The Adventures of Jack and Jill

                      The Adventures of Jack and Jill - Chapter 8

 

      Had not Evelyn Stanton chose this particular time to allow Jack to leave her office, a totally chastised and whimpering student of St. Switchers Academy for Wayward Teens, the other new student, his sister, might have suffered irreparable harm, perhaps even death, at the hands of the headmaster. Gerald had completely lost his moral compass, that is if he ever had one. His rage had overwhelmed his intellect and he was in the process of forcing the girl to have anal sex with him.

 

      Poor Jill was in dire straits, her naked body bowed backwards into a painful arc. Gerald Stanton had both hands around her throat and was squeezing the life from her. His knee was wedged between her thighs to keep her in this awkward position. He was thrusting his massive cock against the girl's bottom, trying to locate her unblinking brown eye so he could plunge it into her bowels and begin the process of sodomizing the academy's latest student. Jill's eyes were bulging from their sockets and it was beginning to get dark as far as she was concerned. She was mere moments away from passing out and having that monster member begin plowing deep into her rectum.

 

      Suddenly there was a pounding on the door of his study and Evelyn's voice screaming for him to let her enter. He tried to ignore her, still seeking the entrance to the teen's lower intestines so he could begin to rout the demon that dwelled within. The pounding and yelling continued unabated, and a new voice was added to the pleadings for him to let them into his office. Jill began to shudder and her face took on a mottled color that he did not see, being too busy preparing to rape her asshole.

 

      Evidently Evelyn had gone back to her office and retrieved the key that would open his study, that is provided the door had not been barred. Fortunately for Jill, this time in his excitement he had neglected to prevent everyone, including his wife, from entering his place of refuge. It took the combined efforts of Evelyn and two of the male teachers to separate Gerald from his prey. Jill was more frightened than harmed, and after a few minutes had calmed down enough to be taken to what passed for the school's infirmary, where the woman teacher doubled as the school's nurse.

 

      The next thing Jill knew they had strapped her down to the examining table with her feet in the stirrups and her thighs spread wide and secured to the wings that folded out from the platform she was lying upon. For the next fifteen minutes the three teachers poked and probed her most intimate areas, nodding and grinning at what she displayed. A speculum was slipped into her cunt and opened until she felt as if one more turn would rupture her fun box as one wag described it. Samples from her cunt walls and deeper near her cervix were taken with  swabs and put into vials. Little did she realize that after she was removed from the area, the samples were quickly discarded. As she soon learned, almost everything they did at this prison disguised as a school was more or less a facade to cover what they really did, which was sexually molest and brutalize underage teens.

 

      Jill's cunt was carefully measured; it's length and width recorded for reasons known only to those making them. The thickness of her inner and outer cunt lips were taken, along with how far they could be stretched, a process that brought tears to her eyes. However it was her clit that received the most attention. Calipers were used to measure its diameter before and after stimulation with a pocket rocket vibrator that also managed to bring her very close to an orgasm. This seemed to amuse the teachers who made jokes about how highly sexed this young teenager was. Needle-nosed pliers were used to measure just how far that fleshy nubbin could be stretched. One of the men claimed that the more elastic the clitoris, the more sex was required by the subject. They all laughed at his observation. Poor Jill could only blush at these remarks and hope that this examination would come to a quick conclusion.

 

      Everyone got "deeply" involved in the next measurement, the depth of her cunt. There was some difference of opinion on exactly how to make this critical determination, with the major issue having to do with the elasticity of Jill's still maturing cervix. It was finally agreed that everyone would make an independent test and the results would be averaged to produce her cunt depth, which turned out to be a little under ten inches. This resulted in another round of bad jokes at her expense. Two of the male teachers offered to use their cocks to settle the issue, but were rebuffed for the moment at least.

 

      Jill underwent more tests on her budding breasts, their size (top to bottom and end to end),  weight

(a very tricky measurement), elasticity (a very painful measurement using tongs), plus the length and diameter of her nipples when stimulated and at rest. Still they were not satisfied until the depth of her armpits, the length of her arms and legs plus the standard chest, waist and hip tapings were completed. Jill heaved a sigh of relief when they all agreed that enough data on her body, especially those regions usually playing a major role during sex, had been taken and accurately recorded.

 

      Then one of the teachers innocently mentioned that they had no knowledge of her anus, except he called it her asshole. This evoked roars of laughter from the trio at the joke they had just played on their newest student. Of course this entire procedure was nothing but a farce, so why not go whole hog. Jill got a very nauseous feeling at that moment, realizing she was far from being out of the woods. It also struck her that her  twin brother would sooner or later go through the same humiliating game at his expense.

 

      The next thing Jill knew, her asshole was carefully lubricated and a tapered rod was slowly inserted into her rectum, stretching her sphincter wider and wider as it traveled into her lower bowel. What started out as a dull ache soon graduated to steady pain as the ring of muscle guarding her interior was widened further. Now the pain was sharper as her asshole approached its limit of elasticity. She started to moan and then cry as the pain increased in response to the growing pressure on the entrance to her rectum. Beads of sweat soon dotted her forehead as she struggled to stay relaxed, knowing full well from previous experience that any resistance on her part was only going to cause higher levels of pain.

 

      Then she let out a hoarse scream of agony as she felt something beginning to tear in the vicinity of where the tapered rod was making slow, incremental progress. All movement abruptly stopped and then the rod was slowly withdrawn from her sore asshole. "I see blood, we have a legitimate measurement", an excited voice exclaimed. Jill started to blubber and writhe against the straps holding her down. The pain had not gone away, it remained. Moments later the "nurse" swabbed the area with some kind of ointment that numbed the flesh. Jill tried to get a grip on her emotions and regain her composure. What she had experienced was no worse than some of the anal rapes she had endured previously. If she could survive those, she could also deal with this one as well. 

 

      It took some time for it to sink into Jill that they were not done with her just yet. She could see their faces breaking into evil grins and the knowing glances that passed between them. The poor girl had no idea of what to expect next, then she saw them beginning to don latex gloves and she blanched. She was about to be invaded in a way that was not unknown to her. The only issue facing the teen was the size of the fists involved in this new torment. Rather than draw straws to determine the order in which they would fist her, it was decided to start with the smallest fist and graduate to the largest. In that way Jill would always be encountering a higher level of pain as they progressed.

 

      The nurse-teacher, Ms Wippett, an ideal name for a faculty member at St. Switchers, approached the table, her eyes fixed on the teen's pinkish slit. She wondered if the girl was moist, which would take some of the edge off the pain she could create. Ms Wippet inserted two fingers and wiggled them about, discovering a desert within the teen's cunt. She smiled evilly and began working the first four fingers into Jill, making good progress despite the teen's outcries as she tried to escape the intruders by wiggling her body. Her reward for these efforts was a swift slap across her belly and a warning that the next one would be a fist and even lower. Jill was smart enough to control herself and so the four fingers soon were joined by the woman's thumb and then the five digits were formed into a fist.

 

      The trio decided to turn this event into a race to Jill's cervix. The starting line was when the teacher's wrist was completely within the teen's cunt as agreed upon by all the contestants. Then the race would begin and anything went. Suddenly the previous measurement of Jill's birth canal distance made some outrageous sense. Evidently this was not the first time that this kind of race had been run. Jill's musings were interrupted by the sharp pain she felt as the woman's bony fist started churning away inside her very dry fuck tunnel. All she could do was grit her teeth and hope for the best. It was slow going and the fist made a number of stops in order for the teacher to regain her strength before plowing forward towards the goal line of Jill's still maturing cervix.

 

      The woman quit half the way up Jill's fun box from total exhaustion. However she made the teenager pay for her lack of cooperation by using her fingernails on the girl's cunt walls as she extricated her tired arm and aching hand while her two opponents smirked and gave her a hard time for a less than sterling attempt to reach "Mount Cervix".

 

      Now it was the turn of the first male teacher, Brad,  whose last name she hadn't heard. Unlike the woman, he took the opportunity to slather some lube over his latex gloved fist. Even with the assistance of the lubricant, it was torture for Jill as he fought to seat his fist properly within her twat. She was in a world of hurt even before he launched his fist up her fuck tube to the mocking cheers of the other two. Brad knew what he was doing, much to the dismay of Jill. His fist marched steadily down the path to the finish line in bursts of power that  gobbled up inches at a time on his way to the promised land. Unlike the nurse-teacher, he hunched over so he could deliver maximum pressure to the teen's twat, forcing it to yield to his fist.

 

      When he was within a few inches of the goal he adopted a different tactic, moving back and then plunging forward, instead of the slow constant pressure he generated during the first leg of the race. This back and forth fisting was not only more painful but it delivered results. Jill let everyone know that he had crossed the finish line when she let out a howl of agony as his fist contacted her cervix, or as he called it, "knocking on heaven's door", after the song of the same name. His time was duly noted, then with a big smile he removed his arm with a loud pop from her well stretched and traveled cunt.

 

      Poor Jill then had the unappetizing task of cleaning whatever had accumulated on his fist and arm while he tunneled through her dry twat. The teen was experienced enough to realize that her failure to do this little job would result in some serious pain as a consequence. So while everyone watched, she applied herself diligently to the task at hand, if you'll pardon the pun, and was rewarded with a pat on her head as if she were a dog that had just done a trick for its master.

 

      The last contestant was the one who had escorted the naked female teen into the headmaster's office and then participated in her beating. This did not give Jill a warm feeling, and he quickly demonstrated the accuracy of her assessment. He began by threatening the girl if she didn't cooperate while he was fisting her. To emphasize his threat, he slapped her across the face a number of times and then viciously pinched her cunt lips until she blinked tears that ran down her cheeks. While she recovered from his brutal assault, he was busy slapping on the lubricant and making sure it coated his hairy arm as well; something that the others had not done.

 

      His method of inserting his fist was brutally effective and made Jill scream her head off. He  grabbed her cunt lip with one hand and yanked it back as far as it would stretch, thus opening her cunt mouth much wider than anyone else had. He then jammed his well lubricated fist into her fuck box and seated it as the teenager wailed in agony. He grinned wolfishly at his opponents and waited for the signal to begin the trek up her fuck tunnel. The woman nodded and he drew back his arm and punched Jill inthe cunt as hard as he could.

 

      The blow drove the wind from her lungs and made her almost vomit. It also got his fist half way up her cunt. Twice more he used the same technique, smashing his fist with all his power to drive it further and further into Jill's pouty, puckered pussy. He was now scant inches from the goal, one more brutal punch was all it would take. By the time his fist encountered the entrance to the teen's uterus she was unconscious from the terrible damage those four punches had caused in her tender twat. She was just another in a long line of female students here at St. Switchers, who had fallen victim to this horrible game and his brutal way of always winning.

 

                        (To be continued - rolf palsy)