Mr. Mack hardly sleeps a wink on the final night. He’s too keyed up imagining what he will do the next day. He spends most of the evening languidly masturbating to the photos he took of Oliver the previous afternoon. He knows he will only have one more day with the boy, and he must make it count. This is the day to indulge his true fantasies.
What little sleep he does get is wracked with dreams about the boy: Oliver, sucking him off. Oliver, begging Mr. Mack to fuck him. Oliver, writhing in pleasure as he is impaled on Mr. Mack’s fist.
He’s a bit more tired than he would like when he comes into the shop in the morning, but he’s prepared to power through it. He’s also prepared for this to last as long as he can possibly make it: in his pocket is a pack of mostly-legal pills that advertise the “endurance of a true stallion,” whatever that means. Mr. Mack figures that if they give him some kind of sudden heart failure while fucking the boy, at least he’ll die happy.
Oliver once again arrives early, which is a good sign. Mr. Mack has cleaned the maid outfit of their previous interaction, and holds it out to Oliver with a smile. Oliver takes it without comment and makes his way to the bathroom to change. Mr. Mack is only now struck by the ludicrousness of the boy being too shy to change in front of him, considering what Mr. Mack is about to do to his body.
While he waits, Mr. Mack pops one of his mysterious pills. He doesn’t notice any immediate effects, but he imagines they will take a little time to kick in. If there were immediate effects, he’s not sure he would notice regardless; he’s been half-hard all day in anticipation of this event.
Olly appears, once more in the maid costume. He’s like a pinup; an angel at once wholly innocent and utterly filthy. Mr. Mack finds himself captivated by the creamy stripe of flesh between the top of the boy’s tall white socks and the white lace of his panties. Utterly delectable.
Today, Mr. Mack won’t worry about frightening Oliver away. Today, he won’t worry about getting caught, or about doing something that might be difficult to explain to the boy. Today he will indulge himself.
Oliver hops up onto the desk for the final time and points his ass at Mr. Mack. Mr. Mack takes a moment to caress it; he grabs the cheeks in each hand and squeezes, loving their soft give. The flesh dimples under his eager fingers. Mr. Mack massages, squeezes, presses the cheeks together, then runs a thumb down the cleft between them. It’s like having a banquet laid out before him; though his mouth is watering he wants to take a moment to savor the aromas before digging in.
He teases the boy’s asshole with a single finger through the cloth, pressing against the pucker, pushing as far forward as the taut satin fabric will permit. The boy wiggles his ass impatiently, seeking out more contact. Mr. Mack’s pulse soars with bliss, his breathing suddenly labored. Perhaps it’s merely the pill kicking in.
He fumbles with the lube, manages to squeeze the tube with shaking fingers. He coats his entire hand, just in case, and places the tube on the desk instead of back in the box so that it’s within easy reach.
He slides a glistening hand up the boy’s thighs and slips it under the panties, fingers seeking out the boy’s hole like an animal diving for its burrow. The hand slides up and over the soft mound of the boy’s buttock and two fingers slip into the soft, welcoming hole waiting beneath the fabric. The boy’s flesh is warm and tight around his digits.
He makes unerringly for the prostate this time. His fingers find it from muscle memory, engraved into Mr. Mack’s subconscious now like following a map to the holy grail. He rubs his fingers into the spot and pulls a gratifying moan from Oliver.
No games today. With his other hand, Mr. Mack reachers between the boy’s thighs and begins to rub up and down the length of the boy’s shaft through the fabric of the maid panties. Olly’s small penis is just as cute and perfect in his hand as he imagined it would be. He slides his palm against it, feeling its heat, feeling it pulse as it eagerly wakes.
If Oliver finds it strange that Mr. Mack is touching his penis, he says nothing about it. His eyes are tightly clenched shut.
Mr. Mack moves his two hands in tandem, ruthlessly milking the boy’s pleasure for everything he can. He feels Oliver writhe between his hands, gasping and squirming, unaccustomed to such an onslaught. He’s fully hard with astonishing speed, the tip of his penis tenting the underwear.
Mr. Mack bites his lip, yanks his two fingers from the boy’s passage, and frantically claws the boy’s panties down around his knees. As much as he loves the article of clothing, he’s desperate to see the miraculous little pucker of flesh in all its exposed glory. Besides, the panties look delightfully obscene pulled down like that, clinging to the boy’s thighs and manacling his legs together.
Within moments he’s back to pleasuring the boy. This time he plunges all four of his fingers unceremoniously into the boy’s rectum, fueled by something like desperation. He smears his other hand through the runoff already dripping from the boy’s hole and, so lubed, curls the free hand around the boy’s shaft and begins pumping him in earnest.
Oliver cries out as Mr. Mack strokes him and jabs furiously at his prostate. Mr. Mack has a vivid mental image of turning the boy around and forcing the boy’s face down onto Mr. Mack’s now-straining cock, impaling his mouth and choking him while simultaneously pleasuring Oliver’s ass and penis, attacking him from three angles at once. But even now, he’s not sure how to broach the subject of oral. Besides, Mr. Mack is pretty sure that if he tried that he’d immediately come down the boy’s throat, and he absolutely cannot afford the risk of missing the chance to fuck Oliver’s ass.
Oliver is whimpering now, begging in wordless pleas, hips undulating back and forth as his ass seeks more pleasure, then his cock, then his ass again. He’s wild with need, desperate for his release. Mr. Mack is only too happy to give it to him, milking and milking and milking until Oliver spills himself, shaking, over Mr. Mack’s fist.
The boy slumps exhausted onto the desk, limbs loose as jelly. Mr. Mack feels the boy’s rectum unclench from its desperate embrace of his fingers, and pulls them loose. While the boy catches his breath, Mr. Mack takes the time to uncap the lube once more, pull out his own cock, and coat it liberally.
With unsteady hands he pulls at Oliver, turning him to the side so he faces the wall. Instead of laying lengthwise across the desk, he positions the boy so Oliver’s back half slides off the desk’s edge, next to the chair, his legs dangling. He puts a knee between the boy’s thighs, trying to spread them until he realizes that he can’t; the panties still cling to the boy’s plump, delicious thighs, tying them together. Mr. Mack considers for a moment, but decides to leave them where they are.
Thinking ahead, he also reaches once more down into the box and pulls out the little bullet vibe. He’s not sure whether he’ll use it, but best to be prepared. He puts it down on the desk next to the lube.
He glances to the side, where the full-length mirror from yesterday is still set up. He sees himself standing behind Oliver, penis out and straining towards the boy. He sees the lift of the boy’s skirt, the way the underside of it is crushed against the desk. He sees the boy’s legs dangling over the edge of the desk, the wrinkled roll of the panties like a giant pair of handcuffs around the tender thighs.
Mr. Mack takes a deep, shaking breath. Carefully, he guides the tip of his penis to sit right at the entrance of the boy’s hole. With one hand on his member, he takes the other hand and grips the boy’s left buttock, his thumb at the boy’s anus, pulling at the flesh, prying it open as he leans forward, guides himself in, encounters resistance, takes another deep breath and pushes-
It’s everything he hoped it would be. It’s heat and tightness and choirs of angels singing hallelujah. It feels as though his life is flashing before him; it’s all he can do not to pass out from the sheer pleasure. Underneath him, Oliver groans as Mr. Mack slides inside him.
When he’s fully seated—several slow, agonizing seconds later—Mr. Mack has to pause to compose himself, to catch his breath. It’s tighter than he’d expected, a desperate high-pressure embrace that seems to be trying to wring the very life from him.
Oliver, for his part, was apparently too dazed from his orgasm to realize what Mr. Mack was doing until the man pushed into him. Now he squirms weakly, although whether in protest is unclear. Mr. Mack reaches up and lovingly strokes the boy’s hair to calm him. The strands are silky-soft against his fingers. He trails his hands down the boy’s back, absently smoothing the fabric of the costume, petting him and cooing to him, until his fingers brush across the skirt and finally come to rest on the boy’s buttocks.
He squeezes the soft mounds once more, marveling to see himself cleaving the young flesh. He steals another glance at the mirror to his left, drinks in the image of his reflection spearing the boy. He looks down, pulls the buttocks apart to better see the penetration, then pushes them closed around his cock, jiggling them a bit playfully.
“You’re so good,” he tells Oliver hoarsely, voice as strangled as his cock. “You’re so beautiful, your ass is so amazing Oliver, you’re amazing.”
He pulls halfway out, grinds his way back in. Still amazingly, gloriously tight. He wonders how he’ll even fuck the boy, with his hole this tight. “Amazing,” he repeats.
But the lube does its job. As tight as the boy is, the slide of Mr. Mack’s cock isn’t painful—at least not for Mr. Mack. He pulls halfway out again, and rams home with a shudder.
He fucks the boy with agonizing slowness. Each retreat and thrust take several seconds, a slow draw out, and a relentless, inevitable push back in. His hands are now locked around Oliver’s hips, fingers white-knuckle-gripped onto the fabric as he holds the boy steady. Out. In. Out. In. Deep breaths, steadying him, guiding his timing. Each moment inside the boy’s blessed body is heaven, ecstasy.
Mr. Mack alternates between watching himself fuck the boy in the mirror and staring at the cleave of the boy’s ass where he’s impaled, watching the greedy little mouth gobble him down, twitch and swallow him, ever eager for more. Mr. Mack runs a finger along the seam of the penetration, marveling that such a tiny young hole can stretch so wide to take him in.
Oliver is starting to squirm again, as he comes down from his orgasm into renewed awareness of what’s being done to his body. It’s delightful in some ways, including the spasmodic clenching of the boy’s rectum around Mr. Mack’s invading member. But it does make Mr. Mack’s thrusts harder to control.
He takes firm hold of the boy’s hips, stilling and steadying him, pinning him against the desk, and begins to increase the speed of his thrusts. He works up to a steady pace, machine-like, each in-and-out thrust timed at about a second, each slam forward driven home into the boy with all the force he can muster. His hips drive his cock into the boy like a piston, fucking deep into the boy’s passage.
There’s a clock in the office, a cheap old analogue timepiece hanging on the back wall. Mr. Mack paces himself to the tick-tick-tick of the second hand, driving into the boy again and again and again and again. The pill seems to be working; Mr. Mack is surprised he’s even lasted this long, and yet he feels like he could go on forever.
He loses himself in pounding the boy’s ass. Time becomes meaningless. His focus narrows to the slam, slam, slam of his hips. His cock is endlessly hard. He could fuck this boy literally forever. Oliver is everything he’s ever dreamed of, every fantasy come to life. He wants to permanently fuse the boy onto his cock, to go about his daily life buried in the perfect ecstasy of Olly’s passage. He wants to start and end every day by coming into this boy’s amazing hole, to spend every waking hour driving himself into it over and over.
He’s not sure how long he’s been fucking Olly when he catches a sudden glimpse in the mirror. On the apex of his thrust, burying himself so deep in Olly that the boy is thrust forward slightly, Oliver’s hips lift up and reveal an exciting truth: the boy is hard again.
Mr. Mack thrills. The boy is hard from being fucked. Oliver is turned on by Mr. Mack’s cock riding him. Wonder of all wonders. Mr. Mack falls in love with the boy all over again. Swallowing hard, Mr. Mack glances around for inspiration, some way to reward him.
His eyes fall on the bullet vibe he left out earlier. With a smile he picks it up and stills his thrusts.
It’s a little tough to maneuver enough to get a hand underneath where they are joined, but Oliver is thankfully light enough that Mr. Mack can partially lift the boy’s body as necessary. Mr. Mack takes the bullet in his fingers and reaches under his own cock, pressing it up against the bottom of Oliver’s hole.
Though it seems impossible, given how tight the boy feels, the bullet begins to slip in as Mr. Mack pushes it with his thumb. The boy’s hole is by now oozing with lube, crying rivulets of it, so friction is of little issue. The tough part is just getting it started, getting the boy’s anus to part ever-so-slightly more to accommodate the tiny vibrator. Once it starts to ease into him it goes quickly, popping inside with a satisfying little slurp as his warm little tunnel welcomes it in.
Mr. Mack reaches in after the toy with his pointer finger and tries to maneuver it to roughly where he knows the boy’s prostate is. It’s difficult from this angle. He fishes it around for a little bit until he’s satisfied with its placement, and then withdraws his finger and turns on the switch.
Immediately, Oliver yelps at the sudden vibration. Mr. Mack is pretty overwhelmed himself. The combination of the new vibration with the already-overwhelming tightness is almost more than he can bear. It’s all he can do to keep from coming immediately.
Mr. Mack knows he can’t last long like this. He abandons all pretense of a restrained rhythm and begins to slam into the boy wildly, his thrusts desperate and animal. Half-blind with pleasure, he reaches under the boy’s hips to his little cock and takes it in his fist, pumping it with abandon.
Oliver cries out, writhing on Mr. Mack’s impaling cock. Mr. Mack fucks him hard, wild, uses the hand on the boy’s cock to slam Oliver’s hips even harder backwards onto his penetration. He doesn’t pull out so much as gyrate, burying himself as deep as he can in the boy’s welcoming heat as though he could somehow fuck himself into the boy entirely, force the little hole to swallow up his entire body.
Oliver cries out and whimpers and shakes, his own little cock hard and weeping. He makes desperate, barely-sensical pleas for more, for some release to this tortuous pleasure. Mr. Mack grants as much as he can, slams forward as hard as he’s able, buries his cock as deep as it will go.
He tries to hold back. He summons as much self-discipline as he can muster to keep fucking the boy. Each thrust is an agony of pleasure, an assault of perfection. But he wants to wait for the boy, wants to feel-
And there it is. Oliver’s hips buck once more, cock spilling itself over Mr. Mack’s fist, and Mr. Mack is finally treated to the absolutely delicious sensation of Oliver’s rectum spasming around his dick as the boy comes. Breathlessly, Mr. Mack lets himself follow, driving forward in four more devastatingly deep thrusts before he too is coming, finally finally finally pouring his seed into the boy’s passage, staining it with his essence, emptying himself as deep into the boy’s body as he possibly can.
Wrecked, Mr. Mack slumps forward over Oliver, pinning him to the desk, panting for breath. Behind him, the clock ticks away its cooling seconds as he slowly descends back to earth from his heavenly perch.
Oliver has started to fidget restlessly beneath him when Mr. Mack’s cock finally softens enough to slip out of the boy’s passage. An obscene mess begins to drip down the inside of the boy’s thighs, staining the panties he still wears.
Mr. Mack straightens and takes a stumbling step back to view the boy in all his conquered, ruined glory. Once again he can’t stop himself from reaching for his phone, snapping a few pictures. The soft, black-clad form slumped over the desk. A close-up of the distended, gaping red asshole that even now twitches to have Mr. Mack’s cock back in it. Though he may never see this boy again, Mr. Mack knows that these pictures will keep him warm for years to come.
They both take a few more minutes of just breathing, coming back to themselves gradually. With a soft feeling akin to regret, Mr. Mack reaches to remove the boy’s panties and help him out of the costume and back into his street clothes. The sopping panties sit on the edge of the desk like a trophy, an indisputable reminder of what Mr. Mack has achieved.
Together, silently, Mr. Mack and Oliver walk back into the store. Mr. Mack reaches up onto the shelf above the model rocket and takes down one of the large, unopened boxes. He solemnly places the plastic-wrapped parcel into the boy’s waiting arms and smiles at him. The boy smiles half-heartedly back.
Mr. Mack walks him to the front door, his heart clenched. But he refuses to be sad. He’s gotten so much more than he ever dreamed from his bargain; to be sad would do such joy a disservice.
Oliver pauses in the doorway, staring at his feet and shuffling his shoes. He looks like he wants to say something. Mr. Mack waits.
“There’s, umm...” Oliver starts after a few seconds, then hesitates. He takes a breath, his shoulders rising as though gathering courage, and says in a rush, “There’s other stuff, you know, that I want from the store. We could... if you wanted to keep, um, doing stuff, there’s... we could... we could keep going.”
The world has stopped. Time has ceased in the face of the blinding, overwhelming joy that seizes Mr. Mack’s heart. For a moment he can’t bring himself to answer, so high-soaring is his giddiness. He smiles an unbearable smile.
“Certainly Oliver, if that’s what you want. I’d be more than happy to make another deal.”