The three days that follow are the most nightmarish thing Tommy has ever experienced. The four men who’d kidnapped him keep him tied up on the couch and sate themselves with his body whenever they feel like it. It becomes almost routine, the feeling of a cock sliding up into him, or hands forcing his mouth open. At some point Tommy finally plucks up the guts to try and bite one of the men as they force him to blow them, but the only result is that he gets the ring gag put back into his mouth for his trouble.
They’re not all around all of the time, but there’s always at least someone there to watch him, to stop him from trying to escape. Time begins to blur together into an endless sea of waking and sleeping and waking up to one or two of the men fucking him once more.
Three days must eventually pass; Tommy has long since lost track of the time. He wakes up from several hours worth of sleeping to find himself, strangely, being cleaned up.
One of the men is dragging a soft, damp washcloth along his thighs, cleaning up days worth of dried cum. Tommy is startled into waking from where he’d been dozing on the dirty couch, fear spiking once again through his veins. What now? The cool sensation trails up and up until they get to his ass, wiping it thoroughly clean and even going so far as to stick a corner of the cloth up his rectum, twisting it around almost playfully before pulling it back out. Another of the men gives the same attention to his face, removing the ring gag and cleaning dried cum from his cheeks, chin, forehead, nose, and hair. There’s a substantial amount to remove.
After these ministrations, the men man-handle him back into his pants (they’d long since removed them for ease of access) and drag him to, surprisingly, a cage.
He hadn’t seen it around the warehouse before; he’s not sure where it came from. One of the men must have brought it when they last went out. It’s one of those animal cages intended for large dogs; not spacious, by any means, but large enough that Tommy can fit into it entirely without touching any of the sides. The men don’t untie Tommy’s bonds before throwing him in, and padlock the door behind him for good measure. Then, finally, they load him back up into the back of the van that had first brought him to this hellscape.
Only two of the men come with this time: the driver, Andy, and one person in the back of the van with Tommy, the man with the cap. Tommy isn’t fully certain of their names, but he thinks this one might be called Hank.
The men are silent as they drive Tommy to whatever mystery destination they have planned. They don’t bother to tell him where they’re going; Tommy doubts they would even if he asked, so he just stays silent.
Eventually the van comes to a stop. To Tommy’s surprise, Hank throws a cloth over the cage before the van doors open, leaving Tommy almost entirely in the dark. He hears the car doors slam and open, and feels the cage being lifted. They’re carrying him somewhere.
It takes a while. He hears the low murmur of voices behind the cloth, like he might be traveling through a semi-crowded space, but he’s afraid to cry out for fear of who might be on the other side. He hears a ding, and feels the tell-tale stomach swoop of traveling on an elevator. Where are they taking him?
Eventually, he feels his carrying container being set down. Everything is silent for a moment. Then, the sound of a door opening. The murmur of soft voices. “Hello again. He should be here any moment. Thank you for waiting.” And then another door.
“Alright Gentlemen.” This new voice is deep and smooth, calm and composed as a news anchor. “I’m afraid I don’t have a lot of time here. Let’s see the goods so you can get your payment.”
The cloth is suddenly, blindingly stripped from Tommy’s cage. He blinks in the unexpected light. When his eyes adjust, he finds himself in a round, red room with multiple doors along the walls. A large plush couch, round and flat like a giant ottoman, sits in the center of the space. There are five men in the room. In addition to the two that brought Tommy here, there is a man in a tweed vest and large glasses who looks like a professor, another man more fashionably dressed with multiple piercings in one ear and, finally, an imposing man in a professional-looking suit who stands over Tommy’s cage and looks down at him.
The man’s face shows no particular expression. He looks nearly bored, like he’s waiting in line at the supermarket. He surveys Tommy briefly, obviously evaluating but betraying none of what he’s thinking. After his cursory appraisal, he nods. “A little on the older side, but he’ll do. At that age they sell better trained. Cecil, put him on the schedule.”
The man in the fashionable outfit nods and makes a note on a clipboard. The man in the suit snaps at the two kidnappers and points at the door to the cage. “Open it. I want the doctor to look him over before you get paid.”
The two men who brought Tommy hasten to obey, unlocking the padlock and dragging Tommy bodily out of the cage. Tommy wants to struggle, but he’s weak from three days of almost nothing to eat. There’s little he can do as he’s thrown bodily face-down on the couch.
The man in the tweed vest, the doctor apparently, approaches Tommy, pulling on a pair of latex gloves. When he reaches him, he removes a flashlight from his pocket and begins inspecting Tommy as he would for any other physical the boy has ever been to: shining a light into his eyes and ears, telling him to say “ahh.”
“Now,” says the man in the suit as the doctor pokes and prods Tommy. “I want you to tell me that this boy is a virgin.”
“Yes Sir,” lies Hank. “One-hundred-percent grade-A fresh holes. As requested.”
“Good,” says the man, just as the doctor gets behind Tommy and pulls his ass cheeks apart, investigating his anus with the same efficient thoroughness as he’s done everything else.
He runs a gloved fingertip along the edge of Tommy’s hole and then presses the tips of his finger and thumb inside, spreading it apart to get a look at the interior. The fingers disappear and then Tommy hears the tell-tale snap of a cap of lubricant before a slick digit returns, sliding up his rectum and feeling around inside him. Tommy whimpers as it brushes his prostate experimentally.
The finger is removed, and Tommy feels himself being turned over. The doctor hefts his cock and balls in one hand, turning them and looking at them closely. It would be intimate if it wasn’t so clinical.
Finally the doctor turns and nods to the man in the suit. The man nods and reaches out a hand to Hank, who takes it and shakes it. “Very good then. Your payment will be waiting for you at the front desk when you leave. Pleasure doing business with you.” He turns to the man he had called Cecil. “He’s all yours.”
“Roger that Boss,” Cecil responds. His voice is laconic, an unhurried drawl like a predatory cat waking up to stretch for the day. He smiles down at Tommy. “Your lucky day, Boy, we’re about to have some fun.”
As the other men leave the room, Tommy is surprised by Cecil cutting through the restraints on his legs. He hauls him to his feet by the remaining ribbons binding his arms; Tommy stumbles as blood rushes back into his numbed lower limbs.
Cecil opens one of the doors along the wall into what looks like nothing so much as a hotel bedroom. It’s lavish, with soft plush furnishings in shades of red and brown and an enormous bed that takes up most of the space. There’s even a tiny fridge and a TV, along with a door in one corner that looks like it leads into a bathroom.
Cecil throws him unceremoniously onto the bed. “Alrighty, Boy, listen up,” he says. “Here are the rules. Your name is Boy. Or John, or Elliot, or Gertrude, or whatever the fuck I or the man fucking you tells you it is. This arrangement is simple: you do what I say? You eat. You do it quietly, obediently, and with general good behavior? You keep your privileges, like this nice room with a soft bed. You fail to do these things, and we put you back in the cage on a cement floor and have men fuck you through the bars until you wise up and change your mind. Got it?”
Tommy says nothing, dazed and horrified by what he’s hearing, until Cecil swats him on the ass. “I said, ‘got it’? That’s a ‘Yes Sir’ if you can hear me.”
“Y-yes Sir,” says Tommy, cowed.
“Good,” says Cecil. “Now, we’re gonna start by teaching you how to blow a man. Let’s see what you’re working with.”
And so begins Tommy’s education. Cecil is exacting, but not unnecessarily cruel. He begins with oral sex, forcing Tommy to blow him immediately and then several times a day from then on. He persists without mercy, forcing his cock deeper and deeper each time until Tommy finally learns to relax his muscles and deep-throat. The first time Cecil manages to get Tommy to swallow his considerable cock all the way down to the balls, he pets the boy’s hair fondly. “See?” he says, “I knew you could do it. You’re a quick study. Plenty of other boys need months before they can take so much cock.”
His ass is not safe either, although Cecil doesn’t fuck it himself. Instead, he uses toys. On the second day of Tommy’s new life, the man presents him with a large dildo attached to straps that secure around his legs and buttocks. He lubes it up and forces it up Tommy’s ass, securing it in place so that the toy remains nestled inside of him. “This is your trainer,” he informs Tommy. “You are to keep it inside you at all times except to use the bathroom or unless I remove it.” He gives it a little pat. “This is to get you used to having a single, average cock in you. We’ll work our way up to more advanced configurations.”
Tommy does his best to obey and, as promised, finds he is not punished. In many ways, it’s at least better than the warehouse. He has his own bathroom here, and real food in his little mini-fridge. Even television and a few books to read if he gets bored. And the bed is certainly softer than sleeping out on the street. The door back into the circular room is, however, locked; comfy as it is, his two rooms are nevertheless still just a larger cage.
He is, for the most part, able to follow directions. He only slips up once in the first week, when the toy he is forced to walk around with becomes unbearable. He unstraps it, sighing in relief as he draws the thick silicone object out of his rectum, figuring he’ll just put it back in before Cecil returns and the man will be none the wiser.
It doesn’t, however, go as he plans. He’s unprepared when he hears the door begin to unlock, and as much as he struggles, he’s unable to get the toy back inside himself before Cecil catches him.
The man shakes his head and clicks his tongue softly in disappointment. “And you were doing so well, Boy,” he says. “I had high hopes for you.”
The retribution is immediate and brutal. Cecil moves with lightning speed that Tommy was not expecting. He twists Tommy’s arm painfully behind his back and forces him down onto the bed while he ties him up, restraining Tommy’s arms. Then he grabs the boy by the hair and force-marches him out of the room, back into the circular room and out another door into a stark, cement hallway.
He drags Tommy into a room that looks like a janitor’s closet and, as promised, throws him once more into the dog cage that he’d been secured in when he arrived. The cage is fetched up against a corner of the room between a cement pillar and some kind of large piece of machinery. Before Tommy can so much as struggle, Cecil has strapped him in further; his thighs are belted to the bars of the cage, leaving his bare ass pressed invitingly up against the side opposite the pillar.
“You’re in luck,” Cecil says, his voice still perfectly calm. “Since you haven’t started taking customers yet, you won’t have to deal with their abuse while you’re in here. We’ll just have to settle for this instead.”
Tommy can’t see what he’s doing, unable to crane his head back far enough to get a glimpse. With his arms secured behind his back, he can’t even lift his torso up from the ground. He certainly feels it, however, when a phallus-shaped object is deftly inserted into his anus through the bars of the cage, sliding all the way inside him.
“Please!” he tries to protest, afraid of what is about to happen to him. “Please, I didn’t mean it! I just wanted a break, I won’t do it again! Please!”
“If you really want your punishment to be over quickly,” Cecil informs him, “then just accept it and endure it quietly. The more obedient you are, the more quickly it will be over.”
Cecil stands up, and moments later Tommy hears the whirr of a motor starting up. The fake cock inside his ass begins to move. Tommy’s eyes widen.
The machine next to Tommy’s cage is, as it turns out, a fucking machine. It rams the cock-shaped toy into Tommy again and again in a cold, unceasing rhythm. There is nothing Tommy can do to protest or even try to squirm away as he is penetrated over and over and over by the action of the mechanical pistons.
Cecil leaves him there, locked in the cage and being fucked by the machine. The only light in the room comes from a small, tiny window high up on the wall. There are few other features around him to offer any kind of distraction.
Tommy assumes Cecil intends to leave him like this for a few hours, but eventually night falls with no end to his torment in sight. The machine continues to fuck Tommy over and over and over until eventually he passes out, waking up the next morning to the machine’s continued attentions.
Cecil leaves him in the room for two days, until Tommy’s ass is raw and sore and he’s so hungry he passes out every few hours. When the man finally deigns to unstrap him, Tommy’s entire lower half is too numb to feel.
“Have you learned your lesson?” Cecil asks him calmly.
“Yes!” Tommy screams between thrusts. “Yes! Please! Just let me out! I swear I’ll do whatever you want, just please!”
“Please?” Cecil asks with an eyebrow raised.
Tommy swallows. “Please, Sir.”
“That’s better,” says Cecil, and turns off the machine.
He has to carry Tommy back to the room; the boy’s legs are too numb to stand. When they arrive he applies a soothing cream to Tommy’s red, heavily-abused anus. He leaves him there with some kind of nutritional drink within reach on the bedside table. Tommy drinks it and falls fitfully in and out of sleep for the rest of the day.
Cecil still comes in for his thrice-daily blowjobs, but leaves Tommy’s ass alone for several days until he’s fully healed from the ordeal. Then, Tommy’s training begins once more. In addition to the toy that he is to keep strapped up his ass at all times, Cecil occasionally comes by with a vibrator, which he sticks in beside the existing toy and turns on.
“You might be called upon for double-penetration,” he explains. “It’s important you be able to take both cocks without tearing. The men who pay for you likely won’t be as gentle with your holes as I am.”
But perhaps the worst of the training, at least in Tommy’s mind, is when Cecil comes into his room one day, sits down on the bed with one leg crossed over the other, and says simply, “Seduce me.”
“I-I’m sorry?” Tommy asks in confusion, belatedly adding an obedient, “Sir?”
“As part of your training,” Cecil explains, “your customer may want to know that you want it, and want it bad. I want you to show me that. Bedroom eyes, slinky walk, a desperate hunger to have a dick put in you. I want to see it from you.”
“I... I don’t know how,” Tommy admits.
“Give me your best shot,” Cecil instructs, “and I’ll guide you from there.”
And so Tommy learns to put on a show. Cecil shows him how to approach a man, tells him what compliments to use, how to talk dirty. How to gauge whether his customer wants enthusiasm or shyness. He shows him how to be sexy while preparing himself for penetration. They even use an anatomically-correct dummy to teach Tommy how to properly ride a cock for a man who doesn’t want to put in the effort. Every single stage of it is humiliating, and makes Tommy feel like he’s dying a little bit on the inside, but at this point he’s utterly terrified of the consequences. All he can do is obey Cecil the best he can and pray he meets expectations.
Tommy doesn’t have a calendar in his little room, but he thinks it’s roughly a month or so after his initial imprisonment when Cecil finally enters his room and says, “Good news kid, it’s graduation day.”
“What?” asks Tommy, confused.
“Today’s the day we make sure you pass all the tests. Then we put you out on the market. Our premiere customers will have a chance to bid on you as a permanent accessory while you’re still virginal, or if no one wants you that bad you’ll go into general rental rotation until such a time as someone decides to actually purchase you. Congrats.”
“I-” Tommy starts, stunned, but then catches sight of Cecil’s expression. “Yes Sir,” he says meekly. “Thank you Sir.”
“Attaboy,” Cecil says with a smile. “Now, show me what you’ve learned.”
He sits on the bed. Swallowing his bile, Tommy does his best slinky walk over to him, climbing onto the covers and crawling over to him. He reaches for the fastening on Cecil’s tight, peach-colored pants. “May I please suck your cock, Sir?” he asks. “Please? It’s been so long, I want something in me so bad. Please can I make your cock nice and wet for my ass, Sir?”
Cecil grins and leans back on the bed, making a “have at it,” sort of gesture towards his penis.
Tommy can feel his mouth starting to water in a pavlovian reaction. He swallows, then leans forward to take Cecil’s cock between his lips.
He bobs up and down on it with well-practiced motions, sliding it in and out of his throat. As he does so, he reaches down with one hand and begins to pull down his own pants, exposing his ass to the open air. For once he’s not wearing the dildo; for the few days Cecil has let him go without. Now he knows why, Tommy supposes.
He massages his own asshole with the fingertips of one hand, making himself moan around the cock in his mouth. He tries to make enthusiastic noises around the spike of meat, as he was taught, conveying how happy he is to be swallowing Cecil’s manhood.
When Cecil’s cock is good and wet, Tommy begins to draw back to get the lube. But Cecil’s hand in his hair stops him.
“Just finished what you started,” Cecil commands. “It’s not my cock that’s going up your ass for now anyway, so you might as well. Be patient; we’ll get there.”
Tommy swallows and does as he’s told, continuing to deepthroat Cecil’s cock. He forces it deep into himself over and over and over, swirling his tongue around the head every time he pulls off and swallowing around the base every time he goes down. He tries his best to show off what he’s learned, kneeling with his face low and ass presented invitingly in the air as he helps Cecil fuck his face.
Eventually, he feels the man’s balls tighten. He swallows earnestly as Cecil begins to come inside him, drinking the liquid down in eager gulps, leaving the cock deep in his throat until he’s gotten every last drop.
He licks his lips self-consciously as he draws back, looking to Cecil for what he wants him to do next.
Cecil reaches under one of the pillows and pulls out an enormous black dildo, at least twice the size of the one Tommy was trained on. Tommy’s eyes widen when he sees it.
Cecil grins and hands it to him, along with a small tube of lube. “Fuck yourself with this,” he instructs, “and pretend it’s me. Talk to me as though I’m the one fucking you. Keep going until you come just from the toy. No touching yourself.”
Tommy swallows once more and takes what he’s handed. His mind races as he tries to imagine how on earth he’s going to fit this damn monstrosity inside him, let alone come from it. No way. No way! What is he going to do? Eventually he smiles as best he can at Cecil and finishes removing his own pants.
He lubes his fingers, lays back, and begins to finger himself open. “Mm,” he moans. “My hole wants it so bad. But you’re so big, just give me a second to get myself ready. Otherwise you’ll definitely break me with that monster cock. Here, let me just...”
As he continues to finger himself with one hand, Tommy lifts the fake cock to his lips with the other and lathes it with his tongue. It’s actually too big to fit in his mouth, but he does the best he can to get it as wet as possible, even while he smears lube hastily around his insides.
He can’t get his fingers deep enough inside himself as he knows he really needs to for a toy of this size, but he also knows he doesn’t have much of a choice. Unfortunately, the little prep he’s able to do will have to suffice. Tommy sits up once more and hastily coats the toy in as much lube as he can manage.
“Here we go,” he says, trying his best to sound upbeat and seductive. “Now you’re ready. Good thing too, my hole is aching for you. Won’t you please put it in me?” He waggles his ass slightly before lining the toy up with his entrance.
‘Here goes nothing,’ he thinks, and begins to push in.
It’s so big that at first he’s too distracted to remember to talk. The damn thing feels like it’s cleaving him in half. He’s panting with exertion before he’s even fully gotten the head of the toy inside him.
As the initial pain of the penetration subsides, Tommy remembers himself and opens his mouth again. “Oh god, so big!” he says. “That’s it. That’s the monster cock I wanted. Yes, please, fill me up baby. Put it all the way inside me! Stuff me full of your meat!”
He keeps pushing, but it’s slow going. It’s not going to fit. He knows it’s not all going to fit; the thing is nearly the size of his forearm. But he does his best. Inch by inch he feels the toy disappear inside him, feels the way his own hole twitches around it and swallows it deeper. He tries to keep up the dirty talk around his panting. “Yes! Yes! Oh god, deeper, yes!”
Finally, he gets it in as far as he can manage. It’s barely over half of the thing’s length, but it’s all he can do. Gritting his teeth, he starts to fuck himself with it.
“That’s so good,” he says through his clenched jaw. “Yeah, fuck me as hard as you can. Yeah, break my ass in half. Do it!” He swivels the toy in and out of himself.
All well and good, but how the hell is he supposed to come from this? Tommy wiggles his ass, clenching and unclenching around the toy and rubbing it up against his insides, trying to rub it up against his prostate as best he can. “That’s it,” he mutters, “come on baby.”
He’s come from just prostate stimulation before; Cecil had insisted on it. In fact, he rarely lets Tommy touch himself during lessons. But usually someone or something else has been stimulating him, and never with something this big. It’s a struggle to get it to press against the right spot without causing just as much pain as pleasure. The way the toy is splitting him in half is practically unbearable.
But he persists. Little by little, Tommy feels himself getting hard. He tries to focus on the pleasurable feeling, and ignore how cleaved-open he is. He uses short, fast thrusts of the toy, pulling it out to a shallow depth so he can really drive the head home into his prostate. He throws his head back and moans; only the fact that he has both hands on the toy is keeping himself from reaching up and trying to tug himself off.
Finally, finally, after ages of Cecil watching him fuck himself, Tommy finally feels the waves of pleasure begin to crescendo. “Yeeees!” he wails. “That’s it! That’s the spot! Yes! Fuck me! Fuck me fuck me fuck meeeee!”
And then he’s coming, spilling all over his chest and stomach, feeling his rectum tighten fiercely around the toy. He nearly sobs in relief as his body shudders through wave after wave of orgasm.
And then, before he’s even fully finished the spasms, Cecil reaches forward to the base of the toy and shoves the entire length of it up into him in one sharp motion.
Tommy screams, feeling like his eyes are going to bug out of his head. He’s never taken something so deep before. It’s so far inside him he imagines he can feel it in his throat when he swallows. He writhes on it, desperate to get it out but so far gone that he can’t do anything useful.
Eventually he subsides with a whimper, the toy cock still fully inside him. He’s panting heavily, his breath hitching in pain and humiliation. He can’t even take the thing out himself. He feels utterly broken.
“There we go,” says Cecil pleasantly. “Now, what do we say?”
Tommy gulps. “Th-thank you for the cock, Sir.”
“Good boy.” Cecil ruffles his hair. “You did an excellent job. Passed with flying colors, I’d say. You’re ready for your debut. I’ll send the doctor in to give you one last check-over, and then you should get some rest. Tomorrow’s a big day!”
Tommy lays silent in the middle of the bed, cleaved in half by the enormous sex toy, and tries not to think about what might come next.