The Jackpot

Author's note:

This story contains the following (among other things): noncon, stretching, lubeplay, objectification, and a little transphobic language. Basically i'm just warning you that our main character is an ass. If that doesn't float your boat then i might suggest reading a different story. All characters are over 18 of course.

If people end up liking this I might write more. We'll see.

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By the time I arrive at the house it's raining, except that word alone isn't enough to do the weather justice. It's pouring. Cats and dogs just beating on my windshield as I hook my mask around my ears. My umbrella's under the seat but I've already decided to leave it behind.

There's a strategy to it.

I jog through the rain and up the short sidewalk to the front door. There's no cover aside from a very narrow lip above me and the rain isn't as warm as you'd think it'd be by late April. I ring the doorbell and knock for good measure, anticipation aching behind my teeth. Less than a minute passes before it opens.

"Sorry—" There's a young man at the door, can't be older than twenty, with pale skin and short honey-brown hair. I can't help the smile that breaks across my face and I'm glad he can't see it behind my mask.

"Max?" I hold up the black bag containing his order.

"Yeah." He waves me inside. "Come in, sorry, real quick."

I step inside without question and there in the entrance hall I take a good look at him when he turns. He's on the short side—can't be more than five nine—and thin. His outfit looks barely thrown together. No mask. A loose gray shirt and green running shorts. I'm talking about the short kind that don't even reach the knee. Really does wonders for his ass and legs though.

"I need to grab your tip," Max explains. He sounds—sweet. "Didn't wanna make you stand in the rain. Wait here a sec I'll be right back."

As he walks down the hallway I know now's the time to take the plunge. The excitement is almost too much cause this guy is hot. It's been ages since I've encountered such a cute customer on my route. Sometimes I get bored on the job and settle for people that are only hot if you squint. That won't be the case today and I want to have as much fun as possible.

See, most people don't know what I can do. I tug my right earlobe and feel that particular twist in my stomach. Instantly the rain stops. Well, sort of. It hasn't stopped, not really, not for anyone except me. For me the entire world is at a standstill and I'm the only one left moving. Max is frozen in the hall, paused mid step.

I take a quick look around, making a mental note of where I am. Then I set my delivery bag down and wander closer. The mask is stuffy on my face and I rip it off as I circle around Max. He's hot. I lean in to admire his gentle face, his full lips. He smells like soap and I confirm my suspicions when I run a hand through his hair. It's damp at the roots, meaning he'd taken a shower earlier, maybe just before I got here.

Great. I crouch down in front of him, eager to see what I'm dealing with. Looks small just from here. Barely any bulge. Cut or uncut? That's always the first question I wonder about in advance. Hooking my fingers over the rim of his shorts and underwear, I yank them down to his bare ankles with one quick motion.

"Oh," I say aloud. Max isn't cut or uncut because he's got a cunt between his legs and no cock at all. For a moment I stare. His pussy is practically bare, with only a tiny trail of hairs leading down from his flat stomach. He must have shaved today and running my thumb over his smooth skin confirms it. His clit is huge too, fat between his lips.

"That's surprising," I tell Max, though he can't hear me. I'm not complaining, it's just unexpected. But looking at his cute little cunt sparks arousal in me. I reach up under Max's shirt for a second to make sure that he does indeed have a flat chest before pressing my thumb into him. It's warm, but not wet enough yet, so I withdraw my hand and lick two fingers and push them inside next. Yeah—god he's tight. I can already imagine this perfect body squeezing my dick.

For a minute I jackhammer my fingers in and out and being this close I can hear the obscene squishing and squashing sounds that his body makes. Speaks straight to my cock since I can feel heat burning in me now. A fire that never really goes out.

Patience, I remind myself. This guy is the jackpot. A honeypot. And I wanna savor this experience cause who knows when I'll get to fuck a guy this cute.

I withdraw my fingers, now glistening, and instead turn my attention to his clit. Would Max think of it as his cock? I certainly wouldn't. I'll show Max what a real cock is like later. For now I pinch the tip, twist it a little. Flick it up and down against the edge of my hand.

"That's for surprising me." I pinch and pull, not meanly, but not gently either. Definitely enough to sting. "Now I have to stay longer cause there's an extra hole to fill." I enjoy talking to them—the people I use when time has stopped. It's fun because they can't respond so you can say whatever you like. Fills up the silence too.

Once I've thoroughly abused his fat clit I squeeze Max's ass once (small and round. A borderline bubble.) and pull his underwear and shorts back up. His legs are toned and soft so I give them a quick feel too. More to come later.

I return to my spot by the door and pull my mask up over my nose again, then I tug my ear.

For Max no time has passed at all, except I see the way he stumbles, no doubt suddenly feeling the wrath I'd brought upon his clit. I hear his sharp intake of breath and that's all as he hurries down to the end of the hall. By the end of it, near a closed door that must be his bedroom he turns and I see how wide and bewildered his green stare is.

"Uh—be right back, one sec," he squeaks.

I watch him slip into the room, out of sight. What might he be feeling? Is he confused? Aroused? Aching?

I do it again—feel that unique hitch beneath my lungs—and the rain stops, once more plunging the world into quiet. This time I take off my shoes, leaving them right where I was standing as a marker. Then I venture down towards the door. This place looks nice and I wonder if Max lives alone. He seems a little young to be living by himself in a house like this, cause even though it's small it's fancy looking and the neighborhood is wealthy. The entrance hall opens on the right to a living room and kitchen. The furniture looks expensive, if not a bit messy.

"You got money, Max?" I wonder as I get to the end of the hall and push the door open. It's his bedroom. "That's a yes." He's gotta be rich. His bed's huge, queen sized and soft looking. Max is frozen by his desk on the other side of the room, hand outstretched towards his wallet. I get there before he does, thumbing through the contents. There's plenty of cash in there and I pocket an extra five. Not like he'll really notice. He might be wondering where his money went but I'll still be by the door when this is all over.

Anyway, my cock strains against my pants and I wanna get down to it. I hook my hands around Max's hips and pull him back, bend him over the desk. Then I yank down his shorts and underwear again. From the back his ass is perfectly pale and I can't resist slapping it a couple times, just to put some color on his skin. His pussy is plump and pretty between his legs and I reach under to finger him again, finding him even wetter than earlier. All that clit pinching must have gone to his legs whether he'd wanted it or not.

"You liked that, huh? Or I guess your cunt did," I chuckle. I wonder how much experience this guy has. Is he adventurous? Does he get fucked on weekends? Or maybe he's shy and dry, which would be a shame for someone with a body like his.

I hurry to take off my pants and free my dick, it's deliriously hard and I shuffle closer, rubbing my cock between Max's cuntlips, getting it nice and slick. Really savoring the feel. I expected ass at least. Pussy is a surprise.

The moment where I first push in is my favorite. He is stupid tight and it always feels the best, pushing in and getting to feel a slick cunt wrap around you. I push deeper, inch by inch until my full length is inside him and my thighs are pressed against his. For a moment I am still, just enjoying the feeling of being inside. I sweep my hand through his soft hair, mess it up with my fingers. Then when my anticipation is too much I pull all the way back, till only the head of my cock is still inside.

"You're gonna be sore after this."

I pull him back onto my cock when I ram him, and god it feels good. Once I start I just can't stop. I like to be rough, like to leave bruises. That's why I love doing it like this. Cause I can be as rough as I want and nobody says anything about it. Max's cunt seems to want me, practically invites me deeper and I'll accept that invitation without question. I pound his velvety heat all the way, balls slapping against his ass as he rocks against the desk.

I tell him "You feel so fuckin' perfect," and pull his hair, try and imagine what he'd sound like. Would he be breathless or would he be loud? Maybe begging me to slow down or touch his little clitty. I won't. Don't even have to think about pleasuring anyone but myself so I fuck him as hard as I can, just to see how loud I can make the slap of skin on skin. There's gonna be bruises on his hips but I don't care.

"Fuck," I growl. "Fuck, fuck." I thrust one more time and hold Max against me, groan as I come deep inside his sweet pussy. Is he on birth control? The thought is fleeting since it won't matter to me. Not like that'll keep me from coming inside every time.

In the afterglow I lean against his back, catching my breath against his shirt. After a minute I pull out and when I look down there's a bead of white between his cuntlips. A little sign that I've been there.

"I'm not done with you yet," I warn him. I straighten him up and take his shirt off, just to see the rest of him. His skin is clear and his shoulders are dotted with freckles. I carry him to the bed and lay him out on the soft covers, naked and spread like one of those funny looking blow up dolls. He looks spaced out, pink lips barely parted, staring into nothingness.

While I wait for my energy to return, basking in the afterglow, I root around Max's room, looking for something fun. And I find it, buried in his chest of drawers there's a bottle of lube and a small collection of colorful dildos and plugs. No cheap shit either.

I pull the toys out one by one, weighing 'em in my hand. Most of them are silicone but there's a sinfully wide metal plug too and a yellow vibrator that looks expensive. I try and imagine what Max would look like using it. Would he rub it buzzing against his little cock, or would he bury it in himself? That's the annoying thing about my gift. Sometimes it leaves a lot of questions unanswered. No matter, I don't let it bother me too much.

"So you're kinda a slut, huh? But you get no dick?" I bring some of the toys to the bed and crawl between his legs. That's my guess at least. I pinch Max's clit some more, really wanna make it throb. It's slippery between my fingers. When I get bored of that I pull on his nipples. He's got no big top surgery scars, just a little mark beneath each pink nub and that's all. I wonder if he would have let me fuck him. I know I'm young and not bad looking at all. Could get any guy or gal with just a little effort, but this is too fun and the best part is still ahead.

An idea finds me. I grab the lube and drizzle cold slick onto my fingers before plunging them inside Max's waiting pussy. He's already fucked open but I spend a little bit of time just stretching him out even more, getting him nice and prepared for what I have planned. To test out my idea I take one of Max's dildos, an ordinary looking silicone cock. It's thinner than I was so I easily slide it all the way in.

"So fucking loose." I take another dildo, about the same length but a little thicker and in purple. Fit that one in too with just a little wiggling, shove it all the way to the base as well.

I test how tight he is with a finger, wedge it in alongside the toys. It's a tight squeeze, definitely, but it's fun to really push the limits. There's a little room left. I select another one of his toys. This one is real thin, not too much wider than my finger is, but it's got an unnaturally wide head. I lube it up and set the blunt tip against him. It's fucked up, treating him like he's some sort of toy, but what's he gonna do? I said I was gonna savor this one.

For a moment I don't think it'll fit. Maybe I have to use a different toy, then abruptly, with just a little more force, there's that magical instant where you can see his body accept it and the fat head of the toy pops in and then the rest of it too. My cock twitches at the sight, his pussy stuffed obscenely full, the ends of three dildos crammed inside. Can't resist snapping a quick picture on my phone.

I study his face, still lifeless. Eyes glazed. "Just a rehearsal," I explain as I take out the toys and lay them aside. That show will be later and I'm way too excited for it.

With that prepped though, I flip Max over and manhandle him until he's bent, propped up on his knees with his ass all the way up and his face hidden in the covers. There's only so much time I can spend looking at people's frozen expressions. The face ain't important anyway, it's the holes, and I'm about to leave my mark on Max's ass next.

It's impossible not to give him a little handling first, just spread his cheeks and smooth my palms over his backside cause it's actually too good to be true. I play a beat on his skin, drum my palms against him cause I really want him to feel it later. Dunno why. I think I just want this to be something Max dreams about. A fever dream he has no control over.

My fingers are still a little damp but I lick em once anyway to rewet the lube and prod the pink pucker of Max's ass. It gives way surprisingly easy and after a moment of exploration I discover that his ass is already clean, actually. Makes me suspect that he was up to no good earlier. Or maybe I was wrong and he does get laid. Either way that makes my task easier. In only a few minutes I have Max loose enough to use, scissoring my fingers in him. His entrance is hot too and I hurriedly slick up my cock and line it up.

"Hang tight."

In one solid thrust of my hips I enter him, all the way to the hilt. A satisfied groan escapes me.

"Fucking—anal slut." He feels too perfect on my cock. "You're fuckin' made for this." The jackpot. That's what Max is.

The yellow vibrator rests on the bed by the other toys and I get another idea. I lean over to snag the toy and fumble with it under Max until I manage to blindly jam it in his cunt. Then there's more brief fumbling as I mess with the switches until—

"Shit," I grumble as the vibrator buzzes to life. I can feel it on my cock too, through the thin wall separating his ass and pussy, but it's faint. I fiddle with the switch and set it to full power and then it feels good. Not as intense as I expected but intense enough to add another layer of fun to this adventure.

I pound him, hammer him into the bed covers like the world will end if I don't fuck him as hard as I can. Max is just too perfect and I tell him that. Call him a rich slut too cause he's gotta be. "Best fuck I've had in a long time," I tell him. "Maybe—ever. Coming from a boy with a pussy." The vibrator continues to buzz and I slap his ass some more, every second thrust.

"This is what a real dick feels like," I grunt. "Not that tiny thing you got." Real cocks are probably better off inside him anyway.

It doesn't take long to come. I'm lost in the moment, so busy fucking that when the vibrator falls out of Max's loose cunt I hardly even notice. This is my second go and I sag against him as I pump his ass full of sticky white, panting. God it feels good. After I pull out his ass stays open briefly before it lazily slips closed. I wipe a stray drop of cum off his hole and smear it against his thigh. Jackpot.

I take another break before clean up time begins. I sit on the fancy looking couch in the living room and spend some time rooting through the cabinets for a snack. Looking around the house I get the impression that he really does live alone.

Finally I return and Max is still in the same position, head down, ass up, holes full of cum. I take a couple more pictures for later, in case my buddies beg for details. This part is always the most tedious. I put all the toys away, dress both of us, and set Max back up in relatively the same position. Might be a little off but that's okay. Afterwards I backtrack to where I left my shoes. Put them on, put my mask on, pick up the bag of food that'll still be warm.

Time starts again and even down the hall I hear a sudden crash and a sound. Not a moan but not a scream either. Just a noise.

"Everything good?" I call down the hall.

I wait, silence answering me until the door opens and Max stumbles out. His face is red and his eyes are wide with confusion as he comes back down the hall, wallet in hand.

"Y-Yeah—sorry." He stammers, pulling a ten out of his wallet and holding it out. His legs are trembling. Once I take the bill I sneak my hand up and pull on my ear, one last time. This is the icing on the cake, arguably the best part of a day like today. Getting to see his reaction. His complete bewilderment when there's a stranger's cum leaking from his body. I think it's a little too soon to really go again but I push Max down to his knees and squeeze his cheeks so that his mouth opens wider. Unbuttoning my jeans I feed the tip of my half hard cock into his mouth, wary of teeth. His mouth is warm and wet and when my dick reaches the back of his throat

I guess my body decides that I can cum again after all. I hold his head between my hands and move it back and forth on my cock, first slowly, then faster as I find a rhythm, balls bumping his chin. It's tradition for me to christen every hole and Max happens to have three so I gotta put a bit more effort into it. When I do dump my load I make sure to pull his head away a little, so some cum gets on his tongue and doesn't just spill down his throat. I want him to taste me. Want me to live in his mind for hours after this is all over.

I tip him onto the hardwood floor, prop him up on his face and knees like he was on the bed earlier, and pull his bottoms down. Then I run to the bedroom again and bring back the three dildos, a buttplug, and the bottle of lube.

The first thing I do is unscrew the top of the lube entirely. I press the open end against Max's asshole and squeeze almost half of the bottle's contents into his waiting entrance. I just want him to be messy beyond belief. He'll wonder what the fuck happened, find himself sopping and stuffed full. Picking up the teardrop shaped buttplug I slick it up and press the cold tip against him. It's big and metal, maybe three inches at its widest point. I push it in slowly, first a little at a time, then pulling it back, then deeper again. It's just fascinating seeing the rim of his hole stretch and shrink.

Eventually I ease in the widest part and watch with bated breath as Max's ass closes around the neck of the massive toy, accepting the intruder as part of him and sealing the lube inside. I make sure the base of the plug is flat against him before I flip him over and get to work on his pussy.

I pour a quarter of the bottle inside his hungry little cunt and insert the toys in the same order as earlier. It's a bit tighter this time. The buttplug adds pressure and as I push in the second dildo lube oozes out onto the floor. I'm undeterred. I can make everything fit because I've made it fit before. The final dildo goes in much like it did earlier. Initially I start to doubt and then abruptly it pops inside and fits snugly with the rest of the toys.