Cute Singles In Your Area

Jack doesn’t think much about the child’s picture as he swipes to the right on his hookup app. It’s not unheard of for men on this app to post their childhood pictures in some kind of optimistic gesture towards youthfulness. Right now Jack is just horny as hell and swiping right on every twink in a ten-mile radius. He’ll worry more about the details later. So at the time it registers as only a mild blip across the surface of his consciousness.

He only really processes it later when he matches with this so-called “Luca” and discovers that this is, in fact, the only picture he’s uploaded. With a frown he hits the “message” button and starts typing. Luca is online, and he gets a response immediately.

Jack raises an eyebrow. He’s not a hundred percent sure what’s going on, but maybe this is someone whose kink is being treated like a child? Whatever. At this point his horniness is making him impatient and this at least seems like he’ll maybe get a funny story out of it, if nothing else. Besides, the kid’s pic is cute: tousled brown hair and a cute little button nose with a smattering of freckles across his cheeks. He looks like he should be on the cover of one of those “Adventures for Little Boys” books. If he grew up to look anything like he did as a kid, he’s probably still pretty attractive. At any rate, he can always call it off if the guy turns out to be, like, old or ugly or whatever in person.

Jack chuckles to himself. Definitely a weird story.

Jack closes the app and grabs his keys. He’s weirdly curious now and looking forward to seeing this guy. He puts on the same hat he uses in his profile picture to make himself more recognizable; he’s not sure he’ll be able to pick out Luca from just a picture of him when he was eleven. Hopefully Luca will be able to spot him instead.

It’s an overcast, somewhat windy day, and so the park is fairly empty when Jack arrives. This is probably a good thing; no one is there to see his absolutely floored expression when an actual honest-to-god 11-year-old boy sees him and comes running towards him with a huge grin.

“Hi!” says the kid, louder than Jack is comfortable with. “You must be JackOffroad69! I’m Luca!”

“Uh,” says Jack stupidly, his mind racing. “Call me Jack. Are you... you’re really Luca?”

Luca nods. “You said you can give me a ride, right? I have to be back by dinner or my mom will notice I’m gone.”

“And you didn’t...” Jack licks his lips. “You didn’t come with anyone...? No one knows you’re here...?”

Luca rolls his eyes. He looks exactly like his picture. “I’m not gonna tell my mom about being on that app. She’d take away my phone. I’m not supposed to lie about my age on the internet, she says. But it’s not like it’s hard! They don’t check or anything!”

“Okay,” says Jack. Then again, “Okay.” He takes a deep breath. “Come on then. This way.”

He gestures towards his car and Luca goes bounding ahead. Following behind him, Jack can already see the cute little roundness of his butt through his tiny shorts. God, he’s so small. Jack bites his lower lip. His dick twitches in his pants. Is he really going to have an opportunity to...?

His knuckles are clenched white on the steering wheel the entire way home. When they arrive he quickly ushers Luca into the house, glancing around as subtly as he can to make sure none of his neighbors are watching him bring an underaged kid home.

Once inside he takes off his jacket and opens the door to the downstairs den. He gestures at the carpeted stairs. “This way,” he tells Luca.

Luca once again bounds ahead of him with his apparently dauntless energy. He hears the boy stop abruptly when he reaches the bottom of the stairs. “Whoah...”

Jack has worked hard to make the downstairs den into a proper BDSM parlor. There’s all kinds of whips and straps and oversized dildoes hanging on the walls, surrounding an enormous pink-clad bed with silk sheets. Even the lighting is a soft, gauzy red.

Jack clears his throat as he comes up behind Luca. “So,” he says. “What do you already know about fucking?”

Luca tears his eyes away from the implements on the wall and turns back to him. “It’s sex, right? It’s, like, a thing where you get naked and touch each other. Adults do it and they think kids don’t know about it. Everyone’s always trying to tell me I’m too young for stuff, but I’m not too young! I bet I’ll be really good at it!”

Jack coughs, feeling torn between laughing and crying. “That’s more or less it. How about I show you how men on that app do fucking then, huh? You’re a little... small for it. It might take some work. I’m not totally sure you’ll be able to, to be honest.”

“I can!” Luca insists. “I’ll do whatever! I’ll show you! I work hard at things!”

“I’m sure you do,” says Jack. “Take off your clothes.”

Luca does so immediately, with no shame or even embarrassment. His young body is lithe and smooth, barely out of the chubbiness of childhood. His butt in particular is beautifully round once out of its confinement, like two large grapefruits. His tiny little cock nestles like a promise between his legs.

“Here.” Jack pats the bed and grabs one of the large black straps attached to the bedposts at the head. He begins to adjust it; he’ll need all the length he can get out of them for someone so small. “I want you to lie face-down in the center of the bed here with your knees slightly bent so your a- your butt is in the air. I’m going to use these straps to tie you in place so you don’t move around too much.”

“You don’t need to tie me up,” Luca protests. “I won’t run away.”

“Trust me,” Jack says. “This is how it’s done.”

This is apparently enough for Luca, and he assumes the requested position without further protest. Jack practically drools at the sight of his young, supple ass presented so unsuspectingly in the air. He can’t help but lightly caress one of the globes; it’s just as soft as he imagined. He hurries to finish strapping the boy in.

He fastens the boy’s ankles to the head posts and his wrists to the foot of the bed so that he can’t get any additional slack by flattening himself out or lowering his hips. Then he retrieves a blindfold from the drawer of the bedside and casually slips it over Luca’s eyes.

“Huh?” asks Luca, confused. “What’s this for?”

“This is how men fuck,” Jack insists. “Not being able to see will help you concentrate more on what you’re feeling.” He rubs his hands together, almost unsure where to start. “Now,” he says, “you were basically right about fucking. What’s gonna happen is that I’m going to put my genitals—that is, my cock—inside your butt. But unfortunately since you’re so small, it’s going to take a little while to be able to work up to that. If you want me to be able to fuck you, we’re going to have to practice getting you opened up first. Okay?”

“I can handle it!” Luca insists again.

Jack smiles, the anticipation so thick it’s almost making him sick. “Alright then, let’s see if you can.”

He retrieves the bottle of lube he keeps on the bedside table and snaps the cap open. Jack himself is still fully dressed except for his shoes as he mounts the bed behind the boy, coating the fingers of one hand in lube.

Jack reaches down to the delightfully-presented ass with his dry hand and pries one ass cheek to the side, using his thumb to massage the newly-revealed hole. He bites his lip as he pushes the digit against the tight ring of muscle in a steady rhythm, teasing at the opening and trying to get the boy used to the sensation of being touched there. He wants more than anything to just dive right in, but he doesn’t want to push his luck; if the boy gets too upset too quickly, it may be difficult to do as much to him as Jack wants.

With a few last firm pushes against Luca’s asshole, Jack again uses the dry hand to pry apart Luca’s buttcheeks and begins the penetration. Slowly, carefully, he starts to slide two lubed fingers up inside Luca’s tight, virgin hole.

Luca groans. “Is that it?” he asks. “Is that your c- your cock?”

Jack chuckles. “Oh no, not even remotely. We have a long way to go before that.”

He doesn’t fuck Luca with his fingers for too long. He’s impatient, but he at least tries to be thorough. He moves the digits in and out of the boy until he can hear it squelching, coating the boy’s passage, and then scissors them apart a few times for good measure. While he does so, he eyes his wall of implements: a buffet of delights for him to experiment with.

It doesn’t take long to decide what should come next. Jack leaves the bed and grabs up a vibrator from the wall. It’s definitely on the small side—smaller than his own cock, certainly—but it’s one of his favorites nevertheless because of the intensity of the vibration and its squirming gyrations. If this doesn’t soften up the boy’s insides, he doesn’t know what will.

Jack takes a brief moment to coat the toy in its own layer of lube before returning to the bed. Luca’s butt is still thrust up into the air like an offering; not that he can move out of the position anyway.

Once more Jack parts Luca’s buttocks and places the tip of the vibrator against the pucker of his hole. “Here’s the first training object,” he warns Luca. Then he starts to push, piercing the entrance.

The boy’s asshole doesn’t swallow up the toy quite as eagerly as he’d hoped. He has to force it past some resistance, jamming it down mercilessly inch by unyielding inch. Luca starts to whimper, his hips shaking back and forth as though he’s trying to move out of the way of the painful intruder. But the straps do their job and keep him firmly in place, ass in the air. He cannot escape the slow, relentless invasion.

Jack continues the unceasing push, slow but steady, until he has seated the entire toy in Luca’s young passage. Then, with a grin of anticipation, he flips the switch.

Luca yelps as the toy suddenly begins to writhe and vibrate inside him. He strains against the straps, but to no avail. The dildo continues its happy little whirring, massaging him from the inside.

Jack nonchalantly leaves the bed once more, content for the moment just to watch Luca endure the toy’s ministrations. He takes his time unclothing himself to the delightful soundtrack of buzzing, squelching, and whimpering coming from the bed.

Once he’s fully nude, Jack takes a moment to indulge in the boy’s body. He runs his hands along it, squeezing the butt cheeks, trailing fingers up the boy’s thighs, reveling in the softness of the skin. He feels his way up the boy’s sides and ribs, coming around to the nipples and giving them a rough tweak. Luca cries out and twists in his bonds. Jack does it again, abusing the poor little nubs, pinching and squeezing, pulling at them like he’s trying to milk the boy.

They seem especially sensitive, to Jack’s delight. He rubs them some more before pinching them up again into little peaks. Every time he touches them it makes Luca squirm. Jack decides it’s unconscionable to just leave such cute little playthings entirely bereft, so he takes another detour back to his wall for a pair of clamps.

They’re classy objects, as clamps go; when he fastens them tight to the boy’s nipples they dangle down a small, clouded white jewel below them, like a large frozen droplet of cum. Jack gives the dangling stones a playful little brush, setting them swinging, before returning to his exploration of the boy’s body.

He feels up the side of the boy’s neck and cheeks, runs his fingers along the soft, dusky lips. He even slips his digits inside the boy’s mouth, feeling the insides of his cheeks and tongue, keeping his jaw open until a little trickle of drool forms at the corner of his mouth. He wonders if he should try to fuck the boy’s face. Or gag him, perhaps? He does have a variety that might be small enough...

Jack glances back at Luca’s ass and notices that it has managed to reject several inches of the vibrator, pushing them back out. He clucks his tongue and removes his fingers from the boy’s mouth. “Now, this just won’t do. We have to make sure this hungry little hole of yours stays filled. Let’s hammer that back in a bit, shall we?”

Jack retrieves a wooden paddle from the wall, one of his favorites. He returns to Luca and, without warning, rams the toy as deep into the boy as it will go with the heel of his hand. Then, with barely a pause, he raises the paddle and brings it down on the boy’s buttocks with a sharp smack. Luca cries out as Jack proceeds to harshly spank him, bringing the wooden board down again and again on the soft young flesh. The round globes quickly redden as each blow enforces the depth of the toy, keeping it lodged inside the boy as far as it will go.

Jack notices tears on the boy’s cheeks by the time he’s finished paddling him, although to Luca’s credit he hasn’t yet asked Jack to stop. Jack’s lust is at a furious volume by this point, and he doesn’t think he can wait any longer to have this young body.

“Okay,” he says, “time for your next training object. Let’s see if we can go a little bigger.”

Jack once again mounts the bed behind Luca and turns off the vibrator in the boy’s ass. As he had hoped, the flesh is soft and loose now, numbed and worked-open by the toy’s ministrations. Instead of drawing the object back out, Jack simply uses one hand to pull it downwards and the other to pry the boy’s tired flesh even further open. He places the head of his eagerly-straining cock at the forced-wide entrance and begins to push himself inside beside the existing dildo.

“Here it comes,” he warns Luca as his cock begins to cleave the boy open. Once he’s managed to force the head inside he moves his hands to the boy’s thighs to better yank him back onto the spear of penetration. As before he does not stop once in his long, slow slide, sinking inch by inch into the boy until he’s fully buried, flush against the reddened ass.

Jack sighs in contentment. “Okay, let’s work this one around inside of you a little as well to get you used to it. After all, we really need to spread you open if we’re eventually going to fuck you.”

He smiles and begins to thrust into the boy. It’s a tight fit with the other phallus, but Luca takes it like a champ. His pained whimpers continue, but no worse than before. Jack proceeds to fuck the living daylights out of him, thrusting harder and with more enthusiasm than he ever has in his life. The boy is just so tight—it’s practically miraculous! Jack’s hips piston in and out and in and out relentlessly, drowning in the pleasure of the tight heat.

He takes his time, in no particular rush. They have hours still until he needs to start worrying about cleaning the boy up. Jack drills into him over and over, fucking him and fucking him and fucking him until he sees stars. Eventually he just can’t contain himself anymore and comes harder than he’s ever come before up the boy’s ass.

With a happy sigh, Jack withdraws his softening cock from the boy’s abused hole, noting with pleasure the way his cum begins to dribble out around the still-present vibrator soon after. “That was some good practice,” he tells Luca. “We’re almost ready for you to get fucked. Just one more little trial...”

He’s not sure how much more Luca can handle; to be honest, he’s astonished they’ve even managed to get this far. But Jack can’t help himself. He knows he’ll likely never have another chance like this again, so he’s determined to see just how far he can push it.

Jack removes the vibrator from Luca’s ass; the boy’s hole is positively gushing at this point, dripping a mix of sweat and lube and Jack’s own cum. Jack bites his lip and, without warning, forces his entire forearm up Luca’s ass.

Luca screams, but Jack only laughs. He begins to thrust, pulling his arm back and forth in the tight passage, occasionally opening up his hand and wiggling his fingers for additional stimulation. He fists the boy with a cheerful nonchalance, despite the way Luca writhes and cries on the enormous girth penetrating him, straining as hard as he can against his bonds.

“Do you like that?” Jack coos at him. “This is almost as wide as my cock is, you know. If you want to get fucked, you’re going to have to get used to taking something this big. Feels good, doesn’t it?” He rams his forearm home a few more times in emphasis.

His dick twitches, which makes him dizzy. No way is he actually getting hard again this quickly; he couldn’t possibly. But as he continues to punch his way over and over into the boy’s rectum, he finds to his absolute astonishment that he is. It’s slow to rise, but his dick is definitely determined to get in a round two. Jack delays by continuing to fist the boy, prolonging it as much as he can to give himself time to catch his breath. He focuses on the delightful stretch of the muscle of Luca’s anus as it struggles to swallow the girth of his arm, twitching and shuddering. For a few minutes Jack just leaves his arm still, embedded up to the elbow, and marvels at the way the clever ring hiccups around him, as though it can’t decide whether to reject him or try to draw him in further.

Finally, after perhaps ten to fifteen minutes of fisting the boy, Jack’s cock is fully hard once more and raring to go. Jack withdraws his arm, and is equal parts proud and appalled to see the boy’s hole barely shrinks behind it. It stays gaping and fucked-open, begging for something enormous to be crammed inside. Jack snorts. He’s not going to get any more tightness or pressure from the boy’s ass during this session, he can tell. Ah well, there are alternatives.

“Alright,” he tells Luca, “it’s finally time. Are you ready? I’m going to put my cock in you now.”

“No please!” Luca protests. “Please, it’s too much! I- it hurts, I don’t want-”

“Hey now!” Jack gives Luca’s buttocks a warning spank. “No more talk like that. You said you could handle it. We can’t just go through all of this preparation only for you to back out now. I think we need to work on that attitude of yours...”

Jack returns once more to his wall and his selection of gags. He takes only a moment to pick one out; a large, stiff rubber ring designed to fit over the teeth and keep the mouth forced open. He moves to Luca’s head and forces his fingers once more into the boy’s mouth, prying open his jaw and jamming the ring into place. He fastens the device around the back of Luca’s head, over the strap of the blindfold. Luca’s protests continue, but are unintelligible now around the gag.

Satisfied, Jack roots through his equipment until he locates the largest expander in his collection. He returns to Luca’s twitching hole and places it just outside the wrecked orifice. “Are you ready?” he asks rhetorically. “Here comes my cock, finally ready to fuck you. Get ready.”

He begins to slide the inflator into the greedy opening. In its base state, the inflator looks like an enormous black dildo. It’s shorter than Jack’s arm, but only slightly narrower. It goes in easier than anything has since Jack’s fingers, parting the tired flesh like slipping into a warm bath. Then, once the full ten inches or so are fully seated inside Luca, Jack turns it on.

The toy begins to inflate, growing wider and wider and wider until it strains against Luca’s flesh, forcing his hips open. Luca cries out once again, giving Jack an excuse to return to his head.

“Hey now,” he says, “what did I say about protesting? Don’t you like the way my cock feels in your ass? You know if you want to be an adult and get fucked, you’re going to have to get used to taking something this big inside you. Now, no more complaints!” With this declaration, he places his cock at the entrance to Luca’s mouth created by the ring gag and begins to push inside.

Luca’s mouth is not as tight as his ass was, but to be fair it’s probably still tighter than his ass is right now. Jack chuckles to himself at the thought as he continues to slide his cock deep into Luca’s mouth and then down his throat, feeling the boy gag around the invading flesh. It probably doesn’t taste great, Jack assumes, given where it’s been, but he doesn’t really care that much at this point.

He begins to fuck the boy’s face while the inflator reaches full size in the boy’s ass. “Your ass loves my cock so much!” he teases Luca. “Feel how big and hard I got inside you? That’s because of how nice your hole is welcoming me! Now, let me just...”

He waits for a second; the inflator has a small piston in the base that kicks on when it reaches full size. Any second now... there! He hears it kick on as it begins to thrust the enormous phallus in and out of Luca’s hole. It’s not much; the machinery is only capable of moving the toy a few inches back and forth. But with the size of the penetration it’s more than enough.

He feels Luca’s scream vibrating the boy’s throat around his cock and shudders in pleasure. He resumes his ministrations, fucking the boy’s mouth in tandem with the toy pistoning deeper into his ass. He can’t help but think that this is it; this is the peak. He’s ruined for all other sex after this. Nothing is ever going to be this good again.

So he draws it out as much as he can. He’s able to last longer the second time, now that he’s already nutted in the boy once. He savors the hot wet slide of the boy’s mouth around his cock, the way his throat clenches and spasms whenever he makes the boy gag at the height of his thrusts. He fucks the boy’s face over and over, on and on and on for as long as he can make it last, until the boy’s muffled screams fade to whimpers and then to simple tears running down his cheeks.

Finally, inevitably, the end comes. Jack can’t contain himself forever and eventually finds himself jizzing down Luca’s throat, burying his cock as deep as he can inside the boy as it twitches and empties a second load. Jack sighs in contentment and withdraws. He takes his time cleaning himself up, letting the toy inside Luca’s anus continue to pound away as he washes his hands and his cock and puts his clothes back on. He takes the ring gag out of the boy and washes that as well, returning it to its place on the wall.

One last task: Jack takes out his phone and takes several pictures and a short video of the boy’s penetration, storing the image and sounds of the toy working Luca’s ass for future jack-off sessions to come. Only when he’s satisfied that he’s captured the necessary angles does he finally turn the toy off and remove it from the boy’s exhausted, tortured hole. (He gets a few pictures of that as well: the gaping crimson flesh, wide and oozing, the buttocks on either side still pink from the earlier spanking.) Luca’s body sags as much as it can against the bonds.

Finally, Jack undoes the straps around the boy and helps him remove the blindfold. “There you go,” he says. “You got what you wanted: properly fucked. If you can handle that, then maybe you actually can do adult stuff, just like you said. Now, let’s get you cleaned up.

“And hey.” Here he winks at the boy. “If you ever want another adult experience, just hit me up on the app again sometime. More than happy to fuck you again whenever you feel like it.”

Luca stays silent. Jack can’t tell if the boy would ever actually consider such a thing; he’s probably too traumatized for a repeat of this particular performance. But either way, Jack is satisfied. He got more than he ever dreamed from this encounter, and he will forever have the pleasure of knowing that he was the first to ruin that adorable little hole.