It had begun as just a Saturday job. Her boss, had asked her to accompany him to the jail to take notes, filing etc as he visited his bevy of illustrious in custody clients. Sarah had jumped at the chance. Sarah and Jonathan had a great working relationship but this would be their first time together at the jail. He had many clientele stuck in jail during the Covid lockdown and that meant weekends had to be a renewed effort to get organized and see if any matters could resolve.
Sarah prided herself on her appearance. But turning up in black seamed nylons and glasses at a men’s prison is tantamount to a suicide mission. They had to walk through a sectioned off pathway that was covered in mesh wire. She was barely through the gate when catcalls began to ring out.
‘Oh, baby… show me your tits… oh, you’ve got great tits.’
‘Oh, boys look at that. I haven’t had a woman in five years.’
‘Come on and just back it up to the bars so I can slide it in for a quickie — I’ll even let you decide which hole sweetie!’
‘That’s it baby… look at what I got here for you. A nice juicy black cock. All hard and thicker than you’ve ever had, just waiting for you to screw yourself with…’
‘You look like you know what to do between the sheets honey. We have five guys in our crew that would love to show you a good time in the showers. Do you want us all at once or should we line up to take turns fucking that hot pussy?’
She shuddered in mock revulsion as one after another lewd suggestion was barked at her as she walked down the range. From the corner of her eye, one inmate, standing well over six feet tall and wearing beanie cap winked at her. The innocence of it, in comparison to the calls of “get your tits out babe” made her falter. Jonathan whisked her through into a hallway that led to a disused meeting room.
‘Legal aid is a bitch but it pays the rent,’ said Jonathan as he dropped his briefcase to the desk. ‘Are you alright?’
Sarah sagged at the desk. ‘Yeah, no biggie. I’ve heard that shit since I was 15 years old.’
Privately, she was horrified to realize that the lewd comments had made her wet and thoughts of their suggestions were going to drive her to many more earth shattering orgasms the moment she could find the privacy to fondle herself.
One by one the clients came in. Young, old, warn out completely, ruggedly attractive. All of them menacing. All of them looking at her as though they knew exactly what she looked like under her clothes. Jonathan was professional and carefully kept them in line but she had to admit that she was a little rattled by her true response to the jail house experience.
Nonetheless, she ran out to the car that next rainy Saturday morning ready to do it all over again. She slipped in and noticed Jonathan’s predictable perusal of her legs as she allowed her new summer dress to ride up her thighs just enough to hint at what hides beneath.
‘Ever the professional, eh, Sarah,’ he said as he manoeuvred into the traffic.
There were fewer prisoners in the yard that day. She ignored the jeers, finding herself smiling at some as they walked down the “lab rats’ pass” as Jonathan called it. Beanie cap was there again. Sarah couldn’t help but notice how like Clive Owen he was. Taller than the others. Less soiled by the environment. He leaned against the fence and winked at her again, this time while holding his crotch in his right hand. She smiled back, feeling oddly confident all of a sudden.
They had met with four clients already that day and the anticipation of seeing the last one had caused Sarah’s heart to accelerate noticeably.
Lyle Davis, Prisoner no 15687. Assault with a deadly weapon among other charges….
Sarah had more than infrequent thoughts of him since the day he went away. She’d thought of him many times while lying in bed or in the privacy of the shower. As Lyle entered the secured meeting room Sarah couldn’t help herself and gave his orange jumpsuited crotch a glance as he sat down. Deadly weapon indeed!
Davis was soon to appear before the parole board and Jonathan was not very confident he’d get it.
‘You assaulted a police officer.’
‘He assaulted me first,’ Lyle said, his eyes focused on Sarah’s as she began to take notes. She shifted in the seat as the flush raced from her neckline to her face. She was wearing a thong that was wedged not uncomfortably in the place where she was wettest. Jonathan continued to speak but Sarah didn’t hear him. She ran her tongue across her lips and Lyle’s eyes narrowed. Sarah winked at him and tilted her head slightly.
What are you doing?
Sarah didn’t behave like this. She was a good girl — or at least tried to sell that appearance when she wasn’t cranked up with her girl posse at Danny’s strip club. But there was something so… mysterious about him… so dangerous. And sexy. This inmate was definitely sexy.
Lyle gave a heavy sigh and ran a hand across his jaw. Sarah leaned forward and plucked a pencil from Jonathan’s briefcase. The movement revealed an inch more cleavage than it should’ve. He smiled broadly at her.
‘Vanilla,’ he said suddenly. Jonathan glanced at him. ‘What?’
‘Your secretary… is wearing vanilla perfume.’ He said helpfully as he folded his arms across his chest and sat with a confident grin. Jonathan didn’t seem to understand. Poor Jonathan didn’t feel the air thicken around him as Sarah, who had gone without sex for almost six months, flirted with the prisoner who had been inside for almost two years. Oh, if he only knew of the affect this criminal was having on her! It felt as though every hair on her body was standing straight up and her nipples stood hard and proud straining against the soft cotton of her bra.
‘I’d like to see you again next Saturday,’ Jonathan said as Lyle stood to leave. A guard swung the door open. Lyle took one last look at Sarah.
‘You can bet your life on it.’
By the third Saturday, Sarah walked in like a seasoned pro. She didn’t even hear the abuse as she crossed over to the building. She scanned the crowd for Lyle and saw him off to the side with a number of others. He had that confident smile and Sarah wondered what he must be telling his fellow inmates about the hot secretary he was meeting.
He mouthed something to her as she passed but Sarah didn’t catch it as she followed Jonathan to the interview room. As had become routine, one by one they filed in, ogled her while pretending to listen to Jonathan outline their chance for parole or bail or early release. With most of the men Sarah sat impassive and mildly disinterested as they stared at her pushed up breasts and her chestnut brown hair, clipped back in a neat pony tail.
In any given situation Sarah was aware of men’s stares and usually conscious of their nasty thoughts. But here she was in a prison where men were mostly denied the sexual release they might find on the outside. In here, she was so much more a piece of meat and the inmates made no effort to hide their lust.
Sarah felt it devilishly thrilling to know how many erections she was causing. Simply walking through the cell block meant that she was sending blood coursing through every cock she walked by. The thought of so many men stroking their cocks to thoughts of ravishing her body gave her a thrill unlike any she’d ever imagined.
And then he finally arrived — and Sarah shivered as he smiled broadly at her. Somewhere south of her abdomen gave a little flare and she felt her stomach sink. She was seriously attracted to this guy even though much about him scared the shit out of her. It wasn’t that she was looking for a boyfriend, she just wanted to fuck him. No, she wanted to suck his cock and then have him fuck her and hard!
Last Saturday, after Jonathan had dropped her home, she’d raced inside, slammed closed her bedroom door, fallen onto her bed, fished out her favourite purple vibrator and brought herself to the most thundering orgasm of her life.
Today, she’d made it a little more exciting. Today, Sarah had decided to walk into a men’s prison without any panties on. She uncrossed her legs as the moisture streamed out and made her asshole every bit as wet as her pussy. Lyle’s eyes flickered to her knees under the table and his lips parted.
Sweet Jesus, he knew! She sat bolt upright in her seat and fussed with his file.
Jonathan swore under his breath. ‘Shit, I’ve left the application in the fucking car.’
Sarah’s face dropped as she watched Jonathan rise from the chair and rap on the steel door.
‘Jonathan, where are you going?’ she bleated. Lyle sat forward and ran his tongue across his lower lip.
‘I’ve got to get the application… I’ll be fifteen minutes. Don’t worry, the guard will stay with you.’
She felt her insides tighten as Jonathan’s frame disappeared out the door and a hulking guard came in to watch over Lyle.
Lyle leaned close to her.
‘You’re not wearing any panties are you?‘ his voice was coaxing. She squirmed.
‘Don’t speak to me.’
‘You’re not! Naughty girl. Walking into a prison without any underwear on… Think it’s funny, do you? To get inmates all hot and then wander out of here without a second glance. I can see the attraction… must give you some thrill to be that… alluring. A lot of these men would shag their mothers if they got the chance but a piece of ass like yours…’ He gave a whistle. The guard smiled.
‘Stop that Davis. Or I’ll revoke your privileges,’ he said, in a tone that let her know he was enjoying Lyle’s speech.
She looked up into his limpid green eyes.
Maybe. Why? Are you all hot? Or are you just all talk? Does your cell mate get the brunt of your frustrations or are you saving yourself for the first woman you meet when you walk out of here?’
She couldn’t believe she’d said it. Neither could the guard. He chuckled into his fist as Lyle winked at him.
‘She’s got a mouth on her, Davis!’
‘Oh yeah. And a nice one at that.’
Sarah smiled again. Right now, she’d have shagged him on a table in the canteen for the whole prison to see.
The thought of fucking Lyle with so many watching was another perverse thrill from the darkest regions of Sarah’s ever increasingly risqué desires.
‘Do I scare you?’ he asked suddenly.
Did he scare her? No. To her utter shock, he didn’t. He seemed so serene. They could’ve been in a bar or a restaurant. And he was just like some bloke that was hitting on her. And she liked it.
‘You can leave us, guard.’ Her voice seemed to come from another place. The guard did a double take. ‘Are you serious?’
‘I want a moment alone with our client.’
Lyle’s smile never faltered. The guard poked him in the shoulder.
‘Not a word about this Davis or… oh fuck it… what do I care… knock yourselves out.’
The guard slipped out the door and turned the key in the lock.
Sarah folded her arms across her chest. Lyle mimicked her.
‘Well?’ he asked after a time.
‘So are you wearing panties?’
She shivered, her face was red and her bottom was suddenly burning hot. She nodded slowly attempting to appear more confident than she truly felt inside.
‘What will it take for you to believe me?’
She knew where this was going. Knew she was going to lose the challenge. Knew that what she was playing was the most dangerous game she would ever play. Yet she was still rolling the dice.
‘Show you. What if I am lying?’
‘Then I guess I still end up with the pleasure of seeing your wetness soaking through a pair of panties.‘
As though she were watching herself from outside her body, Sarah rose from the cheap plastic chair and slowly hiked the fabric of her summer dress up over her knees.
Lyle’s smile faded as she revealed inch after inch of glossy black thigh, pausing for a moment as the bare skin above her stocking appeared. Her heart was hammering in her chest as the hem refused to come easily over her bum and then… she flipped up the front and revealed her neatly trimmed bush and smoothly shaven pussy lips. For a second, there was silence and then he exhaled heavily.
‘More than anything… I want to fuck you right now. You should know that.’ His arms never left his chest but his eyes were fixated on her brazen display and the smell of sex permeated the air. The key churned in the lock and Sarah quickly yanked her skirt back down and took her seat.
Jonathan shuffled back into the room and sat down. It didn’t seem to dawn on him that the guard was no longer there. He resumed his babble, completely unaware of his companions staring each other down. Before Lyle left he slipped a note into her hand. Sarah clutched it until she got home and repeated last Saturday’s performance.
The note was short and succinct.
Next Saturday is not a good day to come.
Accompanying the brief note was a drawing he had done of her naked and masturbating while standing against the wall of a men’s bathroom. It was surprisingly well done and was pretty close to accurate as though she had posed nude for him. Sarah made a note to ask for more of his drawings to see just how he imagined her while alone and jerking off in his cell.
She gave a little shiver as she rocked herself to another orgasm. Prisoner 15687 did not seem to realize that Saturdays were the highlight of her week now, and she wasn’t about to give that up.
So the following Saturday, they arrived at the prison as usual and were taken across the walkway. As usual she was asked to suck this and fuck that and she shook her head to Jonathan as one would if acknowledging a naughty schoolchild. The IC met them at the door.
‘Jonathan… what the hell were you thinking?’ he barked as they entered the building.
‘I beg your pardon?’
The IC glanced at Sarah. ‘Taking a woman across the yard like that… I am trying to keep these men calm… and look at her!’
Sarah clutched her coat around her. She was wearing a black partially seethru blouse that showed off the frilled edge around the top of each bra cup. Her outfit was finished off with a complimentary skirt as well as her regulation seamed nylons. She was dressed as a secretary albeit a naughty one.
‘I’m sorry miss but you shouldn’t have been paraded across the yard like that. Especially when you’re dressed like the fantasy of every adolescent schoolboy!’
Sarah felt a retort rise in her throat but Jonathan cut her off.
‘I’m sorry. I presumed it would be the same as every Saturday… the guards allowed us in… we didn’t know that there would be any problems…’
The governor shook his head. ‘Look just don’t do it again-‘
Suddenly a siren began to wail over their heads and there was a roar from outside. Sarah gripped Jonathan’s arm as the guards swung open the door behind them and revealed the inmates clipping through the mesh fence.
‘RIOT!’ They roared and raced out to beat the inmates back from the fence. The governor grabbed Jonathan’s arm while he pulled Sarah along with him.
‘Come on and for God’s sake run.’
Down the corridor they went and up a flight of stairs. The noise was following them but they couldn’t tell how close it really was. They went through a series of doors which the IC duly locked behind them. Finally, they seemed to be approaching a part of the building that was carpeted and seemed like an office area. And then the lights went out.
Sarah shrieked as Jonathan screamed and tripped. Footsteps approached and Sarah felt intense fear rise in her throat as a hand closed over her mouth and she was tugged backwards along the corridor.
Jonathan was still bellowing and the governor was barking at him to for God’s sake shut up when Sarah heard two swift thwacks and they were silent. Sarah had seen enough movies to know that they were unconscious. Her feet left the ground as she was dragged through the darkness and suddenly dumped unceremoniously onto a thin mattress.
Her senses screamed. She was… oh shit… she was in a cell. Suddenly, an alarm screech and the cell doors slid shut and the lights flickered on. She sat up and came face to face with her abductor.
‘You fucking bastard,’ she breathed when Lyle dropped to his knees in front of her. He glanced at a scratch on her forehead.
‘You’ll thank me later.’
‘Yes. I told you not to come.’
‘It’s my job.’
‘Well, when the convicted criminal tells the secretary it’s not safe to come to prison, the secretary usually listens. They’ve been planning a riot for months.’ He peered out through the bars.
Sarah glanced around her. The cell was small and neat. A small desk in the corner was piled high with books and a small TV adorned the wall. But terror shot through her. Lyle was ripping a sheet from the bunk above her and draping it across the bars. Soon they were obscured from view.
‘What are you doing?’
‘Well, in here, a sheet across the bars means one thing and one thing only. Boys getting friendly with one another. I’m not big on the details but apparently some men get lonely enough to do anything. I’ve never been partial myself.’
Lyle’s face darkened. ‘Don’t flatter yourself. If they found you wandering around in the dark they’d take turns until you passed out and then revive you with some more. And let me tell you, this prison is full of every sized dick you could imagine and I’m here to tell you from my observations in the shower that there are a whole lot of huge cocks you never want to find between your legs no matter how much you’ve enjoyed a big one. This is prison, sweetheart. I just saved your life.’
She watched him as he listened to the chaos outside the cell door. The noise was deafening and yet she was safe as houses. In here. With him. Her stomach lurched. God but he was sexy. He was wearing a white tee shirt and faded Levi’s and soft leather shoes. Expensive leather shoes.
‘How did you get…? I mean, you seem dressed so… normal… and yet you’re in here.’
‘They caught me,’ he said sagging down on the mattress. ‘Simple really. I’m not one for guns or weapons. I’m in here because I took a gun from an over zealous fucker who later said I assaulted him with it. I may be a thief but I’m certainly not a thug. But that doesn’t really wash when the judge is a collector who views your theft as a personal attack.’
The noise receded.
‘They’re on the roof. We could be here for a while.’
Sarah felt her pulse quicken. ‘A while?’
He was looking at her, smiling. ‘So if you’ve got any prison fantasies you want to fulfil… now’s your chance.’
She gave a jittery laugh. ‘You really are a piece of work.’
‘Aren’t I though?’
‘So Lyle… you’ve rescued the damsel in distress. What happens next?’
Lyle glanced down the front of her blouse to where her breasts were just hidden yet swelled riotously against the fabric. Sarah breathed in deeply. The air was heavy. She could hear his breathing and it matched her own. Carnality was raging through her. In all her life she’d never felt so grateful to someone and so overwhelmed with the desire to tongue every inch of his body.
‘I’d probably drop dead if you were to pull out a breast now. I’m not a rapist, Sarah. I may have wanked my own body weight in semen in the last four weeks thinking about you but I’m not about to take something that you don’t want to give.’
Sarah slowly raised a hand and popped the top button of her blouse.
‘And if it were to be given willingly… if the damsel in distress had thought about nothing but the bad man for four weeks as well. If he knew that she had gone to sleep with her fingers drenched in her own juices thinking about him. If he knew that she was willing to do anything…?’
Sarah popped another button and revealed the top of the lacy cups of her black bra, ‘anything to thank him for saving her life.’
Another button. His tawny skin blushed as the creamy globes of her breasts plopped out.
‘What would his fantasy be? What would that bad man want,’ asked Sarah?
Lyle ran a hand across his jaw. She knew he was wondering if this was really happening. If a woman, a flesh and blood woman were in his cell, offering to fuck him senseless. Had it really been two years?
‘He’d like to see her completely naked to begin with.’
Summoning all of the courage she could muster, Sarah rose slowly and turned to face him. She undid the rest of the buttons and pulled back the shirt to reveal her not unsubstantial breasts in their gossamer fine holdings. Her breaths were jerky and her nipples stood proud from arousal and fear.
‘But then he’d realized he couldn’t wait that long,’ Lyle said suddenly, launching off the bed at her and pinning her to the wall.
His mouth was on hers, his lips and tongue searching every crevice of her mouth as his hand placed a firm but measured grip around her throat. Her fingers undid his buckle and pushed down jeans and prison issue boxer shorts to the floor. She cupped his sack, relishing his groan against her mouth, delighting in the silky feel of his hard cock as it jerked in her hand. He felt good. He felt weighty. Not so big that you’d gasp but big enough to make you sigh. Sarah felt her head spin as he lifted her and wrapped his legs around his waist, grinding himself against her. She gasped as his hands drove her skirt up her thighs and discovered she was again, sans panties.
Lyle’s cock sawed between her lips and across her clit almost as though he was savouring the moment until he could stand it no longer. Predictably, this act couldn’t last very long before he would succumb to his search for the ultimate treasure.
‘Dear Jesus, he groaned into her as he slowly drove himself into her. The head of his cock was firmly lodged against her cervix. His girth was such that every inch of her vaginal canal was stretched pleasantly around his rigid shaft of meaty flesh. They both shuddered, staying in that position for what seemed like an age. Sarah needed a moment to get used to his thickness. She had put a lot of miles on her collection of vibrators but none of them had quite the spongy girth of Lyle’s steel cock.
‘Yep,’ he panted into her ear. ‘Just as I imagined. Hot, wet and tight.’
Sarah gave a little moan as he popped her breasts out of their cups and he grazed each nipple with the front of his teeth. With his body and one arm supporting her weight, his other hand delved lower until he found what he was looking for. The erect little pearl of her arousal, wet and slippery and waiting for him.
‘This may not last long… forgive me,’ he grated as he slowly began to move his hips. Sarah didn’t hear him as she was already tightening, bunching like a fist around him, feeling the palsy as it overtook her, the naughty secretary being fucked hard by the criminal inside the prison cell. She writhed against him, getting the stimulation she needed and more. His finger was skilled and a little too eager but it was enough when he gave one strong tweak for her to crash over the edge, panting into his ear that she was cumming, she was cumming. He gave a masculine grunt as her contractions gripped him and he gave up the ghost and came for what seemed like an age. He kissed her mouth again, his tongue soft and probing with all of the skill of earlier but less of the frenzy.
‘I’m sorry,’ he said, setting her to her feet and pulling up his jeans.
‘Why? That was amazing.’
‘I’m not usually as… quick.’
Sarah felt the sudden shift in his humour. Was he embarrassed? Had she royally fucked it up now by being so quick to let him have her?
‘Really. I see. Well, you can understand if I have to take your word on that…’
His eyes snapped to hers.
‘I mean, you’re not exactly giving me a frame of reference here.’
He smiled at her. ‘What frame of reference would you need?’
Sarah sighed and dropped to her knees in front of him. His penis had certainly softened but even flaccid it was not without surprising weight to her experience.
What Lyle was now discovering was that Sarah had never viewed blowjobs as work or obligation. Rather, she enjoyed the sense of power that her skillful mouth and lips gave her over a man. And to her experience, there was nothing at all repugnant about the taste or texture of sperm so Sarah was one of the uncommon recipients who was more than eager to swallow a man’s emissions unless of course he got off as many did by cumming on her face which was equally fine to Sarah as well.
‘So, I’d need at least two more incidences to make an informed decision…’
And so for the next four hours, she did everything he bid her. She gripped the end of the bed while he pounded her from behind and probed the length of his thumb in and out of her asshole. Riding her hard with animalistic passion, her neck strained back at the pressure of his firm hold on her ponytail.
She got naked and bounced joyfully up and down on his cock while he sat on his small chair. First facing him and then away.
Again, she let him take her up against the wall and thrilled as the violent force of each thrust raised her up on the balls of her feet and slammed the cheeks of her ass against the cold brick of the prison wall.
Between each change of position Sarah went back between his thighs and bobbed her experienced mouth up and down his cock for as long as he could take it until needing to be back inside her again.
This criminal of hers’ turned out to be a skilled and giving partner as well. In their time together he spent a considerable time nestled between her legs using his fingers and tongue with a sense of craving. Sarah cried out almost constantly with every flick of his tongue across her sensitive clit. Intermittently, Lyle forced his tongue as far between her folds as possible. Indeed, this man’s tongue went deeper inside her than some of her less fortunate lovers had ever reached.
And finally, he lay on top of her in the good old fashioned missionary position, hands entwined over her head, eyes and groins locked. Finally, when they could do no more, they dressed and sat on the edge of his bunk, waiting patiently, smiling at one another silently in the afterglow of a fantastic sexual escapade.
And then… the outside came in and Lyle was dragged from his cell and Sarah had to throw herself across Lyle to tell the governor that he had saved her. The last she saw of him was as he was being dragged away and she was quickly escorted out to a waiting police car.
10 weeks later…..
The small newspaper article said that a female legal secretary had testified that one inmate had saved her life, taking her into a cell just before the prison had been locked down. There, he had been an utter gentleman and made sure she was not harmed. The same inmate had had his parole application approved and been commended by the warden as an example to all inmates. Sarah had not gone back to the prison, except to give a statement of what had happened. And then she had testified at his parole hearing.
To her disappointment, she’d been hoping to see him there but these matters were all conducted in private. She’d said that Prisoner no 15687 had found her wandering around in the dark and had taken her into his cell where he’d explained that she was in danger and that he could trust her. There he had treated her with the utmost courtesy and respect. He had even draped a sheet across his cell so as to prevent the rampaging inmates from discovering her.
Jonathan had received a concussion but had recovered and was now working insurance cases. And she was back spending her Saturdays in her little apartment with her dull roommate and fantasizing about her prisoner. Sarah drained her coffee cup and balled the paper up and threw it in the recycling bin. Her roommate was out on a date and she was alone in the apartment. Everyone had been telling her that she needed to see a therapist after the supposed dreadful things that had happened to her. But how could she tell them that she’d spent the best sexual day of her life in a tiny 10 x 6 cell with a convicted criminal.
Sarah undressed in her room in just the light of her bedside lamp and lay down on the crisp bed linen. She opened the drawer and took out her new pink vibrator that had been her bed companion every night since she had first spotted the beanie wearing inmate in the exercise yard who had so cheekily winked at her. She lay back against the covers and sighed as she flicked it on and let her legs fall apart.
‘That’s just rude,’ said a deep voice from the darkness the other side of the room. Startled, she sat up and opened her mouth to scream and then the voice spoke again and she smiled.
‘I mean… I come in here and I find you… pleasuring yourself and you don’t even have the manners to invite me to join in?’
Lyle approached the bed. He was sharply dressed in a charcoal grey suit and snow white shirt. His blonde hair was longer and he smelled of some expensive cologne. Same prisoner. Just dressed better. And looking, if it were humanly possible, even more sexy than ever.
‘Really? Perhaps you’d like to do the honours,’ she laughed, flicking off the vibrator and dropping it back into the drawer.
Lyle allowed his eyes to travel the length of her. She stretched out luxuriously. Let him look. She’d be naked in his company forever.
Lyle offered out his hand and Sarah took it and rose from the bed. Without undressing, Lyle sat down and quickly put Sarah over his lap with her ass sticking up in the air. With no idea where this was going Sarah was completely caught by surprise by the first firm but gentle slap of his strong hand on the naked cheek of her ass. With each insistent slap the breath caught in her throat as she felt the skin of her backside heating up.
‘I have an idea,’ he said, dangling a pair of handcuffs in front of her. ‘Perhaps this time, you can be the prisoner…