Note: This story was dynamically reformatted for online reading convenience. Welcome to the world of Little Girl Discipline; a world where adults enjoy strictly disciplining little girls' bare bottoms (and other places). I do hope you enjoy this story. I am always looking for inspiration so please email me at and share your experiences / thoughts. --------------------------------------------------------------------------- ---- BATTLE OF THE BABYSITTERS (Ff/gg, NC, spanking, ped, enema) CHAPTER 1 - A visit to the Orphanage The State Girls Babysitting Championships were fast approaching. In towns up and down the length of the State girls, generally in their late teens, practiced their babysitting skills in readiness for the great event. Winning, or even being a runner up, guaranteed a college place and sponsorship from one of the School Boards. Many School Principles, Heads of Orphanages, Directors of Education and the like were ex babysitting champions. The most important thing to the state was to have the people responsible for its children skilled in and dedicated to the severe punishment of any child that stepped out of line. Even small towns had their own orphanages, although these weren't really for orphans anymore. Instead, they were secure places where children who misbehaved were sent to be taught a severe lesson until their behaviour improved. Such was the social disgrace of having a child placed in an Orphanage that parents who lacked the disciplinary skills themselves were happy to pay babysitters to come and do the job for them. Championship babysitters were in high demand and could charge $200 - $300 for an evening's work. Sixteen year old Amy Jefferson and seventeen year old Mary Jennings were both front runners for this year's championships. They both lived in the same large industrial town and both had been allocated State Coaches to help them develop their babysitting skills. Babysitting coaches were always a male and female couple and almost always the female was an ex babysitting champion herself. To help out with this process the State made available to licensed coaches, and other privileged citizens, young girls from the local orphanages. These girls, so called `punishment girls', were generally between the ages of eight and twelve and were made available for the explicit purpose of strict disciplinary sessions. Both Amy and Mary were born babysitters. The moment they saw a bratty little girl they itched to have her panties down and her bottom burning like a furnace. At the very thought their fresh teen pussies would tingle and become wet and slippery. From the State's point of view this was excellent news and the sexual arousal and pleasure of babysitters was not only nurtured, but was part of the competition itself. Mary's state allocated coaches were Steven and Alison. At 35 and 33 respectively they had almost ten year's successful coaching behind them. In the last five years they had achieved one outright winner and four runners up. They were generally acknowledged to be amongst the State's top coaches. Like most coaches they held down professional jobs during the day and dedicated their spare time to coaching. Amy's coaches were Jason and Sarah. At 28 and 27 respectively they were just starting to be recognised as good coaches. In the five years they had been coaching all their girls had appeared in the top five. It was the general consensus that they were getting better and it was only a matter of time until they had a champion or runner up. The main time for training sessions across the State was Friday night. This coincided with when the Orphanages signed girls out for punishment. Training sessions focussed on the main categories judged at the championships: bathtime, personal care, freestyle punishment and pleasing the parents. `Bathtime' was where the babysitter got the chance to prepare their young charges for the punishment to come. Points were awarded for humiliation, fear and increasing the sensitivity of the skin. `Personal care' could take a number of forms but was focussed on the little pussies and bottom holes of their charges. Points were awarded for humiliation, fear and discomfort. `Freestyle punishment' was the opportunity for the teen girls to express their individuality through severe punishment of their charges. Points were awarded for style, innovation, level of pain induced and control exhibited over the young girl. `Pleasing the parents' was the final category where the babysitter could demonstrate to the judges how sexually excited she had been by administering the punishments. Usually the babysitter chose the male as a partner for this. Occasionally they chose the female and this was also perfectly acceptable to the judges. Official babysitting coaches were entitled to State aid to modify their homes for training. The set up was usually the same; a child's bedroom, with various punishment equipment, separated from an adult's bedroom by a large ceiling-to-floor two way mirror. There was sound and vision monitoring equipment in the lounge, bathroom and garden. Radio headsets were provided to allow the babysitter and coaches to communicate during the sessions. Alison and Sarah both had the first job of the night. They had to pick up the `punishment girls' from the orphanage. Alison had booked two girls for the night; if Mary could control both of them they might go for a combination at the finals. This would attract additional points. Sarah had booked one girl for the night. In Jason's and her view it best to keep thing simple. That way less could go wrong on the night. Amy was very inventive and Sarah was confident that would get extra points. Alison arrived at the Orphanage and was shown to the waiting room. There were a number of ladies already waiting there, amongst them Sarah. Alison recognised the competing trainer and nodded politely. Sarah nodded back acknowledging her. While they were both fierce competitors they held each other in professional regard. Alison drank in the sight and smells of the Orphanage. It was light, stark and barren; no home comforts here. The air smelt of disinfectant. Life for the young girls in its halls was unpleasant, unfair and frequently painful. If a girl was `adopted' then things had to be pretty bad at their new home for it to be worse than here. It was an open secret that girls would willingly accept sex from their new adoptive `Daddy' rather than return. Why, only last week she had sat next to Mr. Montegue at church and his newly adopted young `daughter' Charlene. The poor ten year old couldn't sit still on the pew; a result, Mr. Montegue claimed, of an early morning bare bottom whipping. In Alison's view, judging from the girl's movements, it had more to do with Mr. Montegue making good use of his new little `daughter's' holes. Alison suspected that as Mr. Montegue had been single for the past five years poor Charlene was getting little rest. An official came to collect the ladies from the waiting room. Alison's pussy started to tingle. The route to the collection point took them past the Orphanage's punishment suite. It was rarely unoccupied and the Orphanage staff were masters at their art. As they approached the suite the unmistakable sounds of little girl shrieks and howls began to echo down the corridor. Alison's pussy gave a hard throb. As the double doors were opened a cacophony of punishment sounds assaulted their ears. All five rooms in the suite were occupied. Each door had a one foot square two way mirror allowing those outside to see in. The procession of ladies stopped for a moment as they took a good look at the punishments in progress. In the first room a lady in her late fifties with her white hair tied back in a bun had a little blond girl of about ten years old over her knee. She was spanking her vigorously with a huge paddle, almost the size of the girl's bottom. The little girl was screaming blue murder and her legs kicked furiously with the pain. The viewers were treated to a clear view of her young pussy. Her bottom had already turned a deep red and laid out on the table was big shiny black leather strap. Clearly this little girl was going to be sleeping on her tummy tonight. In the second room a completely naked dark haired girl of about eleven bent over touching her toes. A svelte woman of about thirty had a long whippy cane in her hand. The girl's bottom was a mass of scarlet wheals and her howling made Alison's pussy throb. Standing naked in the corner of the room with her hands on her head stood a weeping girl of about nine. She was waiting her turn for a bare naked cane whipping. The way her big friend squealed as the cane bit into her cheeks left her in no doubt as to how much this was going to hurt. In the third room a brown haired girl of about ten was lying on a bed with her legs spread wide. It appeared her punishment was over and her little bottom and the backs of her thighs were in a real state. The whole area was vivid dark red, badly swollen and crisscrossed with painful raised lines. The cause was plain to see; a thick wooden paddle and wicked thin switch lay on the table. The girl was wailing and moaning as a pretty young nurse callously pinched and mauled the girl's bottom cheeks on the pretext of applying antiseptic cream. In the fourth room a very cute little girl of about nine was being undressed by a smartly dressed young lady in her mid twenties. There was a twinkle in the lady's eyes as she pulled the clothes off the weeping girl. The girl pouted miserably and her eyes constantly flitted to where a sturdy hairbrush and long thin cane were waiting to be used on her bottom. The awful wailing and squealing from the other rooms made her cry even more. In the fifth room there were two women in their early forties. They were smiling and laughing. Between them, bent over a chair and tied down was a naked girl of about twelve. She was just on the edge of puberty with a full bottom, small budding breasts and a little fringe at the top of her pussy. She was shrieking in agony as the two women both whipped away at her horribly welted bottom with long thick switches. On the table stood a large inflatable butt plug and tube of lubrication gel. Those two ladies were going to make that little brat suffer tonight. The official herded the ladies on to where the `punishment girls' were waiting for them. As they arrived at the room a line of young girls stood to attention; backs straight and arms stiff by their sides. All were dressed in their outside uniforms of pale blue gingham check summer dresses and white knee socks. The dresses had short puffy sleeves and their hems stopped just above the girls' crotches. Each girl was wearing a little g-string that barely covered their small pussies and left their bottom cheeks entirely bare. The ladies were called out one by one to be introduced to their girls and informed of their crimes. Alison was called first. "Alison Peters! This is Kelly, she's ten. And this is Jennifer, she's nine. Kelly has been very naughty this week. She did not do as she was told to on two separate occasions. Maybe you can teach her to listen. Jennifer is new with us. Her first week has been very poor. Her attention and grades are very bad. Maybe you can get her to smarten up her thinking!" the official said. Alison was delighted. The two were absolutely adorable; cute and frightened as little kittens taken from their mum. Kelly was a tall thin dark haired girl with pale skin. Jennifer was shorter with an impish face, brown hair and a little bottom that jutted out just asking for hard punishment. It was such a bonus getting a new girl as well; her little bum would still be fresh and sensitive. Alison knew Mary would have real fun with this one. She signed the two papers the official offered her. Sarah was called next. "Sarah Rollings! This is Jessica, she's eleven. Jessica has been caught masturbating." the official said. There was a collective gasp from the ladies and Jessica flushed a deep red. "I recommend a very very severe punishment for Jessica." the official observed. Jessica bit her lip, the tears pressing just behind her eyes. She had a pretty face and her brown hair had been tied up into cute bunches. Her body showed signs of developing early; maybe that was why that thing between her legs seemed to have that funny itch and wanted to be rubbed all the time. Sarah couldn't believe her luck; just wait till she told Amy. With her notorious imagination Amy was bound to come up with some really unpleasant ways to teach Jessica not to play between her legs. Sarah's pussy throbbed joyfully at the thought. She signed the paper that the official held out for her. The ladies walked back to the main door. As they approached the punishment suite they heard the unmistakeable sound of a thin whippy flexible cane coming into high speed contact with cringing little girl bottom cheeks. This was inevitably followed by an ear splitting scream as the bottom's owner told the world how much that wicked cane hurt. When they reached the suite they could see that only one of the rooms was now occupied. It was room four where they had seen the little nine year old being stripped off ready for the hairbrush and cane. Through the two way mirror they could see that the little girl had been bent over the foot of the bed and her hands secured with leather cuffs. The girl's bum and thighs had been blistered by the hairbrush and heavily marked by the cane. Her voice was hoarse with howling but each time the cane whipped around her cheeks she found new voice and squealed like a branded pig. The smartly dressed young lady who wielded the cane was flushed red and her hips kept giving involuntary wriggles. The other ladies knew that feeling well. Alison knelt down between her two girls and put an arm round each of their shoulders. "You see that cane?" she said, looking at up at the one being used so effectively. The girls nodded miserably. "Well, the girl who is going to baby-sit you tonight has got a much bigger one than that!" she gloated. Alison felt Jennifer's little shoulders start to tremble as the girl began to cry quiet little sobs. "Oh no darling! Don't cry!" Alison comforted, "My babysitter wants to hurt you first before you do that." Jennifer's quiet sobs became louder as Alison lead the girls out to the car. CHAPTER 2 - Mary babysits Kelly and Jennifer Alison arrived home and ushered the two little girls in. Mary was waiting in the lounge. The seventeen year old was dressed in tight jeans and a small T shirt that showed off her big young breasts nicely. Alison spoke to the girls. "Kelly and Jennifer, this is Mary. I've got to go out so she's going to babysit you. Now, because you were naughty this week, I've had to give Mary full punishment rights so she can take care of you. Say hello to Mary please girls." The girls regarded the muscular teen with fear. They both managed to splutter out their hellos. Alison left the lounge and then she opened and closed the front door. To the girls it would sound like she had left. She sneaked back into her bedroom. Steve was waiting for her. He was lying on the bed naked and his big cock was hard and ready. Alison was horny as hell after her trip to the Orphanage and she tore her clothes off. She was wearing red lacy underwear and the panties were soaked through. She dragged them off and bent over. Steve came up behind her and she felt his cock stretching and filling her pussy. He stayed still and let her wriggle herself up and down his shaft. It felt great, she was so wet and desperate to get herself off. Within a few minutes she climaxed hard and then slipped off him. They put their radio headsets on and settled down to begin the coaching session. Mary knelt between the two girls and put an arm around each of them hugging them close. "Well, Kelly and Jennifer," she said, "I hope that you're going to be good for me tonight. I do like looking after little girls." Mary started to play with their exposed little bottoms, slipping her fingers inside the G-strings and down their cracks. "I hear that you've both been very naughty!" she whispered, "Your bottoms both feel lovely and soft. I'm going to have to hurt them both really badly before you go to bed!" Kelly was crying harder than Jennifer now. "Oh please Mary! Please don't! Don't hurt me like the other babysitter!" Kelly begged. "What other babysitter?" asked Mary. "It was last year." sobbed Kelly, "She hurt me so much! Please Mary! Don't hurt me like she did!" "Oh, you silly goose!" giggled Mary, "Of course I'm going to hurt you more than she did! Why, I've got the biggest hairbrush and longest cane you've ever seen. I'm going to hurt your little bottom worse than it has ever been hurt before. And your little friend's bottom too. What do you think of that Kelly?" "Boo hoo! Boo hoo! Please Mary! Don't hurt my bummy! I'll be really good for you! I promise!" the little girl sobbed. "I do hope so!" smiled Mary, "Now let's go and give you two a bath. I want your bottoms to be nice and clean for when I punish them!" Mary took the sobbing girls to the bathroom. She turned on the hot water and started to strip the girls off. Alison and Steve had a good view of the action from a camera mounted behind the bathroom mirror. Mary stripped an unresisting Kelly naked first. Her pale skin was going to mark up really well and now her clothes were off you could see that her bum was quite wide and her pussy very pronounced. Jennifer resisted Mary's efforts to undress her. Mary heard Alison on her headset. "Smack her across the face." Mary's smacked the left cheek of Jennifer's face leaving a red handprint. The little girl began wailing but offered no more resistance as Mary stripped her. When she was in the nude little Jennifer's bum could be seen in all its glory. Seemingly out of proportion to the impish nine year old its large rounded shape would guarantee its little owner a very painful evening as Mary got to work. Mary turned the tap off and tested the water. "OK girls, you can get in now." she said. Both girls got in but began to complain almost immediately. "It's too hot!" wailed Kelly as she stamped her feet in the water. "It's hurting me!" Jennifer shouted as she tried to get out. Mary grabbed both the girls and forced them down into a sitting position. Then she grabbed a sponge and began to wash the girls with the hot water. The girls thrashed around crying and shouting as she washed them. "Yahhhhhhhh! Boo hoo! It's too hot! Let me out! Please!" sobbed Kelly. "Eeeeeeeee! It's burning me! I wanna get out! Please Mary! I'll be good!" yelled Jennifer. "Right, both of you stand up." said Mary. The two girls jumped up wriggling their bodies and fanning their hot skin. Alison felt Steve's cock slip back into her wet pussy. This time he needed it. "Like two little lobsters." he breathed into her ear. Alison began slowly moving her bum sliding her pussy over Steve's cock. Mary reached up onto a shelf and took a plastic nailbrush. It had a handle on the back and stiff nylon bristles. Mary rubbed the bristles onto a bar of soap. "Kelly, come here! I want to make sure you're good and clean." Mary said. Kelly could see the brush in Mary's hand and she knew what it meant. "Please! Please!" she sobbed, "Don't! Please!" "Hands on head and legs apart." said Mary. The sobbing girl falteringly put her hands up on her head and shuffled her feet apart. "Further apart!" insisted Mary. Kelly moved her feet until her legs were spread wide. Then a frightened little Kelly closed her eyes shut tight and wished with all her might to be somewhere else. Mary held Kelly tightly round the waist to stop her wriggling too much and started to vigorously scrub between the girls legs. The stiff hard bristles roughly scraped Kelly's soft sensitive little pussy and bottom hole. "Ahhhhhhhhh! Stop! Please! It hurts! You're scrubbing too hard! Yeeeeeeee! Boo hoo!" wailed Kelly. Mary scrubbed even harder; all over the most delicate intimate bits of Kelly's private person. Mary felt her own pussy start to throb as she watched Kelly wailing and dancing to avoid the brush. When Mary finished the whole of the area from the top of Kelly's pronounced little mons, right through her legs, up inside her bottom crack to the very top was red raw. Kelly howled and stamped her feet holding herself between the legs as Mary lifted her out of the bath. Mary put some more soap on the brush and turned to the petrified Jennifer. "Your turn now!" Mary smiled. Mary helped the younger girl get into position. Jennifer babbled incoherent pleas for mercy. She'd be good forever if only Mary didn't scrub her! She'd seen how Kelly had shrieked and wailed as got scrubbed. She looked down and saw Mary's hand and the brush go between her legs. Then the dreadful scrubbing noise started. "Yeeeeeeeeeeee!" squealed Jennifer. It was even worse than she'd thought. It felt like having a cheese grater rubbed hard between her legs. Her hands came off her head but Mary grabbed hold of them and held them tight. The scrubbing continued whilst Jennifer shrieked and danced in the bath. Only when Mary saw that Jennifer was as red raw as Kelly did she release Jennifer and lift her out of the bath. The howling stamping girl grabbed desperately between her legs trying to squeeze the pain out. Alison felt Steve's cock start to jump inside her. She rapidly increased the pace of her bottom movements so her bum cheeks slapped against his stomach and her pussy pumped his cock. Grunting Steve came deep in her. Mary wasn't finished with the girls quite yet. She reached up onto a shelf and took down a bottle of medical alcohol and poured some of the liquid into her cupped palm. Then she took Kelly and administered the liquid between the girl's legs. The result was instantaneous; Kelly let loose a blood curdling scream and grabbed herself between the legs. It felt like she was on fire; just like someone had poured petrol on her private bits and set it alight. Poor Jennifer was next. Mary held the squirming girl tightly with her hands out of the way and then slowly, deliberately poured the liquid into her palm and administered it to the pleading girl's waiting pussy. The shrieks and squeals filled the bathroom as Jennifer cavorted round the room. "Oh yes!" Alison spoke into the headpiece, "Full marks for bathtime." Mary nodded at the camera behind the bathroom mirror. She could feel that her pussy was throbbing nicely. She couldn't wait to get at their lovely little bottoms. Mary marched the miserable pair into the bedroom, both of them sobbing as they nursed their stinging little privates. When they reached the bedroom Mary threw the door open with a flourish. The girls were shocked into momentary silence. The room was decorated with cute little girl wallpaper and pictures and had a bed in the middle, but the girls' eyes were elsewhere. On the wall opposite the door was a board on which hung virtually every punishment implement an unfortunate little girl's bottom might encounter. There were straps, paddles, two canes, two hairbrushes, a wicked looking bath brush and several switches. There was a small leather topped child size vaulting horse, a sturdy straight backed chair and a low heavy stool. All these items had multiple Velcro straps attached. It was clear to even Kelly and Jennifer that these were for restraining naughty little girls while they were having their bare bottoms soundly whipped. Kelly started to cry noisily and Jennifer started to panic. "Please Mary! I'll be good! Don't hurt me!" Jennifer wailed, "Don't use those things on me! Please! I'll be good! I promise! I don't want the cane! Please!" "I'll have a look at your report from the Orphanage in a little while." said Mary sweetly, "If it's good then I'm sure you have nothing to worry about." Jennifer started to sob uncontrollably. She knew her bottom was going to be hurt really badly. "Girls," said Mary, "I want you to kneel up on the bed, put your heads down and stick those bottoms out. Before I deal with you I need to check your temperature." Crying the girls did as they were told. Alison and Steve were treated to the sight of those two little asses pushed out towards the two way mirror. Licking her lips Mary opened the drawer where the punishment thermometers were kept. She chose two `grade 2' models. Fashioned from medical steel they were shaped like butt plugs with a button and small LCD screen on the handle end. The `grade 2' model was an inch and a half thick, quite enough punish a nine and ten year olds tight holes. Mary smiled as she fondly remembered the time she has used a `grade 5'. At three inches wide she had treated a wailing twelve year old girl's anus to an excruciating half hour stretching session. The way the girl had howled and begged! Mary had actually climaxed during the session itself. Mary applied liberal lubrication to both thermometers. She started with Jennifer first. The cold metal tip entered the girl's exposed hole. "Waaaaah! Boo hoo! Don't! Please Mary! I'm sorry!" sobbed Jennifer. Mary paid no attention and pushed on firmly. The anus dilated to an inch. "Ahhhhhhhh! Stop! It hurts! I'll be good! I promise! Please!" Jennifer wailed. Mary pushed the rest of the thermometer home. "Eeeeeeeeeee! It's too big! It hurts! It hurts! Take it out! Please Mary! I want it out! Please!" Jennifer howled. Mary pressed the button on the base of the thermometer and a small beep sounded. The LCD display started to flash as it measured the temperature. Mary turned her attention to Kelly. "You've been at the Orphanage a while now, haven't you?" Mary asked. "Yes Mary, two years." sobbed Kelly. "When was your bottom last stretched?" Mary asked. "Two weeks ago." Kelly answered truthfully. "What grade did they use?" asked Mary. "Grade 1. They said my hole was really tight." Kelly replied, her voice barely a whisper. "Well I'm going to give you a grade 2!" Mary said, "Same as Jennifer's got. Your hole won't be so tight when I've finished with you. And I'll let the Orphanage know they can use something bigger on you now!" "Please Mary! Please Don't! It hurts me so bad! My hole's really small! It won't take a grade 2! I know it won't! Please! I beg you! Don't!" Kelly blubbered. Mary took the thermometer and started to drive it up the wailing girl's cute little bottom hole. Kelly was right, her hole was tight. But Mary had a point to prove and, slowly but surely, the squealing girl's anus was firmly stretched to accommodate the full width of the thermometer. As her bottom hole closed to accept the bulb of the thermometer Kelly wailed out "Ahhhhhhhh! It hurt's! Take it out! I'll be good! Please! Mary! Please!" Mary ignored her and pressed the button to start taking the temperature. Jennifer's thermometer gave a longer beep to say it had finished and a few minutes later so did Kelly's. Mary checked the screens; both girls were perfectly healthy. Nothing could save their bottoms now. She grabbed hold of both thermometers and yanked them out roughly. The girls' shrieks were deafening. Mary felt her pussy throb wildly. She was going to hurt those cute little bums so badly now. Alison's voice came over the headpiece, "Great personal care. That's a nine out of ten." Alison turned and looked down at Steve's cock. It was rock hard again. He loved to see little girl's holes being punished. Alison backed up onto him so his big cock filled her pussy. She started to grind onto him slowly. He'd already cum once so he was going to last for ages this time. Alison loved the bottom punishments. These two were just so cute she couldn't wait for Mary to start hurting those wobbly little bums. Mary took the reports from the Orphanage and read them. "So Kelly," she said, "not doing as you were told. And Jennifer, poor attention and bad grades. I'm afraid I'm going to have to punish you both very severely. This is going to be a real lesson to both of you to behave better." Mary went over to the board and selected the larger of the two hairbrushes. She brought it back to the girls. "Look at this, girls!" Mary said, brandishing the hairbrush in front of them. She laid it against Jennifer's little ass. "Why it's as big as your whole bum." she said, "Oooo, this is really going to hurt both of you. Who wants to go first?" Sobbing both girls indicated the other. "Hmmm. I think I'll choose you!" said Mary grabbing Jennifer. Jennifer started to wail miserably as Mary sat in the straight backed chair and pulled Jennifer across her lap. The girl's feet pointed towards the two way mirror making sure that Alison and Steve were able to see every detail as the girl kicked and splayed her legs. Mary held Jennifer's hands tightly out of the way and rubbed the back of the hairbrush firmly across the wriggling bottom cheeks. "Are you ready for your spanking?" Mary asked maliciously. "Boo hoo! Boo hoo! Please Mary! Please don't hurt me! I'll be good! Boo hoo! Don't! Please!" Jennifer pleaded. Mary tensed herself and began an explosive volley of spanks to the fleshy little bum cheeks in front of her. Jennifer was shocked into momentary silence and then began to shriek at the top of her voice. "AHHHHHHHHH! STOP! NO! NO! STOP! YHAAAAAAA!" she howled. Mary continued her vigorous application of the hairbrush to that delicious wobbly bottom. CRACK!-CRACK!-CRACK!-CRACK!-CRACK! It was getting nice and red now. "YEEEEEEEEEE! IT HURTS! MY BOTTOM! WHAAAAAAAA!" Mary started on the backs of Jennifer's thighs. CRACK!-CRACK!-CRACK!-CRACK!-CRACK! "AHHHHHHH! NOOOO! NOT THERE! NOT THERE! IT STINGS! PLEASE! STOP!" CRACK!-CRACK!-CRACK!-CRACK!-CRACK! Mary was having a field day. The girl was kicking like mad and Alison and Steve would love that. Her teen pussy felt so good as she walloped the squealing little girl's naked ass cheeks. Her clit pulsated strongly. Mary saw the first blisters start to form on the right bottom cheek. She stopped and let Jennifer go; after all, there was still plenty of cane yet to come for that little bottom and its shrieking owner. Kelly sobbed miserably as she watched the athletic young teen give a hairbrush spanking that the strictest matron at the Orphanage would have been proud of. The way that Jennifer howled and danced around the room grabbing at her bottom cheeks left Kelly in no doubt of what it felt like. "Kelly!" Mary called. Kelly turned and saw that Mary was smacking the hairbrush down into her open hand and looking at Kelly meaningfully. "Come on darling, over my knees. Your turn next." Mary said. On shaky legs Kelly went to her bare bottom doom. She climbed over Mary's lap and felt her hands being held tightly. The brush rested across her bottom, the varnished wooden surface felt hard and cool. Then it began. CRACK!-CRACK!-CRACK!-CRACK!-CRACK! "YAAAAAAAAH! TOO HARD!" Kelly yelled. Kelly started to panic. Even at the Orphanage they didn't spank this hard. Mary was going to take the skin right off her bottom. CRACK!-CRACK!-CRACK!-CRACK!-CRACK! "EEEEEEEEEEEE! IT STINGS! IT STINGS! STOP! MARY! PLEASE!" CRACK!-CRACK!-CRACK!-CRACK!-CRACK! "TOO HARD! MY BOTTOM! DON'T! PLEASE!" Steve and Alison luxuriated in their slow hot sex as the howling Kelly got her bare bottom hairbrush spanking. Alison slid up and down her husband's hard big penis. Alison loved the way Mary spanked so hard and made little girls shriek. Steve felt his wife's pussy starting to convulse around his cock; she was cuming really strongly. He felt her relax but she was still moving on his prick. Mary was going to cane the girls soon and he knew that would make Alison cum all over again. CRACK!-CRACK!-CRACK!-CRACK!-CRACK! "WAAAAAAAAAAH! MARYEEEEEE! PLEEEEEEASE YAAAAAAAAH!" Mary spanked away at the burning red bottom and thighs as her pussy throbbed joyfully. Kelly screamed and howled as the huge heavy hairbrush smacked away time and again at her agonised bum. Mary only stopped when she saw the first blisters appear. She let Kelly up for the naked little girl's screaming prancing war dance as a hard session with the babysitter's hairbrush showed its effect. Mary moved the child size vaulting horse so that the long side faced the two way mirror. She went to the board, hung the hairbrush back up and took down the longer of the two canes. It was a wicked looking thing; three and a half feet long, thin and very flexible. Kelly was still howling and jumping around so Mary went to Jennifer who was weeping and rubbing her burning bottom. She knelt down next to the girl and put the tip of the cane on the floor in front of Jennifer. "Look Jennifer," Mary said, "my cane is almost the same height as you! I bet you've never seen a cane as long as this before! And guess what darling? The longer they are the more they sting. How does your bottom feel now?" Mary cupped the little girl's sore cheeks and stroked and petted them. "I think this little bottom's ready for the cane now, Jennifer! Don't you?" Mary whispered in Jennifer's ear. "Please Mary! Don't cane me! I beg you! I'll be good! Not the cane! Please" Jennifer snivelled as Mary led her by the hand to the horse. Mary bent the pleading Jennifer over the long side of the horse. Using the Velcro straps she tied Jennifer's hands to one set of the horse's legs and Jennifer's ankles to the other set. Mary stood back to admire the thrust up bottom with the widely spread legs beneath. Nothing was left to the imagination as Jennifer's little pussy gaped open and her buttocks were parted to show her cute bottom hole. Mary's sopping pussy seemed to have a life of its own; tingling and throbbing as Mary swished the cane through the air ready to administer a squeal inducing cane session to the naughty Orphanage `punishment girl'. The cane sliced though the air and made contact with the little bottom. THWICK! Jennifer shrieked "YAAAAAAAAAAAAH!" Mary drew the cane up in the air again poised and ready to strike. She waited for a couple of seconds until the little bottom really felt the pain. THWICK! "WAAAAAAAAAH! NOOOOOOO!" THWICK! "EEEEEEEEEE! MY BOTTYEEEEEEEEEE! WAAAAAAAAAH!" THWICK! "AAAAAAAAAAH! MARYEEEEEEEEE! STOP! NOOOOO!" THWICK! "NYAAAAAAAAAAAA! SORRYEEEEEEEEE! I'M SORRYEEE!" Mary admired the pretty bum, so red and swollen and marked now. How many more could Jennifer take? Another ten? Another fifteen? Both Mary and Jennifer were going to find out. For the next ten minutes the whipping noises of the cane, the meaty thwacks as it met Jennifer's sorry bottom and the shrieks of a little girl receiving good hard bare bottom discipline filled the room. Jennifer's big fleshy bottom found room for another twenty strokes of the cane before the crisscrossed scarlet ridges covered the whole surface of the wriggling cheeks. Jennifer had screamed herself hoarse and her rasping hicuppy sobs served as evidence of a job well done. Mary unfastened Jennifer and lifted her onto the bed where she laid face down writhing in agony as her hands stroked and pawed at her swollen cheeks. Alison started to pant and shudder. Steve knew that Alison was ready for a really big orgasm. He started sliding his cock in and out of her pussy more quickly, pounding it into her. Alison tensed rigid as wave after wave of pleasure flooded her body. Nothing turned her on more than little girls receiving severe naked bare bottom punishments. Mary turned to the shaking Kelly. "How many smacks with the cane do you think I should give you, darling?" Mary teased, "Why, your little friend here took twenty five. Shall I give you fifty? What do you think?" "Boo hoo! Boo hoo! Please Mary! No! Don't! I'll be good now! I'll be good forever! Not fifty! Please! Boo hoo! I've only had thirty before! Fifty would kill me! I know it would! I'll do anything! Not fifty! Please! Pleeeeease!" Mary tapped the top of the horse with cane. "Come on Kelly." Mary instructed, "You know what to do." Sobbing loudly Kelly bent over the horse and put her arms and legs ready to be tied. "I'm sorry! I'm sorry! I'm sorry!" Kelly repeated endlessly as Mary tied her into position. Mary could see now that the cane was going to really sting as it wrapped itself round Kelly's wide sensitive bottom cheeks. Mary stood back and raised the cane for the first stroke. Sensing what was going to happen, Kelly started to shout. "NO! NO! NO! NO!" Mary whipped the cane across the little girl's obscenely thrust out bum cheeks. THWICK! "EEEEEEEEEEEEEEEEEE! NYAAAAAAAAAAAAAA!" Kelly's shrieks were far louder than Jennifer's. The elder girl felt the cane so very keenly. Professional pride meant that Mary was going to give Kelly's bottom more than thirty strokes, but Mary doubted the girl's limit would be much more. She would have to judge this carefully. THWICK! "WAAAAAAAAAAH! NOOOOOOOOOO!" THWICK! "EEEEEEEEEEEEEEEEEE! IT HURT'S!" THWICK! "YAAAAAAAAAAAH! I'M SORRYEEEEEEE! I'M SORRYEEEEEEE!" THWICK! "NYAAAAAAAAAAAAA! MARYEEEEEEE! STOP!" THWICK! "EEEEEEEEEEEEEEEE! PLEEEEEEEEASE! STOP!" Carefully Mary caned the little girl's bare bottom. As the number of strokes built up Jennifer became hoarse with howling and her bottom jerked spasmodically. Mary's pussy throbbed angrily; it needed attention. She slowly reached thirty strokes and stopped to survey the damage. The bottom cheeks were a scarlet splodge of cane marks and the skin looked in danger of breaking. Mary stood back and gave Kelly one more stroke of the cane just where her buttocks joined her thighs. She was rewarded with a hoarse wailing. Mary felt a grudging respect for the Orphanage, they knew their business alright. Now Mary's pussy needed attention. It needed hard adult cock. Mary unfastened Kelly's hands but left her legs tied; she wanted a good look at that spread bum when she was in the next room getting her pussy seen to. She left the wailing girls and went to see Alison and Steve. When she opened the door she was greeted by the sight of Alison bouncing up and down on Steve's cock as she drove herself to her next orgasm. Mary could see Alison's pussy slide almost all the way up revealing Steve's big penis and then slam back down. Alison started to moan and shudder and then fall forwards to embrace her husband. In a few moments Alison got off Steve's still erect cock and smiled at Mary. "You were really on form tonight!" she congratulated the teen. "Thanks Alison. Look at my jeans!" Mary said indicating a dark blue wet patch around her crotch. "Wow!" said Alison, "You'll get extra points for that. The judges like to see a girl who enjoys her work. So, I bet you're ready for Steve now! "Gosh, yes!" said Mary, "I'm so horny and his cock looks so hard and lovely!" "Oh it is!" said Alison laughing, "It's certainly made me feel good tonight. I can see you've left Kelly tied. Does that mean you want to look at the girls whilst you're having fun with Steve?" "Yes please!" said Mary blushing prettily. "OK then." said Alison, "Why don't you kneel on the bed facing the girls and then Steve can kneel behind you and put that nice big thing of his right up you." Mary needed no second bidding. In a fit of indecent haste she pulled her clothes off, jumped onto the bed, knelt down and stuck her cute seventeen year old ass up at Steve. Mary gritted her teeth with exquisite pleasure as she felt that big old cock slip up her. She looked up at the girls; Jennifer was still lying face down on the bed rubbing her bum whereas Kelly's bottom was still in its immediate after punishment agony. The girl was wailing hoarsely as she grabbed and squeezed big handfuls of her bottom cheeks opening up her pussy and anus to the excited watchers. Mary felt Steve's cock riding in and out of her. She pushed back to meet his thrusts so his belly slapped into her ass. She could feel it coming now; at first that intense twitchy tingling around her clit then the waves of pleasure deep in the bowels of her pussy itself. She mewled and stuck her ass out for more as the feeling seemed to go on forever. After Mary had recovered and put her clothes back on Alison offered her a lift back home. It would take Alison almost an hour to do the round trip. She looked back at Steve; he was still lying on the bed with that enormous erection of his and greedily eyeing the little sweeties in the next room. Alison winked at Steve and he winked back; she knew that the moment she left he would introduce his cock to the girls and give them some rather more intimate and painful punishments than either Mary's or her own anatomy permitted. Still, the little brats deserved to be hurt some more. Lucky Steve, she thought! CHAPTER 3 - Amy babysits Jessica Sarah bustled into the lounge where Amy was waiting. The cute sixteen year old wore a short pleated skirt and a cropped top. Sarah guessed from experience that Amy wasn't wearing any panties. During the punishment session Amy's pussy would become swollen, wet and highly sensitive; having any material rubbing on it was uncomfortable. "Amy, this is Jessica." said Sarah, "Jessica is eleven and has been caught masturbating and is to be given a very severe punishment. I have to go out tonight so can I ask you to carry out this chore?" "Of course, Mrs Rollings!" Amy answered, "I'll take care she's properly dealt with." "Thank you, Amy. I know I can rely on you." said Sarah and left the room. Sarah pulled the usual trick of closing the front door from the inside and then sneaking back to the bedroom. Jason was lying naked, his short thick cock hard and bulging. Sarah noticed the pubes around the base of his cock were wet. "Amy give you a blow job?" she asked smiling at him. "Yeah, just a quick one so I was ready for you." he said. Sarah had to admit, as she stripped off her clothes, that had been very thoughtful of Amy. She would have to thank her later. Sarah bent over and presented her curvaceous ass to her husband pulling the cheeks apart to give him a good view of her drooling pussy. "The Orphanage was really hot tonight." she moaned, wriggling her butt. Jason came up behind her and squeezed his cock into her pussy. Sarah never tired of the feeling of that cock filling her. It stretched her nicely giving friction where she wanted it the most. Jason stood still whilst his wife energetically moved her ass back and forth as she vigorously wanked her pussy off on his cock. In the lounge Amy surveyed the delightful girl standing in front of her. It was going to be such fun humiliating her and hurting her bottom. Amy felt her pussy give a little throb. She wondered how much encouragement the girl would need to get herself in even more trouble. Amy was an experienced masturbatrix and humiliated many of her young charges on the end of her experienced fingers. Only a few nights ago nine year old Sophie Newton had stood naked with her hands on her head in front of Amy. With her Mummy and Daddy looking on Sophie had wriggled and ground herself onto Amy's stroking probing fingers. Her parents had kept saying how naughty she was and to stop right away but Sophie just couldn't. When the nine year old had cum over Amy's fingers her mother handed Amy the most enormous paddle. Sophie went over Amy's knee for a bottom blistering fifty with the paddle. How that little girl had screamed! Amy could feel she was getting wet just thinking about it. Nice and gentle at first to lull her into a false sense of security. "Well, Hi Jessica. You can call me Miss Amy." she said. "Hi Miss Amy." replied the little `punishment girl', not quite sure what to think. "Before I put you to bed why don't I give you a nice hot bath?" asked Amy, "You know, wash away all that dirt and grime from the Orphanage. You've only got showers there, right?" "OK!" said Jessica. She thought it seemed like a nice idea. It was a long time since she'd had a real bath and this babysitter seemed kind and friendly. "Alright then! Let's go to the bathroom. I'll run you a nice bath and then help you get washed." said Amy. Jessica wasn't sure about having someone else wash her but she didn't want to say no to such a nice babysitter. Amy ran the water. She made it hot, but not so hot as to hurt the girl. If she played this right there would be more opportunity to do that to her later. Amy helped the girl get undressed. Off with the socks and short summer dress, oh that little g-string looked so cute. As Amy helped to peel the g-string down she noticed the slight stickiness between the young girl's legs. Jessica's pussy was a little treasure with small puffy developing lips. Amy put Jessica in the bath, sponged her down and then soaped her up. She paid lots of attention between Jessica's legs, her soapy hand carefully sliding over sensitive bits whilst Jessica wriggled. Amy got Jessica out of the water and towelled her dry with a big fluffy bath towel. Jessica thought she was in heaven. "Oh, that little thing between your legs looks sore." said Amy, pointing at Jessica's pussy. Instinctively the young girl covered herself as Amy pointed at her private place. "I think I better put some soothing cream on for you." said Amy, taking a tube of lubricating gel off the shelf. Amy squeezed the gel onto her fingers and moved Jessica's covering hand gently away. "I do this for lots of the girls I babysit for." Amy whispered as her fingers slickly spread the gel over Jessica's tingly pussy. Amy began to slowly move her fingers over the pussy lips, tracing the edge of the hole and grazing the erect little clit. Jessica's pussy was on fire! Touching herself was nothing like this. Miss Amy's fingers were making the hard tingles come really quickly. Amy slipped a finger up into Jessica's pussy, her thumb making circular movements over the sensitive clit. Jessica started to pant and push her crotch against the fingers. The sensation in her little pussy was amazing. It was going to happen, that special feeling, any moment NOW! Jessica gave a muffled groan as the strongest ever special feeling overtook her. She opened her eyes and looked at Amy but Amy's expression had changed. Her face was full of anger and disgust. Jessica started to shake. What had she just done! Oh God! She was going to be in real trouble if Amy told. Jessica felt the tears forming behind her eyes. One of them broke free and slid down her face. "You dirty little girl." spat Amy, "I put cream on you because you're sore and you actually masturbate on my hand! Just wait until I tell the Orphanage! I bet they'll send you to reform school. And we all know what happens there. Don't we!" Jessica started crying properly. At the Orphanage you got punished for being naughty. At the Reform School you got punished for being there. And they used whips to punish naughty bottoms too. "Please Miss Amy! Don't tell!" Jessica begged. "You dirty dirty girl! Why shouldn't I?" asked Amy. "Please don't! I'll be really good! I won't do it again! I promise!" sobbed Jessica. "You deserve to be punished big time!" said Amy. "Please Miss Amy!" snivelled Jessica, "Don't tell! You punish me! Please don't tell!" "OK, I'll give you a chance then." said Amy, "If you can take one of my special punishments without having to be tied then I won't tell. But it's going to hurt bad. Real bad!" "I'll be good Miss Amy. I'll take my lickin' from you real good. I'll keep position. I promise!" "OK Jessica. I believe you. I think the reason you got such an itch in your front hole is that your back hole is dirty. So I'm going to give you a good hot punishment enema to start with. Kneel on the floor, spread those legs and stick that bum out for me." said Amy. "Boo hoo! Not an enema! Please Miss Amy! I hate them! The hot ones are worst!" cried Jessica. "Should I tell?" Amy wondered aloud. "I'm sorry Miss Amy! Look, I'm doing it! I'm getting down! See! I'm really sticking my bum out now!" Jessica sobbed as she knelt on the floor and stuck her little bottom out for the horrible enema. Sarah's voice came over Amy's headpiece "That's a great combination `bathtime' and `personal care' you're working on. You've really got her scared. If the enema is good you're looking at full marks in both!" Amy nodded towards the bathroom mirror where the camera was. Sarah knew that Jason loved watching little girls receiving hard punishment enemas. Personally she preferred watching their little cheeks being whipped. But she wanted Jason to enjoy himself too. He was lying behind her and she could feel his hard cock resting between her bum cheeks. Sarah raised her uppermost leg opening her pussy to him. "Go on darling." she said, "You can put that thing of yours up me and use me whilst you watch." Sarah felt Jason's hard cock spreading and entering her. She lowered her leg pushing her bum out into his groin and began to slowly grind her hips, enjoying the feel of that big thing inside her. Amy took the enema kit off the shelf and, looking at the cute little rosebud presented to her, selected a `grade 3' punishment enema nozzle. At two inches wide the cold medical steel nozzle was going to stretch and hurt that little bottom hole plenty. "Look Jessica!" she said showing the nozzle to the little girl, "I'm going to put a grade 3 up your bottom! Do you think that's going to hurt?" "Boo hoo! Yes Miss Amy! Ooo it's really big! Please give me a grade 2! Please!" begged Jessica. "Oh no Jessica! You've earned this! I'm going to stretch the little bottom of yours nicely!" Amy smiled. Jessica sobbed fearfully sending little tingles of pleasure through Amy's pussy as she liberally spread the lubricating gel over the fearsome looking enema nozzle. Amy knelt down behind Jessica and put the tip of the nozzle against the little bottom hole. "Please Miss Amy! I'm sorry! Please!" sobbed Jessica but her miserable pleading only made Amy's pussy get even stickier. Amy started to firmly push the nozzle into the hole, rotating it as she went. Jessica wriggled her little bum and wailed as her hole was stretched wide. "Oooo! No! Please Miss Amy! It's too big! Stop now! Please!" she cried. Amy's pussy throbbed repeatedly; she loved hurting little bottoms this way. She kept up the firm pressure and cruel twisting motion and very slowly Jessica's tight little girl bottom hole was opened up to the full excruciating two inches. "Waaaaaah! Boo hoo! It hurts! Yaaaaaaaaah! Take it out! Please! Take it out!" Jessica wailed. Amy ignored her as she prepared the enema bag. The water was hot to the point that the girl was going to really feel it and Amy made it good and soapy so that when it went inside it irritated and hurt even more. Sarah could feel Jason's cock throbbing in her. She slowed her movements down to prolong Jason's pleasure. Amy purged the enema pipe of air and connected it to the nozzle. She opened the valve and the enema mix started to flow into the little girl. "Yaaaaaaaaaaaah! It's hot! Nooooo! Stop it! It's burning!" howled Jessica. "This is what naughty girls get." said Amy smugly. "Waaaaaaaaaaaaah! It hurt's! It's stinging! What did you put in!?" cried Jessica. "It's my special mix!" said Amy proudly, "Do you like it?" "Boo hoo! Boo hoo! Nooooo! It hurts! Stop! Pleeeeeeease!" wailed Jessica. Amy checked the bag and found there was about half left. It was time for her special move. She grabbed the enema bag and squeezed it hard. "YAAAAAAAAAAH!" howled Jessica. The feeling of the extra volume of hot irritating liquid suddenly entering her hurt more than any enema she'd had before. "WAAAAAAAAAAH! IT HURTS! IT HURTS!" Jessica shouted. Sarah felt Jason's hand firmly grasping her shoulder and felt his cock starting to jerk involuntarily. She started to slam her butt back into him riding the whole length of his straining cock. She heard him gasping and felt his cock jumping and spasming inside her as he came really hard. Amy turned the valve off and disconnected the pipe. She made the sobbing Jessica stand up and put her hands on her head so she could admire the miserable little girl already in such discomfort. The griping pains had begun and Jessica bent double, rubbing her tummy. "Please Miss Amy! I have to go! Please! Take the thing out of my bottom! Please! begged Jessica. "OK Jessica!" said Amy, "It works like this. Where you're ready for the biggest bare bottom punishment of your life then you just let me know. Then I'll take the nozzle out, you can go poo poo and then I can take you and your bare bottom to the bedroom for the nastiest thrashing you've ever had. So, you just let me know." Crying loudly and stamping her feet with the pain Jessica hung on. She hated even getting her bottom spanked. What was this horrible cruel babysitter going to do to her? But she was fighting a losing battle. The soap Amy had put in was doing its job well and the whole of Jessica's gut was experiencing a horrid burning sensation. The urge to poo became overwhelming. "Please Miss Amy! I have to go!" sobbed Jessica "Are you ready for your punishment?" asked Amy. "Yes Miss Amy." Jessica answered. "Beg me for it!" smiled Amy. "Please Miss Amy! Give me my bare bottom punishment!" blubbered Jessica. "Not good enough!" said Amy, "Try again!" The cramps were coming again. This time worse than ever. Jessica doubled up. "Please Miss Amy! I beg you! Take me and hurt my bare bottom with hard punishment! Do it as hard as you can! Make me scream and cry!" Jessica wailed. "Go to the toilet." Amy commanded. Jessica stumbled to the seat while Amy put rubber gloves on. Amy reached behind Jessica, took a firm hold of the nozzle and dragged it out of the squealing girl. Amy threw the article into a bucket of disinfectant while Jessica stamped her feet and drummed her fists as she expelled the liquid. Amy flushed several times and cleaned Jessica with wipes until the girl was fresh and cleansed. "Time for your bare bottom to be punished now!" Amy said as she led the shaking girl into the bedroom. Sarah's voice came over Amy's headpiece "Full marks for `bathtime' and `personal care'." she said. Like all babysitting coaches' houses Sarah's and Jason's was modified in the same way. As Jessica entered the room she saw the board with its huge array of punishment implements, the leather topped child size vaulting horse, the sturdy straight backed chair and the low heavy stool; each of them fitted with sets of restraint straps. The meaning of the room was immediately clear to Jessica; her bottom was going to get hurt very badly indeed. She started to shake and wail, putting her hands protectively over her bottom cheeks. "You don't want me to tell the Orphanage!" Amy reminded her, "Hands on head please!" Sobbing Jessica removed her hands from her bottom and put them on her head. Through blurred tear filled eyes she watched Amy cross over to the board to select something to punish her with. "Please don't! Not something hard! I'll be good!" Jessica sobbed almost incoherently. Amy selected a large heavy wooden paddle with many holes drilled in it. She held it up for Jessica to see. "I call this my `blisterer'." Amy announced, "When I spank a little girl's bottom hard with this it always gets lots of blisters. When I've finished you're not going to be able to sit down for weeks!" Amy could feel the slick wetness on her inner thighs now. Her pussy was leaking copious amounts of sticky juice. She knew it wouldn't be long before her pussy took matters into its own hands and made her cum without even touching herself. Jason's cock had already recovered and Sarah positioned him lying on the bed facing the two way mirror into the bedroom. With her back to his face she sat astride him and lowered herself onto his cock. She wanted to be in control of working that big thing in and out of herself as she watched the exciting action in the next room. Amy sat in the straight backed chair side on to the two way mirror. She dragged the wailing Jessica across her lap so her bum was facing the mirror. Making sure she had Jessica's hands held out of the way Amy rubbed the paddle against Jessica's cringing little bottom cheeks. "This is for your own good, sweetie!" Amy smiled, "You can blame that naughty little thing between your legs for this!" Amy lifted the paddle up to the height of her head. Jessica had a beautiful little bottom; full and firm but softly padded with puppy fat that meant there was plenty of surface for Amy to work on. This spanking was going to last a long time and was going to hurt Jessica real bad. CRACK! Amy whacked the paddle down hard across both little cheeks. "EEEEEEEEEEEEEEEE!" screamed Jessica, her bottom bucking in response to the wicked strike. CRACK! "YAAAAAAAAAAAAAAH!" howled Jessica. The red image of the first smack from the paddle was showing nicely. CRACK! CRACK! CRACK! The pistol shot retorts of hard wood making high speed impact with sensitive little girl bottom flesh, played counterpoint to the agonized howls and shrieks as Jessica sang the unmistakable shrill song of a young girl being spanked. "YAAAAAAAAAAAH! EEEEEEEEEEEEEEEE! WAAAAAAAAAAH! BOO HOO!" she howled. CRACK! CRACK! CRACK! CRACK! CRACK! Amy was into her stride now, spanking away to her hearts content. Jessica's legs opened wide as her legs kicked widely. Her screeching filled the house. CRACK! CRACK! CRACK! CRACK! CRACK! "EEEEEEEEEEEEEE! WAAAAAAAAAAH! STOP! PLEEEEEEASE!" Jessica screamed. The little bottom was a hot deep red now and Amy turned her attention to the thighs. CRACK! CRACK! CRACK! CRACK! CRACK! "EEEEEEEEEEEEEEE! NOOOOO! NO! NOT THERE! AAAAAAAAAAAAH!" squealed Jessica. Amy's pussy was throbbing uncontrollably now. Some more really nice hard ones on the backs of the thighs should do the trick. CRACK! CRACK! CRACK! CRACK! CRACK! "YAAAAAAAAAAAAAAAAH! BOO HOO! BWAAAAAAAAAAAH! OH NO! STOP! IT HURTS!" Jessica sang. Amy's pussy convulsed, shaking her body with a shuddering orgasm. The sight of Amy cuming, glassy eyed and slack mouthed, as she paddled the little girl's bottom brought Sarah on too. She bounced up and down on Jason's cock stifling her squeals of pleasure as a powerful orgasm took her body. The consummate professional that Amy was she never broke the rhythm of her spanking once during her climax. Jessica's bottom wasn't blistered yet and so Amy gave her another twenty hard spanks until she saw the blisters start to form down the backs of the thighs. She stopped short of blistering Jessica's bottom; there was plenty more to come for those sensitive little cheeks. Amy released the howling Jessica to watch the twisting contortions of the naked eleven year old. Jessica jumped and skipped, shrieking in pain as her hands tried to rub the sting away. Amy admired the dark red swollen bottom and blistered thighs. How lovely and sexy they looked. This one really deserved everything she got. What a dirty little bratty girl she was. And with one word Amy could have her sent to Reform School for what she'd done. Amy resolved to make her take the most severe punishment that a babysitter was permitted to give. When Jessica had calmed down and the wails had quietened to heartfelt sobs Amy spoke to her. "That was just a little taster of what you're going to get, Jessica. If you don't want me to tell you're going to have to be good now. Are you going to be good and do what I say?" Amy asked. "Boo hoo! Boo hoo! Yes Miss Amy! I'll be good! Don't tell! Please! Oh my bum! My poor bum! You really hurt it! Ooooo it hurts!" Jessica sobbed. "Come with me, Jessica." said Amy, beckoning the little girl to follow her. Amy led the red bottomed little girl through the house and out of the back door. Amy paused to pick up some pruning clippers. She marched Jessica down the garden to the old willow tree. "Cut me three nice switches, Jessica." she said, handing the clippers to the little girl. "Boo hoo! Boo hoo! Boo hoo!" Jessica sobbed continuously as she went about her task. Jessica took the switches to Amy and with trembling hands held them up for her to see. "Not long enough." Amy said and threw them over her shoulder. "Try again!" Sobbing bitterly Jessica cut the three longest switches a naughty little girl has ever had the misfortune to encounter. They were all about four foot long, thin pliable whippy sticks with cruel buds down the length that would sting and mark the skin. She took the switches to Amy and presented them again. Amy took them and spent her time testing them; bending them and whipping them dramatically through the air whilst watching the terrified girl shaking with fear of the pain they were going to give her bare bottom. Amy turned round to take Jessica back to the house and noticed that their appearance had drawn some attention. Looking over the fence on one side was a smartly dressed woman of perhaps thirty five. Peering over the fence on the other side was a boy of perhaps the same age of Jessica. Amy marched the crying Jessica over to meet the woman whose eyes lit up at the lovely sight being presented to her. "Hi, I'm Amy and I'm babysitting Jessica tonight." said Amy offering the lady her hand to shake. The woman took her hand shaking it firmly. "I'm Louise. That's a mighty fine job you're doing there." she said pointing at Jessica, "You going to be swichin' her next?" "Oh yes!" said Amy, "Good and hard!" "You know," said Louise conspiratorially, "I'm getting a little bit too much sass from mine at the moment." She indicated further up her garden where a young girl of ten was trying to her best not to be seen. "How much do you charge for a session?" Louise asked, "I think she needs a good workout!" "I charge $200 and that includes everything, including `pleasing the parents'." said Amy, "Would it be you or your husband who would require pleasing?" "Hmmm! Well, it'll be my husband's money so I guess he'll want the pleasing!" said Louise a little disappointedly. The idea of this cute young teen licking and sucking at her engorged pussy and clit was quite appealing. "I'm very severe." said Amy, "You understand that your little girl's buttocks will be heavily marked when I'm finished." "Yes I do." said Louise, "And she'll have earned every welt." "Excellent!" said Amy, "Would Tuesday night at 7.00 be OK?" "That would be good. I'll leave you to your work." said Louise hurrying off. She couldn't wait to see the look on her daughter's face when she found out the fate that awaited her bottom and her husband's look when he found out he was going to get some tight teen pussy. Amy turned and walked Jessica over to where the young boy was peering over the fence. As she approached Amy could see the boy quickly taking his hand out of his pants. "Hi, what's your name?" Amy asked the boy. "I'm Anthony." the boy said and then blurted out "You're Amy Jefferson, aren't you?" "How do you know me?" said Amy intrigued. "Oh, my Dad and me are real babysitting fans!" he said, "Dad's got all the videos of the championships. He say's your going to win for sure! We've got out tickets booked for the final. We're going to be cheering for you! Yah! Come on Amy!" Amy laughed. What a little cutie! Putting his hands up to do the cheer she could see pants tented out with his little erection. If it wasn't a training session Amy would have let him come and watch the punishment and play with himself as much as he liked. Still, if nothing else a little treat was in order. "So Anthony, what do you like looking at best, a girl's front or her back?" asked Amy. "Well, I like them both but I like the bottom best." Anthony answered truthfully. Amy turned to Jessica and pushed her forward until she was standing only a few feet from Anthony's eager eyes. Amy stood behind Jessica, reached down with both hands and spread Jessica's pussy wide open for Anthony to look. "That's where lots of men like to stick their willies." said Amy, "Little Jessica here likes to keep playing with hers. She's already in the Orphanage. If she doesn't stop soon it's going to be a Reform School for her." She let Anthony have a good long look. "Jessica," Amy said, "I want you to turn round, put your feet apart and put the palms of your hands onto the ground. If you can't get your whole palm right down then just keep moving your legs apart until you can." The snivelling and humiliated Jessica did as she was told and Anthony was treated to the sight of a girl, just a little older than himself, showing him her completely exposed and gaping pussy and anus, both framed her heavily swollen and vivid red buttocks and thighs. Amy stood next to Anthony and put her hand over the fence. She slipped it down the front of Anthony's pants, took hold of his little willy and began to play with it for him. "Ooooo, that feels so nice Amy!" he panted. "See the way her bottom hole's gaping open?" said Amy, "I gave her a hot enema with a grade 3 nozzle earlier." hAmy felt Anthony's legs tremble and his little cock jumped in her hand as he came. "Gosh, thank you Amy!" he said gratefully, "That was lovely!" "No problem!" said Amy waving at him as she led the miserable Jessica away for the thrashing of her lifetime. When they got back into the kitchen Amy laid the switches down on the table. She fetched some fine wire and proceeded to bind the bottom of the switches together, winding the wire round and round the three long sticks. She tied the wire and then cut it with pliers. Finally she took some Duck tape and wound it round the wire making a comfortable handle for herself. She lifted the finished article up and showed it to the terrified Jessica. It was a fearsome item; the sticks, not being entirely straight, fanned out at different angles creating a spread that would cover almost the entire area of Jessica's bottom. Amy swished it through the air. The multiple sticks made a frightening humming noise. This was going to hurt. They went back to the bedroom. Jessica's head hung and she sobbed loudly as they walked. There was no getting out now; that thing Amy had made was worse than anything she had ever seen before. Jessica could just picture it ripping her bottom to shreds as Amy enthusiastically thrashed her. When they got to the bedroom Amy moved the child size vaulting horse into position to give Sarah and Jason the best view. "Jessica!" Amy said, "Remember what we agreed. If you can take this punishment without being tied then I won't tell. But if I have to tie you then you're going to be sent to Reform School. And I'm sure you don't want that, do you?" "Boo hoo! Not Reform School! I'll do as you say, Miss Amy! I promise!" pleaded Jessica. "I want you to bend over this bench, Jessica." Amy said, "Spread your legs wide apart so that your feet touch the bench legs, bend over the bench, stick your bottom out and hold onto the bench legs the other side." Jessica did as she was told; that cute fleshy little bottom was beautifully presented for its switching. Amy took up position behind and to one side of Jessica using the length of the sticks to judge the right distance. Sarah hollowed her back towards Jason and felt his thick hard cock dilate her pussy and slide up. "This is going to be awesome!" she whispered to him and started to pump her ass. Amy lifted her arm so that the switch was high in the air. The pounding in her pussy was almost unbearable. Her clit had erected and stood proud of her puffy lips. Her thighs slipped together with the copious amounts of juice that oozed out. Jessica sensed that her time had come and started to babble whining pleas for mercy. "Boo hoo! Don't Amy! Please! Not with that thing! I'll be good! Please! I promise! Don't! No!" she cried. Whooooosh! The sticks whipped through the air. THWAP! "AHHHHHHHHHHHHHHHHH!" Jessica howled. Amy caught Jessica perfectly on the stickiest out bit of her bulging sit-upon. Jessica's whole body seemed to rise up as the sticks made contact. For a moment Amy thought that Jessica was going to manage to hold her position, but the silly girl grabbed her bum, jumped up and started to dance around. Amy took a firm hold of the girl, pushed her back over the vaulting horse and tied her legs. "Last chance, Jessica!" Amy said, "If you can't keep your hands off your bum whilst I whip you then you're going to Reform School." Whooooosh! THWAP! "NYAAAAAAAAAAAAAH!" screamed Jessica. Her bum weaved around madly and her hands waved behind her but she just managed not to put them on her bum. "Very good." said Amy. She'd soon put a stop to that. She aimed the sticks at the most sensitive bits of Jessica's bum where it met the thighs. There was a good change that some of the blisters on Jessica's thighs might catch this one. Whooooosh! THWAP! "EEEEEEEEEEEEEEEEEEEEEEE!" Jessica shrieked. Instantly her hands glued themselves to her bum and then, just as suddenly, pulled away. But it was too late. Amy had got what she wanted. "You silly girl! You silly silly girl! What did I tell you?! What did I tell you not to do?!" Amy lectured. "Please Miss Amy! Please no! Please don't' tell! Oh God don't! I don't want to go to Reform School! I beg you! Don't tell! I'll be good!" Jessica sobbed desperately. Ignoring her pleas, Amy fastened the wailing little girl's hands to the vaulting horse. Amy picked up the bundle of switches ready to start properly. "You silly girl! You've brought this on yourself! Now you're going to Reform School!" Amy berated her. Whooooosh! THWAP! "EEEEEEEEEEEEEEEEEE! NOOOOOO!" Jessica howled. "When you get there this is going to feel like a walk in the park!" Amy hollered above the agonised shrieks from Jessica. "You'll get worse than this every day!" Whooooosh! THWAP! "WAAAAAAAAAAAAH! DON'T TELL! PLEEEEEEASE!" "I'll tell! I'll tell all I like!" Amy shouted, "They've got things there that they stick up you and the put electricity through! They make girls dance and scream like that!" Whooooosh! THWAP! "NYAAAAAAAAAAAH! PLEEEEEEASE! I DON'T WANT TO GO! PLEEEEASE!" "Well you're going now!" Amy shouted shrilly, "Just you wait until you see how they stretch girl's bottoms there! In Reform School they have up to grade 10 bottom stretchers! Just wait until you get one of those forced up your hole! You won't stop screaming for a week!" Whooooosh! THWAP! "EEEEEEEEEEEEEEEEEEEEEE! WHAAAAAA! I'M SORRYEEEEEEEEE! DON'T!" Amy felt her pussy contracting. It was almost here! She stepped up a pace. THWAP! "Silly!" THWAP! "Silly!" THWAP! "Little!" THWAP! "Girl!" "EEEEEEEEEEEEEE! YAAAAAAAAAAH! IT'S CUTTING ME! IT'S RIPPING ME! NOOOOOOO!" THWAP! "I'll!" THWAP! "Whip!" THWAP! "This!" THWAP! "Little!" THWAP! "Bottom!" THWAP! "Right!" THWAP! "Off!" THWAP! "EEEEEEEEEEEEEEEEE! EEEEEEEEEEEEEEEE! WHAAAAAAAA!" Jessica screamed and howled non-stop. Amy's legs started to shake. It was going to be massive! Her pussy convulsed squirting liquid down her legs whilst an intense orgasm wracked her body. Like earlier, the sight of Amy cumming so hard made Sarah's pussy start to cum in unison as she pumped hard on Jason's big cock. Jason gritted his teeth. The feeling of his wife's pussy clamping around his cock was exquisite but he had to hold back. In just a few moments the cutest tightest teen pussy he had enjoyed was going to be squeezed round his cock demanding a long hard rough screwing. Amy recovered and checked Jessica's bottom. Perfect! The skin wasn't broken but otherwise it was a real mess. Weal after raised weal crossed each other until the bottom seemed to become one big blistered ball. Amy released Jessica's hands so that she could watch as the squealing girl put on a raw display of agonised rubbing and squeezing. God, it was so sexy watching those holes being exposed and spread like that. Amy left and went to the adult's room. She needed something big, hard and male up her. In Jason and Sarah's room Sarah had got off Jason and was sitting naked in a chair. Her legs were spread and her sopping open pussy was in full view. Jason was lying on the bed, his big cock hard and ready for Amy. "Great work!" said Sarah as Amy entered the room, "Ten out of ten. We loved the outdoor humiliation as well. Keep it up like that and you're going to win." "Thanks, Sarah!" said Amy as she stripped her few clothes off, "I owe it all to yours and Jason's coaching." Amy looked hungrily at Jason's cock. She couldn't wait. Sarah laughed, "OK Miss hot pants! Go on! Jump up!" Amy needed no second bidding. She crawled over Jason, took his cock and positioned the head against her pussy and then sat back forcing it up herself. She began to bounce her ass up and down working the whole cock length in and out of her tight pussy. "Sounds like she's missing you!" remarked Sarah and she turned the intercom up. Jessica's hoarse wailing voice filled the room. "Waaaaaaaaah! Boo hoo! Come back Miss Amy! Please! Don't tell! I don't want to be sent to Reform School! Please! I'll do anything you want! Please! Just come back! I'll kiss you between the legs! As much as you like! Just don't tell! You can take me home! I'll be your family sex slave! Everyone can spank and use me! Not the Reform School! Anything else! Anything! Please come back! Don't tell!" Amy plunged the cock in and out of herself as she watched Jessica playing with her whipped bottom cheeks and making every obscene suggestion her young mind could come up with of how she might please Amy in return for not being sent to Reform School. Amy felt the tingling start way in the back of her pussy and then her clit throbbing and pulsating as another great climax swept though her. This time Jason couldn't hold back. The feeling of the tight energetic teen pussy cumming all over him was too much. With a great moan he pushed his body up making sure every last inch of his cock was in her and began to shoot blast after blast of cum up her tight squeezing pussy. On the way back in the car Sarah turned to Amy. "Are you really going to get Jessica sent to Reform School?" she asked. "Oh yeah!" answered Amy, "Her little ass was made for it!" "She's a little brat. Deserves everything she gets!" said Sarah, nodding with agreement. Amy sat back. In a few weeks time Jessica would be safely locked up in the local reform school. There she would learn the awful truth that Amy was a part time Assistant with the power to discipline any of the girls as she saw fit. Reform School had none of the regulations or safeguards of the local Orphanage. In the sealed punishment rooms there were no windows or cameras; just the little girl being punished and the wicked imagination of the punisher. All those lovely things little Jessica had promised her at the end. They were all going to come true, and so much more as well! Amy's pussy started to wet again. DISCLAIMER: This is a work of fiction not fact. The two are very different.