Chapter Text
October 31, the fabled holiday of Halloween, Most would be out and about, wearing costumes of things that would typically be related to this kind of holiday, such as demons, witches/wizards, mummies and whatnot, going from house to house Trick or Treating for Candy. Some others would prefer to say home to give out the candy or host halloween parties at their houses. And others, would just like to spend the day quietly. Rio was a bit of a mixed bag. The green-eyed, brown-haired male’s life had become quite… interesting over the years ever since he met a particular person. At first, he never really found the joy in Halloween and would just spend the day at home by himself, either watching movies or playing video games with his friends over a Discord call. However, all of that changed on one fateful Halloween day, where he met a particular Hellhound girl.
Her name was Sinder and she was a Hellhound that was essentially kicked out of hell, and ‘cursed’ with a half human, half hellhound body as her punishment due to her having a heart of gold filled with pure empathy and love for everyone around her. Considering that she was basically stranded, she started to look around for any place to live. However, practically everywhere she tried, required her to have some form of currency to pay and she… well, being a literal species from hell, did not have such things on her. So, she was homeless and broke and she would have probably stayed like that for a good while… if not for this wonderful guy helping her out. Of course, that guy was Rio, who had decided to help her out, by offering her his place to stay until she could get a job and get her own place.
Sinder was a bit skeptical of his kindness, wondering if he had some ulterior motives that included her, but… she was thankfully proven wrong. Rio was the nicest human she’s ever met up to that point! So you could believe how internally grateful she was that she decided to trust him. Ever since that day, Sinder and Rio had lived together under the same roof. The Hellhound even picked up a hobby of hers aside from gaming and making ASMR roleplay videos, which was streaming. Sinder’s streaming career took off quite quickly as she was quickly gaining many subs and followers, her beloved Pyro Pups on twitch. Heck, she even began to make friends with other streams like herself, some of which being Akuma Nihmune , a self-declared “badass demon girl” who was quite well known for being “a bottom” , Bao , a whale girl who has had… interesting tastes to say the least, Trickywi , an egyptian harpy dragon with an adorable personality but an immense fear of spiders, Vienna , a cosmic dragon girl who’s extremely passionate about things she dislikes, such as spaghetti and Sanagi Yuzu , a silk moth spirit who has absolutely ZERO sense of direction; quite an interesting, quirky group of girls. Rio would occasionally find himself interacting with the others in this little circle of friends Sinder gained, which ended up becoming named the “Girliepops” , but she also has friends outside of this little group, such as Shylily, Cottontail, Lucy Pyre, Filian and Buffpup to name a few.
At first, there wasn't much verbal interaction, mainly due to Rio finding himself feeling out of place in a group of unique girls, all of which with a different abnormal origin while he himself was just human. So whenever they’d be in a discord call or just hanging out together, Rio would gradually isolate himself from them, feeling like he was intruding on their time. But after some much needed encouragement from Sinder, which involved a little push and with her purposely moving the conversation to him to get him, Rio would soon find himself more involved with Girliepops. even joining in their streams for collabs and even hanging out with them away from the cameras, where… more often than not, something ‘interesting’ would happen. But in the end, they all would end up enjoying each other’s company.
What also probably helped was the fact that… well, all of these girls were hella attractive, both physically and personality wise in their own way to Rio. From Snider's infectious laugh, to Numi’s stuttering whenever she gets embarrassed or flirted with; from the cute Harpy Dragon noises Tricky makes to how Yuzu’s wings begin to flap gradually whenever she’s happy, each and every one of the girls that Rio met were all attractive in their own ways, along with their general very attractive appearances. So it was understandable that Rio would sometimes look at his friends in a different light. He had multiple stories of situations he found himself accidentally being in with the girls, but those would be for another time.
So for this year’s Halloween, Sinder asked Rio if they could host a Halloween party today and invite all of their friends over for the night. While Rio would usually take a bit of time to think about her idea, Sinder practically begged him this time… and Rio would find it hard to turn her down. He didn’t know why, but something about the way she looked up at him with those adorable fiery orange eyes with her hellhound ears flattening and her large tail drooping downwards, making herself look like some kind of sad puppy. It was a classic tactic that Sinder used on him whenever she really wanted to do something that she knew he’d probably try and talk her out of, and 9 times out of 10, it worked.
He remembered her reaction to his answer, a happy and joy filled “yay!” followed by her basically tackling him down. She’d repeatedly thank him as she nuzzled into him like she was truly being a puppy, despite her on multiple occasions, denying that she was and that she’s a Hellhound.
All of that led to today, the day of the Party. The previous night, Sinder and Rio spend the entire day preparing the house for the party by putting up decorations, getting the food, drinks, games and everything. As for their costumes, Sinder already had hers from last year, her succubus outfit while Rio had decided to get a new outfit in advance, which was that of a vampire. So everything was ready. All that was left now was to wait until nighttime and wait until the others arrived before the party could start.
Considering it was still quite early in the afternoon, Rio decided to take a nap in his room so that he’d have enough energy for the night. (He would desperately need it). So there he was, lying on his bed, his eyes closed as his breaths were slow and gentle. A gentle hum would soon leave his lips as it seemed that he was having a nice dream and he was indeed. However, a small groan would suddenly leave his mouth as his body would slightly twitch, the warm and wet feeling on his crotch becoming harder and harder to ignore.
Finally, he opened his eyes. He was about to complain about his dream being interrupted when he was treated to a specific sight, one that he was quite familiar with. It was his housemate herself, Sinder the Hellhound.
A light *pop* was heard as the hellhound girl released his cock’s tip from the embrace of her lips, which soon curved into a seductive and downright sexy teasing grin as she moved her massive tits up and down at a steady pace, the sight of his cock’s tip appearing and disappearing within the depths of her cleavage arousing her further as her tail wagged back and forth happily.
Sinder: “ Happy Halloween, dear~ !” She sang, her tone with a sweet yet almost addictingly alluring sound.
Rio: “S-Sinder…?” he managed to force out, trying to hold back a moan that nearly left him. “W-What are you–”
Sinder: “Don’t worry about it~. Think of it as the Halloween Treat I have just for you.” The brown-haired male tried to let out a sound of protest, but holy hell he just couldn’t. He already knew how god-like Sinder’s body was. In fact, he had multiple personal experiences of it. It wasn’t the first time he’d wake up to her doing this to him after all.
Rio: “But the party, the other’s will be–”
Sinder: “We still have time.” She answered, as Rio slightly glanced at the clock in the room. 3pm. He lightly sighed, it sounding a bit more erotic than he intended it to be due to the massive watermelons currently acting like pussy to his cock. His reaction enticed a small giggle from Sinder, with her feeling more and more proud of her actions. She knew he loved her body and she was more than willing to let him fully indulge himself in it. After all, so long as they remained ‘friends’ , she was his and he was hers.
Rio: “What… am I going to do with you, you cheeky hellhound.” It was obviously a rhetorical question. Sinder was well aware of that, but chose to answer anyway.
Sinder: “Who knows… Face fuck me and make me drink up every last drop of your pent up cum~? Or perhaps pin me down to the bed and fuck my brains out so that I can’t even walk straight during the party~? Or maybe–”
Rio: “Rhetorical Question, Sinder!” he yelled, his face turning slightly red as the hellhound’s laughter filled the room. God, her laugh. That infectious, pure joy laugh of hers that sounded so adorable. It drove him crazy! All of her suggestions began to put clear memories in his mind as both of these kinda happened in the past.
Rio remembered at one point, face fucking Sinder while they were in the shower, the Hellhound just happily taking every inch of his dick in her mouth as the hot steamy water ran down their bodies. The other memory was a more spicier one. During one of the many drips that he and Sinder went on with their friends, there would be moments where Rio would find himself, bending Sinder over and fucking her from behind into the bed of his hotel room, all the while the girls were in the other rooms. Though he vividly remembered hearing the sounds of moans, which made it clear to him that the other girls heard their rather… steamy session. It became more evident that the next day, he’d catch Numi and Bao in particularly eyeing him and when he’d look in their direction, they’d look away while blushing, Bao trying to play it off casually while Numi would just become a stuttering mess as she usually did.
Sinder: “Ehehe~ I know, I know!” She laughed, enjoying his reaction as she continued the titjob she was giving him. She began to focus more, with her holding her tongue out, allowing a bit of saliva from her tongue to drip onto his tip, acting more like lubricant and allowing her to gradually ramp up the intensity of the titjob. “You love it, right dear~? Feeling my tits smothering your girthy, aching, pent up cock~” Almost immediately, they got a reply.
Rio: “You fucking bet I do… You’re tits are fucking heavenly… as ironic as that is.” Sinder felt her face flush with a light blush from the praise, but of course, she enjoyed it immensely, most evident by how much her tail was wagging back and forth. A small giggle left her lips as she hummed sensationally, moving her tits up and down more rapidly by the second.
Sinder: “I’m glad. After all, hearing you moan and praise me the way you do makes me feel even hotter~.” If there was anything Sinder really loved, it was making others feel happy and for Rio, she had multiple methods of doing that. From cuddling with him and kissing him, but she definitely loved making him feel the pure euphoric sensation of arousal but what she loved even more, was making him bust his load, whether it's all over her or in her.
Rio: “Shiiittt….~ Holy fuck, Sinder…” He’d moan, his head resting on his pillow as his half-opened hazy eyes managed to look at her. While he couldn’t fully make out her expression anymore, he could tell that she was getting more and more into it as she continued using her tits like an extremely soft fleshlight for him. In fact, it wouldn’t take that long for Rio to start feeling that sensation bubbling up within his shaft. Precum began to leak onto her tits as his cock would twitch and throb between them. “S-Sinder…~”
Sinder: “You gonna cum~?” She questioned, her smile never leaving here expression as she tit-fucked him with growing aggression. He quickly nodded his head but was grinding his teeth together to try and hold it all back. Sinder however, didn’t lead up. In fact, it just encouraged her to get more determined to make him cover her tits and face in his seed. “Then go on and cum. Cover my tits in your thick, baby-making milk. Cum, cum, cum~!”
She continued to repeat those words, her tone sounding more and more cute and enthusiastic while she moved her tits more rapidly. Rio was being pushed over the edge at this point. How in the hell did this one woman… this Hellhound have some of the best pair of tits he’s ever seen? Even then, he wouldn't be able to find his answer as he was taken for a ride of pure euphoria. A louder groan was forced out of his throat as Rio thrusts his hips upwards, grinding his teeth together as his cock finally erupted, the tip shooting out string after string of cum, staining her tits and some even landing on her face.
A pleased hum was Snider's response, the small flames in her hellhound ears slightly flaring up in excitement as she held her tongue out, managing to catch some of the falling substance on her tongue. A quick taste was all she needed to start cleaning herself up by picking up some with her hands and licking it all off. Rio in the meanwhile was taking this brief moment to catch his breath but the moment his eyes laid on the Hellhound before him, he could feel himself wanting more already. Sinder had cleaned herself up, her eyes closed as her pleased hums acted like music to his ears, but the moment she reopened her eyes, everything settled in. Her fiery orange eyes were filled with lust and desire, her breath becoming visible as she panted like an excited puppy.
Rio: “S-Sinder…” Hearing her name be called in such a way made the fire burn brighter in Snider's chest. Now that she was on all fours, she crawled over to him, with her grasping his phallus in her hand, causing him to let out a light grunt.
Sinder: “ Darling~ ”
Her tone was purely filled with passion and lust now as her eyes were fully set on the man before her. She stared directly into his eyes as she began to jerk him off, wanting him to be at his hardest when she eventually gets penetrated. The brown-haired male gasped in pleasure, the soft and silky texture of Snider's palm causing his already sensitive phallus to start hardening again. Rio continued to stare back at her, his eyes slowly trailing down from her eyes to her inviting lips. He began to sit up a bit, but Sinder already beat him to the punch as she lunged a bit forwards and pinned him back down, her lips crashing against his.
The kiss was heated, literally. Rio’s body felt as if it was on fire the moment their lips met, possibly due to Snider's natural heat due to her being a Hellhound, though thankfully due to them living together for quite some time now, he’s built up a semi-immunity to Snider's heat… well at least when she’s not unleashing her full capabilities, which she thankfully never had a reason to. The handjob Sinder was giving the male felt like pure divinity, especially when she had kept her hand near the base of his shaft, using two of her fingers to stroke his balls in the process, sending shivers down his spine as a semi-louder muffled moan was forced from his throat. With the kiss being temporarily broken, Rio out of pure instinct decided to let the Hellhound know how good her hand felt.
Rio: “F-Fuck… Shit, Sinder… you’re a fucking god at this…~ At this rate, you’ll make me cum again…” It was true. Thanks to her boobjob and blowjob earlier, Rio’s cock was already a bit sensitive and Snider's handjob certainly wasn’t helping him hold back.. A flattered laugh left the Hellhound as she licked her lips seductively, staring down at her beloved roommate like he was a delicious meal for her.
Sinder: “You’re gonna cum again~?”
The brown-haired male nodded, his breathing becoming ragged as she jerked him off faster. However, a groan of confusion and frustration would soon leave him as Sinder suddenly pulled hand back, stopping her handjob and essentially edging him. Before he could complain however, he was silenced by the Hellhound pressing her lips against his again. In an instant, he reciprocated her affection, kissing her back with equal passion and love. Sinder, on the other hand, began to lift her leg as she slowly began to fully mount the man, promptly sitting on his crotch, allowing his swollen shaft to rest between her asscheeks. It was only then, he realized what she had planned.
Sinder: “If that’s the case…” She broke the kiss and stared into his green eyes, her fiery orange eyes glowing as they were noticeably heart-shaped. She then leaned down to him, her lips stopping right next to his ear… “ Cum inside of me~ ”
Rio struggled to even get words out, Snider's words alone effectively stunlocking him into an aroused silence. With her hand gently caressing his shaft, Sinder began to gradually raise herself up and line him up with her entrance. The moment his tip came in contact with her hot, swollen and sensitive nether lips, they both shuttered, a soft moan exiting their lips. And then, she did something that the male didn’t expect she’d do. With one swift motion, Sinder dropped herself down on his cock, taking in the entire thing in an instant and slamming herself down into his lap. As the Hellhound arched her back, letting out her howls of pleasure from being filled instantly with his entire shaft, Rio was squirming around underneath her, his cock throbbing intensely inside of her warm insides. Even though he tried to hold back, his attempts proved futile as with a shout, he orgasmed right inside of her cunt, filling her pussy to the brim with his warm seed.
Sinder: “Mmm~! Ahh~!” She moaned happily and in delight, wiggling her hips and grinding against him as she milked his cock, her tail wagging back and forth rapidly as she felt herself have an orgasm as well, her pussy squeezing his shaft intensely. “S-So much, and it’s just your second~ My pussy feels that good, huh~?” With a few breaths after his orgasm, Rio looked up at her, his left hand Hellhound’s right thigh.
Rio: “You… fucking cheeky Hellhound…~” She giggled and held a playful and teasing smirk.
Sinder: “Ehehe. You love me~.”
Rio: “You’re fucking right I do.”
With his other hand, he gripped the back of her head and pulled her down, enticing a surprised squeak from the Hellhound as their lips instantly connected again. With zero hesitation, Sinder kissed him back, after all, aside from draining him dry with various methods or cuddling him, she loved kissing this man, showing him how much she just appreciated him. The moment the kiss broke, they stared at each other silently, their gazes locked eternally as their heavy and husky breathing was the only thing audible in the room at the moment before she began to move.
With her warm canal nice and wet for him and filled with his seed, Sinder began her movements, starting slow as she began rocking her hips back and forth. The feeling of his cock sliding in and out of her, rubbing against her sensitive walls nearly made her howl like crazy and she wasn’t the only one. Rio was in a similar state of euphoria, lying there as his roommate rode his cock in such an erotic manner by grinding on him.
Sinder: “F-Fuuaah…~ So fucking good…~” She swore, feeling his seed being stirred up inside of her as she continued grinding on him all the while panting like an excited puppy and wagging her tail. Then, she began to get slightly rougher.
No longer just purely grinding on him, Sinder truly began her ride. She began to bounce her ass up and down, an audible and slightly wet *plap* as their pelvises smacked together lightly, the oozing semen dripping down his cock from her pussy. The sex was beginning to ramp up now, their breathing was getting heavier now and more erotic. The look in their eyes said it all, that they were enjoying this to the fullest and didn’t want it to end. Rio’s hands dug into her thighs as he helped her with her movements, though in reality, his hands holding her in this manner only just encouraged her to keep riding like her life depended on it. As she crashed down on his pelvis, she felt his cock’s tip hit the entrance to her womb, causing her to slightly tense up and whine in delight, but instantly leaned back down to kiss him.
Their tongues danced around in their mouths as the woman on top continued to slam her hips down on him, making sure that she felt every inch of him inside of her hitting her in all of the right places. Snider's hands squeezed his shoulders, her nails slightly digging into him, enticing a slight muffled grunt from Rio, but he didn’t mind it. The sheer heat from fucking her pussy and making out with her more than made up for it. Then she felt his right hand slowly running up her left thigh and curving around her round and well-shaped ass before–
*SMACK*
Sinder: “A-Ahh, fuck~!”
The kiss broke with that cry of arousal, which accompanied her walls tightening suddenly as she had hit her orgasm suddenly. Sinder felt sensitive from both that and the sting on her ass from where Rio had spanked her, but that was the moment that her feral side began to show more, especially with the fact that now, the normal fiery-orange highlights in her hair and the flames in her ears and tail and her beating heart-shaped eyes changing color, turning a bright, lustful pink.
With her tongue hanging from her mouth, keeping the line of saliva connected with his tongue, Sinder began to move faster. Her hips went up and down at a faster pace, the audible smacks of skin getting louder and more intense. The bed creaked beneath them as the sex was ramping up more, becoming more filled with passion and lust now.
As she bounced on him, Rio was treated to the sight of her lewd and pleasure-driven expression, along with her bouncing tits that pressed against his chest with every move she made. It made him want to just kiss her and fuck her into complete submission but it seemed like Sinder beat him to the punch as she clashed her lips against his again. As they made out, she began to grind on him again, only this time, in a much more aggressive and erotic manner. It felt like she was giving him an intense lapdance with how she moved her hips, and fucking hell did it feel immensely amazing to Rio. It felt like he was ready to just cum right then and there in fact, but he was holding it in, wanting this to last for as long as it could.
The bed rocked back and forth, the bed head banging against the room’s wall as Snider's hips worked their magic, grinding and bouncing on his cock, her walls squeezing his entire length as if she was trying to milk him, like a farmer milking their cows’ udders for milk, and fuck was her methods working.
The moment their lips disconnected, Sinder saw that look in his eyes, the same one he’d always have whenever he was ready to fuck her brains out… and it made her even more excited.
Rio: “Sinder…~!”
With both hands squeezing her asscheeks, Rio now began to move. His hips began to work, thrusting upwards as he fucked her like she was the last woman on earth. His cock continuously banged against her cervix, almost as if he was trying to impregnate her.
Sinder: “Rio~! F-Fuuuccckk~ Fuck me harder ~!” She didn’t need to tell him twice as the brown-haired male had nothing else in mind, aside from fucking her until she couldn’t walk straight during the Halloween party that they both had promptly forgotten about. “Mm, just like that~ Yes, yes~! Oh fuck I’m gonna cum again~!”
She wasn’t lying as she could feel the building up of her third climax now. The room was filled with the loud clapping of skin and the creaking of the bed. With a spank to her ass by her roommate which left a noticeable handprint on her, Sinder began to contribute to the movements as well, as she began bouncing her hips in rhythm to his thrusts. Their bodies worked together like a well-oiled machine, both working each other closer to their climaxes. The bed creaked loudly as they both bounced a bit, the sex getting more intense and rougher. Snider's tail was wagging back and forth crazily, the pink flames in her wolf ears and on the tip of her tail burning brighter. Her cries of pleasure peaking, her eyes squeezed shut as she had started to become a bit overwhelmed by the intense pleasure she was feeling and it wasn’t only her. Rio too felt himself becoming overwhelmed by the pleasure, the sheer heat and moist nature of her cunt as it squeezed his swollen and twitching phallus as it plowed her into submission, so much so that the Hellhound couldn’t even form words at this point. All she could do was moan like a girl driven by sex and pant like a dog. All of this pleasure the two would feel would eventually boil over.
With sharp gasps, the two slammed into each other one more time as their pleasure overfilled. Sinder quite literally howled in the lewdest way possible as she hugged the man below her tightly, her intense climax taking place as Rio’s cock filled her womb to the brim with hot, sticky, cum. It felt as if their bodies felt a massive relief as the euphoria of their climaxes fully took over, their bodies shuttering from how intense the feeling was. Rio felt like he was seeing white as all he focused on was the pleasure of giving his beloved roommate the creampie of her dreams. Sinder slowly grinded her hips back and forth, making sure that her pussy milked his balls completely dry, her long awaited Halloween Treat. Her favorite kind of treat. Nothing else could match this kind of feeling for them.
Their breaths were heavy and tired, their bodies lightly trembling from the sensitivity. Snider's tail drooped downwards as her highlights, eyes and flames slowly reverted back to their normal orange color. She locked eyes with Rio, her hands gently cupping his cheeks as she stared at him, with pure… love.
Sinder: “I wuv yu…~” Despite the slurring of her words, it was clear what she said.
Rio: “I love you too…~”
Nothing else was needed to be said as their lips met, a more gentle and loving kiss taking place now. They held each other, their warm and sweaty bodies pressed together as Sinder continued to stir the cum inside of her with slow, gentle grinds. With her movements coming to a gentle stop, their eyes opened as the kiss broke once more, their tongue remaining in contact as their hot breath brushed against their mouths.
Nothing could ever interrupt them now as they were locked in this state of euphoria…
*Doorbell Ring*
Or so they thought…
The sound of the doorbell startled them both, the two gasping in surprise as they remembered the time. Looking at it, it was already 5pm. Two hours had gone by since they had started their session, a surprise to the two but they were then hit with the realization.
Sinder and Rio: “The Halloween Party!”
With how much they had gotten into the sex session, they had completely forgotten about the party they had prepared for. Numi, Yuzu and the other Girliepops were probably outside of the house right now, waiting to be let in and it was only proven more by there being a second doorbell ring, followed by the loud yet very noticeable yell of Bao. The two looked at each other silently.
Rio: “Take a quick shower and get your costume on. I’ll let the girls in.”
Sinder: “R-Right.”
There was no need for a debate.
Hours went by and the Halloween Party was going by as anyone would expect with this group. A bunch of fun games, conversations, jokes and other stuff, including food and a lot of drinks. As the party went on, Rio found himself being more and more involved in the activities and conversations as the girls seemed to be very ‘ interested’ in his vampire outfit while Sinder continued on like nothing happened, with her even encouraging all of the teasing and whatnot, despite her recent confession of love to the male. However, even despite all of the fun that they were experiencing, Sinder still couldn’t fully ignore the burning sensation in her loins along with the hot, steaming creampie nesting in her womb, which thankfully never decided to start oozing out and staining her succubus outfit. But there was one thing for sure…
After the party, even when everyone’s sleeping in the guest bedrooms, she and Rio were going to fuck more, even if the risk of her friends hearing there, because she couldn’t help but crave more of his Halloween Treat.
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