The last of Mr. Mack’s packages arrives on Wednesday evening. Mr. Mack grabs it, along with a full-length mirror hanging on the back door of his closet, and puts them in a pile to take with him to work the next day.
Oliver, for a change of pace, arrives nearly ten minutes early on Thursday. Mr. Mack almost isn’t ready for him, caught mid-fantasy as the bell on the door jingles. He smiles widely as Oliver comes in and quickly rushes over to perform the usual ritual of locking the door and turning the sign.
The boy seems much less morose than the previous day. Mr. Mack fancies there is even a sort of suppressed excitement about him, but that might just be his own wishful thinking.
Mr. Mack has thought all morning about how to broach the subject of his newest acquisition with Oliver, what lies to tell or what cajoling he might do, promises he might make. In the end however, he simply hands Oliver the package and says, “I got you something I was hoping you might wear for our... encounter today. Would you mind?”
The boy shrugs and takes the package, not really looking at it. “Sure, I guess.”
Mr. Mack smiles. “Good, good. You can change in the bathroom. Here.” He directs Oliver into the shop’s tiny restroom in the back. “I’ll be waiting in the office when you’re ready.”
Mr. Mack heads for the office room and waits next to the desk, fidgeting with impatience. He wrings his hands self-consciously, shifts his weight from foot to foot. The clock on the wall ticks with exaggerated slowness, carving time into seemingly endless chunks.
Finally, movement in the doorway, and Mr. Mack looks up to see a sight straight out of his fantasies: Oliver in a french maid costume. Mr. Mack gulps audibly.
Oliver pulls unhappily at the skirt. “These are girls’ clothes,” he protests.
They are, in fact. Mr. Mack had been worried that he wouldn’t be able to find a sexy french maid outfit in a child’s size, but as luck would have it the first halloween costume site he’d been to had offered this delectable morsel as an option in the section for young girls. Down to and including the frilly white panties. He’d even gotten it on sale cheap because it was the off-season for Halloween apparel. Honestly, Mr. Mack had thought, what were standards of decency coming to these days.
“No, no, of course not,” Mr. Mack assures. “You’re a boy, aren’t you? So any clothes you wear are boys’ clothes. It looks fantastic on you. Just perfectly what I was hoping for.”
Oliver moves over to the desk and starts to pull down the lacy white panties, but Mr. Mack stops him with a gentle hand on the boy’s wrist. “No no, leave those on. I’ll work around them.”
Oliver shrugs, looking skeptical, but gets up onto the desk, assuming his usual position. The skirt part of the costume is slightly stiff, and raises into the air, exposing his beautifully white-clad bottom. The costume didn’t come with shoes, more’s the pity, but it did contain white knee-high socks, which Oliver is now obediently wearing.
Mr. Mack caresses the satiny fabric lovingly, petting its delectable softness. Unable to help himself, he lowers his face to the boy’s bottom and rubs his cheek against it, feeling the fabric against his stubbled face. So perfect. He runs a finger just under the elastic where it hugs the boy’s thigh. His eyes run similarly over the lines of the costume: the white bow of the apron tied around the boy’s back, the puffy black shoulders. He’d even put on the little black-and-white-frilled headband that had come with the outfit. It’s beautiful against the boy’s tawny, tousled hair.
Mr. Mack licks his lips. Despoiling the boy when he’s like this will be something magical, that much is certain. But he’d thought long and hard after their encounter the previous day, and he’s decided that today will be first and foremost about the boy’s pleasure.
Mr. Mack reaches into his toy box for the lube and begins the ritual of lubing up his fingers. With one hand he grabs the stretch of white fabric that covers the boy’s anus and pulls it to one side, rather than removing the boy’s underwear. The tight little pucker of muscle looks somehow much more obscene when framed this way with the lacy undergarment than it did when the boy was fully naked from the waist down.
Biting his lip, Mr. Mack pops two fingers into the boy straight away. It’s a bit of a risk, but this is the fourth day in a row they’ve done this now, and the boy’s muscles seem inclined to relax quickly. With a pleased smile, Mr. Mack twists the fingers back and forth a bit until they’re well-seated inside Oliver, fucks them in and out a few times, and then begins his exploration.
It doesn’t take long before he finds what he’s looking for. His fingers remember well the location of the boy’s prostate, and after a telling jolt of Oliver’s hips, Mr. Mack zeroes in on the location. He begins to massage the boy’s gland with his fingers, pulsing and pressing and kneading the spot. He even puts a hand on the boy’s lower back for leverage, crushing down the black fabric and fluffy white tulle of the maid skirt under his palm.
Oliver groans, cutting off into a whimper. Mr. Mack continues, relentless, pushing and pushing and pushing, grinding his fingers against the spot until he finally gets the result he wanted: the white lace panties begin to tent under the boy’s burgeoning erection.
This is phase one. Mr. Mack carefully and deeply massages the boy’s prostate until Oliver’s erection is straining, desperate against its fabric prison. When Mr. Mack pulls his fingers out, he hears an audible sigh of disappointment from Oliver. His heart thrills. His fantasies overcome him once again as he imagines forcing the boy to beg for it. ‘Say please,’ he imagines commanding Olly. ‘Say, please fuck my ass, Mr. Mack, with your wonderful cock.’
“Did that feel good?” he asks out loud, letting the fabric once more stretch to cover Oliver’s precious little opening as he rummages in the box. Oliver doesn’t respond verbally, but he does nod after a moment’s hesitation. Mr. Mack feels like dancing.
Mr. Mack fishes out the beads again that they’d used the previous day, lubing them as quickly as he can. He doesn’t want to keep that delightful bottom waiting. When he pulls back the fabric once more, he sees Olly’s anus twitching and shivering, clearly desperate for more. What a lovely, greedy little hole it is.
Mr. Mack pops the first bead into the boy’s ass and turns on the vibration. Once again, Olly moans low in his throat. Mr. Mack adds the second bead immediately before re-inserting his fingers to once more seek out Oliver’s prostate.
He pushes the beads into the boy’s gland, grinding the vibration against his most sensitive inner treasure, and is rewarded with a squeal from the boy. “Theeere we go,” he murmurs. He resumes his earlier motions using the beads this time, pushing them again and again into the spot that makes Olly shiver and his fingers clench.
Olly whimpers, his hips bucking, and then slowly, gradually, begins to fuck back against Mr. Mack’s fingers. His hips thrust backwards on each pulse, clearly driving towards some need that the boy does not yet fully understand. His body is practically begging, pleading with him as it grinds against his fingers and seeks out the vibration, searching desperately for something more. The thrusts onto his fingers become more and more vigorous with each passing second, until Mr. Mack can practically hold his fingers still and feel the boy’s rectum clench rhythmically around him.
With a feeling like triumph, Mr. Mack takes up the opposite end of the vibrating bead string with his free hand and, almost nonchalantly, lifts it up to the front of Olly’s panties.
It could almost be an accident; certainly it’s a general enough motion for plausible deniability. His hand is just coming up to steady himself against Olly. Just happens to be holding the rest of the beads in it. If it happens to flatten the string of vibrating orbs against Oliver’s straining penis, well, that’s just coincidence.
Oliver lets out a shout and comes immediately, soaking the panties gratuitously. Mr. Mack thrills, triumphant. The boy’s hips buck and buck as he frantically spills himself. Mr. Mack firmly presses both ends of the bead string against the boy’s prostate and penis, holding pressure until the last seismic pulses of the boy’s orgasm finally pass.
Oliver is breathing hard, panting. The muscles of his rectum are loose with release, sloppy and relaxed. Mr. Mack pulls the string of beads out of Olly’s shuddering body with satisfaction and drops it back in the box. He plunges the four fingers of his left hand idly into the boy’s anus so it won’t get lonely while he roots around in the box with his right for an appropriate implement. The tired ring of muscle accepts him without complaint, stretching wide to accommodate Mr. Mack’s every whim.
There’s so much to choose from in the box that Mr. Mack is spoiled for choice. He doesn’t want to simply repeat all the implements he used the previous day. In the end he finds a simple dildo, silicone black and absurdly sized. It’s still not quite what they’d need to use before Oliver could be ready for fisting, but it’s at least a step in that direction.
With a grin, Mr. Mack takes his hand out of Olly and flips him over. The boy is unresisting, dazed with the pleasure of his climax. He blinks at Mr. Mack in uncomprehending confusion.
“Look what else I have, Olly,” says Mr. Mack. He steps to the side so Oliver can see the full-length mirror that Mr. Mack mounted to the wall. The boy still looks confused.
“I want you to be able to see what’s giving you so much pleasure,” Mr. Mack explains. “It’s really quite amazing to see what your beautiful little hole can do.” He hands the boy his own knees and, when he’s sure Oliver is holding them tight, reaches down again to pull the fabric of the boy’s panties aside once more.
“See Oliver?” he says. “Watch the mirror.”
Oliver’s eyes fix on his own reflection, a cute little boy in a frilly black-and-white dress, headband slightly askew and panties wet with his own cum. His face is flushed, as is the newly-revealed pucker.
“Watch closely now,” Mr. Mack instructs, and lines the big black head of the dildo up with the boy’s anus. He tries to hold it from beneath so that the image in the mirror is clear and unobstructed. He observes closely as Oliver’s eyes widen when he sees the enormous phallus come to rest at the entrance to his seemingly tiny orifice. Then he begins to push.
The toy slides into the boy with surprising ease. Mr. Mack is satisfied to watch as inch after inch is slurped up into the boy’s eager passage, disappearing like a magic trick. Oliver squirms with embarrassment, but Mr. Mack holds him steady and continues the relentless onslaught of the toy, pushing it further and further and further until he probably has a good ten inches of the thing in the boy.
“Look how beautiful that is,” Mr. Mack croons, letting go of the toy and using both hands to spread open Oliver’s asscheecks as far as he can so they can gaze together at the point of penetration. “So perfect. So lovely. It’s like your body was just made for this.”
Mr. Mack grabs the end of the dildo firmly in one hand and begins to thrust it in and out of the boy in sharp, hard movements. Once again the boy has reached the point where his ass is squelching with the frothy lube coating his insides. Every time Mr. Mack drives the toy deep into the boy’s body, his ass mumbles as though speaking its appreciation. And every time he draws it out for leverage to thrust again it clenches and grabs at the phallus as though desperately seeking its return. Olly himself is flushed red in both face and ass, a delightful contrast to his black and white ensemble.
This dildo is not, itself, a vibrator, but Mr. Mack feels there should be vibration here, and so he nestles the big black manhood as deep as he can in the boy’s ass and goes rummaging around in his box once more. He finds a small bullet vibrator, smooth and pink, that should do the job, and returns to Oliver’s side.
Mr. Mack pauses with one hand on the dildo and waits until Oliver meets his eyes in the mirror. With a smile, Mr. Mack pulls up on the dildo with one hand and uses the fingers of his other hand to slip the bullet in underneath it, trying once again to find that delicious sensitive spot just inside Olly’s passage. Oliver’s body barely seems to register the additional penetration, until Mr. Mack flips the switch on the controller and turns the bullet on.
Oliver’s whole body tenses and shudders as the vibrating bullet is trapped between his prostate and the thick black dildo. The vibrations travel all throughout the length of the toy, buzzing it from the distended flesh of his anus, all the way deep down into his passage where the head of the toy rests buried inside him.
Mr. Mack grabs up the end of the dildo once more and resumes pumping it in and out of Oliver’s asshole. Oliver twists and writhes and cries out. To Mr. Mack’s delight, he seems to be growing hard again. Ah, to have the resilience of youth.
As they did with Mr. Mack’s fingers, Oliver’s hips begin to buck up to meet the thrusts of the toy. Desperately he tenses up off the desk, leaning into the penetration as Mr. Mack rams the dildo home each time. He’s started to mutter to himself, first incoherently, until Mr. Mack catches a few words—“please,” and “need,” and “can you” and “again.”
He knows what Oliver’s asking for, even if Oliver himself doesn’t yet know the words for it. “Shh, shh,” Mr. Mack soothes. “Of course. Just a moment.” With a grin, Mr. Mack plunges the dildo deep and lets go so he can flip Oliver over onto his knees again. The boy’s eyes are squeezed shut anyway, no longer observing his own penetration.
Which is a shame, because the boy’s fucked-full ass looks delightful. Mr. Mack pauses a moment to admire it, taking a step back. The lacy white panties are held to the side by the several inches of the dildo’s base that protrude from the boy’s well-stuffed anus. Rivulets of lube run down from his hole, staining the fabric and glistening on the flesh of his trembling thighs. The reddened muscle of his asshole twitches and gasps around the penetration.
Overcome past the point of caution, Mr. Mack takes out his phone and quickly snaps a picture of the delightful sight, careful to crop out the boy’s face so he can’t be recognized. One picture of the body, splayed out on his desk, and one close-up of the boy’s ass, impaled and rosy and waiting for him.
Mr. Mack puts the phone away and grabs hold of the dildo once more, resuming his thrusts. The wet spot on Oliver’s panties is starting to strain forward once again as his young member comes back to life. But Mr. Mack isn’t quite ready to satisfy it yet.
Instead he pleasures himself first. Continuing his thrusts with the dildo, Mr. Mack reaches into his own pants and pulls out his length, pumping it quickly and efficiently. He steps closer to the boy and pushes his member up against the soft, silky fabric of the panties, rubbing himself frantically against the boy’s bottom.
If Oliver notices the extra sensation beyond the relentless penetration of the dildo, he doesn’t say anything. Mr. Mack continues to rub himself against the panties, grinding against the soft fabric and the even softer flesh beneath. With the hand not spearing the boy he reaches up and grabs the black fabric of the skirt, pulling it down to rub the top of his shaft even as he continues to thrust up against the boy’s bottom.
Oliver is whimpering and mewling by the time Mr. Mack comes all over his fabric-covered ass and the underside of the boy’s skirt. The panties soak in the wetness, but what’s one more stain? Mr. Mack will have to wash the clothes anyway. As he strives to catch his breath, Mr. Mack yanks the bullet vibe out from the boy’s anus by the cord, causing Olly to gasp.
Mr. Mack puts himself away, zips up his pants, and then resumes his ministrations. With one hand he continues to jackhammer the dildo into the boy, and with the other he reaches up with the bullet vibe and slides it up and over the boy’s testicles to press against his cloth-covered erection.
Again the boy comes almost immediately. He’s practically sobbing with relief when he does. Mr. Mack holds the vibrator steady and thrusts through the boy’s shudders, finally plunging the toy as deep as he can when it seems like the boy is in the final throes of his orgasm. He sees the boy’s anus clench painfully tight around the toy, desperate and needy, before relaxing into post-orgasmic calm.
When Mr. Mack finally pulls out the dildo, he keeps hold of the panties for a moment to watch the boy’s anus with a glow of pride. It’s a sloppy mess, as usual, well-used. He takes the camera once more out of his pocket and snaps a final close-up of the boy’s loose and tired asshole, red and heaving with its exertion. Then he lets the fabric fall back in place and pats the cloth-covered spot affectionately.
“There we go,” he says. “All done for today. You can change out of the costume. Thank you for indulging me. Was it good?”
“...Yes,” says Olly after a moment, his voice tiny with embarrassment.
Mr. Mack puffs up with pride. Success. “Only one more day, and then you get your spaceship,” he says, not without some regret.
Olly nods and tries to sit up, but winces hard at the soreness of his bottom and has to lie on his side a moment, still breathing heavy. Mr. Mack pets his hair gently around the maid headband. “Take as long as you need,” he says. “You can stay here until you’re ready.”