This is a story based on a number of events that occured over a period within the uk prison system, while not all the incidents happened to the same person for the sake of ease of reading I have written them as though they did, also some aspects have been changed slightly to avoid possible identification of anyone involved. it features events that while covering boots also covers other things which I feel that you, the reader, may enjoy.
Best wishes, Owlman.
Not everyone is suited to work within a prison environment, some people want to work there because they enjoy controlling others, some are bullys who are on a power trip and some are just well, too nice or naive to be allowed anywhere near the type of person often found within these establishments. If you think of a prison as being like a large lake, you won't be far out, look at a large lake, generally it's quite a pleasant place on first glance, ok on the fringes in the reeds you'll find odd bits of rubbish, discarded plastic bottles, crisp packets, sweet wrappers, the general detritus abandonded by a modern society in its quest to enjoy itself. However pull on your nice rubber waders and poke about under the smooth surface of the lake and you'll no doubt soon discover a lot more unpleasant things that have been abandoned there, as the old saying goes, out of sight out of mind, well the prison system is not to much different, the modern world has a few ways of getting rid of its unwanted human detritus, psychiatric hospitals and prisons are two of the common favourites.
It was into this environment that a young lady one day found herself thrown, well meaning and convent school educated Sian had decided to dedicate her working life to helping others less fortunate than herself and from what she'd heard a prison seemed the ideal environment, after all weren't most people in there only there due to circumstances ? If, she reasoned, they'd had a better start in life then they wouldn't be locked up in a small prison cell, Very soon she'd realise that as with a lot of things in life the reality was far different from her own perceptions.
She found herself working in a prison not as a prison officer, or screw as they are more commonly known, but as OSG, or operational support grade, these staff carry out a wide range of tasks but one thing they don't do is lock prisoners behind their doors, that is still done by the 'screws'. Sian ended up working with prisoners in a sort of secretarial role, helping them with anything from writing letters home to helping them understand letters sent to them regarding appeals,or other stuff. With some of the more dangerous or volatile prisoners she'd be accompanied by a screw just to prevent her being physically assaulted, but most of the time she was in a small office just her and the prisoner, for safety at various points around the room were positioned alarm buttons, hit one of those and within moments screws would come rushing to her aid, thankfully in the short time she'd worked there she'd only pressed the button once, when she was told to press in on her first day, to show her that it did work.
Also in that environment was a prisoner, lets call him Wilson, now from outward appearances he was a pretty insignificant individual, not particulary well built, not a member of the prison gym set who spent all their free time in the gym pumping iron. He wasn't the type of prisoner who'd go out of his way to cause the staff problems, was very rarely known to get in fights with other cons, he generally seemed the type of prisoner who you might imagine was doing a short sentence for a motoring offence or a business fraud, the reality was he was doing a long sentence for a vey nasty offence involving a young lady who having been tricked into delivering a parcel of drugs for him had been unfortunate enough to lose it after she was attacked by the very people she was delivering it too, after recovering from the injuries she'd suffered during the attack to get the drugs she was then to face the wrath of Wilson, for losing them, having found herself stripped naked and abused for several days by him and several of his mates, she was found chained to a pipe in the filthy cellar, and this was only due to the fact that having not paid his electricity bill entry had been forced into the building to cut off his supply.
Dressed in her smart white polo necked jumper, black knee length skirt and pointy toe'd pixie boots Sian had done her best to dress in a way that while not making her look frumpy didn't make her look too sexual either, one of the first things she'd been told when she'd done the prison service training was that no matter what, she shouldn't dress in a way that could be considered flirty or two revealing, one thing an inmate wasn't allowed was any form of sexual contact with a female and being deprived of female company even the slightest glimpse of a thigh or a bra thru a blouse could be enough to make a member of the female prison staff the object of desire for a number of inmates and so she'd chosen her outfit with much care, not even the slighest glimpse of her shapely thighs or her pert 34B brests could be seen.
One of the most important things when working in a prison environment is what is called jailcraft, it's not something you get taught on the courses, more something you sort of absorb and not everybody is able to do it, it's the ability to sort of 'feel' when something isn't right on a wing, or to look at the way an inmate is behaving and realise that it's not how he normally acts and that usually means he is up to something, had a more experienced member of staff been with Sian on her first encounter with Wilson, its possible they'd have picked up on something and the events that followed would not have taken place, sadly for this 21 year old convent educated girl it didnt happen and as a result not only did she lose her job and her dignity she also ended up with a prison sentence and a criminal record, anyway hopefully dear reader you now have at least some idea of how the system works, so lets move on.
Sian headed into work on that fateful morning blissfully unaware that today would see a chain of events set in motion that would end several months later in a court case and her finding herself on the wrong side of a set of prison bars!
She stood up from her seat behind her desk and walked to her office door opened it and looked into the corridor, sat with his head down was Wilson, hearing the door click he looked up and saw Sian, the barely perceptible flash in his eyes would had she had the experience possibly alerted her to the potential for danger, sadly she hadn't got the experience and therefore missed this crucial warning sign. "please come in lets see how i may be able to help you" she said, stepping back into her office, Wilson got up from his seat and followed her slowly into the office, his eyes taking in every aspect of the image in front of him, from the pointy black pixie boots past the shapely lower legs up the skirt that clung to her shapely rear and past her waist, he saw the way the outline of her bra was just about visible under her tight jumper and allowed himself a little smile, game on!
Sian liked these meetings to appear not too formal and as usual rather than sitting behind her desk opted to sit at the table in the middle of the room and indicated to Wilson to sit opposite her, he smiled pleasantly as he sat down, taking a few seconds to take in the way her dark shoulder legth hair framed her pretty face, he didn't exactly miss the two small bulges in her jumper and guessed that she was a B cup, just the size he liked, unlike most prisoners who tended to find bigger breasts more attractive, he found smaller better, perhaps in his twisted mind, he thought of smaller breasted women as being younger and therefore he felt more able to manipulate them.
It was nothing too taxing that he wanted, just some help filling in some forms for compensation for stuff that had been lost from his house after he'd been arrested, naturally, Sian didn't ask why he was in prison, it wasn't something she needed to know so she went thru the forms and began to fill them in, She was pleasantly suprised at how attentive Wilson was, he kept his eyes focused on the paperwork and when they chatted he'd look up and make eye contact, he was polite and pleasant and at no time during the meeting did he give even the slightest hint of any improper behaviour, not a look, not a rude comment, nothing, and even to someone with her limited experience in the job that was a pleasant change, most of the prisoners made some personal comment, anything from how pretty she looked to if she had a boyfriend, and she never gave an answer to that question, another thing you are told in prison is never let the inamtes know anything about your personal circumstances.
Paprework completed she told him she'd send it off and as soon as she received a reply she'd get him back in to continue the claim, he thanked her and left her office, after a break for coffee her day continued uneventfully, or so she thought.
About a week later the reply to the letter landed on her desk, yes things hand't been done as they should and therefore the prisoner was entitled to compensation, the only question was how much? Sian arranged for him to be brought to her office the following morning so they could prepare a list of what he'd lost, this was the difficult part as well she knew, it wasn't only prisoners who seemed to think that an item bought 5 years ago was still worth the amount they'd paid for it and most people had never heard of depreciation, Sian swallowed the last of her coffee let out a sigh and went to open the office door.
To her suprise Wilson was already standing there waiting, "good morning Miss, it's so kind of you to help with this" he said, eyes meeting hers, that same slight smile on his face, she walked back to the table as he closed the door and followed behind her, for saftety she should have been behind him, thats something else you get taught, never let a prisoner get behind you, too many officers have been attacked that way. They were about to sit down at the table when Wilson spoke, "excuse me Miss, could we sit at your desk today, my back hurts a little and I think sitting upright would be better for me " she nodded and took her usual seat behind her desk, Wilson sat upright in the other chair facing her hands folded in his lap.
Sian explained what she'd read in the letter and how they would have to make a list of all his property and its approximate value, she also took pains to explain that although he might have paid £400 for a tv 5 years ago didn't meanhe'd get £400 compensation for it. "yes Miss, I understand all about depreciation" he replied. They got down to making a list, first on a sheet of paper and once they'd listed everything and agreed a value she'd write it on the paperwork and send it back.
Wilson chatted about what he'd lost explaining that he wasn't bothered about a lot of the stuff, he wasn't petty, small stuff like books, pictures and such werent worth claiming for, after all they'd have been no use to him in prison, no it was things like his TV, his furniture and most importantly his car, for while they were not of massive value they could have been sold and the money put in his prisoners bank account to enable him to have a few luxuries during his time in prison, he had limited funds and no family to help him and to him even a bar of chocolate was a luxury. Feeling slightly sorry for him and remembering she had a small tin of travel sweets in her bag, again something she shouldnt really have brought into the prison, she took them out, and handed them to Wilson, "here, you keep these, it's not much but i can get some more when i go shopping" in handing him the sweets she'd unwittingly sealed her own fate.
Having finished the paperwork, she was about to end the meeting when he asked her if she'd mind doing something else for him, he appologized profusley for taking up so much of her valuable time but he wanted to buy a small radio for in his cell, could she possibly do a bit of research for him on the best radio for about £40. Sian told him not to worry,she was here to help it was what she got paid for, besides, he wasn't rude or making sexual inuendo's like a lot of prisoners, she actually enjoyed her time with him, she'd just make mistake number two!
Sian was kept busy for the next week or so and it was almost a fortnight later when she got around to seeing Wilson again, it wasn't that she'd forgotten about him merely that she'd had a lot of work to do, various prisoners were coming up to their release date and she'd been busy arranging appointments with benefits claims advisors, or finding accomodation for some of them on their release. She went into work armed with some printouts of various radio's that were available, the sheets explained the features each had plus a picture of the item, the price and the store it could be ordered from, rather helpfully the prison had someone who's sole job it was was to order stuff on behalf of the inmates, all he had to do was chose one, take the number to this person and they'd order it, payment would then be taken from his prison bank account, yes prisoners even have bank accounts in prison!
Going through her mail that morning she discovered a reply to his compensation request, 'hmmm that came back quickly' she thought to herself, she smiled a little as now not only would she be able to help him get his radio but she could help him get the compensation which she thought he richly deserved, after all she couldn't imagine how she'd feel if after being locked up for a relatively minor offence all her posessions had been thrown in a skip!
She sailed through her mornings work and after lunch found herself once more sitting at her desk, sat in front of her, hands in his lap, polite and charming as ever, was Wilson.She gave him the leaflets on the radio's to look at while she carried out some other small jobs at her desk and said that she'd give him time to look at them and then, when she'd finished they'd go through the paperwork regarding his compensation claim, he smiled, nodded and Sian began to read some of the paperwork on her desk.
Not long after she became aware of a rustling sound and glanced up from her paperwork, Wilson seemed absorbed in the leaflets and didn't seem to notice her, the rustling sound went on, she glanced around the office but couldnt see anything that could explain the noise, eventually she looked down under her desk and got the shock of her life, Wilson had one hand in his loose fitting tracksuit bottoms and appeared to be, well as she'd heard it put so often, having a wank!
Sian let out a loud gasp of shock and Wilson casually glanced up from his leaflets, "something the matter Miss?" he casually enquired, Sian glanced over at the alarm button, "I really would't press that Miss" he said in a menacing tone she'd never heard before, Still moving his hand in his pants he continued to speak, "You see what we have here is what you might call a 'situation' and one of you're own making" he hissed, " did you really think you could walk around like that and not get some reaction you little slut?" he went on, Sian sat in silence, a mixture of felings engulfed her, fear, shock, confusion, she'd tried to dress in a demure manner and besides, she reasoned, if her outfit was at all slutty why hadn't one of the officers said something?
"now, the first thing you're going to do is lift up that top and let me see those tits arent you, what size are they?" he hissed , Sian took a deep breath, "that's got nothing to do with you, how dare you make such rude comments, I think it's time you left" she replied, trying her best to sound in control, and I might add, failing badly! " oh I think not, you see you're the one in trouble, not me, who gave whom a tin of sweets then?" he told her, "yes ok I gave you some sweets, whats the problem?" she stammered, Wilson smiled, "you should know its against the rules to give a con anything, anything at all" he replied, a little smirk on his face, "well I'll deny it, you could have bought them from the prison store" she replied, feeling a little panicked now, "wrooong," he replied, "the prison store selling M and S sweets, get real you stupid bitch" he snarled, "it's bloody obvious they came from outside, and who said there was just sweets in the tin, imagine how it would end if the screws knew you'd been bringing drugs into the nick, you'd end up in one yourself, now i'll ask again cow, what size are those tits?"
Sian could feel the tears welling up in her eyes, how could she have been so stupid, hadn't she been warned about this happening " 34B" she sniffled, "WHAT, what's 34B? " he snarled, "my breasts, they're 34B" she replied, "hah posh little cow, my breasts are 34B" he mimicked, "they're not breasts, they're tits and you're going to take that top off, now say it and do it". Sian felt the tears on her cheeks, "ok my tits are 34B" she sobbed, "ok now lets see them" he growled, Sian slowly pulled the tight jumper over her head revealing her white bra beneath, " hmm now the bra, that can come off too" he ordered. Sian paused for a second, in one respect she longed for someone, anyone, to walk in to her office before things went too far, the other thought was how it would look if someone did walk in and she was sat there topless, she was bound to lose her job, she took off her bra, hoping against hope that once he'd had a look he'd let her get dressed and that would be that.
"hmmm, nice little tits, and what pretty nipples they have, make them hard for me" he told her, he didn't sound as aggressive now but there was still menace in his voice. "how do i do that? " Sian asked, "I dont fucking care how you do it, lickthem, rub them, unless you want me to get them hard for you?" he snarled, his temper revealing itself once more, "it's ok, I'll manage" she answered as she began to stoke her nipples with her finger, "lick it, make it look good slut" he growled, licking her finger she once more began to play with her nipples and they became erect in no time.
"hmmm, good slut, now get the top back on, leave the bra off, after all imagine anyone walking in and seeing you sat there, a filthy little slut with her tits out" , she quickly put her top back on, ok she was now covered but her nipples were clearly visible poking through the thin fabric, seeing this Wilson smiled, "hmmm, I think you're going to be a good little slut for me, now move your chair around, let me get a proper look at you" he said, pointing to a space at the side of her desk, getting up he strolled towards the door and kicked the door wedge to within an inch or two of the door, now anyone opening it would drive it onto the wedge stopping it opening any farther, and it could easily be explained away as an accident, he turned and made his way back to the desk turned his seat to face hers and sat down, "best keep those nipples hard bitch, unless you want to take that top off again" Sian shook her head and began to rub her nipples through her jumper.
Wilson reached out to her desk and picked up her bra, rubbing the soft silky material in his fingers he smiled, "name slut?" , Sian, stopped rubbing, "it's Sian, and please stop calling me a slut, its not very nice you know", Wilson grinned, "hmmm, Sian the slut, i like that, well Sian, best keep rubbing those tits, or shall I do it? "he asked as he reached out and roughly pinched one of her nipples through her jumper causing her to yelp in pain. She went back to rubbing, she dind't have a lot of sexual experience but was doing her best to keep him happy and therefore hopefully prevent him from going any farther. he fingered her bra for a minute or two as she continued rubbing her nipples, "bet they're fucking soaking aren't they, oh and do they match then slut?" Sian was in truth a little bit wet 'down there' as she called it, but felt horrified at the fact that despite the situation she was getting wet, she mentally tried to take herself out of the situation by imagining herself somewhere else, doing this for someone she had feelings for. "well slut, are they" he growled, "are what what?" she snapped, suddenly back in reality, "don't get fucking nasty with me you little bitch, I asked a question, are your pants wet and do they match the bra?" forgetting herself for a moment she replied, "actaully that's two questions, and yes they're wet and yes they match" then for no reason added, "white silk, full cut actually". Turning his seat so he was sitting square on to her he smiled, "stand up, lets see them then" Sian gasped, "get up lift that skirt slut, or shall I lift it for you? "
Sian got to her feet and with a little wiggle slid her skirt up exposing her underwear, to her horror she saw that her panties weren't just damp, they were soaked, so much so that her dark pubic hair was clearly visible beneath them.
The Shaming of Sian
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owlman
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: The Shaming of Sian pt 2
Wilson had watched her as she wiggled and slowly slid her skirt up to her thighs, he enjoyed controlling and humiliating women as his previous victim had soon found out, when he had been arrested and sent down he'd had to satisfy himself by replaying those events over and over in his mind, he would never had believed he'd get the chance to control another woman for a long time and certainly not one of the women who was supposed to have control over him.
He smiled as he stared at the wet patch in her panties, this was even better than what he'd done to land him in here, actually doing this inside a prison, the last place he'd either expected, or was supposed to be able to get away with stuff like this, the question was, how long could he keep it going for?
"awww, it seems my little slut has pissed her pants, are you that scared then slut, sondering what i'm going to do to you? " . Stood there holding her skirt up, exposing herself to someone she was rapidly realising was a pervert Sian felt herself bristling, "for your information I haven't wee'd my panties, so there" she said sharply, "hmmm, so you find this a turn on then slut, showing how cheap you really are to someone you're supposed to be in control of?" he pointed to the chair indicating for her to sit down, "leave the skirt up, and spread those legs slut" . As her bottom made contact with the hard cold plastic seat Sian was brought back to reality with a jolt, it's funny how a thin skirt can make the chair seem warm, she thought to herself.
Wilson began to lower his tracksuit bottoms, "might as well get comfy and enjoy this" he said, seeing the shocked look on her face as not only his tracksuit bottoms but also his underpants came down in one smooth movement.
Before she could say anything he began to wank himself off, long slow strokes and a hideous smile on his face, "are those nipples going soft again?" Sian immediately went bact to rubbing them through her jumper, this looked dangerous, if she had to play with herself while he satisfied himself that was bad enough, what she didnt want was him deciding to take things any further. he seemed to speed up his strokes and motioned her to move her chair closer, now she may not have had much experience with men but she knew enough to know what was about to happen, hesitantly she moved her chair closer, "put them together slut" he whispered, even a whisper from him sounded sinister she thought and moved her chair until the seats were touching, to acheive this meant spreading her legs so wide they were aside the chair, he smiled. "left leg up slut" he said tapping his right thigh, she obediently placed her booted foot on his left thigh and shivered as he began to stroke her boot, "hmmm, I loved how slutty you look in these the first time i saw you, you been fucked in them yet?" Sian felt a frisson of fear run through her body and a little trickle of urine esaped involuntarily through her panties, "oops, feeling afraid slut?" he asked as it pooled on the plastic seat, "no, i've never had sex in these boots" she replied, ignoring his other question, "oh well, maybe you will one day" came his hissed reply. hopefully not by you, Sian thought to herself.
Wilson felt a familiar feeling in his balls and knew he wasnt far off cumming, in one smooth movement he slipped the boot from Sians foot and held it so the tip of his cock was inside it, four more strokes and he began to spurt, now this being a meticulously planned event he'd abstained from wanking for almost a week, knowin that when he did release it would be a decent quantity. He smiled as three thick ropes of cum shot into her boot, then stopped stroking, he was far from spent, he was simply saving the rest, well for a minute or two.
Sian grimmaced as she felt his thick sticky cum on her foot as he gently slipped the boot back on her foot before placing it back on the floor, suddenly he was back stroking again, Sian was so busy watching him she forgot she was still rubbing her nipples through her jumper, the warm sticky mess hitting the front of her wet panties shocked her back into reality!
The amount he unloaded onto the front of her panties was incredible, there must have been ten thick spurts, each one hitting the same spot and dribbling slowly onto the seat in front of her, finally he had finished, he put his cock back in his pants and smiled, "forwards slut, sit in it", Sian slid forward reluctantly, feeling the warm sticky mess, soaking into her panties, oh my god, whats next i wonder, she thought to herself, she'd not have to wait long to find out.
"okay slut, i've had my fun now its time you had yours I think" he sat back in his chair looking totally relaxed, "now lets see my little slut make herself cum i think she's earned it" . Sian didn't move, "unless she wants me to make her cum" he added, by way of encouragement, she shook her head, "ok well since we dont know each other that well I'll give you a choice, you can either drop them pants and do it like you normally would, or providing you can do it, you can do it thru the pants, up to you, can you cum like that slut?" Sian nodded feeling his mess on her fingers as they shot down to her panties, "well at least its well lubricated slut" he laughed, "not that it matters to me, but you wont get pregnant will you?" . She shook her head but didnt elaborate on why she couldnt get pregnant, if he knew it couldnt happen there was always the possibility he'd decide to dump a load in her. slowly she rubbed her slit, feeling her folds part as she rubbed gently and felt his mess being pushied through her panties, knowing it was in contact now with her most private parts, "harder slut, work that clit, moan, enjoy it, you know you like it, showing off for me". Sian closed her eyes trying to imagine she was somewhere anywhere else, surely she couldnt get herself off in this situation, after all it wasn't like she wanted it. she worked her fingers up and down and found her clit, she rubbed it frantically and to her suprise a few minutes later felt her breathing quicken, oh my god, she was actually getting aroused, "good slut, cum those pants make a filthy mess, lets see how much you love this". A few minutes later she felt two things happen at once, her face began to redden with shame and her pants began to get really wet, she was actually squirting!
Sian opened her eyes and looked at the clock on the wall and blinked, was the clock right, she looked at her watch, it was, the whole ordeal had lasted just under an hour, so thats why nobody had come to check on her, they usually checked every hour and a half, he'd clearly worked it all out in advance. "hmmm, you did enjoy that didn't you my little slut?" Wilson said smiling as he looked at her before reaching out and rubbing a finger along her sopping slit. "now, you're going to stand up and take those nasty wet pants off, cant have you in them all day you know". she got to her feet, slid the chair back and slid her panties down her legs, he reached out and helped them over her boots, she held out her hand to take them from him, "I think I'll keep hold of these for a little while" he said as he carefully folded then and slipped them into his underpants. "but i need to wipe, look at me" Sian replied, pointing to her glistening pussy which was already begining to drip its juices onto the floor. "too bad, hopefully nobody will notice, now drop the skirt, oh best put those tits back in the bra, don't want the screws noticing, do we? " .
Sian removed her top once more, quickly put her bra back on and then her jumper, she hoped dearly that she wouldnt drip anywhere and get noticed, she was still hoping to get him out of her office then report what had happened, but, she was in for a shock, this was a well thought out plan and it wasnt going to end here.
He stood up, placed his arm around her and gave her bottom such a hard squeeze it hurt, a spurt of urine shot out and trickled down her leg, thankfully he didnt notice it, " well Miss slut, I shall expect to hear from you next thursday, I'd love to see you sooner but we dont want to draw attention to our 'relationship' do we?" she shook her head, "oh and don't think of telling anyone, remember not only do i have the tin of sweets, but I hve your pants too, and since they have both our DNA on it would be a hard one to explain don't you think?" Sian sighed, he might not have physically put his cock inside her, but she was fucked none the less, considering her education, she couldnt belive how stupid she'd been, the only question now was how far was he going to take it, would he ultimately make her have full sex with her, and for how long was he going to keep it going, her only way out now was to leave the job, and she didn't want to do that.
The week seemed to fly by and all too soon there he was again, outside her office, she invited him in and he sat down, he wasn't as polite as before, clearly he'd drawn her in and the politeness was just a front. he sat down and indicated for her to stand in front of him, he kicked her legs roughly apart and slid her skirt up, this time she was wearing little black panties, he smiled he liked black underwear. "top match too? he asked, she nodded,"ok lets see it then" she swiftly pulled up her black jumper revealing a little black half cup bra, he reached out and squeezed her tits with both hands, she yelped with the pain, "don't piss yourself slut, well not yet anyway" he said as he pulled her down onto his knee, as her bottom came into contact with his body she could feel something hard pushing against her bottom, he had an erection, oh shit is this it, she thought to herself.
"relax, enjoy yourself while we have a little chat, I know I'm going to" he said as he fondled her breasts through her bra, he smiled as her nipples began to harden, "see slut, I told you you'd get to like it", he played with her for several minutes and she realised to her shame that her panties were begining to get wet, whats wrong with me, she thought, I shouldnt be enjoying this. After a few minutes he stopped playing and she felt one hand go onto her panties, then into them, oh my god, he's fingering me, she thought as she felt not one, but two fingers slip inside her, she could also feel the bulge growing in his pants and began to fear the worst. "ok slut, stand up lets have those pants off" he ordered, Sian got up, stepped forward and slowly took off her panties, "good, now spread those legs for me" he went on at the same time taking the black panties from her hand.
He put them in his pocket and at the same time removed a Mars Bar which he unwrapped and placed on the chair in front of her, then from his other pocket he produced a condom and slowly unwrapped it, fuck this is it, he's going to make me have sex with him, she thought, but whats the chocloate for?
Wilson saw the worried look on her face, "relax slut, I'm not going to fuck you, well not just yet" she watched as he took the Mars Bar, slipped it into the condom and handed it to her, "put it in slut" she looked at him puzzled, "in your cunt slut, put it in" she blushed as she took it from him and slowly pushed the condom wrapped chocolate bar inside her until only the tip protruded, "all the way slut" he barked, she pushed a little more and it slipped inside her, her pussy lips closing behind it, it felt strange inside her, strange but not as bad as she thought. "now slut, lets see you walk with it in, go on, up and down the room" Sian felt more than a little conscious as clad in only her bra and boots with her skirt around her waist she paraded herself up and down the office for him, god knows what she'd do if anyone walked in, remembering last week she walked toward the door and kicked the wedge into position, the door could still open but only just and at least it would give her time to make herself decent, she hoped.
"ok slut, come here" she walked back to the desk and stood in front of him, "ok give it back" he held out his hand for the package, she slipped a couple of fingers inside herself and attempted to retrieve the chocolate bar, it wouldnt come out !
She groped around for a couple of minutes, Wilson began to lose patience, "push slut, push" she stared at him blankly wondering what he meant, "listen bitch i want it out, now push, like you're having a shit, do it" Sian began to panic a little, she'd heard that women giving birth had described the pushing as similar to going to the toilet, but she wasn't actually giving birth, and what if she really did go to the toilet, what then! Wilson began to look annoyed, "ok i'll get it, come here and drop the pants" , she looked at the size of his hands and imagined how rough he'd be getting it out, as bad as it was soiling her panties wasnt going to be anywhere near as bad as him poking around inside her, "it's ok I can manage" she replied as she squatted slightly and began to push, thankfully the only thing that began to emerge into her panties was a condom covered Mars Bar, she slipped a hand into her pants, took hold of it and stopped pushing, it was out and thankfully her panties were still clean, she handed it to Wilson, "here you are".
He placed it on the desk and reached out and removed her black panties, sliding them down her legs and over her pixie boots, he took them and began to push them inside her, he was she thought suprisingly gentle. Once they were inside her he slipped one hand under her bra and exposed her pert breasts, he fondled them gently and smiled as he saw the way her nipples began to harden, with his other hand he rubbed her clitoris and it wasnt long before she began to get a familiar feeling, she was almost at the point of orgasm. Sensing this Wilson slowly began to pull the panties out of her until they were half in and half hanging out, she glanced down and thought how glad she was nobody could see her, she looked like a common slut!
He went back to her clitoris and began to play, each time she was about to cum he backed off, then went again eventually she could stand it no longer and found herself begging him to allow her the orgasm he kept denying her and she so badly desired. A powerful surge flowed through her body causing her to shake violently, she felt a warmth running down her thighs, oh fuck, I've wet myself, she thought, then realised it wasnt urine, it was her juices, she'd never experienced a feeling like this before.
She eventually stopped shaking and he gently removed the sodden panties from inside her, "hmm the lads will love these won't they slut?" he said as he dropped them into a plastic zip lock bag and sealed it before placing it inside his own underpants, "oh by the way I thought I'd best return these" he said as from inside his pants he produced her white panties, the ones she'd worn last week, it was clear from the stains that someone had been enjoying them in her absence, "I was telling my mates about you, well I din't actually name you but I did say I was having a bit of fun with one of the staff, they were well keen to get their hands on your pants, I hand to keep them on me all week in case someone went into my pad and robbed them, anyway, I'm sure they'll enjoy the black ones, and besides, they're nice and fresh" he told her to put the soiled white panties back on, she did and they looked a real mess, she was glad nobody was going to see her in them.
She got herself dressed again and just when she thought it was over he handed her the chocolate bar, "best pop this back in, get used to it being there" she reluctantly raised her skirt, parted her legs and pulling the panties aside slipped it back inside her, as it disappeared she let go of the panties and they snapped back over her pussy, now there was no sign whatsoever of waht was inside her.
"get used to carrying that, you're going to meet me in here again next Tuesday, but on Monday night you'll go to the pub down the road at eight and meet a mate of mine, he'll know who you are, i told him black skirt, white blouse and pixie boots, he'll give you a package of the same size, relax its only a mobile phone, put it in straight away and bring it in for me on Tuesday, oh and any funny business and the governor might suddenly come into posetion of a pair of your panties, he'll know they're yours from your DNA, but they'll wonder who's the six other types are, still so long as they catch a slut who's been screwing cons i dont suppose which cons really matters does it" .
Sian spent the rest of the day walking around with the package inside her, she didnt actually feel uncomfortable and nobody noticed, the only scary moment came just before clocking off time when she needed a bowel movement, as she sat on the toilet and gave a push, she felt the package begin to emerge from its hiding place, she gently pushed it back inside, finished her toilet and headed for home.
As part of the security team I often got called in to meetings with the governor and that Monday morning was nothing out of the ordinary, or so i thought, I, along with two other members of staff, another male and two females, had been called in to discuss a security operation that was to take place the following morning, during the meeting i was handed a ziploc back and I opened it, tipping the contents onto the desk I discovered it was a pair of black ladies panties, but not just any pair, these were liberally coated in semen!
Monday came and dressed as instructed Sian made her way to the pub as she'd been told to, as she approched the bar a young man handed her a drink and whispered, "well I take it you're Sian the slut, glad to meet you". He gently steered her to a small dimly lit room just off the main room and they sat down, apart from them the room was empty, the man explained he'd got a package for her and he'd hand it over shortly, he wanted to be sure she was alone first, after several drinks he turned to her, "ok slut get that skirt up, lets do his". Sian gasped, "I'll do it in the loo if you dont mind" he shook his head, "oh no I have ot make sure you dont lose it, now come on, after all you're not usually shy about people seeing your cuntare you slut?"
Sian reluctantly slid her skirt up to her waist exposing her panties, pulled them aside and quickly slipped the package inside her, snapping them back into place she was about to pull her skirt down when he palced his hand on her crotch and began to rub, "been told to make you cum before you leave, so relax enjoy it" he told her, she just sat there hoping nobody walked in as he did what he did, he wasnt as experienced as Wilson and it took a good fifteen minutes before she felt a familiar feeling and her pants became wet. "there we go you enjoyed that didn't you slut? " he told her as though he was doing her a great favour, she finished her drink and went home.
The following daY i went into work early ready for the drugs operation, Sian got up, showered, got dressed and headed into work as usual, she went through the main gate and as she entered the building a couple of women staff approached her and asked her to accompany them upstairs, I watched from the window and even at that distance I could see the colour drain from her face. She was brought into the office where myself and one of my colleagues were waiting, the first thing she saw on entering was the panties on the table and she knew the game was up, she let out a gasp of shock and i told her we had reason to believe she was bringing something into the prison that she shouldnt be and she would be subjected to a search by the two women officers in a seperate room, I'd barely finished speaking when I heard a soft pattering sound, looking down I saw a a puddle forming beneath Sian, she was actually pissing herself and began to sob. I dont normally feel sorry for people caught smuggling but this case was different, she looked completely beaten. "it's ok, no need for a fuss" she replied between sobs and before anyone could stop her she pulled up her skirt, pulled her panties aside and ejected the package into her hand. "no point being shy about it now is there, not after what I've been through, and no doubt whats to come" she sniffled, "and all for a bloody mobile phone" I took the package from her, wiped it on a tissue and opened it, yes there was indeed a small mobile phone in there but wrapped around it was a plastic bag containing about £1000 of class A drugs.
Sian was arrested and soon after appeared in court charged with trafficking drugs and misconduct in a public office, she got eight years! As she was led down the steps of the court to be taken to prison i looked at her an attractive and naive young girl and wondered how many times during her sentence she'd be forced to take down her underwear to pleasure some big butch female prisoner, I shuddered at the thought
THE END
He smiled as he stared at the wet patch in her panties, this was even better than what he'd done to land him in here, actually doing this inside a prison, the last place he'd either expected, or was supposed to be able to get away with stuff like this, the question was, how long could he keep it going for?
"awww, it seems my little slut has pissed her pants, are you that scared then slut, sondering what i'm going to do to you? " . Stood there holding her skirt up, exposing herself to someone she was rapidly realising was a pervert Sian felt herself bristling, "for your information I haven't wee'd my panties, so there" she said sharply, "hmmm, so you find this a turn on then slut, showing how cheap you really are to someone you're supposed to be in control of?" he pointed to the chair indicating for her to sit down, "leave the skirt up, and spread those legs slut" . As her bottom made contact with the hard cold plastic seat Sian was brought back to reality with a jolt, it's funny how a thin skirt can make the chair seem warm, she thought to herself.
Wilson began to lower his tracksuit bottoms, "might as well get comfy and enjoy this" he said, seeing the shocked look on her face as not only his tracksuit bottoms but also his underpants came down in one smooth movement.
Before she could say anything he began to wank himself off, long slow strokes and a hideous smile on his face, "are those nipples going soft again?" Sian immediately went bact to rubbing them through her jumper, this looked dangerous, if she had to play with herself while he satisfied himself that was bad enough, what she didnt want was him deciding to take things any further. he seemed to speed up his strokes and motioned her to move her chair closer, now she may not have had much experience with men but she knew enough to know what was about to happen, hesitantly she moved her chair closer, "put them together slut" he whispered, even a whisper from him sounded sinister she thought and moved her chair until the seats were touching, to acheive this meant spreading her legs so wide they were aside the chair, he smiled. "left leg up slut" he said tapping his right thigh, she obediently placed her booted foot on his left thigh and shivered as he began to stroke her boot, "hmmm, I loved how slutty you look in these the first time i saw you, you been fucked in them yet?" Sian felt a frisson of fear run through her body and a little trickle of urine esaped involuntarily through her panties, "oops, feeling afraid slut?" he asked as it pooled on the plastic seat, "no, i've never had sex in these boots" she replied, ignoring his other question, "oh well, maybe you will one day" came his hissed reply. hopefully not by you, Sian thought to herself.
Wilson felt a familiar feeling in his balls and knew he wasnt far off cumming, in one smooth movement he slipped the boot from Sians foot and held it so the tip of his cock was inside it, four more strokes and he began to spurt, now this being a meticulously planned event he'd abstained from wanking for almost a week, knowin that when he did release it would be a decent quantity. He smiled as three thick ropes of cum shot into her boot, then stopped stroking, he was far from spent, he was simply saving the rest, well for a minute or two.
Sian grimmaced as she felt his thick sticky cum on her foot as he gently slipped the boot back on her foot before placing it back on the floor, suddenly he was back stroking again, Sian was so busy watching him she forgot she was still rubbing her nipples through her jumper, the warm sticky mess hitting the front of her wet panties shocked her back into reality!
The amount he unloaded onto the front of her panties was incredible, there must have been ten thick spurts, each one hitting the same spot and dribbling slowly onto the seat in front of her, finally he had finished, he put his cock back in his pants and smiled, "forwards slut, sit in it", Sian slid forward reluctantly, feeling the warm sticky mess, soaking into her panties, oh my god, whats next i wonder, she thought to herself, she'd not have to wait long to find out.
"okay slut, i've had my fun now its time you had yours I think" he sat back in his chair looking totally relaxed, "now lets see my little slut make herself cum i think she's earned it" . Sian didn't move, "unless she wants me to make her cum" he added, by way of encouragement, she shook her head, "ok well since we dont know each other that well I'll give you a choice, you can either drop them pants and do it like you normally would, or providing you can do it, you can do it thru the pants, up to you, can you cum like that slut?" Sian nodded feeling his mess on her fingers as they shot down to her panties, "well at least its well lubricated slut" he laughed, "not that it matters to me, but you wont get pregnant will you?" . She shook her head but didnt elaborate on why she couldnt get pregnant, if he knew it couldnt happen there was always the possibility he'd decide to dump a load in her. slowly she rubbed her slit, feeling her folds part as she rubbed gently and felt his mess being pushied through her panties, knowing it was in contact now with her most private parts, "harder slut, work that clit, moan, enjoy it, you know you like it, showing off for me". Sian closed her eyes trying to imagine she was somewhere anywhere else, surely she couldnt get herself off in this situation, after all it wasn't like she wanted it. she worked her fingers up and down and found her clit, she rubbed it frantically and to her suprise a few minutes later felt her breathing quicken, oh my god, she was actually getting aroused, "good slut, cum those pants make a filthy mess, lets see how much you love this". A few minutes later she felt two things happen at once, her face began to redden with shame and her pants began to get really wet, she was actually squirting!
Sian opened her eyes and looked at the clock on the wall and blinked, was the clock right, she looked at her watch, it was, the whole ordeal had lasted just under an hour, so thats why nobody had come to check on her, they usually checked every hour and a half, he'd clearly worked it all out in advance. "hmmm, you did enjoy that didn't you my little slut?" Wilson said smiling as he looked at her before reaching out and rubbing a finger along her sopping slit. "now, you're going to stand up and take those nasty wet pants off, cant have you in them all day you know". she got to her feet, slid the chair back and slid her panties down her legs, he reached out and helped them over her boots, she held out her hand to take them from him, "I think I'll keep hold of these for a little while" he said as he carefully folded then and slipped them into his underpants. "but i need to wipe, look at me" Sian replied, pointing to her glistening pussy which was already begining to drip its juices onto the floor. "too bad, hopefully nobody will notice, now drop the skirt, oh best put those tits back in the bra, don't want the screws noticing, do we? " .
Sian removed her top once more, quickly put her bra back on and then her jumper, she hoped dearly that she wouldnt drip anywhere and get noticed, she was still hoping to get him out of her office then report what had happened, but, she was in for a shock, this was a well thought out plan and it wasnt going to end here.
He stood up, placed his arm around her and gave her bottom such a hard squeeze it hurt, a spurt of urine shot out and trickled down her leg, thankfully he didnt notice it, " well Miss slut, I shall expect to hear from you next thursday, I'd love to see you sooner but we dont want to draw attention to our 'relationship' do we?" she shook her head, "oh and don't think of telling anyone, remember not only do i have the tin of sweets, but I hve your pants too, and since they have both our DNA on it would be a hard one to explain don't you think?" Sian sighed, he might not have physically put his cock inside her, but she was fucked none the less, considering her education, she couldnt belive how stupid she'd been, the only question now was how far was he going to take it, would he ultimately make her have full sex with her, and for how long was he going to keep it going, her only way out now was to leave the job, and she didn't want to do that.
The week seemed to fly by and all too soon there he was again, outside her office, she invited him in and he sat down, he wasn't as polite as before, clearly he'd drawn her in and the politeness was just a front. he sat down and indicated for her to stand in front of him, he kicked her legs roughly apart and slid her skirt up, this time she was wearing little black panties, he smiled he liked black underwear. "top match too? he asked, she nodded,"ok lets see it then" she swiftly pulled up her black jumper revealing a little black half cup bra, he reached out and squeezed her tits with both hands, she yelped with the pain, "don't piss yourself slut, well not yet anyway" he said as he pulled her down onto his knee, as her bottom came into contact with his body she could feel something hard pushing against her bottom, he had an erection, oh shit is this it, she thought to herself.
"relax, enjoy yourself while we have a little chat, I know I'm going to" he said as he fondled her breasts through her bra, he smiled as her nipples began to harden, "see slut, I told you you'd get to like it", he played with her for several minutes and she realised to her shame that her panties were begining to get wet, whats wrong with me, she thought, I shouldnt be enjoying this. After a few minutes he stopped playing and she felt one hand go onto her panties, then into them, oh my god, he's fingering me, she thought as she felt not one, but two fingers slip inside her, she could also feel the bulge growing in his pants and began to fear the worst. "ok slut, stand up lets have those pants off" he ordered, Sian got up, stepped forward and slowly took off her panties, "good, now spread those legs for me" he went on at the same time taking the black panties from her hand.
He put them in his pocket and at the same time removed a Mars Bar which he unwrapped and placed on the chair in front of her, then from his other pocket he produced a condom and slowly unwrapped it, fuck this is it, he's going to make me have sex with him, she thought, but whats the chocloate for?
Wilson saw the worried look on her face, "relax slut, I'm not going to fuck you, well not just yet" she watched as he took the Mars Bar, slipped it into the condom and handed it to her, "put it in slut" she looked at him puzzled, "in your cunt slut, put it in" she blushed as she took it from him and slowly pushed the condom wrapped chocolate bar inside her until only the tip protruded, "all the way slut" he barked, she pushed a little more and it slipped inside her, her pussy lips closing behind it, it felt strange inside her, strange but not as bad as she thought. "now slut, lets see you walk with it in, go on, up and down the room" Sian felt more than a little conscious as clad in only her bra and boots with her skirt around her waist she paraded herself up and down the office for him, god knows what she'd do if anyone walked in, remembering last week she walked toward the door and kicked the wedge into position, the door could still open but only just and at least it would give her time to make herself decent, she hoped.
"ok slut, come here" she walked back to the desk and stood in front of him, "ok give it back" he held out his hand for the package, she slipped a couple of fingers inside herself and attempted to retrieve the chocolate bar, it wouldnt come out !
She groped around for a couple of minutes, Wilson began to lose patience, "push slut, push" she stared at him blankly wondering what he meant, "listen bitch i want it out, now push, like you're having a shit, do it" Sian began to panic a little, she'd heard that women giving birth had described the pushing as similar to going to the toilet, but she wasn't actually giving birth, and what if she really did go to the toilet, what then! Wilson began to look annoyed, "ok i'll get it, come here and drop the pants" , she looked at the size of his hands and imagined how rough he'd be getting it out, as bad as it was soiling her panties wasnt going to be anywhere near as bad as him poking around inside her, "it's ok I can manage" she replied as she squatted slightly and began to push, thankfully the only thing that began to emerge into her panties was a condom covered Mars Bar, she slipped a hand into her pants, took hold of it and stopped pushing, it was out and thankfully her panties were still clean, she handed it to Wilson, "here you are".
He placed it on the desk and reached out and removed her black panties, sliding them down her legs and over her pixie boots, he took them and began to push them inside her, he was she thought suprisingly gentle. Once they were inside her he slipped one hand under her bra and exposed her pert breasts, he fondled them gently and smiled as he saw the way her nipples began to harden, with his other hand he rubbed her clitoris and it wasnt long before she began to get a familiar feeling, she was almost at the point of orgasm. Sensing this Wilson slowly began to pull the panties out of her until they were half in and half hanging out, she glanced down and thought how glad she was nobody could see her, she looked like a common slut!
He went back to her clitoris and began to play, each time she was about to cum he backed off, then went again eventually she could stand it no longer and found herself begging him to allow her the orgasm he kept denying her and she so badly desired. A powerful surge flowed through her body causing her to shake violently, she felt a warmth running down her thighs, oh fuck, I've wet myself, she thought, then realised it wasnt urine, it was her juices, she'd never experienced a feeling like this before.
She eventually stopped shaking and he gently removed the sodden panties from inside her, "hmm the lads will love these won't they slut?" he said as he dropped them into a plastic zip lock bag and sealed it before placing it inside his own underpants, "oh by the way I thought I'd best return these" he said as from inside his pants he produced her white panties, the ones she'd worn last week, it was clear from the stains that someone had been enjoying them in her absence, "I was telling my mates about you, well I din't actually name you but I did say I was having a bit of fun with one of the staff, they were well keen to get their hands on your pants, I hand to keep them on me all week in case someone went into my pad and robbed them, anyway, I'm sure they'll enjoy the black ones, and besides, they're nice and fresh" he told her to put the soiled white panties back on, she did and they looked a real mess, she was glad nobody was going to see her in them.
She got herself dressed again and just when she thought it was over he handed her the chocolate bar, "best pop this back in, get used to it being there" she reluctantly raised her skirt, parted her legs and pulling the panties aside slipped it back inside her, as it disappeared she let go of the panties and they snapped back over her pussy, now there was no sign whatsoever of waht was inside her.
"get used to carrying that, you're going to meet me in here again next Tuesday, but on Monday night you'll go to the pub down the road at eight and meet a mate of mine, he'll know who you are, i told him black skirt, white blouse and pixie boots, he'll give you a package of the same size, relax its only a mobile phone, put it in straight away and bring it in for me on Tuesday, oh and any funny business and the governor might suddenly come into posetion of a pair of your panties, he'll know they're yours from your DNA, but they'll wonder who's the six other types are, still so long as they catch a slut who's been screwing cons i dont suppose which cons really matters does it" .
Sian spent the rest of the day walking around with the package inside her, she didnt actually feel uncomfortable and nobody noticed, the only scary moment came just before clocking off time when she needed a bowel movement, as she sat on the toilet and gave a push, she felt the package begin to emerge from its hiding place, she gently pushed it back inside, finished her toilet and headed for home.
As part of the security team I often got called in to meetings with the governor and that Monday morning was nothing out of the ordinary, or so i thought, I, along with two other members of staff, another male and two females, had been called in to discuss a security operation that was to take place the following morning, during the meeting i was handed a ziploc back and I opened it, tipping the contents onto the desk I discovered it was a pair of black ladies panties, but not just any pair, these were liberally coated in semen!
Monday came and dressed as instructed Sian made her way to the pub as she'd been told to, as she approched the bar a young man handed her a drink and whispered, "well I take it you're Sian the slut, glad to meet you". He gently steered her to a small dimly lit room just off the main room and they sat down, apart from them the room was empty, the man explained he'd got a package for her and he'd hand it over shortly, he wanted to be sure she was alone first, after several drinks he turned to her, "ok slut get that skirt up, lets do his". Sian gasped, "I'll do it in the loo if you dont mind" he shook his head, "oh no I have ot make sure you dont lose it, now come on, after all you're not usually shy about people seeing your cuntare you slut?"
Sian reluctantly slid her skirt up to her waist exposing her panties, pulled them aside and quickly slipped the package inside her, snapping them back into place she was about to pull her skirt down when he palced his hand on her crotch and began to rub, "been told to make you cum before you leave, so relax enjoy it" he told her, she just sat there hoping nobody walked in as he did what he did, he wasnt as experienced as Wilson and it took a good fifteen minutes before she felt a familiar feeling and her pants became wet. "there we go you enjoyed that didn't you slut? " he told her as though he was doing her a great favour, she finished her drink and went home.
The following daY i went into work early ready for the drugs operation, Sian got up, showered, got dressed and headed into work as usual, she went through the main gate and as she entered the building a couple of women staff approached her and asked her to accompany them upstairs, I watched from the window and even at that distance I could see the colour drain from her face. She was brought into the office where myself and one of my colleagues were waiting, the first thing she saw on entering was the panties on the table and she knew the game was up, she let out a gasp of shock and i told her we had reason to believe she was bringing something into the prison that she shouldnt be and she would be subjected to a search by the two women officers in a seperate room, I'd barely finished speaking when I heard a soft pattering sound, looking down I saw a a puddle forming beneath Sian, she was actually pissing herself and began to sob. I dont normally feel sorry for people caught smuggling but this case was different, she looked completely beaten. "it's ok, no need for a fuss" she replied between sobs and before anyone could stop her she pulled up her skirt, pulled her panties aside and ejected the package into her hand. "no point being shy about it now is there, not after what I've been through, and no doubt whats to come" she sniffled, "and all for a bloody mobile phone" I took the package from her, wiped it on a tissue and opened it, yes there was indeed a small mobile phone in there but wrapped around it was a plastic bag containing about £1000 of class A drugs.
Sian was arrested and soon after appeared in court charged with trafficking drugs and misconduct in a public office, she got eight years! As she was led down the steps of the court to be taken to prison i looked at her an attractive and naive young girl and wondered how many times during her sentence she'd be forced to take down her underwear to pleasure some big butch female prisoner, I shuddered at the thought
THE END
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