The shop bell jingles, and a child of about Oliver’s age breezes in. He has the sort of swagger that is painfully embarrassing in boys his age, and a backwards-turned baseball cap. He saunters up to the heavy wooden counter and eyes Mr. Mack suspiciously.
“Can I help you?” Mr. Mack asks with annoyance.
“Is Oliver here?” the boy demands. “He says he has a job here after school. I was lookin’ for him. Is he here?”
“As you can see,” Mr. Mack says with irritation, “he is not in today. I suggest you go look for him elsewhere.”
“But he said he has a job here,” the boy insists with the stubbornness of his youthful years.
“He does,” Mr. Mack repeats slowly and acidly, “but as I said, clearly he’s not in today. And if he was, he’d be working, and unable to waste time fooling around. You’d be much better off seeking him out on a weekend.”
The boy rolls his eyes, clearly unimpressed. He leaves the counter, but instead of immediately exiting the shop, he wanders the aisles, eyeing the merchandise. Mr. Mack itches to get up and shoo him out, but stays put.
For several minutes, Mr. Mack watches with gritted teeth as the boy trails hands over boxes, picks up action figures and puts them down again, and generally loiters. Finally he appears to grow bored and saunters back to the front door, slamming it unnecessarily behind him.
Mr. Mack rolls his eyes and reaches under the desk. He grabs Oliver’s hair where it is nestled like a little thatch over Mr. Mack’s crotch as the boy kneels between his legs, sucking him off. He takes a moment to admire the boy’s lips around the head of his cock before using his hand in the boy’s hair to push Oliver’s head all the way down and forward. Oliver chokes as his already-full mouth becomes fuller and Mr. Mack’s cock slides its way deep down into his throat. With a happy sigh, Mr. Mack comes hard into the warm, wet cavern. Oliver gags, but obediently does his best to swallow it all down.
When Mr. Mack finally lets go of his head, Oliver draws back and wipes at his spit-stained lips. “Can we go do the butt stuff now?” he asks hopefully, looking up at Mr. Mack.
Mr. Mack smiles. “Yes, I suppose you’ve earned it. Go lock the door and turn the sign. I’ll meet you in the back room.”
As Oliver bounds off to follow instructions, Mr. Mack zips himself back into his trousers. He’ll need a while to recover before he’s ready to fuck the boy properly, but until then there’s plenty they can do with their box of toys.
Mr. Mack stands and moves leisurely back into the office. Oliver speeds past him with the exuberance of youth, shedding pants and underwear as he goes, and hops up onto the desk in a single athletic leap. He sticks his ass into the air eagerly. It’s suspiciously shiny.
Mr. Mack smiles and approaches the boy. He sticks a testing finger into the boy’s anus and, sure enough, finds it well-lubed. “Why you darling little boy,” he says fondly, “did you slick yourself up for me?”
Oliver nods. “I did it in the school bathroom before I left. I wanted to be ready so we could go faster.”
Mr. Mack is touched. He licks his lips at the thought of the boy in a bathroom stall, leaned over the toilet, reaching behind himself with lubed fingers to stretch and open himself in preparation for Mr. Mack’s ministrations. What a darling boy indeed.
“Why don’t you show me?” Mr. Mack suggests. “Just show me what you did to get ready. So I know you did it right and I won’t hurt you,” he adds piously.
“I just did it like you always do,” Oliver says. Without hesitation he reaches behind himself and shoves three fingers into his own ass. Mr. Mack watches happily as he splays them a few times and then fucks himself with the digits in short, shallow thrusts. The angle is a little too awkward for him to get them in very deep, but he does the best he can, moving the hand around and loosening himself, preparing his passage.
“Good job,” says Mr. Mack. “That’s very good. Well then, let’s go right to something interesting, shall we?” He reaches into the box and takes out the large, gyrating dildo that always makes Oliver squirm. He takes a second to line up the toy and then slides it into Oliver in a single, fluid motion. Oliver groans as it sinks into him, and then groans again when Mr. Mack flicks it on and it begins to wriggle and thrust itself inside him.
Mr. Mack leaves Oliver to the toy’s ministrations and rifles through the box as he contemplates his plan of action. Maybe this should be the day. Oliver has been so good, and has proved just how eager he really is with his self-preparation. Maybe this should be the day they finally try fisting. Well, he’ll have to ease up to it. Test the waters, see how far Oliver is willing to go.
After a moment’s thought, he decides that phrasing it as a challenge is the most likely way to go. Oliver likes to prove that he can do things; Mr. Mack has used this to his advantage before.
“I’ve been thinking,” Mr. Mack says aloud. “I think you might be ready to try something a little more intense. I’m not sure though. It requires fitting a lot more into your ass than we’ve tried so far. I’m not sure whether you could handle it.”
Oliver groans, but doesn’t answer. It’s not exactly fair to ask him this now, when he’s so distracted. So Mr. Mack makes it even less fair by yanking the still-wriggling toy abruptly out of the boy’s twitching hole and asking again while the muscle gasps desperately to have the penetration returned.
“Huh?” says Oliver, dazed. “Sure. Uh, sure, I can handle it. Put whatever you want in my butt.”
Mr. Mack smiles and slides the toy back in. The gyrations of the thing are so wild that he has to briefly turn it off to still it enough to get it back up Olly’s ass. But once it’s nestled, he turns it immediately back on.
Oliver groans, his body writhing on the desk. His hand reaches down towards his crotch, but Mr. Mack swats the approaching wrist lightly. “Ah ah,” he chastises. You know the rule.”
The rule is that Oliver is not allowed to touch himself unless Mr. Mack’s dick is in Oliver’s ass. If he comes before that, it has to be from the penetration alone. It’s been known to happen.
Oliver groans, but returns his hand to the desk and doesn’t try again. “But it hurts,” he protests. “I want it so bad.”
“Well then, we’ll have to hurry up and put a bunch of stuff in you, won’t we?” says Mr. Mack gleefully. He finally spots the big black latex glove near the bottom of the box and takes it out, setting it aside. The thrill of anticipation makes him shudder nearly as hard as Oliver.
Mr. Mack reaches up and snaps off the switch on Oliver’s vibrator. The boy’s body twitches and shivers, his little hole clenching and unclenching around it.
“Well then, let’s do a test, shall we?” he asks rhetorically. Mr. Mack takes up the string of large vibrating anal beads that he’s had since he first bought toys for his dear Oliver. Each powder-blue sphere is roughly two inches in diameter, and the string contains ten of them. He recalls trying to fit them into the boy in that first week, and only barely being able to get the fifth one inside. Well, time to see how much the boy has improved.
Mr. Mack pushes the first of the beads easily into the boy’s anus, turning on the vibration immediately after burying it inside him. With a self-indulgent smile he reaches in a finger after it and pushes the vibrating ball down against the boy’s prostate. Oliver moans loudly; his tiny hard cock twitches in search of relief.
One by one Mr. Mack begins to push the other beads into Oliver. They slide easily into his slippery little hole. Before he knows it he’s gotten five beads into the boy, and he still feels barely any resistance at all. Mr. Mack’s heart pounds in triumph. The boy has adapted so well. No surprise from such an amazing child as Oliver.
He continues to force each sphere into the boy, barely pausing between them. Each one takes only a mere press of his thumb before the boy’s anus eagerly swallows it up, gulping it inside like a hungry mouth. In no time at all he’s on the last ball; it goes in almost as easily as the first. Olly kneels before him with the entire string of ten beads inside him and plenty of room left.
“I’m so proud of you, Oliver,” says Mr. Mack sincerely, tears at the corners of his eyes. “You fit all ten so easily! You’ve learned so much.”
Oliver just whimpers. “Can you please put your penis in me now?” he whines. “Please?”
Mr. Mack licks his lips. “Patience, my boy. We’re almost there.” Out of curiosity, he pulls another dildo out of the box. It’s not the same monstrous one as before, but much more ordinarily sized. He wants to try...
Holding the ring at the end of the anal beads to prevent them from getting lost inside Oliver’s rectum, Mr. Mack proceeds to slide the dildo in alongside them. As he had hoped, he’s able to get it all the way inside with little trouble. Oliver truly has grown.
“Is it in?” Oliver asks impatiently.
“Now now, you can’t tell the difference between me and your favorite toys?” Mr. Mack chides. He grabs the base of the dildo and rams it home a few times, fucking the boy with it idly. Oliver bites his lip but submits to the ministrations in silence.
But this is not what Mr. Mack has been looking forward to. He pulls the dildo back out of Olly with only mild regret and tugs on the end of the string of beads. Oliver’s hole gives them up reluctantly, each one sliding out of the twitching ring of muscle with its own little pop and a tiny splash of lube.
Finally, Mr. Mack takes a deep breath and puts on the big black glove. It seems intimidatingly large, but he has faith in his boy.
Without further foreplay, Mr. Mack lines up his hand and begins to shove the entire thing into Oliver.
Olly groans when the ball of Mr. Mack’s hand stretches him wide, wide open, then slips suddenly forward up to the wrist. Mr. Mack keeps pushing and keeps pushing, desperately curious how far he’ll be able to go. His hand just keeps going in further and further and further, without stopping. Mr. Mack’s eyes widen as he embeds more and more of his arm in the boy’s rectum, only coming to a final stop when the glove runs out shortly before his elbow.
Oliver writhes on the penetration like he hasn’t done in weeks. “It’s so big,” he murmurs. “It’s too much, it’s weird, it’s so much.”
“Too much?” Mr. Mack questions. He begins to pull his hand back and then rams it forward again, sending a jolt through Oliver’s entire body. He grins and does it again. And again, and again, and on and on, impaling the boy on his forearm over and over. This opens up so very many possibilities for fucking the boy. The sky is truly the limit now. Mr. Mack sighs in utter bliss.
“Please,” Oliver finally whimpers, after Mr. Mack’s arm has been embedded inside and drilling into him for several minutes. “Please, please, I need it so bad, I need to...”
Mr. Mack feels a twinge of pity. The boy has been waiting to come for hours now, including the time he spent sucking off Mr. Mack in the shop earlier. And yet he finds himself reluctant to remove his arm from the boy’s anus, now that he’s finally managed to get it in there. Hmm. Well, perhaps...
Mr. Mack pulls his arm back to the wrist until only his fist remains inside the boy. With a little squirming, he’s able to angle his closed hand so that the circle made by his curled pinky finger is just behind the sphincter of Oliver’s hole.
Grabbing the boy’s hip with his remaining hand, Mr. Mack pulls the boy backwards and guides his cock to the boy’s anus. With a tortuously slow push forward of his hips, he stretches the boy open even wider, forcing his phallus into the welcoming circle of his fingers beyond the boy’s sphincter. It’s unbelievably tight; the boy’s passage parts only very reluctantly around the added girth. But part it does, inch by inch, until Mr. Mack is holding his own cock inside Oliver’s passage.
“There we go Olly,” he says cheerfully. “I’m inside you now.” He begins to thrust. It’s almost like masturbating, with the familiar feeling of his fingers sliding up and down his member. But he doesn’t even have to clench his fist at all to achieve incredible tightness: the walls of Olly’s passage do that for him. The sounds that come from his thrusts are obscene; loud, messy wet squelches as the lube splashes out around Mr. Mack’s cock at each thrust. With another pleased sigh, Mr. Mack finds a rhythm and settles into fucking the boy.
With Mr. Mack’s cock up his ass, Oliver’s hands fly immediately to his own penis, milking himself desperately. He comes almost immediately, and the clenching spasms of his orgasm force Mr. Mack’s fingers to tighten deliciously around his own member.
Mr. Mack continues his thrusts through Oliver’s orgasm and long after the spasms have ceased. After a few moments it’s clear Oliver is being overstimulated with the way he wriggles and groans, but to his credit he does not try to stop Mr. Mack from doing what he wants. Mr. Mack fucks the boy genially, enjoying himself immensely and in no hurry to finish.
Mr. Mack has improved a great deal over the past months as well, his stamina increasing considerably with regular penetrations of the boy. He’s fully capable of fucking Oliver for over half an hour now when he wants to. Perhaps he ought to test his own limits at some point and see how long he can manage. Wouldn’t Oliver look cute, splayed out and writhing on the desk for an hour while Mr. Mack relentlessly pounds his tight little hole?
But not today; Mr. Mack is too delighted by the boy’s prowess in fitting so much inside him, turned on by the sight of his fist still embedded in the boy.
Oliver has grown hard again while being fucked, and reaches down to start pumping himself once more, groaning with wanton pleasure. The sight of the boy so eager to be railed, to have his hole so mercilessly claimed, is the final tipping point for Mr. Mack. He comes sloppily into the boy.
As his softening dick slips out of Oliver’s hole, still distended around Mr. Mack’s fist, Mr. Mack reaches down and gently but firmly removes Oliver’s hands from the boy’s own member.
“But- no! Wait!” the boy cries in distress. “I wasn’t done, I-”
“You know the rule,” Mr. Mack repeats. “I’m done with that hole for now. If you want to come again, you’re going to have to do it without touching.”
Oliver whimpers, making Mr. Mack smile. With an easy, fluid motion he pushes half of his forearm back into the boy, returning to fisting him properly. He plunges his arm into Olly over and over until the boy’s anus is wide and red and weeping from it. Oliver is clearly very hard, but without direct stimulation to his prostate he’s unable to come from just the sheer girth of the limb inside his anus.
Mr. Mack continues to fist the boy, on and on and on, until he feels himself start to grow hard again. He’s lost track of time. How long has he been ramming his fist into the boy? His fingers are starting to feel pruney from the clammy sweat inside the glove. But it’s such a lovely sight, he just can’t help himself. He never wants to take his arm out.
But of course, eventually he’ll have to. Mr. Mack eyes the clock. Oliver will be needing to get home for dinner soon. More’s the pity. Leaving his arm impaled nearly elbow-deep in the boy, Mr. Mack steps around the side of the desk.
“Why don’t you suck me off one more time, hm?” he offers.
Oliver looks up at him with big, pleading eyes. “But I need to- to come.” He’s still getting used to using the proper words for these things. “Won’t you please put your dick back in my ass instead? Pretty please?”
Mr. Mack melts with Olly’s expression. It’s everything he’s ever dreamed of, the pinnacle of what he’s been hoping for. The boy, splayed out in front of him, ass already full and still begging to be fucked.
“Tell you what,” he says sympathetically. “You take my cock in your mouth, and I’ll make sure we get something to hit that special place inside you, okay? Then I’ll put my dick back in you when I’m close, okay?”
Oliver nods in agreement, eyes lowered deferentially. Reluctantly, Mr. Mack pulls his arm out of the distended, weeping wreck of Oliver’s anus. Mr. Mack re-arranges the boy until he is sitting between Mr. Mack’s legs, with the box of toys nearby to hand. As Oliver proceeds to lower his mouth onto Mr. Mack’s dick, Mr. Mack fishes around in the box for the bullet vibe.
As Oliver gags slightly at the taste of lube and his own rectum on Mr. Mack’s cock, Mr. Mack nudges the bullet into the boy’s hole and presses it down against the boy’s prostate with his thumb. Oliver begins to make obscene little gulps and whimpers around Mr. Mack’s cock every time he pulses the little toy against the boy’s sensitive spot. Mr. Mack smiles, taking blissful note of the way the boy’s spit dribbles down his chin as he tries to take all of Mr. Mack at once.
Mr. Mack has already come twice now, and it takes him a long time to get fully hard again. He fingers Olly’s hole idly while the boy’s head works him back up to attention. It’s so loose and open now that it’s tough to get the vibe to stay in place without the additional pressure of his fingers. Mr. Mack easily fits most of his back hand into the hole as he steadily pulses the bullet vibe against Oliver’s prostate again and again. With his free hand he pets Oliver’s hair encouragingly.
The boy is very hard, his tiny dick twitching eagerly with each press of the vibrator. Mr. Mack wonders if he will come just from the prostate stimulation alone. It’s only happened a few times so far, but Mr. Mack is certain that as they continue to practice he can make it happen more and more. The thought of Oliver coming just from being fucked is an unbearable turn-on.
Finally, when Mr. Mack is too close to stand it any longer, his grabs Oliver’s head and forces the boy to deep-throat him one last time before pulling the boy off of him and spinning him around. He plunges into the boy’s ass easily, without bothering to remove the bullet vibe first. In fact, he goes in so easy that he grabs up the smaller dildo from earlier and shoves it back into the boy’s ass alongside his own before he starts his thrusts, just to increase the pressure.
Oliver gasps and squirms and reaches down to tug at himself, gasping in relief as he is finally allowed to touch his penis once more. He hurries to stroke himself, desperate to get off before Mr. Mack can do so first and leave him hard for the rest of the evening.
Moments later Oliver comes, and the desperate spasming clenches of his passage around the combination of the bullet, the dildo, and Mr. Mack’s cock are too delightful to resist. Mr. Mack comes again inside the boy, delivering a second helping of semen as deep into the boy’s rectum as he can get. He lets out a deep, satisfied sigh as the last spurt of his cum fires up into the boy.
Letting himself slip out, Mr. Mack reaches for his nearby phone and takes a few pictures of Oliver’s asshole: it’s more distended and abused than it has ever looked before. Certainly a high bar for future encounters.
“There we go,” Mr. Mack says cheerfully, sliding off the desk and patting Oliver’s dripping behind. “Now, what do we say?” he prompts.
Oliver gulps, still shaking from the intensity of the session. “Th-thank you for fucking me, Mr. Mack,” he says.
Mr. Mack smiles. “What a good boy.”