Jail Break

Introduction:
Jessica walked up to the front of the faceless grey hulk of the prison and pressed the intercom at the staff entrance. The day was already bright, sunny and hot despite the early hour but this did little to alleviate the drab monolith in front of her, its walls topped with razor wire and the tireless all seeing cameras.
The intercom crackled to life, ‘Who is it please?’ said a bored sounding voice.
‘Jessica’ she replied, standing in front of the camera mounted in the door and brandishing her security pass.
There was a sound of bolts being drawn back electronically and the door swung open allowing Jessica to enter the prison. Two guards were there to meet her and escort her to the Warden’s office where she worked, and they both looked her up and down.
‘You sure Warden Makepeace won’t bawl you out for wearing that?’ said one.
‘Oh for fuck’s sake it’s going to be like 95 degrees today and I’m not wearing trousers’.
Jessica was irritable. She was already late due to the traffic and this was making her later. Anyway who the hell did these meatheads think they were? she thought to herself.
‘If the Warden has a problem with my attire I’ll take it up with him’.
Jessica looked in the mirror and smoothed her clothing down. She was wearing a pretty, lightweight dress with a small flower print that was sleeveless and hugged her slim figure perfectly. It was short, but not obscenely so and came to around 4 inches above the knee, showing off her long legs to perfection, while her white, high heeled sandals finished off the ensemble, pushing her calves into a sexy shape. She had not dressed specifically to tease, but this oppressively hot weather required light clothes and she was damned if she was going to sit in the office with its dodgy air con feeling like she was about to melt.
Another buzzer sounded at the inner door and it swung open, leading through to the main complex of the prison. Jessica followed the two guards, her thick, long auburn hair flowing over her shoulders and halfway down her back and entered the main hall. The serried ranks of cells stretched around and above her but there was no sound from the inmates. When Jessica had started this job, she had been greeted by whistles, catcalls and crude remarks but Warden Makepeace had punished those responsible severely so now no one dared to make a comment, but they still watched.
As Jessica walked across the complex, her footsteps echoed in the empty space. She flicked her eyes from side to side and could see the men watching intently like a pride of lions stalking their prey. She had guessed that today’s outfit would attract more attention than usual and she wasn’t wrong. The men viewed her with naked lust, undressing her with their eyes and Jessica found to her surprise that she was extremely turned on by being an object of desire for all these dangerous, horny, sex starved men. By the time she got to the other side of the complex and had passed through the security door she could feel dampness in her knickers and was acutely aware of her hard nipples showing through the thin material of her dress.
Warden Makepeace looked up as Jessica entered the office.
‘Sorry I’m late Warden, the traffic was hell his morning’ she said as she sat down behind her desk and flicked her computer on.
Makepeace looked at her intently, resting his chin on steepled fingers.
‘Jessica, I don’t make dress code rules for fun’. ‘We have a difficult situation here at the moment, the prison is overcrowded and anything can spark off a disturbance’. ‘You must realise that a highly attractive lady like yourself dressed like that could cause…..problems, fights’.
‘Warden, it is going to be 95 degrees and you expect me to sit in this sweatshop in a suit?’. Jessica’s voice was level but held more than a hint of barely suppressed temper.
Makepeace picked up on this. ‘The engineer has promised to fix the aircon this week’ he said in a more conciliatory tone but I would appreciate it if you could come to work more appropriately dressed’.
Jessica sighed to herself. To be honest that was pretty mild by Makepeace’s standards as he had been known to go crazy over minor infringements of the rules, so she settled down to look at her inbox and type up a growing pile of reports, assessments, care plans….everything the modern penal system seemed to throw up these days.
Makepeace looked at Jessica as he organised the paperwork on his desk. He admired her efficiency and the cool, unflustered way in which she handled the pressures of the job. He had four Personal Assistants before she came, none of whom stuck it for longer than a few months so he gave Jessica a bit more latitude than he normally would. He watched her legs under the desk as she stretched them, her skirt riding a little higher and affording him a view of her pale, shapely thigh. His cock stirred in his trousers and he hurriedly looked away in case she caught him looking at her and looked at the latest Government forms he was supposed to fill in or ‘death by red tape’ as he called them.
Jessica concentrated on reducing the pile in her in tray with some success although the wheezy air conditioning was simply not coping with the summer heat and the temperature in the office was rising uncomfortably causing her to feel clammy. She got up to go to the bathroom to get some cool water to dab herself with just as a siren abruptly started wailing in the yard.
Makepeace stabbed a few numbers into his phone.
‘Security, what’s going on?’ he said calmly
‘There’s a disturbance in C wing sir, a fight has broken out and spread over the whole floor’. ‘We have sealed off the wing and it seems to be OK for now’.
‘Very good’ said Makepeace curtly. ‘Call me immediately if you have an update’.
‘Anything we need to worry about?’ asked Jessica.
‘Apparently not’ he replied looking thoughtful. ‘I’m going across to the security centre to look at the remote camera pictures and if I think there is any danger I’ll send guards to get you out as quickly as possible’.
‘Thanks’ she said as Makepeace strode off purposefully down the corridor.
Jessica continued to try and concentrate but it was simply impossible with the infernal racket of the siren so she poked her head out of the office to see if she could see anything of what was happening and walked to the connecting door to the main block. There was little she could see through the small glass portal but the noise from the inmates was deafening. However, the guards were situated in the centre of the hall and the cells were still locked so everything appeared to be under control. Having satisfied herself there was no immediate cause for alarm she returned to her office and once again picked up the report she had been working on.
In C wing the situation was worsening for the prison staff. Although the area had initially been sealed, some prisoners who were skilled in electronics had managed to access the control relays and open the doors by springing the failsafe mechanism.
There were running battles between C wing and B wing and Warden Makepeace was running out of options.
‘Take ten men and go to the armoury’ he ordered. ‘Live rounds but fire above their heads on the first volley and await my instructions’.
The young guard nodded his assent and made off quickly with his companions. The armoury was situated between two heavily reinforced doors at the junction of the main complex and the corridors which led to the three primary wings of the prison and as they arrived, the guard signalled for the armoured door to be opened. As the bolts slid back an alarm went off in the main block and all of the cell doors sprang open, courtesy of the C wing hackers who had compromised the core security system.
The guards looked on horrified as the prisoners swarmed out of their cells, retreating towards the exit doors to try and seal off the main hall but they were too late and were cut off. The guards outside the armoury were trapped and the armoury door swung open just as they were overwhelmed by the baying mob. The prisoners quickly dealt with the remaining guards and burst through the open door and into the armoury.
The fight in the main block was short but brutal. The guards were heavily outnumbered and surrendered quickly as the situation was hopeless. Those that were guilty of mistreating their charges were dealt violent summary justice and were beaten senseless or killed. The rest were herded together and locked in the armoury.
The ringleaders passed out the guns among the men, and they now ran down the main corridor towards C wing whooping with delight while others tried to batter down the doors to get out of the prison.
Warden Makepeace looked ashen faced at the monitors as he watched the armed prisoners stream towards C wing realising that the guards down there were now caught in a pincer. He ordered the head of security to call the Police as he realised the situation has spiralled dangerously out of control and then rang down to his office.
‘Jessica, listen to me, you have to get out and get out now’. ‘Use the service corridor and skirt around the main complex, do not try to go through there’. ‘Head for the trade entrance on the north side of the block, the code for the door is 98326’.
‘How about you?’ said Jessica in a shaky voice.
‘Don’t worry about me, you have to get out’ he said and she could hear a note of panic in his normal calm demeanour.
Jessica quickly turned off her computer, gathered her things and headed out towards the service corridor, her heart thumping in her chest. She quickly reached the narrow entrance and followed the exit signs towards the north side of the prison, her ears straining to hear any sounds that might mean trouble ahead. As she arrived level with the main block she heard a splintering up ahead as a door gave way and shouted voices and footsteps echoing in the corridor. Jessica froze with fear and then quietly began to retrace her steps. Fortunately the footsteps seemed to recede and she guessed that the men were headed for the same exit she was trying to get to, but the bad news was that she was effectively trapped.
There was nowhere to go except back the way she had come and as she neared the Warden’s office she could hear the sounds of it being ransacked and destroyed. She crept past the entrance silently with her heart in her mouth until she reached the door into the main block which was now open, another prize for the C wing hackers.
Jessica cautiously looked through and found that the main block was eerily silent, all the inmates seemingly having headed for one of the exits. There was no way she could stay where she was so she crept into the main block and skirted round the edge, hoping to find somewhere she could hide amongst the debris of the wrecked cells. She reached the stairwell and climbed up the iron steps as quietly as she could, hardly daring to look behind her, fearing the shouts that would mark her discovery. As she reached the top her breathing slowed again and she listened for any noise that might signal that someone was still up here. After a short while she moved on again, doubled over behind the railings to hide her self from being seen from below, heading towards a store at the end of the corridor. If that had been looted then she might be able to shut herself in and hide until help arrived as nobody would bother going back there she thought.
Jessica was now passing the high security cells, all the doors open and as empty as the rest when suddenly an arm shot out and hauled her inside the nearest cell. A hand was clamped over her mouth to prevent her screams which she instinctively bit down on, hearing a howl of pain as she wriggled free.
‘Quite a little firebrand ain’t she’ said a hulking figure in front of her. More men came into the cell from the adjoining areas until there were around ten of them in the small space. Jessica could see from the distinctive uniforms that these were all lifers, men without hope for parole. She recognised the hulk as Matt Lewin from his report card and quickly recalled the details. First degree murder of his girlfriend and another man who he thought she was having an affair with. He had also murdered the man’s brother and his entre family by burning down their house after locking them inside. The man she had bitten was Bubba Marconi, Mafia hitman. She recognised Barry Martin, the poisoner and David Karlsen, the baby faced con man who had swindled several high ranking officials out of millions. What had really sealed his fate was that he had also fucked all their wives.
Christ this was like a Who’s who of America’s most wanted she thought as the grinning men edged towards her.
‘Want me to cut her, make her scream’ said a weasel faced man who she couldn’t quite place. Lewin glared at the weasel who shrank back but still the men came on, their leering looks leaving her in no doubt what they had planned.
Despite her desperate situation, Jessica found herself turned on. These guys were fit, their bodies sculpted from endless hours of exercise in the gym, their sole respite from the numbing boredom of prison life and the obvious bulges in their pants made her wet with anticipation. She needed to find an angle, needed to take the initiative so instead of cowering in the corner she took a step forward, looking Lewin straight in the eye and sank to her knees in front of him. Her hands worked quickly and skilfully at the buttons and soon she had his cock out in the open. Lewin was a big man, tall with big hands and feet and Jessica was delighted to find that his cock was in proportion, at least 8 inches long and as thick as her wrist.
‘Oooh when did this big boy last see some action’ she purred and kissed the tip of his straining cock head, feeling it stiffen as her hand glided over his thick shaft.
Jessica continued to work her hand up and down until she could see a clear drop of precum appear and then stuck out her tongue to lick it off, continuing down until his swollen helmet was engulfed by her moist parted lips. She could see other men releasing their hard pricks out of the corner of her eye as she worked her tongue in quick, lashing movements over Lewin’s cock and wickedly decided to give them a real show. She had seen some models giving really deep throat in one of her husband’s porno films and now she aped them, sucking the huge dick deep into her mouth and working it frantically with her hand.
‘Oh you are so big, your cock is so beautiful’ she moaned as her lips sucked at his member and her tongue wiggled into the sensitive hole at the tip.
‘I’ll give you something to moan about’ said the weasel in a thick voice as he pushed to the front.
Lewin’s hand shot out, catching the weasel by the throat and lifting him easily into the air. The man struggled, choking and spluttering, his face turning red, then purple as Lewin choked the life out of him. At the last moment he dropped the wheezing weasel to the ground.
‘Get rid of that sick fuck, I don’t want to see him in my face again’ he snarled. Remember, no one and I mean no one hurts this bitch unless I say so’.
Through all this, Lewin’s cock seemed to have become even stiffer, an iron bar made flesh and Jessica did not miss a beat, sucking on his big fuck stick and cradling his massive, heavy balls in her hand.
Billy Joe Ray and Mark Walcott picked up the weakly struggling weasel and dragged him quickly down the corridor not wanting to miss the unexpected entertainment back in the cell.
‘What the fuck we goin’ to do with him Mark’ said Billy Joe
.
‘B Wing’ said Mark. ‘They hate his sort there’
.
The men quickly reached B Wing and dragged the weasel inside.
‘Listen up everyone’ yelled Mark ‘who remembers Ben Laforge?’.
The weasel struggled to get free and the men currently trashing B Wing stopped and stared, the light of recognition passing across their faces.
‘Well say hello to your new friends Ben’ laughed Billy Joe propelling him towards the mob as he and Mark turned back the way they had come, leaving the now screaming child rapist to his deserved fate.
Back in the cell Jessica had more cocks to work on as other men joined the fun and she was sucking on their straining pricks for all she was worth as the men stood patiently in a row. This was the most wildly erotic situation she had ever been in, she was powerless and yet somehow all powerful but the real thrill came from the knowledge that she was ultimately at the mercy of these men. As the last two rejoined the group she helped herself to their tools too, counting ten thick pricks in all, glistening with her saliva.
Jessica stood, her body tingling all over with nervous, sexually charged energy and unzipped her dress at the back, sidling sexily back up to the huddled men, letting them tug her dress down so it fell to the floor before spinning away with a dirty grin on her face.
Matt Lewin’s eyes looked like they would pop out of his head as he drank in her perfect, slim body encased in some delicate, lacy underwear recently purchased from Victoria’s Secret. Jessica stood with her legs slightly apart and pushed her hair up on top of her head, raising both arms in a sexy pose and pouted at the men, thrilled by the rapt expressions of attention on their faces.
She now turned her back to them and unclasped her bra, slowly turning back towards them. With crossed arms in front of her, she walked up to Matt, allowing him to pull the bra from her shoulders and feel her firm tits topped with large, prominent rose coloured nipples. Jessica passed down the line allowing each man to feel her, shuddering at their touch as they squeezed her breasts and pulled on the sensitive buds, amazed at the degree of control she had before backing away again and hooking her thumbs into her lacy panties. The gusset was soaked as she slowly slid them down her slender thighs revealing her neatly trimmed auburn pussy to their gaze, running her middle finger down her wet slit and then tasting her own juices with closed eyes, a beatific expression on her face.
She crossed back to the men again, now totally naked apart from her high heeled sandals and the men clustered round her. Lewin’s lips clasped themselves to hers as various hands roamed over her body, seeking out her most secret places. Her erect nipples were receiving a good deal of attention from two wet, sucking mouths and a hand was gently prising her thighs apart while another sought out her clit. Jessica groaned as a thick finger entered her hot pussy and began to pump inside her.
This was too much for Lewin who moved everyone out of the way and laid Jessica on the small bed on one side of the cell, kneeling between her legs so he could taste his first pussy in years. He pushed her thighs up and started at her asshole, gently running his tongue around the puckered hole, making Jessica squirm with pleasure as he traced his tongue over her inner thighs, teasing her, before running his tongue up her wet slit.
Lewin reached the top of her sex and moved deeper, running his wet tongue over her clit causing Jessica to gasp with pleasure. The other men were encouraging Lewin and their crude remarks made her feel even hornier as she felt Bubba’s cock slide across her lips. Jessica opened her mouth and curled her tongue around the tip of his hardening cock, running her fingers lightly down the pulsing vein, drawing him in and sucking deeply as Bubba fucked her mouth. More hands began to paw at her tits and run over her belly and arms, adding to the sensations in her tingling sex, making her lose control by the minute, as she abandoned herself to her forbidden desires.
Matt Lewin was now tonguing her vigorously and deeply, using his thick fingers to stimulate the area around her clit. She gagged on Bubba’s cock as she felt her orgasm rising, showering Lewin’s face with her pungent juices that now dripped off his chin.
‘Oh baby’ Lewin croaked, as he pulled Jessica off the bed to sit astride him and guided his thick, long tool into her soaking snatch.
She soon found that she had two cocks in her face, vying for her attention and found her hands quickly occupied with more rock hard shafts which she proceeded to wank gently. Behind her, a man had greased up his fingers with some looted cream and slid them between her ass cheeks, seeking out her tight little starfish. Jessica relaxed as much as she could while the man lubed her anus and slid a finger inside her tightest hole, making her gasp as he plunged it deep inside. Lewin was pumping her pussy like a man possessed while the guys in front of her were taking turns to fuck her hot mouth, calling her ‘bitch’, ‘whore’…anything they could think of which only served to increase her excitement.
She felt Lewin’s fat cock twitch and spasm inside her and then erupt as he came in wave after wave deep inside her belly, continuing to fuck her to the hilt. As his cock softened it slid out of her well screwed hole with a plop and she now found herself sitting astride Barry Martin, guiding his dick into her dripping cunt. Before she could start riding him she felt another tool prodding at her asshole, demanding entry. Barry pulled her forward and she felt her ass cheeks being pulled apart and a rock hard cock poking at her tight chute. Jessica moaned as she felt the mushroom head stretch her sphincter and then he was inside her, moving deeper and now in tandem with the cock in her pussy, causing the most intense sensations she had ever known. She felt Bubba’s cock in her mouth begin to pulse, covering her face in its sticky seed, immediately replaced by another man she didn’t even recognise.
The heavy balls of the man behind her were slapping her ass at the end of each stroke, the man screwing her pussy was mauling her tits and fingering her clit and the warm, sticky spray on her body told her that the shaft she held in her hand had just shot its load. The sensations all rolled into one as Jessica lost track of time and lost track of who and where she was as panting orgasms wracked her slim body.
Jessica was a plaything for these men, it was as if she had no will of her own as they used her body to relieve their pent up desires. One after the other they pushed her into every position imaginable, serving their deepest fantasies as they plundered every hole until they were spent and she was alone and spread eagled on the floor, covered with the fruits of their lust.
Jessica lay there for a few minutes and then stiffly got to her feet.
‘Any chance of grabbing a shower baby’ she said to Lewin, smiling coyly.
‘Where are you gonna get a shower babe?’ he laughed. ‘Anything that could be ripped out has been ripped out’.
‘Maybe in the Warden’s office?’
Lewin looked her in the eyes. ‘OK, four of you take her to the Warden’s office’. ‘Any trouble come straight back’.
Jessica slipped on her discarded dress and followed the men to her old workplace. The main office had been trashed but the small, private bathroom behind was more or less untouched and Jessica gratefully climbed under the steaming jets. She now had a little time to think – the men didn’t seem to want to harm her but they were dangerous and unstable and she had no idea how long she could keep them sweet.
She finished her shower and dried off quickly on a scrap of towel as the men once again eyed her firm, sexy body and walked back to the cell with them.
‘I have an idea’ she announced to Lewin.
‘Go ahead’ he said with an air of hopelessness. ‘Bubba’s just checked and the whole place is surrounded by cops’. ‘There’s guys out there chucking stuff and taking the odd pot shot with a rifle but we’re screwed basically’.
‘There’s some uniforms, fresh back from the laundry in the Warden’s closet’. ‘The door is intact so they should still be there’. ‘They will know I’m a prisoner and as the only woman, I will be attracting most of the attention’.
‘Go on’ said Lewin, the germ of what she was planning beginning to form in his mind.
‘Are there negotiators out there?’ she asked.
‘Yeah’ said Bubba ‘but they ain’t mentioning you’.
‘Of course not you dumb fuck’ said Jessica exasperatedly. ‘That would be the surest way of getting me gang banged’ she said with more than a hint of irony.
There were sniggers around the cell – not many of them would dare talk to Bubba like that but she had appeared to get away with it.
‘We need someone, a prisoner, to come to the door and say he was releasing us as a goodwill gesture’ she continued.
‘Who is going to volunteer to stay in this stinking hole while the rest of us bunk off’ snapped Lewin.
There was a moment of silence and then an older man stepped forward. ‘I’ll do it’.
‘Frank, why would you do a thing like that?’ said Lewin as if the man was stupid.
‘There’s nothing outside for me Matt, I couldn’t survive outside now, who would want me?’ replied Frank.
Lewin looked at him and made a snap decision.
‘Let’s go’ he said and they all hurried down to the Warden’s office.
Ten minutes later they were making their way down the service corridor dressed as the hated screws towards the north entrance. The door had been battered but the prisoners had not been able to force a way through the armoured structure and it was now abandoned.
Jessica punched in the exit code and was relieved when the door opened. Frank stood behind her and Lewin, pushing them both out the door about 100 yards from the surrounding cordon of Police.
‘I’m releasing some hostages’ he shouted. ‘I don’t want no trouble so don’t shoot or my men will kill ‘em’.
Frank dashed back inside and the rest of the ‘guards’ came out blinking into the light. With their heads down they made their way to the nearest part of the cordon, surprising the confused men on the roof who failed to get a single shot off.
Jessica was immediately engulfed by newsmen and reporters who had instantly recognised her as she crossed no man’s land and she was soon in the middle of an animated and detailed interview. Hardly anyone noticed the guards although they suffered a few sneering looks from the Police officers, who assumed from their crisp uniforms and lack of bruises that they had given up without a fight.
‘OK, you men over here, yelled the District Commissioner at the guards, shaking their hands without even looking at them and smiling a fixed smile as a thin line of photographers reeled off a few shots.
‘Over there for debrief’ he waved airily as he charged into the media scrum for a far better photo opportunity with Jessica.
The ‘guards’ quickly split up and edged away from where they were supposed to go. No one noticed as they quietly made their way through the crowd and disappeared into the surrounding streets.
Lewin stuck his hands in his pockets, relishing his first taste of freedom, and felt a scrap of paper. He pulled it out and read it. It said simply ‘Thanks hun’ luv Jessica and a phone number. Lewin broke into a wide smile and walked a little taller as he turned the corner, losing sight of the prison for the first time in years.

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