The Coopers Chapter 18

The Coopers Chapter 18
By Lee Davey
leedavey_1@lycos.com

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This story is intended for ADULTS ONLY. It contains explicit depictions of sexual activity involving minors. If you are not of a legal age in your locality to view such material or if such material does not appeal to you, do not read further, and do not save this story.
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Coopers 18 - The Price of failure.

A drip of sweat run down his forehead pooled and then dripped onto his nose causing him to wrinkle his nose. Richard tried to ignore the tickling if his nose, a tickling he was unable to relieve as both his hands were busy supporting his weight as he knelt on all fours facing a group of serious looking adults with clipboards. Ugghh... a groan escaped his tight pressed lips as the thick plastic strap-on worn by his sister was thrust forcefully once more into his sore bowels.

Stifling any more signs of discomfort from coming forth he concentrated on helping his sister out, and perhaps just as importantly not giving his mother who stood purse lipped watching an excuse to punish him for not helping his sister pass her anal training Regime badge.

Heather hissed silently under her breath as she noted the groan of pain from her middle son at a particularly deep thrust of his sisters thighs. Damn, the Judges saw it she thought as she saw the 4 Judges all scribble at this sign. I warned Ruth about measuring her thrusts, another error like that and she will never pass the exam. Casting a glance to her left and right she saw the other parents and children who were waiting their time to demonstrate their abilities to the Regime judges. The adults looking on with mild interest, the children all naked looking on either in horror or delight depending on their respective sex.

Damn that girl if she fails today I'm going to make she can't sit down for a week, she promised me she was ready to take the test, and that she had been practicing, not from what I've seen she thought.

Staring down at the smoothly varnished floor he knelt upon Richard was in agony the hard floor was hurting both his hands and knees as he bore the weight of himself and his sister. That discomfort was outweighed by the rawness of his bottom as his sister kept sawing into and out of his bottom. 10 minutes she has been doing this he thought, the other girls and boys who had preceded him and Ruth had managed to get the receiving boy to cum in a few minutes. Ruth however can't seem to find my prostate if I painted it orange and gave her a map Richard thought disgustedly, Thomas can every time, even Lee can, Richard thought back to the regular practice sessions he went through both at home and at school. Damn Ruth would you get a move on the lube is running down, arrrrr, run out Richard winced.

Shit...Shit...Shit, well the hell is it Ruth panicked. I was able to find it no problem when my dad showed me on him and Thomas. Ruth looked up from the sweating back of her younger brother as she continued plowing him hoping to somehow to chance upon her brothers prostate, the key she knew to getting him to cum without playing with his thingy.

Mum is going to kill me she whispered to her self, £60 it cost to put me on this course of 'Orgasm through Anal Stimulation, Preparation for Qualified Babysitters Course', and I was the one for begged my Mum to put me on Ruth remembered uncomfortably; and all because I need this qualification and the other Regime Babysitter courses before I can take a babysitting job. I passed the diaper changing course, the spanking course, and the child feeding courses no problem. A smile passed Ruth's lips as she remembered Thomas's the oldest of the Cooper boys disgust at having to be his sisters training partner for those particular courses. But unless I pass this course none of that means a damn... WELL THE HELL IS IT.. Mum promised me a stroke of the cane for every pound she wastes on my training. I can't take 60 strokes of the cane, not unless you can get a bottom transplant on the NHS? Realising that time was short Ruth began probing in her brothers soft rectum in search of the magic button, determined to avoid her mothers ire.

Richard strangled a scream as his eyes bulged when he felt his sister corkscrew the dildo into him, and more through luck and judgement almost crush his prostate. Despite the pain his tiny penis began to betray him as it stiffened at the relentless assault on his botty button, as his parents required to call his prostate.

Ruth with a look of relief noted the hardening of her brothers willy and renewed her corkscrewing plugging plunging deep and hard into her brothers bumhole, finally beginning to rub her brothers prostate sufficiently to excite her brother small cock and balls towards orgasm.

Richard was not sure whether what had just happened in his bum was a good development or not. While it was true that his balls were beginning to tingle and begin their path to orgasm, his sisters cackhanded method felt like the world heavyweight champion was using his prostate as a punching bag. Despite the pain he knew that even this painful rubbing would have him cum.

Uhh, Uhh, Uhhhh, "I'm Cumming" Richard squeeked as two minutes of this painful fucking he finally reached the edge, he and his sore bottom so eagerly sought, despite the pain and the incredible feeling he always had when he had an orgasm Richard remembered to call his approaching orgasm out, knowing full well the fate that any boy's bottom would suffer if he did not clearly announce an orgasm, irrespective of the fact that there happened to be 50 strangers watching him being firmly buggered by his sister at the moment.

Ruth pulled her dildo out of her brothers red hole, a hole which remained open blinking its discomfort to the world. Standing up she rubbed her knees gingerly, red splotches upon them clear from the pressure of kneeling behind her brother for the last 15 minutes. She turned towards the audience of watching parents and children and addressed the 4 unsmiling Judges who sat at the front, their stern black robes emblazoned with a stylized red 'R' that now represented the Regime authorities.

"I have brought my charge to orgasm through anal stimulation only, Sir, Madam" Ruth declared the required words as she curtsied to the 3 male and 1 female judges. The pink strap on between her legs bobbing comically at her awkward curtsey.

The senior Judge eyed the 14 year old girl his eyes sweeping over her coltish legs and budding breasts. Ignoring her he turned to a obese lady in her 60's who sat off to one side and nodded to her. At the Judges nod the lady stood and waddled over to where Richard still knelt and helped him up, and supporting his rubbery legs helped him walk bow legged to the first aid treatment station she manned.

"Will the Guardian of the Trainee please join her on stage".

Heather stood and made her way to where her daughter stood, her face a cold mask that did not fully hide her displeasure at her daughters poor showing this evening. Standing next to her daughter she rested her hand upon Ruth's bare shoulder, her fingers clutching too tightly for comfort into Ruth's bony frame. Ruth winced at the heavy hand of her mother, not only at the pain in her shoulder but also at what her future looked like holding for her.

"I regret to inform you that you have not successfully passed the test. The candidate failed to demonstrate the ability to manipulate a boys prostate sufficiently well to enable orgasm without other stimulation, within a reasonable time as required to successfully complete this course. Next..." at this the Judge waved the two Cooper women from the stage, and sat back down as a young elfin looking girl of about 8 walked on stage her strap on between her legs appearing huge despite its in truth average size, against the girls small frame, a sheepish boy of 15 or 16 followed her on stage and knelt where Richard had so recently suffered grimacing at the feel of the sweat patches that Richard had left, and mentally prepared himself to 'assist' his little sisters budding career.

Heather literally dragged her daughter from the stage and headed towards the back of the hall where a thick red felt curtain separated the stage from the cloak rooms.

"There, there, does that feel better ducky" the fat nurse asked as she continued to massage white cream into Richards sore anus, still slightly distended from its earlier use. Richard who had found himself brusquely draped over the huge nurses two mountainous legs, his cheeks separated and the nurses fingers inspecting his sore bottom without so much as a by your leave "Yes Ma'am" Richard replied telling the truth as the nurses fingers soothed his botty with the cold cream, "It feels really OWwwww..."

Richard's thanks were cut short as he yelped as the nurse who was paying no attention to his words thrust the tube of an enema bag deep into him, and began squeezing its creamy contents into his abused hole.

"Don't fuss this is just some numbing anaesthetic cream to help the pain, luv" the nurse informed as she continued to fill his bottom up. "Normally I believe boys should feel it when they have been rooted, but your sister went over the top. We don't want you being turned off from getting a good bottom fucking, after all it is going to be a large part of your childhood".

Satisfied at the quantity of cream she had spurted up Richard she with a brusque motion quickly slipped the enema tube from the limp boys bumhole. With an equally quick thrust she plugged Richard's now red and white botty with a small retaining butt plug.

"There you go" she cheerfully started as she gently slapped Richard's bum as she righted him to his feet, "That's just a small plug to make sure you retain and absorb all the goodness from the cream, deary".

Swisshhh, "Arrggghh", Swissshh, "Owwww" Swissh. Richard holding his two cheeks in either hand turned his head as he heard the unmistakable dulcet tones of his sister yell out. He was not the only one as the entire audience as one turned at the noise looking at the curtain, behind which Ruth it was clear, was being severely caned by her angry and £60 poorer mother. The loud retort of the cane only beaten by the shrill cries of Ruth.

A malicious grin crept over his face as his listened in delight to the whipping swish of...a cane... if he was not very much mistaken,,,, impact his sisters bottom repeatedly.

"Remember to get your mother to unplug you before bed, and even with the cream you will still be a little sore" the fat nurse advised a smile crinkling her features into a smile as she too smiled at the sounds of parental discipline being deservedly dished out, "Although at seems you won't be the only one in your house with a bottom to sore to sit upon tonight" the nurse joked as she patted the plugged bottomed boy off bidding him off towards the sound of Ruth's caning.