New Babysitter 4 to 7

By Gerste

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This work is intended for ADULTS ONLY. It may contain 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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"New Babysitter," part IV, by Gerste

The girls continued to examine Josh for upwards of twenty minutes, Jill herself joining in with the rest. The girls were voracious, especially eight year old Christy. Josh wanted to die from all the embarassment, and would have fainted straightaway, but for his fear of the impending belt. The prospect of imminent punishment kept his fainting spell in check. It seemed to Josh to be the longest twenty-three minutes, this time of examination. He thought it'd never end. But finally, Jill announced that it will be time for supper soon, and the girls, momentarily distracted by notions of food, inquired what was for dinner.

   Jill: "We're ordering chicken from a restaurant. Josh here will be going to retrieve the takeout order from there. You girls will accompany him to make sure he's properly guided." She winked knowingly at the girls, who giggled as if in on something to which Josh was not privy.

Jill again, looking at Josh: "Josh, you will be our 'treasurer.' " Josh looked back with a quizzical expression. As if in response, Jill continued: "In OTHER words, Josh, you will have the responsibility of bearing the money used to pay for the meal. But first things first..."

   Alexa: "Way ahead of you, Jill."

   Josh turned to see his older sister rejoining them, emerging from the hallway corridor that adjoined her bedroom to the livingroom and carrying a rope and flexicuffs.

   Jill: "The rope will do for now, Alexa, thank you."

   Alexa the walked over to Josh and bound his hands behind his back. Again, Josh's inquisitive facial expression elicited an answer from Jill: "The rope is so that you can't touch yourself."

   Jill's words had the psychological effect of reminding him that his gentialia still itched. The girls' continual molestation of them, so far from actually scratching them, only served to tickle them still more. Squiriming, Josh was beside himself with anxiety, but he still had the presence of mind to stay in the moment.

   Josh: "But how am I to bear money if I am, well, BARE myself? I don't exactly have pockets, you know. The girls should carry the money. In fact, why would I, who have to stay naked, need to go along at all?"

   Jill: "Why, so that everyone can see your cute little dick and ballsack, of course." That response evoked an outburst of laughter from his giddy "guests," who seemed to think it was the dumbest question in the world. The answer didn't seem so obvious to Josh, however, who was at a loss to understand any of this. Everyone but Josh seemed to see this as a festive occasion.

   Jill continued where she left off: "And as to HOW you will carry it..."

   Josh, interrupting: "Yeah, how am I going to hand it over to the cashier with my hands bound behind my back?"

   Jill: "I'm getting to that. And don't interrupt me again, Josh. This is your only warning. You will not be carrying the money behind your back, at least not with your hands. Why would we risk you dropping it? No, we have a better solution. You will be carrying the money in your asshole."

   Josh's eyes got big, his voice atremble from fear: "Y...y...yu..you m...mmmean, between my buttcheeks, r..ri..rrright? But then I will have to clench my ass the whole time so that the money won't fall to the ground. I can't do that!"

   Jill: "Of course not, silly. Besides, people will be parting your asscheeks plenty along the way. You won't be able to clench them much. The money would get lost for sure. Instead, you will be bearing it in your asshole itself, which is what I said in the first place." Josh's mouth dropped. It was what he feared she meant, but he was hoping to distract the matter by suggestion (to no avail). She intended for his rectal passage to act as a kind of pocket.

   Josh: "B..b..b..but the girls have pockets. Why should I have to bear it in my asshole?" Josh began to cry.

   Jill: "Well, Josh, to be perfectly honest, this is our way of seeing how many people we can get to dig around in your ass." She laughed diabolically. Josh turned an ashen white. Had she only disguised her thinly veiled motives with a lie or justification (such as, "Assholes make better pockets for concealment against loss," "They are better against pickpockets," etc.), it would have been a less bitter pill to swallow (no pun intended), even if it belied an obvious, ulterior motive. But her crass, if candid, answer only served to highlight her sadism in his mind, and his subsequent discomfort as a result.

In a last ditch effort to stave off this further indignity, Josh blurted out, "But the money would get lost in my ass, and the paper money would get soiled, smelly and too wet for use." This seemed as good an excuse as any. Better, in fact, as he had a valid point, and was almost smug in his satisfaction concerning it. But Jill was not to be outdone: "Josh," she rejoined, "We have already thought of that." (Who's WE? Josh noticed the plural first person pronoun, but his thoughts returned to the matter at hand.) Jill continued: "We will put the money, which will be paper currency and some change, in a small plastic baggie, so it won't get soiled or wet." With that, Josh's heart sank. Jill then went to the phone to place the order.

Josh was feeling stress over the thought that his rectal cavity was to become the repository for "transfer funds," when a girl interrupted his doleful mood by pinching his penis. She had been "playing" with it throughout this latter conversation with Jill, but he was too preoccupied with current anxieties to notice (in fact, he had two or three girls playing with his penis, each in turn, throughout that conversation).

"Ouch!" exclaimed Josh at the pinching sensation. "That fucking hurt, you god damn, fucking cunt."

Immediately, Alexa's hand met the side of Josh's face in reprisal. Josh, smarting from the blow, immediately apologized, fearing further reprisals. Alexa: "You'd better apologize, you little shit-wimp!!! That was rude. She has every fucking right to pinch and prod her new play thing. How dare you speak to her so!"

Josh, trying to feign contrition: "Sorry, but it really hurt."

Alexa: "Josh, it doesn't matter if it hurt, if it is HER plaything. HERS! Got it?!?! It is NONE of your concern. NONE!!! You need to mind your OWN business. I will not tolerate a meddler, especially one of YOUR gender."

Josh was trying to follow her "logic," for want of a better, or bitter, word. What could be more "his business" than his own reproductive organ? But he knew he had better play along, or face the wrath of their (or rather, HIS) belt.

Alexa, the inflection in her voice changing slightly, conjoling: "Don't worry, brother. They're not allowed to draw blood or do any real, permanent damage, such as castration or ball rupture. Why would they ruin their own toy? It's community property, after all, this penis and ballsack of 'yours.'" And turning to the girls, she added, "There will be none of that sort of vandalism, will there, girls?"

The female company chimed, almost in unison, "Right!!!...No, there won't be," etc., and one girl reached down and again inordinantly squeezed Josh's penis, eliciting a further yelp. Fortunately for Josh, this outcry was tolerated. Josh hardly noticed that they had stroked and manipulated him to erection, which came partly from embarrassment. (His circumcised, beautiful penis stood an impressive four inches, atop an equally majestic set of muscular abs. The girls were euphoric, eyeing his slender physique in the midst of it all.)

Jill returned from the kitchen with the money in a small baggie, with a sealed zip lock on it. Never before had such a small, innocuous item produced such anxiety in Josh. Jill's face lit up with raptuous anticipation as she announced that it was time to insert the aforementioned item into its destined receptacle.

End of part four.

"New Babysitter," part V, by Gerste:

Josh had to think fast. Then it occurred to him: "Of course!"

Josh: "Jill, if your insert that into my ass, won't it make me feel like I have to have a bowel movement? What if I keep shitting it out on accident?" It was something he had heard years ago about the alimentary system: how the colon involuntarily "feels" like it must empty itself when "full."

Jill stood there silent, stunned by Josh's seemingly amazing powers of deduction. She was taken off guard for a moment. He had a point. She refected a moment, then came up with an extemporaneous and ingenious solution.

Jill: "We will give you an enema."

Josh, confused: "A enemy?" Then, furtively glancing about the room, as if in reference, "I have enough enemies, thank you very much."

Jill: "No, silly, EN-E-MA. It's when we insert a suppository or liquid gel into your rectum...er, I mean, asshole, and artificially induce bowl movement...Well, I maen, shitting."

Josh: "Come again? What do you mean?"

Jill: "I MEAN we're going to put a liquid up your ass to cause you to shit. That way, your body won't shit out the baggie we're going to shove up your ass. Got it NOW?" Her visage resumed its former sinister appearance.

Josh, visibly shaken, knew this could not be good: "Nnnooo!!!! The more I say, the worse it gets!"

Jill, laughing sardonically: "That's irony for ya. YEAH!!!" Then, turning to present company, "Girls, we're going to have some fun."

Moments later, Josh found himself doubled over in the bathtub, with Jill and the girls shoving the hose end of an enema bag into his anus, and some liquid solution streaming into his bowels, engorging them. Jill, who seemed to be a veritable treasure trove of serendipitous, lurid solutions, had a camera handy to record the event in all its sordid details (to include Josh's whole intimate anatomy, anus, adjacent ballsack, and all), to be preserved for VHS and/or DVD viewing and viewing by wide audiences on the internet. Jill used a high definition digital camera for the event. The girls were jubilant as they were told they would each get their own personal copy, to be shared with their classmates, and they, in turn, with their classmates and friends, etc. So they were instructed.

Josh, who felt as if he was going to burst, was ordered to "hold his water" until ordered to defecate. He cringed at the ensuing cramps and acute discomfort. Finally, he could stand it no longer. Just then, Jill, sensing this, ordered him to defecate. He ran to the toilet from the bathtub, almost losing it along the way, and disgorged a volumious amount of exrement into the extra large toilet. The smell permeated the room, and the girls felt revolted at the foul, fecal odor.

"EEEWWW!!!" came the uproar, "You stink!"

Josh hadn't lost his droll sense of humor and shot back, "WHAT? And you guys smell like roses when YOU shit a load?"

One girl took up the cause and responded, "Yeah, compared to THAT we do!"

Even Jill was overwhelmed by the swell.

Jill, attempting an understatement: "Well, I think maybe we accomplished our goal of emptying your intestines."

Just then, Josh ran to the toilet again, and, after flushing it, proceeded once more to evacuate the contents of his innards. The assembly were so taken by the resulting gastric, acrid stench that he unintentionally cleared the room. Josh himself was gasping for air, but had the presence of mind to take full advantage of his temporary solitude. He could now scratch that nagging itch on his testacles. But he had to act quickly. His bound hands made it almost impossible to reach them in front, since he was bound in the back. So he jockied about in a bent over position to reach them from between his legs. He managed to scratch them, as the fallout of odor fortuitously afforded him this fleeting opportunity to relieve himself of the incessant torment.

Moments passed, and Josh again flushed the toilet, and proceeded to re-join his gynic company in the living room, already schemming. He knew that he could not flee, since there was nowhere for a bound, naked boy to go but outside, into public view. He wouldn't get far, and knew he had better submit to their plans in order to get beyond them. When they saw him, they asked if he had wiped properly. He responded in the affirmative, but was made to bend over at the waist for another humiliating examination by each girl to make sure he had.

This went on for about fifteen minutes, when it was unanimously agreed upon that he had indeed wiped properly, despite his hands being bound. He was informed that in the future, a girl or woman must wipe his anus. Allowance was made in the present situation due to "extenuating circumsatnces" (i.e., the repugnant fecal odor). After forming a consensus about his anus, there came the inevitable question about his scrotum:

Jill: "And you had not scratched your itchy nutsack, right?"

Josh had not anticipated this question, and had to appear convincing: "No, of course not."

Jill looked incredulous: "REEALLL-ly? You seem less agitated by that itch you were complaining about earlier!"

Josh, cunningly: "Well, how could I scratch my balls when my hands are tied, remember?"

Jill, still looking unconvinced, batted an eye: "HHHhhhmmm! I think that if you crouched down enough, you could probably reach them. If I untie your hands for a minute, do you want to scratch them?"

Josh was cagey enough to know this could be a trap. So he said, noting her wording ("...could"), "Would I have permission?"

Jill: "Of course!"

Josh: "Of course, YES?"

Jill: "Of course, yes. You have permission."

But Josh did not feel itchy anymore, so he said, "Naw. It's OK."

That, it turned out, was the wrong answer. Jill did not believe for an instance that the itch would just disappear on its own. She drew the only obvious conclusion, at least, in her view: Josh had indeed scratched his scrotum, then covered up his act with a lie.

Jill: "Obviously, if you don't need to scratch them, you must have done so already. It's spanking time."

Josh's heart melted: "NNNNnnnoooo!!!! Not another?!?! And so soon?!?!"

Jill: "Bend over, you fucking asswipe. You thought that enema was a pain in the ass. I'll give you a new pain in the ass, one that will last awhile."

Josh knew he couldn't talk his way out of this one, and was afraid to try. He submitted himself to his fate and bent over in the position she had outlined for him earlier, once again exposing his public anus to all present.

The strokes came at irregular internals, unlike before, so that Josh was not able to guess when the next strike would fall. There was no cadence, like before; but the strokes were still interspersed with right angle strikes, which again wrapped around his underside and struck his testicles on about one third of the strikes. The number of strikes was ninety in total, like before. Josh was reduced to tears, to the delight of his enthralled, applauing female audience.

Jill: "Now stand. It's now time for another pain in the ass: the money." She chuckled at her own spontaneous sense of humor: "This gives new meaning to the idea that money can be a pain in the ass." Everyone laughed--everyone, that is, except Josh.

End of part 5

"New Babysitter," part VI, by Gerste

Jill again approached with the baggie of cash, in order to insert it into Josh's rectal passage, when Josh again attempted to frustrate her efforts.

   Josh: "Eeerrr...You know, Jill, if you insert that baggie up my ass, it'll still be so wet, smelly and rancid that no health food professional will want to handle it." Again, Jill stopped to ponder: "HHhhmmm!!!"

........*pause*........

   Once more Josh found himself doubled over and spread-eagle, this time in the front yard with a garden hose up his rectum and water streaming into his colon.

   Jill: "This'll keep that baggie from getting so smelly and rancid."

   Josh couldn't believe his ill luck. "FUCK!" he mutterd beneath his breath, barely audible, "This just gets worser and worser!" (Normally, Josh would have euphemistically substituted "fudge," but he had made some transition in his attitude since all of this began.)

   Jill heard him, and resonded, indignantly, "You know, we might have to do something about that filthy mouth of yours." Josh leered back at her, as if to say, "I don't give a flying f..." Josh wanted to retort something to the effect, "You're not exactly the consumate moralist, you know," but he couldn't find the right words in "childspeak," and decided it wasn't worth another taste of the built.

   A crowd gathered around the throng of girls. Neighbors, both children and grown ups, were watching this new curiosity with rapt attention. Some digitally recorded the event "for posterity"—visual details, of course, included. Jill pulled out the hose when it became apparent that Josh's abdomen had become distended from all the water and the water gushed out of him onto the lawn, mixed with residual fecal matter. Jill repeated this uncomfortable "cleansing" procedure three times. In ancient Greece, such a method, with the ancient equivalent of the garden hose, of course, was performed annually in some circles; an improvident "medical" procedure, really, given the risk of ridding the colon of "good" bacteria as well as "bad," and that of excessive water absorption through the colon wall (resulting in electrolyte imbalance and possible fatality).

   After Jill was satisfied that Josh had been fully "purged," he was allowed to stand again, this time before a greater number of interested bystanders, one hundred strong, who wanted to examine him like the girls had done. Jill and the girls "generously" insisted on this, telling them that his body, particularly his genitals, were theirs for the molesting. "Fondle him anytime at will," they fervantly urged. After an hour and 26 minutes of just such examinations, Jill announced that it was now time to insert the money "pouch."

   "You know what you can do with all this money, Josh?" one girl quipped, "Stick it up your ASS!" The crowd roared with laughter at the girls' clever sense of humor. Another girl said, "Yeah, Josh, your problems are all BEHIND you! Get it? BEHIND!" More laughter followed. Jill added to the jocularity the following line: "This gives new, or NUDE, meaning to the term 'filthy lucre.' " Only muffled laughter followed, as most of the less mature spectators didn't get it. (Predictably, children of all ages and both genders made up the majority of observers. Adults comprised roughly 25 percent of the audience.) Josh was growing quite weary, and wary, of all the puns at his expense. He didn't quite grasp that "filthy Luther" pun, but he intuitively knew it was in the same line. He was surprised they hadn't called him an "asshole" or "dick," after the subject matter in focus. All the "jokes," such as they were, only seemed to Josh to belie their callousness and insensitivity towards his immediate plight. Not only had they made such insensible remarks while he endured the painful ordeal of having a hose and every neighbor's fingers shoved up his rectal region ("EVERY neighbor's,"...and then some), but he still failed to foil their plans to have his rectum act as a makeshift depository.

   Jill, aware that time was getting away from them (they still had to retrieve their takeout order), turned to Josh with the moneys in hand.

   Jill: "Well now, Josh. It is time for you to carry your load." Josh cringed as he anticipated a pun on "load," but none followed. Josh did, however, detect a "knowing" smirk to her affect. She continued, "Unless, of course, you can think of another reason to delay this any further?"

   Josh realized that his last two artifices only seemed to redound back on himself; that the proverbial "cure," so to speak, was worse than the "disease." So his facial and verbal expressions took on an ironical form as he spoke the words, "No, by all means, insert the damn thing!!!"

END of part 6 (no pun intended)

"New Babysitter," part VII, by Gerste

Josh winced in anticipation as he said the words, "Insert the damn thing." He fully expected a sharp pain at the entry of his rectum any second now. But Jill was savoring the moment as she eyed his pristine, virgin hole ("virgin," that is, not counting the foreign objects that had already invaded it earlier: namely, the enema and garden hoes, plus numerous fingers). Jill snickered as she said, in afterthought, "Load. Carry. Carry your load. Load of shit. Now that's a good worplay." Josh sighed deeply, as much from relief as disappointment, as he was at once anxious to get this over with and anxiety-ridden at the thought of commencing. This was an irksome irony for him. Before, he was apprehensive about having them insert the money into his anal orifice, and they were overly eager. Now, however, he was anxious to get it over with, and they were drawing it out. The girls were quick to gather her meaning.

   First girl: "Load of shit. Carry his load. I get it," chuckle...chuckle.

   Second girl: "Yeah, good one, Jill."

   Josh thought he recognized the voice of the second girl. He looked over to see his younger sister, Christy, enthusiastically adding to the frivolity. He knew she was complicit in this crime, but her flippancy on such a solemn occasion, at that one moment, was simply insufferable. Josh could stand it no longer, as he exclaimed, to Jill, "Are you going to do it and get it over with or what, for fuck's sake?"

   Jill's expression changed. She looked like a woman scorned. Christy, too, was vexed at this latest outburst, and, as if to defend Jill's honor, definsively snipped, "Shove it in, Jill." A second girl synchronously chimed, "Yeah, make it count." No sooner had the latter girl spoken the words than Jill resolutely thrust the phallus-shaped baggie upward into Josh's anus, which hungrily swallowed it whole. Immediately, Josh felt a sharp pain as she shoved the baggie of 57 dollars and 38 cents, ten dollars and 75 cents of which were in quarters, up his rectum (most of the money was in paper currency, in denominations of ones and fives [three of them]). Josh felt the bulky mass fill his rectal canal and rest, through her digital prodding, at the vertical plateau of the sigmoid colon.

   "There," she announced triumphantly, "It is in there securely."

   The initial pain passed after a while, as the item was lubricated to facilitate entry. But Josh could still feel the oblong object lodged in his intestines.

   Jill: "It is now time for you to carry your load," more giggles. To Josh, this line was tedious in its repitition. Jill continued, in a somewhat more serious tone, "Go get our takeout order, Josh. It's up at the 'Prime Chickens' restaurant. It's under the name Jill Wounderad. But they're expecting a naked boy with hands bound behind his back. So you might not need to say anything. On your way, now. The girls will accompany you to make sure you don't get 'lost.' You'll have about a half a mile to walk [in fact, it was .679... of a mile]. You've been there before; you KNOW the way. Go with your 'escort.'" Before they left, little Christy took the opportunity to procure for them a green marker. She then used it to write the following words across Josh's naked front torso: "Please feel my dick and ballsack" (an equidistant arrow beneath the words pointed down). On his back she wrote, "Please stick your fingers in my asshole." Again, a centered arrow beneath the writing pointed downward, towards the sphincter in question, just in case there was any confusion as to which anus was meant. Having done this, she assumed her place in Josh's "escort," which then left for the restaurant on foot.

Josh didn't realize that every household along the way in the sprawling metropolis would turn out to "greet" him. Literally hundreds of people, of all ages and both genders, came to molest Josh and examine every inch of his body, with photoshoots to boot, as he made his way with his female escort of twelve girls (Christy's friends back at the house, plus Josh's two sisters: Christy and Alexa). They all made sure to recruit as many people as possible to "examine" him, while two girls held his arms as they all walked. Josh thought he smelled something, and he noticed that many of the girls seeme to have "wet" themselves through their clothes. He didn't realize it wasn't urine.

One girl was assigned the duty of notetaking (actually, three took turns at this). She meticulously recorded everyone who fondled his genitals and fingered his anus, who, invariably, also examined the rest of him as well. She also took names to ensure that there were no duplicates. She thereby counted 589 such participants. Afterward, she (the final girl) flaunted this record before Josh's nose, and taunted him with the words, "How does it feel to be molested by over half a thousand people, my boytoy?" she herself fondling his penis as she said this, for effect or emphasis. Josh fumed beneath the veil of tears that cascaded down his cute little cheeks. After he had gathered his breath, he spoke in a huff as he blurted, "I didn't know the whole fucking city block was a bunch of perverted child molesters. I hope they pay for this!" Alexa chided him, thus: "Child molesters? It's not as if you're a girl, you know. Your body is their body. How can someone molest themselves? You need to just shut the fuck up, you little sprite. Who the hell cares what your butt-fucking opinion is? It's like I said before: THIS is none of your fucking concern, ass-wipe! You cocksucking little fucker, son-of-a-bitch!!!"

Once they had arrived, they saw that the restaurant was packed to the brim. They entered, as if it was the most natural thing in the world for a boy to be nude and so vulnerable in public. There had to be at least 60 plus people here, thought Josh. In actuality, there were 88, all of whom took the opportunity to examine him there and then, in turn. Girls of all ages, 5 to 18, especially took their time doing so (the latter comprised 34 people, of the restaurant occupants; this does not include the 197 such girls who examined him along the way, besides yard occupants earlier). After everyone there had finished the "examination," the proprietor of the establishment, Mr. Ausseriquence, greeted Josh by molesting his penis and anus repeatedly, as if it was also his right and property, and ordered his staff to bring out the takeout order to them, after, of course, they too "felt up Josh" (his words).

Several of the girls, of course, would have to carry the four boxes of food back, and two were enlisted for the task. (They were relatively small boxes, together containing 45 pieces of chicken and four medium side orders.) Then came the first order of business:

Mr. Ausseriquence: "There is the little matter of pay."

Teen aged Alexa was in charge of the escort, being yet the eldest of the group. She answered: "Oh, THAT? That is in Josh's ass."

Mr. Ausseriquence: "What? What is it doing there? This is most unhygienic. We are a restaurant establishment and we have standards."

Alexa shrugged, innocently: "Don't look at me! HE'S the one with the money up his ass. It's in a plastic bag, so it is pretty much unsoiled. And we repeatedly washed out his ass besides."

Mr. Ausseriquence, turning to Josh: "Just the same, Josh, this means we'll have to probe your ass for our money. How could you?"

Josh, bewildered: "How COULD I? How could I what? This wasn't MY idea."

Alexa: "Oh no, you don't, mister! As I recall, you anxiously said, 'Shove it in.' You're definitely the one at fault here!"

Josh, irate: "At fault?!?! I never wanted it in there to begin with!!! I just wanted to get it over with because YOU people insisted on shoving it up my ass!!! I'm the one who warned you how 'unclean' it would be, remember?!?!"

Alexa: "Calm the fuck down, you little ass-twerp! If anyone is to blame here, YOU are! If you didn't have such a cute, pert little ass, nice body and good looks, we wouldn't have shoved it up there in the first place!"

Mr. Ausseriquence, looking pseudo-impressed at her pseudo-logic: "HHhhmmm! She's got a point, you know!"

Josh: "A point?!?! WHAT point?!?! Who can help how they look?!?!"

Mr. Ausseriquence: "Enough of your damn nonsense, Josh! We need to focus here. We need to get that money out of there, if we ever hope to get paid for services rendered," then, turning to his wait staff, "Who wants to begin feeling out Josh's cute littel bumhole for the money?" Everyone's hand went up, including the hands of the customers.

Mr. Ausseriquence: "Well, that settles it, everyone will have to try and get that thing out."

Josh didn't like where this was going at all. He had already been molested and practically "finger fucked" by everyone in that restaurant and along the way. He didn't need anyone, and EVERYone, now trying to fish out an obstinate object now lodged in his colon. In addition, the owner had asked the question invitingly, as if he was featuring an enticing advertisement. Josh felt he could not take much more of this, even though MUCH more would follow.

(The End)