station there were a whole number of people (including the two cops) who were relishing the thought of it. It was a set up for sure, she realised, as she was led into the station right through the main entrance. There were banks of photographers waiting to see her led humiliatingly past them as their cameras exploded to life and a million questions were shouted out. She should have been given at least a blanket over her head but the two cops led her inside seemingly as slowly as possible and when one of them 'accidentally' bumped into her as they ascended the stone stairs it was enough to dislodge her barely in place torn top and expose her boob to the paparazzi. They all (including Gillian herself) knew it would be front page headlines and pictures for the next day's papers. She could just imagine the headlines.

She dropped her head in shame and allowed herself to be hustled inside where there were even more cops waiting to see her brought inside. Why didn't any of them clear the press away? Spare her some blushes at least. Allow her some shred of dignity to be preserved. But it was like no-one wanted to acknowledge who she was and what she was here in the police force. The Desk Sergeant read her her rights and took her bag and at that point they discovered the large amount of coke in her handbag, she looked at it disbelievingly as he started noting it down, made a call to a detective and she heard the word 'dealing' in his conversation. She struggled, tried to claim her innocence, that she had been set up but no-one had any love lost for her before so they certainly wouldn't help her now. She was led down into the stone bowels of the station and released from her handcuffs as she was placed inside a large holding cell. At least, she thought, it was empty, she did not have to share it with the lower class criminals, not realising the irony of her thoughts.

Now, at last alone in the darkly lit cell, sitting on the edge of the uncomfortable cot and contemplated her future, how she had got into this mess and what she could do to get out of it. The normally cold, hard Police Commander even allowed herself to let go a sob and begin to softly cry. She knew nobody would be sorry to see this happen to her, if only she had made some friends on her meteoric rise in the force rather than alienate everyone she had passed on her way to the top.

Suddenly a voice spoke from the shadows outside the cell and she had to get up to the bars to hear it clearly.

"I told you Commander that if you did all that I asked of you you would have me behind bars by the end of the night, didn't I. Well here I am."

At that the door swung open and a tall, male figure appeared and stepped into the diffused light in the cell. She gasped as her old partner Joe Dupree walked calmly into the cell and smiled at her. He had also advanced in the force while Gillian had scratched her way to the top and he was a Sergeant now.

The door clanged shut behind him but he remained at the door looking at her with a mixture of vindication and triumph written across his face.

"You bastard" Gillian spat as he got to her feet, unsteady on her heels and made to come towards him. But the events of the night had dulled her senses and he easily caught her wrists and pushed her back down onto the cot.

"Now then Commander, you're in enough trouble, don't want to get an assault charge against you too, do you?"

He stood powerfully over her and cast her a mocking glance as she once again tried to cover up her left breast which had come loose from her torn top in her efforts.

"Don't worry about it, I saw them and a whole lot more this afternoon. Remember when you were in the mask?"

God, it seemed so long ago but yes, she remembered this bastard fucked her in the brothel while she wore that mask. She shuddered at the memory. Still at least now she knew her enemy and tormentor and once she got this whole mess explained she would begin to make his and his helpers lives hell.

"You won't get away with this you bastard! I'll prove all the things you made me do and then I'll get you, I'll make you wish you never crossed me!"

He smiled cheekily.

"My god you do look hot when you're angry Gillian. Something to do with that red hair. Turns me on! But I hate to disappoint you but you're going to have to wait to get your revenge. You see it's not just me that desires to see you taught a lesson you'll never forget. There's a whole lot of us that have clubbed together to arrange all this, I'm just the point man in this endeavour. You must really have pissed off a whole lot of people in your years in the force."

Gillian caught movement from the shadows and a line of recognisable faces entered the cell and stood across from her. As she watched them file in the true scale of her plight was starting to reveal itself to her. She recognised each of the men as they filed in. The Honourable Judge Mackie, Kelvin Perry owner of the towns largest news network (TV channel and newspaper), Michael Biskin, the District Attorney, Mayor Joseph Brown and a handful of the cities leading industrialists. Then came the worst, Chief Clancy Simpson, her immediate boss. Joe waited until they were all stood around her in a wide 'U' shape as she sat on the edge of the jail cell cot, about ten feet back and Joe waited until she had glimpsed all their faces before speaking.

"Quite the powerful gathering isn't it Commander? And not only that but they aren't alone in this, their peers and colleagues all know about this plot too and were more than pleased to offer their support and help wherever they could. Seems like a whole lot of people are only too keen to see you taught a lesson."

Gillian was taken aback by the line up and all her thoughts of how she would go about clearing her name were swept away in one fell sweep.

"So let me give you your only options bitch! (the tone as he snarled that word made her wince, he had been so calm up to then). You can plead guilty to the charges we present you with and accept our decided sentence of one years incarceration. Or you can take your chances that whoever you hire to defend you isn't in our employee or the judge isn't or the jury aren't (and make no mistake we'll make sure they are) and end up with a ten year stretch in the hardest prison in state with every single inmate knowing your previous profession."

Her pretty face fell open as the stark options were presented so matter-of-factly to her. She was shocked, upset, her world was crumbling before her eyes and the assembled group of men were enjoying it immensely as they thought back to all the dirty tricks and campaigns and short cuts she had used on her route to the top. She stammered and stuttered, unable to even form a coherent reply. Her whole life had been so comfortable and above everybody else and now she was being reduced to this. It was galling. Her analytical, calculating brain could see the truth in their eyes, she was in deep, deep trouble.

"Please, no, I've done nothing wrong, there must be something I can do."

Dupree smiled like a crocodile.

"Well actually Commander Anderson we were hoping you'd say that because you see there are eleven of us present here as you will see and what we thought was that for every one of us that you let fuck whatever hole we wanted we could knock a month off that sentence. That way you can get that down to just one month in the jail, which I'm sure you could manage, couldn't you? Alright your 'career' might be fucked up but lets face it working the streets and the brothel should have shown you that there is another career more suitable for you than policing. So it's decision time bitch, what's it going to be? Wanna fight your case and risk a long stretch in the prison? Or put your slut's body to some good use and reduce that sentence? It's up to you."

On the spot and under the gun there was little option for her other than to cave in and she whispered in defeat.

"Alright, I'll do it" and dropped her eyes to the stone floor as she uttered her submission.

Dupree clapped his hands and said.

"We knew you would see sense bitch, why don't you get us hard and strip off that hooker gear first. Give us a little dance, eh?"

Gillian started to rise but as she did so she became acutely aware of more movement outside the cell and she watching in growing horror as lines and lines of her subordinate police officers filed in to get a view of what she was going. Dupree saw the look on her face.

"Everybody knows what's going on Commander, like I say you don't have many friends around here and everyone's wants to see what you've been reduced to doing. Word of your antics on the streets tonight certainly seems to have spread!"

The redhead couldn't quite believe the size of the conspiracy against her. How could all of these people despise her so much? I mean Jesus, there were lowly constables there, even civilian receptionists and typists.

"Come on Commander, you really need to learn to be obedient. I told you to start dancing, maybe some of our VIP's here will get bored and leave us and then you won't be able to get that sentence down by 11 months will you?"

Mentally, Gillian was defeated. Maybe there was a way that she could have said no and still beat the rap. But looking at the powerful men around her and her colleagues waiting and watching expectantly outside the cell the only way out she could see was to do as instructed. She rose wearily to her feet and started to sway on her heels, trying to imagine what a lap dancer danced like.

The watching crowd cheered and whistled her efforts, shouting out crude encouragement.

"C'mon Commander shake your booty, bitch!"

"That's it Red, flash your gash!"

Gillian was past the point where she would be embarrassed by what she was doing, past even humiliation. She was consigned to her fate. Her ripped top came away easily and a huge cheer echoed through the stone walls as her heavy, fleshy bosoms bounced into view, her big nipples standing out from the creamy skin. She kicked off her boots and slid down her skirt, wishing that the coke hit from earlier that night was still in her so she wouldn't be so aware of what she was doing. She lowered her stockings and rolled them off, tossing them at her chief tormentor with something approaching disgust. He just smiled back at her, indicating with his finger for her to keep on dancing for the wrapt audience.

Once she had shaken her ass enough for the men and women Dupree walked up to her and pulled her by the hand over towards the cell bars, pushed her arms through and told one of the cops standing outside to handcuff her there. The fresh faced recruit laughed nervously and clipped his cuffs around her wrists.

"Here, pass me your nightstick, son!" ordered Dupree and he took great pleasure running it under Gillian's mouth menacingly.

"I don't know if you've figured it out yet Commander Anderson, but you just aren't that well liked are you? This is for all the people you have stepped on in your relentless march to the top. This is for all the people you have framed and bribed and conned, Here! Spit on the tip of this, I'm going to jam it in your ass so you'd better get it nice and wet!!"

Grimacing at his words and her situation Gillian spat on the tip of the nightstick and felt her ass cheeks parted. She felt the hard wood run down her naked spine and stop on her ass cheeks then slide inside. She bit her lip as the object ventured inside her ass hole and Dupree started to slowly push it in and pull it out of her ass as he continued speaking to her.

"You've cut so many corners, not cared who got hurt and done whatever it took to advance, well isn't it a nice irony that after tonight you are going to be the criminal. I cannot wait until your day in court admitting your guilt over this. And believe me you will plead guilty otherwise we'll see to it you get sent down for a hell of a lot longer than a month or so!"

Some of the people outside the cell looking in frittered away, no doubt with work to do or homes to go to but there were still over twenty people on the other side of the bars peering in as Dupree working the long nightstick deeper and deeper into Gillian's tight asshole. He worked it expertly, as if this was not the first time he had done this and Gillian could not help but think back with shame to what he had done with her in the brothel that afternoon. He pulled the stick from her with an audible 'pop' that got a nervous titter from the assembled audience, both outside and inside the cell. He held the long end of the baton up to her face and spoke with authority.

"Lick it clean bitch! Taste your ass."

There was no hesitation, her pretty head lowered towards the hard object that had just been in her asshole and obediently began to clean it much to the amusement of all the onlookers. She closed her eyes and tried to block out what she was doing but those eyes quickly opened up when she heard the sound of Dupree's zipper being opened behind her. He reached forward and whispered in her ear as he continued to feed her the nightstick's tip.

"I'm going first, and I choose to fuck your ass, and if you want my one month knocked off your sentence you'd better make like you enjoy it, like you love it, understand?"

Gillian screwed her eyes shut and nodded before her whole body was jolted forward when her tormentor penetrated her ass behind her and reached under her to grab her big tits that were hanging down and squeeze and fondle them as he began to pound her. With her wrists cuffed through the bars there was not a lot for her to do but just go with his hard and fast pace.

Gillian played her part, she knew what he wanted her to do and ignoring the humiliation and degradation of the situation she played it up. She knew her hard fought for career was finished now and all that remained was to reduce the sentence this cadre of blackmailers had laid out for her. As the man behind her fucked her roughly she reacted how she thought he wanted, panting and crying out for more, her voice carrying an air of desperation, the watching audience excited at seeing the stuck up bitch like this.

As his heavy, sweaty balls slapped noisily against her ass cheeks he squeezed on her tits and called out.

"Yeah! That's it bitch, take it in your ass! You ain't gonna shit right for a month after I'm done with you!"

Gillian grimaced and continued her attempt at making it appear she was loving this ass fucking and was eventually relieved when her blackmailer supreme stiffened and shot his whole load deep within her bowels. When he pulled out she could feel a slow trickle of his cum descend from here ass and slowly slide down her inside thigh. He didn't care though and spanked her ass and called to his fellow conspirators.

"Come on guys, who's next? This slut has plenty holes left to fill and she's fucking gagging for cock!"

She wasn't of course, but that was the whole point. Dupree told the young cop to unlock her from the cuffs and he pushed her to her knees as the Police Chief approached, undoing his zipper as he approached.

Clancy Simpson was a big man, there was little doubt he would fail the police medical if he was subject to it now, no way could he patrol the streets he used for twenty long years before he had finally got the breaks to make it all the way to Chief of Police with just a few short years before he retired. He really had never much liked Gillian. The way she had been on a fast track to the top had stuck in his throat considering the long and winding road he had had to take to reach his position. It also really grated on him the way she had made no secret of her ruthless ambition and she had all but told him that she was gunning for his job sooner, rather than later. Of course, she had thought she was untouchable, that she had enough power and influence to be like that with impunity, as she rubbed her sore wrists and felt semen slide down her naked thighs she was quickly recognising that this was no longer the case.

"On you knees you fucking bitch! It's about time you learned your place. You thought you were such fucking hot stuff, didn't you? Well see where it's got you?"

Gillian was embarrassed and a little frightened by his tone. He had always been so cool and professional with her (though secretly she had always tried to wind him up into losing his cool, anything to score points off of him), but as his big frame advanced on her she obediently dropped to her knees and looked up into his implacable, dark eyes. He smiled at her like a crocodile, his hands already reaching for his straining crotch. His Chief's uniform was about one size too small and his mass bulged out, she always thought he was pretty gross but now as he neared her she couldn't get over how awful he looked and could barely bring herself to watch his approach. She dropped her eyes to the stone floor, affixing them on a small drop of cum that had spilled from her stretched and used asshole. it took only seconds for her view to be obscured by the Chief's size eleven black brogues. He extended his stubby fingers into Gillian's usually perfect but now ruffled ginger hair and pulled her head up so that she looked right into his eyes. God, he was enjoying this!

"I'm going to fuck your face bitch! I really don't care if you keep up with me or not, in fact, I'm kinda hoping you don't. But one thing's for sure, if you want my month off your sentence you'd better damn well not complain or back out or give me any shit, understand!"

Gillian nodded her head (hard to do with her hair held so tightly) and sighed as she opened her mouth acceptingly. There was an audible intake of breath from the watching men as Chief Simpson finally pulled out his fuck stick. For a man in his fifties he was surely hung like a horse! His dick was stiff and glistening with pre-cum and excitement and he wasted no time plunging it deep into Gillian's waiting mouth. As prepared as she had been for it, the red head could not help but gag as the slimy, cock sank into the back of her mouth and on into her throat. But as she gagged the Chief held his stuck up subordinates head in place and pushed his pelvis on to keep up his forward momentum.

TheDarkCloud
TheDarkCloud
4,494 Followers
12