Date: Wed, 22 Mar 2023 11:59:49 -0500 From: Michael Perry <1mikeperry@gmail.com> Subject: Alan's Beach Chapter 10 Written by Pieter , Charles Well and David Warning: This story is a sexual fantasy about young teen and preteen boys having sex. It was written by adults for the entertainment of other adults. The people, places and events detailed here are made up. The authors would never wish to see the events in this tale happen to anyone in real life. Chapter 10 – Final Preparations Continued Andy Dunn (12) & Carter Boyd (13) – 5 Days Before the MAC Andy was still trying to come to terms with his fast-approaching new life as an Alan's Beach Tailer. It was just 5 days before the MAC. He had signed up initially in an attempt to secure a future he hoped included college, law school, and eventually a successful career in the legal profession. His family were not the poorest folks in their little town, but with three growing sons, there was no way they could ever afford to provide their eldest with any great expectations. No, if not for MAC, Andy's future would inevitably mean working as a hand on his father's fishing boat. That was not what Andy wanted. But the MAC was a double edge sword. It did provide him a way out of Alan's Beach and a better future, but it came at a heavy cost. The full import of that true cost was only gradually brought home to the 12-year-old as he began his dildo training and the campaign for securing votes had started. Even before the final decision was made to run for the MAC, Andy had selected his best friend and classmate, Tim McCoy (12), to act as his campaign manager. Tim was loyal, intelligent, hardworking and he understood the politics of Alan's Beach better than any kid Andy knew. Tim had grown up listening to the men sitting in his dad's barber chair all his life and was usually the first the learn the latest gossip and scandal around town. Picking Tim McCoy as campaign manager had been a good choice. He arranged for Andy to team up with Carter Boyd in the 13-year-old age category and the two of them were able to seek votes as a team – one aged 12 and the other 13. That would suit the needs of several of the large voting blocs from South Valley. In the end, Tim settled on a deal with Horace (Tiny) Mackey and his group which had grown to 18 boys by then. Throughout his training thus far, the only thing that had entered his ass were the dildos. All but the biggest one had been used. But today, his little brother, who was also his training coach, said that was about to end. "First, I am going to fuck you," the eleven-year-old Sim stated with conviction. Before Andy could even think about protesting, he continued. "And poor Tim, he's been aching to do it too. I've watched him, and I know that is true. He won't ask you, but trust me, he wants to do it." Andy looked to his campaign manager, who wouldn't meet his stare. That pretty much confirmed that Sim was right. "I've called Carter, he should be here any minute now. He is going to get fucked too. I've also invited Tiny, and he's bringing his cousin Seth. It is time for you and Carter to begin prepping for the big day. Andy gets fucked by Sim Ten minutes later after Tiny and Seth had arrived. "So, why are you guys still wearing clothes?" Sim yelled as he looked over at Carter and his brother. "Strip now. You have two minutes to be completely naked, or there'll be extra punishment." "Why don't we all strip?" Tiny suggested. "Great idea," everyone agreed, and over the next few minutes a flurry of clothes ended up strewn all over the floor of the old bunkhouse. When everyone was naked, Sim noted with satisfaction that every guy in the room was totally boned up. That included the two boys that were about to be the stars of the show he had planned. It had him a little happier about what he was doing. Andy and Carter weren't going to like what was about to happen to them, but their boners said they didn't entirely hate it either. "I'll go first. Andy, I want you over here," said Sim who was now standing next to the magnificently upholstered overstuffed armchair. Although it had definitely seen better days, the size and faded former grandeur made the easy-chair the central focus of the entire room. "Kneel on the left arm of the chair and lean over onto your elbows on the right arm and spread your legs as wide as you can." Andy reluctantly did as he was told and quickly realized what a degrading position he was in. Everyone would get a perfect view of his asshole and dangling balls. "I want your back straight and stick your ass out more. More! More! Okay that's enough. And your head must be up and you need to look at your betters as I fuck you. No hiding your face. Good, stay like that." Andy couldn't see, but Sim disappeared out the front door of the bunkhouse and returned a minute later with a wooden fruit packing case and placed it behind Andy's upturned ass. His kid-brother had obviously been planning this deflowering for some time. He would need the wooden box to raise himself up enough to do the fucking. Once Andy was in position, Sim grabbed the KY that was sitting on the nearby coffee table and applied generous portions to both his own cock and Andy's asshole. As he did so, the room with the 5 boys, had gone completely quiet, until. "Oh! Shit!" Andy yelled out loud. Sim had startled him by reaching under his prone body and rubbed his fingers around the head of his dick, causing him to gasp and lurch forward, and his dick began drifting from hard to bursting. Andy wished he had jerked off that morning, but he had slept in. Still, he knew what he was required to do. "The duty of a Tailer was to help other boys get off," Tim had emphasized numerous times. Andy reached out behind him and took a hold of his brother's cock. It was warm, fleshy, so alien and yet almost magical to hold. "Oh, he likes you, buddy," proclaimed Sim as Andy started jerking his kid-brother's boner. This caused everyone else in the room to laugh and that action reduced the tension that had been building over the past little while. Andy smiled too, relieved that his brother wasn't being too serious and also glad his first fuck would be from this tiny dick. Well, not tiny exactly. Sim was pretty long for his 11 years, at just under 4 inches, but he wasn't thick. Every kid who ever had direct personal experience with a Tailer Training Kit would thereafter compare every boy's penis to the sacred five – the quintet of divine phalluses. And Sim's cock was definitely thinner than the `Lil Pee-Wee. "I like him, too," Andy staged whispered. Tiny was very pleased to see that both brothers were playing their assigned roles to the hilt. He definitely liked role-play fantasy and this one was hot. Sim smiled back. "So, you want me to slide `buddy' up your butt, nice and easy, give you a good round fucking?" Andy actually laughed. It sounded like he was a little kid being offered some candy. "Yeah, I really do." "Well, you don't get the goods without paying the piper, right? Or in the case, getting laid with pipe. So, you want to get fucked, Andy?" Andy nodded. All fun over. This was going back to the stuff he still felt he was too young for. But they were going to make him play right. "Nodding isn't good enough. You gotta tell me what you want and why." Andy nodded again, but this time reflexively. In the next second he grew up immensely. "I want you to fuck me, Sim. I've got to be ready for MAC Day next week. "All right. Way to go, bro." Sim was very excited and more than looking forward to his fuck, but he told Andy he would go easy at first. Sim entered his brother in one long hard movement and didn't stop until he had no more to give. Then he paused to savor the experience. He was indeed trying to be gentle - well, as gentle as an 11-year-old horny boy could be when being offered such a tight, nice and prepped ass to fuck. All too soon, Sim pulled almost all the way out and pushed in again. The action was repeated and repeated and soon Andy was being fucked at a steady pace, which was noticeably speeding up with each cycle. The whole time Sim pumped him, Andy felt that the younger boy was so hard that he was being lifted up from behind and that the roof of his hole and rectum were being worked out. It wasn't unbearable, but a different layer of discomfort physically, than the dildos had been. But it also left him more ill-at-ease as he couldn't reconcile what was happening to him with his own developing masculine self. It wasn't just that he had asked for this fuck, but some inner part of him was aware that this would be his new life for the greater part of his early adolescence. After MAC Day, he would become the anal toy for any other boy around town of the appropriate age who wanted him. Their fuck hole, basically. It wasn't long, though, before Sim finished, more in a whimper than a scream. Andy knew his brother wasn't making spunk yet. No, that honor, the job of filling his asshole with boy cream, would go to Tiny. And Tiny could definitely shoot. Andy had tasted the spunk produced by those particular balls at least a half-dozen times before today. All part of his training, of course. Carter gets fucked by Tim When Sim pulled out and collapsed onto one of the kitchen chairs that was nearby, Tin McCoy took control. "Okay Carter" he announced ominously. "It's my turn. I'm not exactly a virgin because I've had a lot of blow jobs from you and Andy over the past few weeks, but this is gonna be my first fuck. I guess yours too?" Carter nodded his head, but couldn't speak out loud. Yes, he was technically an anal virgin as far as real boy cock was concerned, but lots of dildo's had already created a well-used pathway up there. But now that the actual act was nigh, he couldn't verbalize his humiliation. He didn't want any of this and he had only been forced into it because of the traitorous betrayal by Landon Kelly. The only slight consolation he had was that Landon had signed up for MAC as well, and he might be going through this same experience at that very moment. Carter looked over at Tim McCoy. The kid had obviously said something and was standing there waiting, expectantly. Tim patted the arm of the overstuffed armchair that Andy had just vacated moments before. Clearly, he was meant to get into the same position that Andy had been in. He reluctantly did so. "Thanks Carter. I really appreciate you letting me...I mean..." Tim tried explaining as he carefully lubed the bent over ass and his own cock. He was clearly a little nervous about what was shortly to happen. "Okay, that should be enough. Right Carter?" Without further comment, he felt Tim lean in with the full weight of his body. Carter has seen that Tim was fairly typical in size for a 12-year-old at 4.3 inches long and about one inch diameter in thickness. Carter reflexively pushed backward. This was the technique he and Andy had employed as each new wooden dildo had been inserted back there. His anal muscle opened and wrapped around that large head, pulling it into his bottom. Tim's cock felt big, and he was now glad of all the experience he had on the training bench. He grit his teeth on the dull pain that spread through him, as the familiar sensation of being stretched open was met with feeling and understanding that a long shaft was dragging his anal rim inward as it slid deeper inside. He felt the bulbous head lead the way, opening him up, and striking a place deep inside as first the hairs at the base of Tim's dick tickled the now sensitive skin of his creamy butt cheeks. Then the flat of Tim's lower stomach pressed those same butt cheeks inward. Carter was now fully and completely embedded with dick – real cock, not some fake wooden thing. Although he had taken much bigger dildos from the training box, this sensation was different. There was a real boy at the end of the cock. Worse still, that cock belonged to a younger kid, someone he'd see at school every day. Barely did the cock rest there before it pulled out an inch and was rapidly thrust back in giving Carter a rocking sensation of a deep thrust and a pounding on his perineum. The helmet of dickhead plumbed his inner rectum, and pulled out just as fast. For Tim, the physical and sexual feelings were indescribably intense, with the incredibly tight embrace of almost virgin muscle wrapped wholly around his shaft, dragging that sensitive underside in every which way as he moved it in and out, and sucking that head deep within in warm suppliant entreaty. He couldn't give thought to allowing the boy to adjust, but had to have his repetitive fix of euphoric stimulation along his preteen length, the whole four and-a-bit inches demanding equal share of orgasmic succulence. Carter gripped the arm of the easy chair in front of him, now feeling whole inches tug outward and slam inward in a rapid-fire assault on his hole, his barely accommodating rectum, and his bruising bare bottom. But he held on, and just as he felt three inches of dick drag out of him and slam back in, he suddenly felt the slams harder, shorter, and with greater urgency. He also recognized the clenching of Tim's hands at his hips, and soon the sensation of a sudden flow of warmth more than four inches deep inside him. Tim just came inside his ass. Carter was no longer, nor never, ever would be again, a virgin. Not in any sense of the word, at least back there. "Did you cum, Tim?" asked Seth Mackey. Tim finished out his few last spasmodic jerks into the barely willing flesh and looked one long last time at the comfortable rear end pressed up against his pubis, his own sparse pubic hairs just visible, and, as he began to pull back slowly, the sight of his thick shaft parting those white, once-virgin cheeks. "Hell yeah," he said exultant, but still a little out of breath. Carter gets fucked by Seth Seth Mackey was Tiny's first cousin and another boy from South Valley Elementary. He had been brought along to provide Carter some experience at being penetrated by a more mature cock. Like Carter, Seth was a good looking, confident 13-years-old, but was extremely well developed for his age at 5-and-a-half-inches long and well over an inch in diameter. Pretty close to the Harry dildo Tiny guessed. Not necessarily typical of other boys that age, but Carter would be facing boys up to 2 years older from day one when he took up the duties of a Tailer, and Seth was certainly in the size range he would face from those guys. "Stay there Carter," ordered Seth. "You might as well get used of taking two cocks – one after the other. On MAC Day, the new Tailers get fucked 3 times in a row, remember?" Although emotionally delicate and easily bruised, tween and teen boys are way short on empathy. That comes later in life, if it comes at all. Seth carefully lubed his own cock and then added extra squirts of KY to Carter's hole, which was already oozing a slight discharge of Tim's seed. "Be ready Carter, you're about to be fucked for real. My cock is bigger and better than the puny thing you've had so far. Sorry, Tim, but no offense!" And without further preliminaries or warning he started sliding his monster dick into poor Carter's already used hole. And shit he wasn't kidding. Carter's tight muscle was pushed in and suddenly expanded over a large, spongy but hard, and insistent knob of hot flesh, and he knew just how that knob was connected to the body of another boy. He felt like he was having Tom, the biggest dildo in the training box, shoved up his asshole, and seemingly without end as the dick relentlessly pressed onward. And he sensed the walls of his anal canal were being stretched so, by an unending tube that pushed through, deep into his gullet, pulling his anal ring along with it mercilessly. Eventually, Seth bottomed out and then began pulling back, now dragging against that anal rim and tugging it in a totally opposite way, Carter knew that he wasn't really prepared for this. Who could ever be? But Seth hadn't warned him out of spite. This was happening. Prepared for it or not, Carter was getting properly fucked that day, and he would soon feel the spurts of a second warm boy's cum deep in his rectum. A rectum that would need to be well trained into receiving such cock in a week's time. Seth's attention soon turned to doing some real fucking and he ran the two inches of dick he had pulled out, straight back in. And the barest hesitation was all he gave the boy before pulling back again two inches, going out at the same rate, but going in a bit faster. Soon he was continuing the same rate of two inches back with an ever-increasing speed for the inward thrusts. He then brought it back to 2 ¼, then 2 ½ (and he really had Carter squirming and moaning - though out of a sense of foreign discomfort, not pleasure) and slamming in fast. Once he was pulling out fully on each go, he then began to speed up his outgoing rate, until he was pounding that ass like a piston. Seth's connections as he bottomed out came out more like whumps than slaps and were cushioned by guttural grunts of pleasure from up top and breathtaking pounds from the boy below. And at that point, he was giving Carter a REAL fucking. And it lasted longer than Carter thought he could take, but finally Seth found the sweet spot on the underside of his dick and ran it with force over that still maturing prostate of Carter's before erupting internally into a white lava flow of blissful release. Andy gets fucked by Tiny "Holy fuck Seth! Tiny exclaimed, "That was amazing. You really gave Carter a proper fuck experience. Well done!" Tiny was a skinny, under-weight kid with curly black hair and brown piercing eyes. Although he had been in Grade 8, the top class at South Valley last school year, Tiny was still only 12-years-old. He had a reputation of being super smart and had skipped a grade a few years back. Even so, he did better, academically, than almost all the kids in his class. Tim, Andy and Sim were all too stunned, and lost in their own thoughts, at what they had seen to comment. Andy was once again reassessing whether he had made the right decision to sign up for the MAC, but that ship had long since sailed. Tim was reassessing whether the deal he agreed to with Tiny was worth it, and Sim was just worried about his brother. "He who fuck's last, fuck's best," Tiny laughed out loud as he announced that his own turn for anal pleasure had arrived. "Andy, over the easy chair again. Maybe I can't fuck you as well as Seth just did with Carter, but I reckon you'll feel me more than your kid-brother." He was already applying lube to his impossibly hard boy cock. Knowing his fate was sealed, Andy knelt back on to the arm of the overstuffed armchair and felt Tiny applying more KY over his already used hole. Tiny felt he had waited long enough for his turn, and slowly pushed his five-and-a-quarter inches into the inviting hole. This was the first, but it wouldn't be his last time. Under the deal he had signed with Tim McCoy, Tiny would get three fucks or BJs per week, from both Andy and Carter, which were not included in the boys' total maximums. Six times a week was pretty good. Even God rested on the Sabbath. But if he was still horny, the two tailers would also have their regular quotas, and there were always a bunch of other Tailers around town. Tiny was feeling pretty pleased with himself and how things had worked out. As he slowly pushed into Andy's asshole, Tiny felt the warm, still-tight envelope spread around and grip his dick, drawing it further inward while at the same time still pulling down the length of it like a perfectly wrapped around hand massage. And he kept pushing and pushing, until his entire five-and-a-quarter inches were buried deep inside. He was not called `Tiny' for nothing and his cock must have ranked in the top percentile in terms of both length and girth for 12-year-olds. As he bottomed out, he enjoyed the sight of his small patch of dark pubes pressed into Andy's unblemished cheeks. "You know I'm gonna want more of this Andy!" Tiny said as he pulled back a few inches, before sliding them back in smoothly and effortlessly. "According to our deal, I get three fucks or blowjobs from you and another three from Carter. I guess they could all be fucks, and not BJs. This is so amazing." Tiny began to repeat the pattern he had started, but with a bit more dick and a bit more flair. Sim was transfixed by Tiny's older and larger dick sliding in and out of that tight hole that he himself had only just recently loosened. The plunges were timed with the heavier grunts from Andy, who had no problem realizing an even bigger dick was running in and out of him back there. "Oh, fuck yeah," Tiny moaned and continued to bottom out slowly over and over and over and over again, taking his time to enjoy dicking this incredibly hot hole. He was in no hurry to shoot and wanted to stretch out this sensation into infinity, if only that were possible. And he kept fucking. And fucking. The thickness of this boner was really testing Andy's staying power. Tiny Mackey grabbed an even tighter hold of poor Andy's hips and began slamming hard, slowing with each slam, yet yielding greater force of ever shorter upthrusts. Andy looked down between his legs at his own body where his now flaccid dick was being bounced about by the hard thrusts. He saw his own developing nuts and few pubic hairs, both of which spoke to his own ability to shoot sperm; something that just made the present loading of his ass all the more acutely shameful. And behind those nuts, he could see Tiny's larger, cum producing balls, slamming him like domination in pictures. All too soon, Tiny couldn't hold it back any longer. He held Andy's ass close into his body and shot deep volley after deep volley of sperm inside him. And Andy felt every hot spurt shoot inside. The shame was intense. And as Tiny finally pulled out, that shame had to compete for attention with the latent pain and spasms that re-rocked Andy's overstretched asshole, showing on the 12-year-old boy's face. The energy was draining from him, and reality of his future as an Alan's Beach Tailer was overwhelming. Billy O'Brien (12) – 5 Days Before the MAC Billy O'Brien played a lot of computer games, looked at internet porn, and had even started writing his own apps that he hoped, one day, might make him the fortune he knew he deserved. He only signed up for MAC to be able to purchase the new computer he needed. The $1,000 entry prize would go a long way towards that. But he was no fool he assured himself. He carefully waited until three serious candidates had already joined in his age group. Ollie Mackey, Hank Boyle, and Andy Dunn all fitted that description and were already advertising their wares around town and clearly seeking every vote they could get. That suited Billy just fine. He didn't want any votes at all. However, a major complication arose for Billy when he was reminded by his father that Boyles from his branch of the family, who joined MAC, shared their prize winnings with the others in his immediate clan. Worse still, he had sold his old computer to Mitch Boyle (14) for $60, which was more than it was worth. Mitch expected it to be delivered to him no later than the day before MAC Day. If not, Billy agreed to call on Mitch and his brother, Kyle (12) to fuck him - on stage, for one dollar each. And the Boyle family took contracts, even verbal ones, as though they were commandments from god. Even a reluctant candidate like Billy O'Brien needed some training. Shit did happen after all. And as part of the deal he made with Mitch, he agreed to have Kyle Boyle (12), Mitch's younger brother, and their cousin, Jim Boyle (11) as his joint dildo coaches. But these two took their new office very seriously and poor Billy spent many painful days leading up to MAC Day on the work bench in the Boyle garage, bent over in the doggy position, as various wooden cocks were pushed into his mouth or ass. As Billy lay awake in bed on those final days before the MAC, he also recalled the other part of the agreement he had made with Mitch. "I'll promise you thirty dollars for every O'Brien and Boyle that you call up to the stage for a blowjob. And that is the minimum, perhaps you can get more from them on your own. However, on MAC Day, you'll let these two fuck you for $10 each and give me a blowjob, for just $5. You can tell the audience it was the price I charged for keeping you from getting voted as a Tailer. But to get that deal, you first have to blow me and these two, today, for free. If you get made a Tailer, Kyle and I can use you once a day for either a fuck or a blowjob, and we can invite a friend. This does not count towards your maximum." Recalling all this, Billy O'Brien knew he was screwed, really screwed, whatever happened on the day. Sam McGill (12) – 5 Days Before the MAC Sam had entered MAC Day only for the entrance price – one thousand dollars. Not enough for the motor bike he wanted, but he knew he could earn the rest. But then came rumors that kids were going to vote for him. Knowing the last thing he wanted was to become a tailer, he took an offer from Adam Jones. And that acceptance involved being fucked, something he had sworn to himself he would never allow. So now he needed training, and a trainer. Once he'd signed up, getting out of the MAC was impossible, so what choice did he have. And who would arrange such training – of course, none other than reliable old Adam Jones. Adam assigned his brother, Leo (12) and Sandy McGill (12) as Sam's joint dildo coaches. Worse still, the two 12-year-old classmates of Sam took on their new jobs with enthusiasm, vigor and determination. Soon Sam was on a strict and somewhat painful practice schedule, four times a day, where fake wooden cocks of different sizes were inserted into both his mouth and ass. Weeks ago, his oral training had gone from the dildoes to his trainer's dicks. He had been regularly blowing Leo and Sandy for weeks. "All part of your training you know." But with MAC Day looming, Adam decided he had graduated from wooden training tools to the real thing for fucking. Sam had begun to wonder whether being chosen as one of the 12-year-old Tailers would be such a bad thing compared to what was happening to him now. At least then he would earn the weekly wages. He arrived at the Jones' house, where three very eager boys awaited. He didn't want to be fucked, period. The two 12-year-olds were going to be bad enough. But Andy was thirteen, a year older than him. He'd sucked that dick, more than once already, and knew its dimensions. It didn't look huge, but once in his mouth it had seemed so much larger. He did not want to feel it in his ass. Fred (Curly) Flynn (12) – 5 Days Before the MAC If Bret and Ollie Mackey weren't living "the dream" the same could not be said for Curly Flynn. Of all the boys undergoing the rigorous pre-MAC Day training with the kits originally carved by Calvin Boyd back in the 1930s, Curly was perhaps the only boy having fun. Real fun - a dream come true type of fun. Curly's dildo coach was Clyde (Rock) McGill, the stunningly handsome 13-year-old 8th grader from North Valley Elementary. Curly had lusted over Rock from afar for years, hoping they might meet up, and have sex. That was the fantasy, and that was all it was, until Curly developed a plan to finally interact with his dreamboat. The plan worked out far better than Curly could ever envisage and now he was getting to spend his days in constant sexual interaction with this Greek god. Curly would never forget his first day of training with Rock, who had appointed himself the boy's dildo coach. He had been told to report to Rock's house at 9:30 AM precisely. "Don't be late," he was warned, "or there'll be punishment. We don't have a day to waste." Curly did report on time, and noted that Rock was checking his watch as he opened the door. He handed him the training kit he had brought with him. "Good, you are punctual. My dad is on the day shift for the next month, so we can have all the privacy we need to do your training," Rock explained. His dad was a cop, one of the two local law enforcement officials, and father and son lived in a decent house provided by the city, just outside the better part of town. Rock's mother had run off years ago with a travelling bible salesman. "Okay, I'm all set up in my bedroom. Follow me." As Curly followed Rock up the stairs, he couldn't miss the luscious buns on this teen hunk and was practically drooling at the thought of being admitted to the most secret sanctum of his trainer. He had dreamed of spending time in Rock's bedroom, and now it was happening. When they arrived upstairs, Rock made a point of stopping and digging through a pile of large signs in a metal basket on a high table next to his bedroom. The signs could be attached to the door by a small alligator clip that had been screwed into place. Curly was a little surprised by the one selected and displayed. "CAUTION. Future Tailer in TRAINING." Curly giggled. Obviously, Rock had printed this up himself, but was it meant as a put-down for Curly or a warning to Rock's dad if he came home from work early. It wasn't clear, so he didn't comment. Once inside, he saw that a large queen-size bed occupied the center of the room with a bedside table on either side. Then there was a dresser, a desk and office chair, a small tower desktop computer and screen and on the far side of the room was a large built-in cupboard. Curly was a little disappointed. Apart from a bunch of very cool posters on the wall, this room wasn't that different from his own. The other difference, of course, was the dark wooden Tailer Training Box that Rock had placed on one of the bedside tables. "Okay, strip, completely naked. That will be your first duty every time you come in here. Then stand in the corner with your hands on your head," Rock ordered. Curly undressed as Rock placed a large towel on the bed before directing the "future tailer" where to wait. "Okay, I'm guessing you already know the purpose of this training and the kit, right?" said Rock as he pointed to the box. " Curly did. Indeed, he was incredibly excited at the prospect. However, he made a point of pretending to be scared and fearful. It would never do to let Rock know his true feelings. "You are gonna be a Tailer, Curly. You know that, right? With only three 13-year-olds signed up, it's gonna happen. So you are gonna need to get used to sucking cock and getting fucked in the ass too. You'll be doing that up to 5 times each day, every day, for the next two years. Understand? This kit's supposed to make that as comfortable as possible for you. Get you used to taking dick in your mouth and up your ass. Right?" "Yes please," Curly wanted to answer, but he just looked down at the floor and tried to think sad thoughts. "And because you are 13, your ass and mouth will be available to any guy up to two years older. That's 15-year-olds. Well, in fact any kid 11 to 15 who wants a go. You understand that too, right?" Curly was perfectly capable of doing the math and was looking forward to meeting those older guys. It would certainly be weird if 11-year-olds started knocking at his door, but he guessed kids of that age would stick to the younger Tailers. "So, you've gotta be trained. Trained to take them really big ones. Some 15-year-old guys are pretty big I reckon. But don't worry," said Rock sympathetically. "I guess it won't be too bad. Lots of other guys have done it and lived to tell the tale. You're getting off easy after pissing in my dad's patrol car you know. He was really pissed when he first smelled it, and I had to help him clean up the stink. But it still smells a little off," Rock giggled. He reached for the Tailer training box and opened it, revealing the wooden dildos and butt plugs of progressively larger sizes. The smallest dildo was artfully carved to resemble the erection of a 12-year-old boy just entering puberty. The largest was longer and thicker than any cock Rock had ever seen and was supposed to represent the rampant dick of a 16-year-old in the full bloom of healthy youth. Each dildo was matched with a butt plug of equivalent length but of thicker girth. The plugs were narrow at the top, had a bulbous middle, and narrowed again just before spreading to a wide base that held it securely in a boy's ass. There were five matched pairs and each had names written in small print on the hinge-side of the lid. The five dildos represented the standard 25-day course of stretching an Alan's Beach Tailer would require to safely undertake his obligations to the community without harm. "Lie back on the bed and pull your legs to your chest," Rock ordered. Curly did as he was told, exposing a small, clean asshole of the same light-skin as the rest of his body. Rock knelt on the floor beside the bed and brought his hands to the boy's butt. He had a large tube of KY ready and commenced by squeezing a large glob of lube and spread the viscus liquid around the work area and then immediately concentrated on the sensitive anal flesh and hole. "Do you know how to unclench your hole?" asked Rock, raising his head from the asshole to look at Curly. "I'll try," But Curly couldn't do it. He just squeezed his anal muscle tighter. "No! Push out like you are taking a shit; don't pull in. Try again." This time the pucker opened slightly, and Rock's finger slipped in. "Oh! Oh!, Oh!" Curly couldn't help moaning. He wanted to say how amazing if felt to have Rock's finger inside him like that, but managed to stifle the words. "Stop your bitching," insisted Rock. "That's just my index finger. Wait till I stick the Lil' Pee-Wee in there." Curly could hardly wait. In the meantime, Rock set up a slow but steady finger fucking routine for the next 3 or 4 minutes and soon noticed that the hole became a little looser as the fingering continued. Eventually, he decided it was time to move on. He grabbed Lil' Pee-Wee, the smallest dildo, the wooden duplicate of a 12-year-old boy's stiff penis, which was mounted on a small wooden handle. The handle ensured that the entire 3.8 inches (9.7 cm) of cock could be inserted into the trainee's bottom. It had the diameter of a man's thumb. Rock squeezed more KY onto his hand, slathering it onto the business-end of the dildo and wiped the rest onto Curly's ass. Then he positioned it at the entrance of Curly's hole and eased it in slowly. "Push out like before," he ordered. As the fake cock slipped into his anus, Curly's eyes lit up and he smiled at his dildo coach. "It doesn't hurt too much!" he said. "It does feel strange... but I can take it." "That's good. Real good. Cause one day soon it's gonna be my cock in there, not this dumb wooden thing," said a smiling Rock. Once again, Curly could hardly wait. Rock began fucking the compact dildo in the boy's hole, sliding it back and forth so Curly could feel the sensations of a dick inside him. Without being touched, the penis of the Tailer-in-training pulsed up into a solid 5 inches of circumcised boy meat. Rock eyed the straining rod for a moment and briefly wondered why the sight didn't disturb him. He wasn't gay. He was pretty sure of that. He had never wanted to stare at other boy's boners before. But somehow, the knowledge that he had created this monster, pleased him. He had spent all of last night researching ass fucking on the internet. He had read about the prostate and how men (and presumably boys) could get erections when that organ was stimulated. He also read about anal orgasms and set this as one of his goals with any of the Tailers he fucked in the future. After all, he was not completely selfish, and would be happy if the Tailer had fun too. In fact, he rather liked the idea of another kid spurting his cum while he fucked him. But he wouldn't be jerking them off, of course. Pure anal orgasms were what he wanted. He stared at Curly's boner finding it beautiful in appearance and surprisingly erotic in its straining stiffness as he continued to fuck the boy with the dildo for the recommended 5 minutes. Then he decided it was time for Curly to do some of the work. "Now let's see how well you can suck me off." Rock knew that the instructions in the training box said they should be practicing cock sucking with the Lil' Pee-Wee dildo. But based on his previous experience, Curly was way beyond that and seemed to be able to easily accommodate larger dicks in his mouth. As part of his extensive research last evening, Rock compared his own penis to those in the box. He concluded he was a slightly generous Tiny Tim at 5.05 inches and he had a diameter of .95 inches. As Curly had blown him twice already, Rock rationalized ignoring the Training Box instructions, "for Curly's own good, of course." And here's something to keep in your ass while you do." Rock took the smallest butt plug from the box and eased it into Curly's hole, which was still slippery with lube. The boy scrunched his face as the bulbous part of the tool passed slowly through the tight circle of anal muscle, but then hid his smile when his asshole was clenched around the narrow portion just above the wide base. "It feels... kind of good. I like how it makes me feel warm and tingly inside!" thought Curly to himself, but he didn't say anything. "OK; switch places with me," said Rock; "and take my dick in your mouth." As Curly got onto his knees on the floor, Rock sat down on the bed and leaned back with his legs spread. "Make my cock stiff and then suck it good!" "Yes, sir," said Curly obediently. He fondled his trainer's penis with stroking fingers, watching with fascination as it stiffened to a youthful erection. "Lick the head first," instructed Rock, and nodded his approval as the boy lapped at the glans like a happy dog. "Now, lick down the shaft and suck on my balls." Curly did as he was ordered, as Rock gave him instructions for sucking and licking each orb separately, then both together. "That's enough with my balls; now wet your lips and slide them over the cock-head... Yeah; like that. Don't let your teeth scrape it! Run your tongue all around the top... Now take it deeper into your mouth. Move your lips up and down; a little further down with each bob of your head; keep working your tongue... Yeah; that's it! Keep going all the way down 'til your lip touches my belly. Take it all!" As the adolescent erection poked at the back of Curly's mouth, the boy gagged instinctively and pulled off. "Sorry!" he said meekly. "Get it back in your mouth and try again," said Rock firmly. "Taking it deep is something you're expected to do as a Tailer. Just go slow and try to relax. Now try again." Rock had no idea whether deep throating a cock was a required duty of a Tailer or not, but it made sense to him that they should. Curly tried several more times, unsuccessfully, to overcome his gag reflex, and he was almost in tears with frustration. "I can't do it!" Curly whined. "I think you need some motivation," said Rock with a sly half-grin. "Get up and lay across my lap." It took a moment for Curly to realize what was about to happen. Getting spanked wasn't something he had ever fantasized about, but today was his chance to experiment with boy-on-boy sexuality. He'd heard about kids that liked spanking, and he was prepared to give it a try. Provided Rock didn't get too carried away. "No! Don't spank me! Please! I'll try again! I'll be good!" Curly said in the best pleading, childish voice he could muster. Even Rock had to realize he was acting a roll. "Don't argue with me!" Rock barked. "Just do what you're told!" "Yes, sir," said Curly gently. Rock sat up straight on the bed with his legs together and drew the naked Tailer-in-training face-down across his lap. Rock felt – for the first time in his life – the thrill of wielding punishment. And he knew that this spanking was justified and would ultimately be beneficial in teaching his young student this essential skill as a cock-sucking Alan's Beach Tailer. Curly's stiff cock was pressing against Rock's own erection, and his beautiful, slender buttocks was just calling out to be spanked. The first swat of Rock's open hand came down hard and fast, and the sharp sound echoed off the walls... followed quickly by a high-pitched yelp of pain. When he was younger, Rock's dad would spank him in this position. He paused, savoring the moment, as his hand moved over the soft barely warm buttocks... and then he spanked the butt again, this time with five wacks in quick succession. Curly began crying out almost immediately, loudly begging for the misery to end. "Shut up, boy!" ordered Rock, as he stopped spanking. "When you get a spanking, you need to stay silent unless I tell you otherwise. So grit your teeth and learn how to take it without complaining." "Yes, sir," whimpered the boy, as he clenched his jaw firmly. The spanking came again in another brief flurry, but this time Curly remained almost silent. Rock was satisfied and let the boy up. "Alright. Try again to take my cock all the way." Rock's erection was stiffer than it had ever been, and he was eager to thrust it into Curly's mouth. The instruction continued for nearly an hour. Curly tried his best to learn, and slowly became more proficient at deep throating Rock's cock. Landon Kelly (13) – 5 Days Before the MAC Like his father, Landon had no moral focus and would happily exploit others in the worst possible way. But this spoilt rich kid did have one goal in life – a fatal flaw perhaps. He was fanatical about receiving the praise and approbation of his father, the widely successful, ruthless, and feared businessman. It was this need that led him to con fellow 13-year-old, Carter Boyd, out of a business idea the kid was trying to promote. Unfortunately, it also ultimately led Landon having to sign up as a contestant for MAC Day. His only goal in doing this was to stop Carter from getting money he needed for his logging business. He might achieve that, but at what cost? Kids who came from the "money families" in Alan's Beach absolutely never signed up as contestants in the MAC. The idea was totally unheard of. But having done so, Landon was likely to get dozens of votes from the poorer boys from North Valley Elementary who would enjoy fucking or getting a blowjob from a truly wealthy kid. By the same token, he was just as likely to receive dozens of votes from the boys at South Valley who knew Landon as an arrogant prick and asshole who needed putting in his place. In his case, there was no need for deals or agreements with influence makers at the different schools. Hatred and loathing for the boy would get him all the votes he needed. To make his life even more upsetting, Landon's father had appointed Shane Flynn (13) to train him. And as much as he'd rather have almost any boy except Flynn as his trainer, he was afraid to try and override his father's choice. Shane wasn't related, nor did he live on the correct side of town. He was a common boy. Yet he demanded Landon do as he said. And today, it was about to get far worse. The training kit had been put away. Shane was smiling as he entered Landon's room without knocking and uninvited. "You need to start practicing for the big day," Shane said. As he stepped beyond the door, three more boys were behind him. "In five days, you are going to be fucked on stage, three times or more. And after that, you can expect to be fucked many times per day. I've invited a few of my friends, and we are going to help you get used to it." Shane then introduced Cory Mackey (13), Adan Jones (14), and Drew McGill (14). "I will lead things off, then Cory will help to open you up, followed by Adan and then Drew. And we may even want a few blowjobs before they have to leave. So go ahead and strip so we can get started." "I deserve some say in who needs to be here," Landon began. "Then go tell that to your father. I report to him, not you. And with just a few days to go, it is time for you to get a true picture of what your life is going to be like after the big day." To be continued...