"Huh, always wondered why this dump was called the Ring of Pride..." Loona mused as her paws clicked along the spotlessly clean pavement.
This was technically her home but she'd never really been outside Imp City, and there seemed to be very little there for anyone to be proud about. Especially her - a hellhound sixteen years old and still not adopted. Hence these dumb-ass work contracts, including the one that forced her to drag her skinny ass all the way out here.
"So let's see, which one of these am I supposed to go to... aww fuck, figures it would be that one!" She said, laying eyes on a mansion that definitely stood out. While the rest of the street was a display of both exceptional wealth and exceptionally bad taste, the edifice her phone insisted was the right place adhered to a more traditional infernal aesthetic. An impressive fence made of bones and wrought iron, imposing black-basalt walls, torches burning in sconces and every window showing nothing but blood-red drapes.
"Yeah, definitely not an imp home..." she said, making her way along the traditional infernal walkway (paved with authentic good intentions) before making use of the sinister door-knocker.
The door was pulled open by a skeleton who bid her enter, the hellhound’s keen ears picking up the subtle wailing seeming to echo from the empty skull, begging for an end to the pain. One of those poor fucks who never read the contract before signing his name in his own blood. There were plenty of other skulls strung out on old rusty chains all about the place. Some of them emitted a baleful red glow from their empty eye sockets, so she guessed this must be the owner's idea of lighting.
"Who dares enter my abode?" came a deep voice, and Loona found her tail clamping down and hear ears folding against her head at the sight of the towering demon who'd asked the question. He was definitely the type they used to send out to scare the shit out of mortals, a hulking winged brute whose scaled hide bore a network of scars.
"I... I'm from the adoption agency?" the hellhound said, cringing at the whine that came out of her muzzle.
"Aahh, the hellhound. It is good you are here. I have hired you to be the keeper of my only son and heir. Undead servants and the damned have proven too... fragile, but one of your kind should be safe. Follow me to the inner sanctum..." the red behemoth said, leaving Loona to follow behind and wonder what she got herself into. The heavy door bore a 'DO NOT ENTER!' sign and she steeled herself for what the spawn of this mean bastard must look like, but was surprised when the door was opened to reveal a shockingly normal room, the type that seemed fitting for the young golden retriever relaxing on his bed with a comic book in his hand and a pair of headphones on his head. Loona turned around and cocked an ear in confusion, surprised to see the terrifying demon hunched over, looking pensive as he wrung his clawed hands.
"Uhh, he's adopted, you see. I'd appreciate it if you kept it a secret." he said awkwardly.
*******
"So... you're the terror? You wore out the other sitters?" Loona asked, cocking one eyebrow as she looked down at the golden-furred pup.
"I don't even need a sitter!" the boy said sullenly.
"So why did your dad hire me then?"
"'Cause he's always away on work. So I guess he feels better if he knows there's someone around to keep an eye on me."
"Okay, sounds easy enough. Just to make things clear - I'm not a push over like some skeleton or a sinner, or whoever you've had up till now. Try any bratty crap with me and you'll see why they call female hellhounds bitches. I'm Loona, by the way..." she said, spotting an empty beanbag and pulling out her phone as she settled down into it.
"A-Andrew. But you can call me Andy..." he said, feeling awkward now that he realized he was alone with a girl in his room.
"What, like 'My friends call me Andy'?"
"I guess. I don't really have any friends..." the boy said, getting no reaction from the female hellhound apart from an arched eyebrow.
"Hmm. Friends are overrated anyway..." Loona replied, sliding her finger across the screen.
"Whatever..." the pup said, getting off his bed and heading for the door.
"And where do you think you're going?" the reclining bitch asked, her eyes still on the phone but her ears perked.
"I dunno. It's a pretty big house..."
"Yeah, that's my point. It's a huge fucking house and I have no intention of chasing you around it."
"What, are you afraid I'd manage to ditch you?" the pup asked.
"Dream on. I don't know how good your nose is, but nothing gets past mine. Hell, I can smell what you're thinking..." the hellhound bragged, all the while taping at the screen as little notifications beeped and chirped.
"Really?"
"Maybe. How would you know? Look, from where I'm sitting, this is a pretty easy job - your ass stays in here with me and you can't make any trouble. So just go back to what you were doing before I came in and we won't have any trouble."
The retriever sat down on his bed, sulking as he fixed a scornful stare at his new sitter. The hellhound completely ignored his, although he could tell by the swivel of her ears that she was paying some attention. A few minutes ticked away and feeling more bored than usual Andy spotted something sticking out of the dingy little backpack his sitter had set down. The hellhound seemed to engrossed with whatever she was doing on her phone and didn't notice or care that he'd fished out the scroll and began to read it.
"What's 'hereafter' mean?" he asked, trying to make sense of the big new words in the document.
"It means 'from here on'..."
"Huh. So 'hereafter referred to as the ward'... guess that's me..." he mumbled, but the hellhound didn't seem to pay him any mind. "What's 'compliance' mean?"
"Doing what you're told. Like when I told you to sit and be quiet, if you actually did it, that would be compliance..." the young bitch said, obviously irritated at these constant interruptions of her effort to waste her time. "Why the fuck are you asking? Your dad seems to have done well for himself, there's got to be a dictionary in this place somewhere... wait, what the fuck are you doing with that!?" she barked once she saw Andy reading the scroll.
"Just reading, like you wanted me to. This is the contract you signed when dad hired you, right?"
"Yeah, and if I wanted you to read that I would have told you to. What kind of fucking twelve-year-old reads a contract? Do you dream of being a lawyer when you grow up?"
"I was just curious what this is..."
"It's the sort of contract you have to sign when you're fucking sixteen and nobody's adopted you." Loona replied, a hint of bitterness creeping into her irate tone. "Now give it back!"
"Yeah but, I don't have to, do I? This... this looks like one of those real infernal contracts. Like the ones my dad tricks mortals into signing. And it says you have to listen to everything he or your 'ward' says. And that's me, right?"
"It's just a piece of paper. I'm bigger than you, older than you and you're doing a good job of pissing me off, so you better..."
"Sit!" Andy said, the wavering tone the command had been issued in didn't seem to change its potency. Loona plopped back into the beanbag instantly, looking surprised for a second before assuming her usual expression of indifference, as if she'd done it because she got bored of standing.
"Fine, keep the damn thing. Just a piece of paper anyway."
"Really? Well, let's see if we can change that cranky mood. Smile!" Andy commanded, and almost winced at the sight of the hellhound grinning as wide as she could, showing a mouth full of impressively sharp teeth. "No, not like that! I mean sort of like...a cute girl smile." the boy said shyly, and to his surprise the muzzle-splitting grin was replaced by a pouty one, which coupled with Loona's now perked ears did look cute.
"Aww, like this? You want a cutsey-wutsey widdle hell-hound puppy to play with?" the bitch said in a sugary voice before continuing in her usually surly tone, all the while smiling a cute smile. "I don't know if you could tell, but I was faking. I figure you should start learning to tell when a girl is faking it, I have a feeling you'll need that skill later in life. I may have to do what you tell me, but no paper can force me to do the impossible. And I don't do cute..." she said, nonplussed by the fact Andy's ears were flat against his head after her little remark.
"Oh yeah? Well maybe I won't need that skill later in life!" he said, wishing he'd phrased it a little better.
"Aww, you've got a little girlfriend?" Loona asked, using the forced smile to mock him.
"No, but I've got a girl in my room who has to do anything I say."
"You...wouldn't... dare!" the young bitch said, her cute smile contrasting with the coldly vicious tone of her voice.
"Oh yeah? How about you dance for me? A sexy dance!"
"You should have asked for something better twerp, seeing how it's going to be your dying wish...” she said, but she did rise and after a few quick taps music began to blare from her phone.
It was something very loud and with a lot of distortion and nothing like Andy thought a sixteen year old girl would dance to. But the surly hellhound in front of him began to move, swinging her hips and tossing her hair in a way that soon had him sitting on the edge of his bed with his hands clasped in his lap. Even though acting cute was apparently beyond her abilities, sexy dancing clearly wasn't and as the beat picked up Loona's movements became showier. She'd run a hand along her thighs, cup her pert breasts, throw her rear out or lift her tail. The pup had never seen a girl doing something like this, and as he watched an idea popped into his mind. Desire warred with fear of going too far, but he was at an age when he had more pent-up needs than common sense.
"Okay, now do a strip-tease!" he said, his voice an embarrassing squeak as he shouted to be heard above the noisy music.
The yellow pup’s tail actually started to wag behind him as the dancing hellhound began to obey, sliding her fingerless gloves off one by one. She continued swinging her hips as she grabbed hold of the torn hem of her crop-top, and Andy felt his claws dig into the bed sheets as she pulled the ratty garment up. He only got a glimpse of Loona’s bare chest before the top was flung at his face, filling his nostrils with her scent before he pulled it off.
The sneaky bitch had turned around while he was distracted, frustrating him with the sight of her naked back to the point he was about to order her to face him again. But when the hellhound’s thumbs hooked into the waistband of her shorts he remained silent, anxiously awaiting his first glimpse of a real-live girl’s…
“Whoah!”
Even above the din of the music, Loona’s ears had caught the young mutt’s gasp, a sure sign that pulling her pants down had given the little dork his first glimpse of actual pussy. For her part, she was glad that no one was around to see her exposing herself to some spoiled brat. Still, she figured if she made this showy enough the kid might just ream his pants and that would be it for his first little foray into pubescence. 
She turned around with a flourish, arching her back and thrusting her chest out because no matter how lame it was that she had to strip for this brat, her tits had just started coming in and if she had to show them she would show them off! The sight of the pert young mounds seemed to mesmerize the boy who got to his feet and made a few trance-like steps towards her. He seemed to snap out only when Loona twirled, purposefully smacking him in the face with her bushy tail.
“Ow! Hold still…” the pup whined, and acting under the compulsion of the infernal contract, the young hellhound did just that, standing with one hand on her hip as she looked down at the kid. 
The show wasn’t enough to make him pop, but she hadn’t been far off in her estimate judging by the prominent tent in the kid’s pants. Not bad for his age, she supposed, and if he’d been at least four years older she might have been tempted to help him out with that. She could see how nervous he was which she supposed was the really big turn off here. She knew some of her friends found the whole innocence thing cute, probably since it was fairly scarce in Hell, but she never could figure out what the appeal was in a male who didn’t have balls.
And when the kid’s arms went up, it only proved her point. He was hesitant, even though the way he stared at her perky tits made it clear how much he wanted to do more than just look at them. But his hands were shaking as they rose, almost as if he was afraid she’d bite him. And when he finally worked up the nerve to touch them, he acted like he was palming a pair of soap-bubbles that might burst and disappear if he applied even the tiniest bit of pressure. Although she had to admit that her budding breasts did look impressively big with such small hands pressed against them, but she still would have preferred a pair of strong paws giving her a proper grope. 
Andy palms seemed to tingle as he gently cupped his first ever boobs, his jaw slightly slack as all of his attention centered on the fluffy mounds. They hadn’t looked all that big under the hellhound’s shirt, but the weight of them in his hands was more thrilling than he’d expected, as well as the soft yet firm feel of the two fleshy globes. His attention shifted to the pale-pink nipples sticking out in the soft white fur and soon enough he was running the pads of his thumbs over them, gasping once he saw the nubs stiffen and stick out in response. That must mean I’m turning her on!
A quick look up dispelled the idea, since Loona was still giving him the same bored-and-annoyed stare. But even the glare of the unenthusiastic young bitch wasn’t enough to pour cold water on the pup’s awakened curiosity, and before he knew it he was on the tips of his toes, his nose twitching as he took in her scent just before he pressed his muzzle against one of the hard nubs.
“Haven’t you been weaned kid? Maybe you should ask your dad to hire a wet-nurse instead of a babysitter…” Loona replied, thanking Satan that none of her friends could see this. 
She wondered if she should just take the initiative, and by initiative she meant the boy’s cock. A stroke or two would probably be enough to push him over, and after he embarrassed himself by popping from just a touch or two he might settle the fuck down and stop nursing from her like she was a fucking dairy cow! But she still hoped she might get out of this without getting a kid off, and even if she wanted to do it her last command had been to stay still, so she didn’t have a lot of choices.
“Look kid, if you want milk I can go and get your bottle, but you aren’t going to get anything out of those…”
“I’m not a little kid!” Andy tossed back, worried that the fact that her nipple was still shiny from his spit might cast doubt on the claim. “Anyway, grown-up men like boobs too!”
“Yeah, as toys, not food. Look, there’s a reason you’re supposed to start this stuff off with a girl your own age – because she won’t know that you have no idea what the fuck you’re doing. You fumble around with a girl for starters, and hopefully in a few years you grow the balls to try it with a woman.” Loona explained, upgrading herself a little. Well, I am a woman compared to this squirt…
“Oh yeah? Well…” Andy began, and struggled for something to say that would salvage the childish sentence. “Get on my bed, on all fours!” Loona heaved a sigh, knowing she had little choice. Her muscles moved in accordance with the compulsion and soon she was on the star-and-moon spangled blanket without anything but her spiked collar to protect her modesty. 
“R-raise your tail…” the voice said from behind her, and the hellhound’s only satisfaction was that Andy was close enough for the bushy appendage to swat his muzzle as it swished up.
“So what now? You have any idea what to do with an actuaaaaAhhh!” Loona yelped out, surprised to suddenly feel a finger poking around her exposed sex.
“Did that hurt?” she heard the pup asked, and the concern in his voice was even more humiliating than his fumbling fingers.
“No! Just… warn a girl before you do that!” she replied sullenly.
“Sorry, just… never seen one of this up close…” she heard the kid mutter, and a second after that his finger managed to find the right spot and sunk an inch or so into her. “Whoah! It’s so hot in there…” he said, and Loona felt the digit push in a little deeper. “Isn’t it supposed to be a bit more…y’know… wet?” the pup asked, stretching her folds as if he was trying to see if anything in there was glistening.
“Look kid, a girl isn’t supposed to get wet for you, you’re supposed to make her wet!” the young bitch barked out, omitting the fact that the sight of a particularly well-build hellhound male is generally enough to get her positively dripping.
Andy had no real idea what the naked hellhound was talking about, or even if she was being serious. When he’d ordered her on all fours and started poking around back there, he’d kind of imagined her mood would improve a little. He knew he was still little, but he was also reasonably sure he was cute. Weren’t girls supposed to like that? Moving his finger around inside her didn’t seem to be doing anything for the snarky bitch, even though it felt amazing for him just poking and rubbing around in there. After another minute or so he pulled his finger out and noticed that it was a little wet. He brought the digit closer to his face and his nostrils flared on their own as he took in the feminine scent.
The smell seemed to trigger something in his young brain. Sort of like smelling good food made him feel hungry right away, the scent of Loona’s sex made him desperate to find out what she tasted like. He knew he could always lick his finger, but the idea was flushed from his mind as his eyes centered on the smooth pink slit exposed in front of him. Forgetting his shyness for the moment, Andy knelt down behind the annoyed hellhound, placing his hands on her firm behind as he stuck his muzzle in her crotch.
“What the… fuck!” Loona almost yelped, feeling the cold sensation of someone huffing and sniffing her privates before a tongue slid across her bared slit. 
The little pervert behind her seemed to like his first taste of pussy because the next thing she felt was the muzzle wedging between her lips as he began to lick deeper and faster. This is ridiculous! I’m naked and on all fours with some dorky little brat going to town on my pussy! In all honesty the tongue slurping away back there didn’t feel bad, even though the pup didn’t have the skills needed to do anything more than just get her riled up. And she might have been tempted to teach him if the tables were turned. If she was the one sitting on the puppy’s golden-furred muzzle with the dweeb begging her to let him cum, she could live with that. Or better yet if it was some really big male behind her, one that could actually palm her cheeks properly with his strong paws while he pushed his muzzle into her smooth little cleft. She’d have no trouble lifting her tail and playing a good bitch for a guy like that, but having some little brat treat her like a sex toy was getting on her nerves.
“Will you get your face out of there already? You don’t even have any idea what you’re doing…”
“Okay then, why don’t you show me!” the pup replied, licking his chops and crossing his arms across his chest.
“Can’t reach genius. I’m a hellhound, not a hellcat.” Loona replied.
“Well you can reach this…” the boy said, sounding annoyed as he lowered his pants and fished out his fully erect cock.
“Okay, so if I stroke you off will you just sit down and shut up for the rest of your day?” she asked, figuring that a few pumps would get the little red rocket spraying.
“Nu-huh. You have to use your mouth on me, same as I did to you.”
“Oh, well whatever you say, master…” Loona said, turning around on all fours and flashing a sinister smile as she fixed her gaze on the yellow pup’s pecker.
“Gah! I mean your tongue! J-just your tongue! No teeth!” the boy stammered as the sight of the hellhound’s grin.
“Pussy…” Loona replied, taking some small satisfaction from the boy’s distress.
But the pup’s fear soon melted as she began to lick along his rosy red length. At first it was just a few lazy strokes with her tongue, but when that failed to make the little coin purse contract and the tip erupt she put some more effort into it. She’d start from the fat little knot at the base, cradling the length as she licked up and finished with a flick of her tongue against the boy’s tip. It got her a lot of gasps and whimpers from the pup, but no spray of tween spunk. She even tried closing her eyes, imagining she was working over a foot of hard doggy-dick before letting its owner push it between her legs and thank her for the attention. She even tried throwing in a few soft moans here and there, hoping it would make the pup pop, but the kid just knelt in front of her breathing hard while his cockle bobbed and twitched.
“You getting close there kid? Contract or no contract, I’m not sure how long I can keep this up…”
“I dunno. Never had a girl do this to me…” the boy said. What he really wanted was to feel that gorgeous muzzle swallow his shaft, but the memory of Loona’s teeth kept his from requesting it. “You know, I’m pretty sure I’d be able to finish if we…”
“Look kid, let me stop you right there. I’ve had real men before so if I were to lift my tail or spread my legs, you’d just get embarrassed when I failed to even feel your little puppy-pecker.” Loona said, omitting the real reason she was hesitant to let the boy mount her. She was close to her heat and didn’t trust the pup to pull out in time, but saying that might give the little punk ideas about a sure-fire way to avoid pregnancy. And I’ll be damned if I’ll let this little brat be the first to take my ass!
“But can’t you… like, shrink?”
“What the fuck are you talking about?” she asked.
“I heard you hellhounds can change shape.”
“Yeah, either into humans or into full canines. They’re disguises for when we go into the living world.” Loona barked back.
“But… if you turn into an actual hound… you’d be smaller, right?” the boy asked.
“Yeah, but what does… oh no! Don’t you fuckin…”
“Turn into a hound!” Andy said, cutting off the bitch’s salty protest. Almost instantly blue flames swirled up and engulfed the furious female, receding to reveal something that might have been mistaken for a common wolf if not for the spiked collar and the vicious anger radiating from her blood-red eyes. “There, see? I bet you don’t weigh any more than I do in this shape. Now turn around and lift your tail.”
Loona actually growled which she knew would be the best she could do. A dog’s voice box was great for those, as well as barks and howls, but she wouldn’t be able to talk until he let her change back into a normal hellhound or (Satan forbid!) a human. She’d hoped the little perv would be put off by fucking something that didn’t look like a girl, but when she felt him poking around her spade she realized he was too horny to care.
“Huh… looks different…” she heard him say before a finger was pushed into her canine sex. “Wow, it feels even tighter!”
After that comment the finger was pulled out and Loona wasn’t surprised to feel the hard, tapered tip poking her fortune cookie. She’d never had sex in this shape, although like most adolescent hellhounds she had spent several evenings as a hound just so that she could lick herself. She knew that her anatomy was a little different now and wasn’t surprised that the puppy’s pecker was thick enough now that several inches of it were pushing into her. 
Andy felt his paws clamp down on Loona’s hips, his mouth slack as he watched his slick red length disappear into the strange canine cunny. Loona’s sex had looked prettier when it was just a smooth pink slit, but the spade he was burying his bone in felt amazing as it pulsed around him, caressing his smooth rod as he slid more of it into the velvety warmth of the hellhounds’ honeypot.
By the time his knot touched the canine cunny wrapped around him, Andy was almost panting. Loona’s tongue had felt amazing and despite what he’d told her it had taken every last bit of restraint to keep him from cumming while she licked along his young cock. But her tongue couldn’t compare to the warm, velvety vise holding him now. The pup had paused to keep himself from popping too soon, knowing that the hellhound was sure to tease him mercilessly if he embarrassed himself like that. And maybe if I make her cum she’ll stop acting like such a bitch…
The retriever took a firm hold of the hellhound’s hips, watching the speared spade cling to him as he slowly pulled out before he buried everything but the knot in again. He repeated the slow stroke a few more times, savoring the sheer tightness of the canine sex before instinct took over and his humps got shorter and faster.
Loona had to admit the kid’s idea had worked, and that in this shape his puppy-pecker actually felt like a decent piece of dick back there. Almost big enough for her to enjoy it, despite the amateurish way the boy was banging her. But she remembered that little coin-purse of his had looked quite full and the idea that the brat might breed her was making it impossible to just lay back and relax. She couldn’t say a word or change back until he let her, and judging by the way he was pumping away at her spade she doubted he’d have the good sense to pull out before it was too late.
And the kid was unlikely to have a long fuse. Even as her body reacted to the sensation of a smooth, slick doggy-dick pistoning in and out of her fortune cookie, she kept wondering if she was about to feel the shaft twitch and flood her with a warm batch of puppy-milk. The kid had a firm grip on her hips and was humping into her faster and faster, and only when she felt the knot bump into her cunny with every thrust did it occur to her that the brat might actually…
Fuck! Loona’s mind screamed, but all that left her muzzle had been a yelp as she felt the familiar and right now very unwelcome sting that could only mean one thing.
“Oh wow! Is… is it supposed to go in?” the boy asked, breathing hard and watching with a stupefied expression at where his crotch met hers. Loona’s quite explicit response came out as just yips and growls, but it seemed enough for the kid to realize that she didn’t want his knot inside her. “All right, I’ll try and get it out…”
Loona clenched her teeth as the kid tried to pull out of her, but when the first few tugs failed to pop the knot out she knew there was little hope. She could feel the red lump growing with every twitch of the boyish cock, the hard mass of flesh going from snug to almost painfully big. Normally it was the kind of pain Loona liked, and when it was a safe day she’d enjoy flexing her sex around some hunk’s knot until she felt the rush of hot gooey spunk spray her insides. But whenever it wasn’t safe she had the guy pull out and finish either in her muzzle or between her tits, and now she was in very real danger of having a puppy give her puppies!
“Ungh… I can’t budge it. Look, I know how to get it out. It always goes down after I… finish so…” the boys said, putting his hands back on her hips as he began to grind away at her rear end. Loona tried to growl at his, and tell him to just stop and wait, or maybe call some of those skeleton servants in to pour buckets of cold water over them, but the kid didn’t understand. “Don’t worry, it’s not like I can get you pregnant when you’re shape-shifted. I’ll just make this quick and let you change back…”
What the… of course you can you little brat! Don’t you know what ‘disguise’ means?
Loona tried to think of something she could do to let the kid know that he was going to become a father before he became a teen if he didn’t stop what he was doing, but as the boy mounting her continued to hump against her rump, thinking became harder and harder. She’d always been a sucker for this, and she could have maintained control if that swollen knot was merely pressing against her g-spot. But even the short thrusts were enough to make the bulge move around inside her, and as the throbbing mass pressed and rubbed her most sensitive spot, the bitch felt herself losing what little control she had. Her growls had turned into whines at some point and when she felt little tremors run along her sleek canine body Loona knew she’d lost the good fight. 
She managed to keep herself from howling, but she doubted the boy would miss the fact she was cumming once her cunny clamped down on him. Her angst and cynicism dissolved if for but an instant as her orgasm hit her, her canine sex gripping the boy’s knot as it began to milk the young cock trapped inside it. She was still riding her high when she heard grunts from behind her just before the cock trapped in her sex began to twitch, sending squirt after squirt of Andy’s spunk into her.
All right you little shitheel, you’ve had your fun! Now let me change back to normal, pop this fucking knot out and if I rinse your mess out in time I might just get lucky and…”
“That…was…awesome!” the kid panted, a yawn interrupting his panting. “Uhh, feel so tired. I’m just gonna close my eyes for a sec…” he said, and the next thing she knew Loona had his arms wrapped around her mid-section as he plopped down on to the bed and pulled her along with him. Any hope she had of the kid returning her to normal and letting her push his knot out of her were dashed when she felt him spoon up and heard soft snores from behind her, the brat drifting off to sleep even though his puppy-pecker was still stuck and still shooting the last of his load into her.
Fuck! I just know the agency’s gonna blame me for this…