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Shopping Trip

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2002-12-31

She had never intended to start shop-lifting, but had just drifted into it by accident. Several weeks ago she had been shopping in this very store when, upset and confused, she had wandered out without paying. She had turned to go back in, but after seeing that no-one had noticed she kept the few tins of food she had walked out with. Desperate to keep things together Jenny had started to visit the store on a regular basis, and each time had found that she had been able to walk out with a few stolen items. This had now become her main way of feeding herself and Toby. She still paid for items each visit, but the expensive items would always go out in her bag. The items she did not want herself would be sold amongst her friends. The panties were for a friend who wanted to surprise her husband on his birthday next week. As she stepped outside the store she breathed her customary sigh of relief and turned towards the bus-stop. It was then that she felt a hand on her shoulder. “Excuse me Miss, I wondered if you can step back into the store for a moment?” said the security guard. “W…what appears to be the problem?” Jenny asked, trying to mask her surprise. “There’s no problem, but I need to look at your bag”. “Shall we step inside so as not to make a scene?” the guard asked. Jenny nodded and allowed herself to be escorted to the security office. The security office was a small dreary room, big enough for 3 people at most.

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   A grey metal desk sat in one corner, the coffee stains and overfilled ashtray served as mute testimony to the boredom filled hours spent behind it. Opposite the desk was a narrow table stacked with various VCR’s and monitors, each monitor showing a different perspective of the store. The guard beckoned for her to take a seat in front of the desk, he then took her bag and began to carefully remove the contents. Jenny watched with trepidation as the guard removed items from her bag, she knew he would find the pilfered items and then she would have to face going to court. The thought of prison filled Jenny with fear, she would lose everything and Toby would be taken into foster care. Tears stung her eyes, as her imagination showed her terrible visions of prison life. When the guard had finished cataloguing the items he sat down at his desk facing Jenny. He was tall, possibly 6’1”, middle-aged, with a kindly face and receding brown hair. “It seems you have several items that aren’t on the receipt Miss”, he said, “You do know that this store always prosecutes thieves?”Jenny could hold back the tears no longer. “I can’t go to Jail”, she wailed. The guard seemed surprised by this reaction. “There, there, miss, I didn’t mean to upset you. ”He walked around the desk and placed a reassuring arm across her shoulders. “Look my name is George, what’s yours?” he enquired. “Jenny” she blurted out.

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   “Ok Jenny you dry those tears and I will make us a nice cup of tea”While they sat and sipped the tea Jenny poured her heart out. She explained about Matt leaving and her money worries. George listened in silence offering reassuring comments here and there. Finally, when she had finished, George sighed and rubbed the bridge of his nose. “Look Jenny, I have kids myself and I know times are hard, but stealing is still a crime” “I know” Said Jenny. “What will happen to me?”George sat in quiet contemplation for a moment, and then advised her of his decision. “I have a child myself Jenny and I wouldn’t like to leave him in foster care, I also know how hard finding money can be”. “The stuff you have taken isn’t worth much so I am prepared to forget all about it if you will do me a little favour”. “What sort of favour?” Jenny enquired dubiously. “I have a new guard starting tonight, He’s young and inexperienced, and I am concerned about leaving him to guard the store”. “I want you to stay here until closing time and help me show this new guard the various ways to steal things, then let him role-play interrogating you”. “Okay”, said Jenny with relief “I can do that”. The shop was due to close in an hour so Jenny and George sat and chatted about raising their mutual children while they waited for the new recruit. The new guard was introduced as Chris, a seventeen year-old whom nature had not been kind to. He was tall and skinny, with lank hair and full moon glasses, and spots of acne dotted his face.

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   He was every inch the stereotypical Nerd. Somehow Jenny could not see anyone being intimidated by him. They spent the next hour in the store, Jenny taking items while George advised Chris of the various things to watch for. Once this was done they went to the office and Chris tried his hardest to interview her. Jenny spent the whole interview trying to stifle a laugh. Once the interview was concluded George advised Jenny that Chris would now pat her down for stolen goods. She did not relish the idea of being touched by Chris but a deal was a deal. “Please stand up and stand facing the far wall Miss” said Chris with a nervous tremble in his voice. Jenny gave him an amused smile but did as requested. Chris stood behind her and began to pat her down, once he was satisfied he asked her to turn around and place her hands on her head. Jenny once again complied. Chris then ran his hands quickly over her legs and stomach, as he reached her breasts though he cupped them and gave them a slight squeeze. Jenny glared at him but chose not to say anything, as she did not want to blow this deal. “Could you remove your trainers and socks and place them on the table. ” Chris instructed.

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   “Why?” asked Jenny. “Chris needs to do a standard search Jenny, therefore he will need to inspect your outer clothing for hidden pockets”, said George. “It’s all part of our standard procedure”. Jenny wanted to object, she did not want to remove her outer clothes, but somehow her protest died when she thought of undergoing the same routine in prison. Once she had removed her trainers and socks she placed them on the table and watched as Chris checked her trainers out. “Now remove your jeans”, instructed Chris. Hands shaking Jenny took off her jeans, grateful that her T-shirt was long enough to cover her. Chris examined the jeans and carefully placed them with her trainers. “Now hand me your T-shirt please”. Shocked that she could be expected to strip down to her underwear Jenny glanced towards George, but he merely nodded to confirm that she should do so. Jenny gripped the hem of her t-shirt and lifted it over her head. She was glad that she had worn sensible white underwear today, the cups of her bra were trimmed with lace, but did not reveal anything, and she had on her plain white knickers. Not lingerie by any stretch of the imagination. Jenny stood in her underwear, her cheeks burning with embarrassment. She was overweight and felt very conscious of the way her soft, plump flesh made slight folds around the elastic on her panties.

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  “Please turn towards around and place your hands against the wall”, Chris instructed her. “Then place your feet at shoulder width apart”. Once Jenny had done so Chris placed both hands on her left ankle and slowly ran them up to her buttock, he then repeated this motion with the right leg. Then he ran his hands from her shoulders down to her hips. Jenny held her breath as Chris placed the flats of his hands on her ample buttocks and began to massage them. “Now turn to face me with your legs still apart, then place your hands on your head”, he ordered with growing confidence. Jenny did not like this new confident tone in his voice and her stomach began to knot with worry. She complied with his instruction and stood, feeling very vulnerable, as Chris looked her slowly up and down. She certainly didn’t like the look of open longing that was on Chris’ face. Again Chris ran his hands over each leg. Jenny saw the amused look in his eyes as he stood in front of her; unable to meet his gaze she turned her head to one side. Jenny was forced to stifle a gasp of horror as Chris placed his right hand on her stomach, and with deliberate slowness, slid it down between her legs. This would be over soon she told herself, as Chris began to knead the soft flesh around her pussy. Growing visibly more daring Chris placed his hands on her breasts and began to squeeze them. Jenny glanced to George.

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   Surely he would stop this; but George just made notes on his pad. Chris slid the straps to her bra from off her shoulders. Then, looking her directly in the eye, he ran his fingertips slowly down from her throat and over the smooth skin of her breasts until his fingertips were pulling on the lace edge of her bra cups. Chris then slid his fingers into the cups and pulled them forward. Unable to stand this anymore Jenny slapped his hands away. “I think we can safely say that I have nothing else on me” she snapped at him. She was embarrassed enough already and there was no way this creep was having a look at her nipples. Jenny folded her arms across her bust in a gesture of defiance. Being felt up had made her skin crawl, but she had accepted it because of the trouble she was in. Jenny had a phobia of Imprisonment that had allowed her to put up with that humiliation of stripping to her undies, but enough was enough. Taken aback by her response Chris turned to George, a questioning look in his eye. “Are you satisfied that she has nothing more hidden on her?” asked George. “Not really, she could still have small valuable items on her” Chris argued. “Very well, continue with your search” agreed George. “I think not” said Jenny with an edge in her voice.

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   “I agreed to let you search me not cop a cheap feel”. George stared at her and with a sigh he put down his pen. “Look Jenny I am trying to help you because I feel sorry for you, but you have to understand that this is standard procedure and you must comply”. “Now shall we call the deal off, or will you allow Chris to continue to search you?”“I didn’t agree to being felt up, and I don’t want to have my bra pulled forward” Jenny protested. “I know I made a mistake but I have to draw a line”. Without saying a word George walked over to the VCR and pressed the play button. Jenny watched in horror as image after image of her stealing flashed on screen. They must have had her on camera every time she had stolen from this store. “I think you will agree that I have enough evidence on tape to see you go to prison for a good few years Jenny”. Unable to speak Jenny just slowly nodded her head. Her phobia of prison was overwhelming her now. For all her bravado Jenny could not stand the thought of incarceration and, worst of all, George obviously knew it. “Now I know you aren’t happy with what’s happening, but either you co-operate or I phone the Police”. “Do you agree to follow Chris’ instructions without further difficulty?” George asked. Again Jenny found she could only nod“We have very strict search rules here which you agreed to help Chris learn, and I expect you to honour that agreement regardless of what you are asked to do”.

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   “Understand that you are a thief and if you want to stay a free thief then you will obey every order without question, do you understand?”The full realisation of her situation was beginning to dawn on Jenny. Deep down she wanted to refuse but Jenny was so terrified of prison that she knew that she would do anything that she was asked to do. Ashamed of her cowardice she could only nod again. “Continue with your search” George ordered Chris. Chris motioned for Jenny to place her hands on her head, once this was done he pulled the cups of her bra forward and stared at her dark-pink nipples. With a snap he released her bra cups and tool a step back. “Remove your bra” ordered Chris. Hands shaking Jenny unhooked the back of her bra, but held it close to her breasts, her heart pounding with fear. Ok, she thought to herself, let him see you topless than they will let you go home. Slowly she moved her arms to her sides, now unsupported the bra fall to the floor. No longer hindered by the undersize bra, Jenny’s huge breasts fell forward, her nipples stiffening in the cold air. “Hands on your head” barked Chris. Once she had placed her hands on her head Chris cupped her breasts in his hands, and began to squeeze and stroke them. He then gripped her nipples between thumb and forefingers and pulled them painfully towards him. Jenny could not help but gasp in pain.

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  “Now place you hands behind your back and bend forward from the waist”Clasping her hands behind her back Jenny leaned forward until her beasts were hanging free. “Now I want you to gently rock your shoulders, keeping your hands firmly behind your back”. As Jenny began to rock her shoulders side to side her full breasts began to swing from side-to-side. Without warning Chris painfully slapped her breast causing them to swing faster. Jenny cried out in pain and stood bolt upright. A vivid red handprint began to form on her right breast. “Bend back over!” snapped ChrisOnce Jenny had bent over Chris began to repeatedly slap her breasts, until the pain made them go numb. Tears fell from Jenny’s eyes onto the floor and she sobbed in pain. “Sorry didn’t mean to hurt you”, said Chris “let me kiss them better”. Before Jenny could object Chris had lifted up her right tit and was sucking on her nipple. Suddenly Chris bit down on her nipple; startled by the pain she almost didn’t feel Chris slide his hand into the back of her panties. As he moved his mouth to her other nipple he began to stroke her buttocks. From Chris’s breathing and increasingly passionate groping she knew he was getting aroused. Struggling to control her mounting fear, Jenny tried to think of how she could get out of this situation. She did not want to be raped, especially by this ugly, greasy teenager, but if she upset him then it was prison for her.

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  She glanced across to George but she could see that he was not going to stop her being violated. The only way she could see to get out of this was to degrade herself a little for Chris, in the hope of avoiding a raping. “Do you like my tits?” asked Jenny. Chris looked at her surprised and took his mouth away from her breast, a strand of saliva extending from his lower lip to her nipple. “Oh yes”, said Chris “they are the best tits I have ever seen”. “It’s getting late now, and I really need to get going”, said Jenny “why don’t we forget the rest of the search, and I will do a little something for you”. Chris seemed confused and looked to George for help. George just shrugged. “What would you do for me?” he asked with a nervous edge in his voice again. Jenny flashed him what she hoped was a seductive smile and slowly knelt down in front of him. She paused for a second while she steeled herself for the degradation she was about to put herself through. Then with hands trembling she undid his trousers and pulled them down. Chris was already erect against the material of his shorts, gently she eased them down to reveal his stiff cock. It seemed Chris didn’t wash this area of his body either. She was revolted by the smell of stale urine and semen, but she had committed herself now.

 

   Jenny eased herself forward and placed his cock between her breasts, gripping each one she began to move them up and down, massaging his stiff member. As she stroked his cock with the soft flesh of her tits Chris placed a hand on her head and ran his finger through her hair. Chris began to breathe faster, his moans showing he was about to cum. Jenny started to use her tits with more speed now. A few more seconds and then done she thought, it was then that she felt Chris place his hand on her head and begin to push her down. “Suck me off” he moaned. Jenny was horrified at the thought, she wanted to refuse but her fear over-ruled her. Jenny struggled for a moment but realised that she simply had no alternative. Afraid of the consequences of upsetting Chris she knew that she would have to make this a good blow job if she wanted to get out of here. She released her breasts and let Chris force her mouth onto his unwashed cock. Resigned to her fate Jenny wrapped her right hand around the shaft of his cock and began to stroke it. She began to quickly flick the tip of her tongue over his swollen head, her hand working his shaft faster and faster. As Chris began to moan she took him fully into her mouth, with her free hand she held his balls and began to roll and squeeze them while she slid her mouth up and down his cock. With her one hand and mouth working his cock, and her other hand on his balls it wasn’t long before Chris came in her mouth. She gagged as the first spurt of cum hit the back of her throat and pulled away, this allowed the remaining jets of cum to shoot over her face and exposed throat.

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   Chris took his cock in hand and shook it, splattering drops of cum over her tits. “Swallow it, bitch!” he sneered at her. Looking him in the eye Jenny let a trail of cum dribble from the corner of her mouth. Then with what she hoped passed for a satisfied sigh, she swallowed the rest. After Chris had taken a moment to recover, he pulled his trousers back up. “That was fantastic Jenny” he gasped. “The best blowjob I have ever had”. The only blowjob he has ever had, thought Jenny to herself. “Now if we can continue with the inspection” he said with an evil grin. “Please stand up and face the wall”. “But I. . . I. .

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  . thought…” stammered Jenny“You offered to reward me if I finished the inspection, I never agreed I would” laughed Chris. “Now stand facing the wall”. Jenny started to sob, she had humiliated and degraded herself, and yet she was still in danger. Still crying, she wiped the semen from her face and stood facing the wall. “Take off your panties” Chris sneered. “Please” begged Jenny “I have been good to you”. “Take your panties off NOW!” shouted Chris. Jenny stood sobbing for a moment, the tears running down her breasts and mingling with the semen sprayed over them. Her hands were shaking with fear now and it was all she could do to grip the sides of her panties. Knowing that each moment of hesitation could only make things worse she lowered her panties to the floor and stepped out of them. “Place your hands against the wall and spread your legs”. Jenny did as she was ordered. Chris stared at her full, plump buttocks and milky white thighs with open lust. Chris stood behind her and placed a hand on each buttock, he them began to painfully squeeze them, digging his nails into the soft flesh.

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   Chris then slid his hand between her buttocks and with his middle finger began to trace circles around her anus. He then eased the tip of his finger into her back passage. “Nice loose arsehole you have Jenny”Suddenly he pulled his finger from her anus and brought the flat of his hand against her right buttock in a vicious slap. Jenny screamed in pain as Chris brought slap after stinging slap down on her exposed buttocks. “Loose enough to hide something in Jenny?” Chris said with a threatening tone in his voice. “Got anything shoved up there?”“No”, whined Jenny “please believe me”“Very well, turn around, stand with your legs apart, and place your hands on your head” ordered Chris. Glad to have his hands off her anus Jenny did so. Chris licked his lips as he looked at her pussy. Jenny had not bothered shaving since Matt left and had allowed her naturally blonde bush to grow unchecked. Chris began to run his fingers through her bush, giving an occasional tug on her pubes. Then he moved his hand between her legs and began to run his middle finger over the lips of her pussy. “Not even moist Jenny?” “I am disappointed”“I want you to walk over to the desk and stand facing it Jenny” said Chris with an almost friendly tone. Jenny stumbled over to the desk and stood in front of it, the cold metal pressing against her thighs. She had heard the friendly tone in Chris’ voice and a glimmer of hope entered her thinking. Perhaps he was done now and would let her go.

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  “Spread your feet to shoulder width and then bend over the desk with your hands on your buttocks. ” Instructed ChrisThe cold desk made her shiver as she lay across it, her feet could not quite touch the floor while lying on the desk but she spread her feet apart as ordered. She placed her hands on her buttocks and awaited her next order. “I think an anal inspection will be needed Jenny” said Chris. “Please let me go” begged Jenny, “I have been good”“You are here because you are a thief Jenny and that hardly qualifies you as good”. “Just do as I say and it will be over quickly”“Use your hands to spread your buttocks nice and wide, so that I can search your anus,” ordered Chris. Hands still trembling, Jenny pulled her ample buttocks apart so that Chris could see her anal passage. Jenny felt cold lubricant being spread on her anus; she braced herself for the inevitable pain. Matt had loved anal and this had loosened her back passage but she had always hated being penetrated anally. It came as some surprise as to find how gently Chris slid his index finger into her. Chris began to probe with his finger, after a few moments he pushed in his middle finger as well. Jenny groaned as her anus was stretched out by both fingers, but she was still in no pain and began to relax, hoping for the ordeal to end soon. Then Chris added another finger, this was stretching her to limit and she moaned in pain. Jenny sighed with relief as Chris withdrew his fingers. She ran a hand through her hair and began to lift herself off the desk.

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   Without warning she felt a sudden, sharp pain in her anus as Chris rammed his cock into her. In pain she tried to stand, but Chris placed his hands on her back and used his weight to pin her down. “Please stop, don’t make me do this” she wailed. In response Chris drove his crotch against her forcing his cock deep into her. Jenny could only scream as Chris began to slowly pump his cock in and out of her tightly stretched arse. “You know Jenny, I love fucking a plump woman up the arse. ” “ I love the feel of your fat buttocks rippling as I slam my cock in”As if to illustrate this Chris began to ram into her faster and faster, each thrust sending waves through her plump buttocks and thighs. Her screams of pain only seemed to fuel his desire and he began to fuck her arse harder and harder. Then with a moan he withdrew and shot his load over her buttocks. Jenny lay sobbing on the desk, her anus sore from the pounding. “Don’t just lie there” said Chris. “Reach behind you and rub my cum into your buttocks, I don’t want a drop wasted”. As Jenny behind to massage the warm semen into the skin of her buttocks Chris gave her a playful spank. “That’s a good girl, keep those buttocks moisturised. ”Chris walked over to his chair and sat down.

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   “Well Jenny I think we can safely say you have nothing on you. ” “Thank you for helping with my training. ”Tears streaming down her cheeks Jenny painfully stood up and began to gather her clothes. Jenny felt mixed emotions, she was glad that the ordeal had ended, but she felt betrayed by George who she had thought was a nice man. It was as she pulled back on her panties that she heard George utter the words that confirmed exactly where she stood in his eyes. “Sorry to criticise Chris, but you have just brought a member of the public in, humiliated her, stripped her and yet found no stolen goods on her, isn’t there something you are forgetting?”“Err” Chris mumbled “should I apologise?”“No!” snapped George. You forgot to fuck her cunt”“Nooooo!” screamed Jenny. “Please don’t rape me; I will do anything else you want”. “Jenny, Chris is going to fuck your cunt, and then you are still going to do anything we want” laughed George. “As long as we have you on tape you are our personal whore”. In desperation Jenny made a break for the door, the fact that she would have to run out of the store in panties and ankle socks was the furthest from her mind. With a feeling of relief she grabbed the door handle and turned it. All her hopes fled , it was locked!Sobbing in terror Jenny stood pressed against the door for what seemed an eternity, the smoked glass of the door cold against her bare breasts. Then she felt excruciating pain as Chris grabbed a handful of her hair and forced her to stand on tip-toe. Using her hair to guide her, Chris turned Jenny around and then pushed her violently from behind.

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   Jenny staggered forward then her loosing her balance she fell onto the floor. Jenny landed heavily on her side and rolled onto her back. The impact had stunned her and for a few seconds she lay on the floor arms and legs spread out wide, these few seconds were all Chris needed to mount her. Chris lay along the length of her body in a gross parody of the missionary position, his abdomen pressed hard against hers preventing her from closing her thighs. Chris grabbed Jenny’s wrists and, in spite of her efforts to resist, he managed to lash them together using a belt. “Don’t do this please” Jenny sobbed, “you can cum in my mouth again if you let me up”. “Understand this” said Chris, “you are so afraid of prison that you will do whatever we want”. “Don’t think tonight is the end either Jenny, you will be phoned periodically and told to come in to help with training, and you know the funniest thing?” “You are such a coward that you will come here every time”. Chris used his left hand to pin her bound wrists above her head; with his right he reached down and grabbed hold of her panties. He began to tug violently at her panties, each pull causing the panties to tear until with one long ripping sound Chris tore them off her body. “Now I think we have heard enough from you”, said Chris. Jenny gagged as Chris forced the ruined panties into her mouth. “That should stop you complaining while we fuck”. Chris placed his hands either side if her head and used them to support his wait. He then pushed his abdomen against hers.

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   Jenny felt the head of Chris’s cock move slowly between her pussy lips, then with a wet sucking sound Chris slid his full length into her. Jenny wanted to struggle but was paralyzed with fear; she could not even bring herself to open her eyes. She could only lie there as Chris began to roughly pound his cock into her, each thrust giving out a wet slap as his groin met her soft, damp crotch. After several minutes Chris hooked his arms around her legs and used his body weight to force her legs back against her body. Her abdomen was raised up at an angle and Chris used this position to thrust into her cunt with increasing force. Then with shudder Chris shot his warm, sticky cum into her pussy. After a moment he stood and ran his fingers through his hair. “Enjoy being fucked Jenny?” Jenny could only lie there, her legs still wide open, the air cold against her damp pussy. Chris then removed the panties from Jenny’s mouth and helped her to her knees. She rested her bound hands in her lap. “I am afraid I don’t have any cum left to take up your kind offer of another blowjob, but I am going to let you lick all of your cunt juices off my crotch” Chris said as he pressed his dick against her face. Her spirit broken, Jenny sucked and licked Chris’ cock and balls. Once he was satisfied she had got every drop Chris gathered his clothes and began to dress. “Very good Jenny, said George. “As Chris informed you I will be calling you from time to time and asking you to help with more training”.

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   “If you ever refuse or turn up late, that tape goes to the police, understand?”“I understand” said Jenny hoarsely. “Can I go now?”Without answering George began to remove his clothes. “What are you doing?” sobbed Jenny. “Haven’t I suffered enough?”“Chris is a trainee Jenny; I have to search you now to make sure he didn’t miss anything”. “Now what shall we search first, mouth, arse, or cunt?”Jenny began to scream but was forced to stop when George rammed his cock into her open mouth. “Chris was far too gentle with you” George said as he began to fuck her mouth. “Now you will see how a stinking, rotten thief really gets raped”. It would be a very long, painful night for Jenny. END.

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