A new lewd chapter is here! Btw just recently played Sonic Frontiers, and let me just say…I'm glad I use Gamefly and didn't pay money to play it. I mean it's just my opinion but I didn't like it. The gameplay wasn't my style, but I admit the story was interesting and the characters were well written, and of course the music was pretty good.

Hoping to try out God of War Ragnarok next, and super excited for my pre-order of Pokemon Violet to come. You'd think I'd choose Scarlet with my love of the color red, but I just like the futuristic legendary mount more.

Btw glad you're enjoying the story Smiling Lemon!

Credit to Pickle-Brick for the wrestling idea.

Slurp Slurp Slurp

"Fuck~ How did you get so much better in such little time?" Max moaned as his knees buckled, the heavenly suction being applied to his cock leaving him weak in the knees. Below him Vaggie was too focused on her actions, a firm determination on her face as she bobbed her head up and down and sucked that human cock so hungrily. To the untrained eye, she looked as if she was angry despite giving Max such an intense blowjob, though she might actually be irritated due to her current attire.

Somehow Charlie and Angel Dust convinced her to wear this skimpy clothing that looked more like a tiny bikini. While it covered her chest well enough, the bottom half was practically useless! All it did was the bare minimum of covering her genitalia while showing off every inch of her plump squishy thighs and that humongous wobbly backside of hers that she calls her butt. To make matters worse, the outfit had these straps and chains on the back that held her hands behind her, leaving her completely helpless.

At first she was worried being in such a state of dress would awaken Max's dominant side, and she wasn't sure if she could take such roughness so early in this strange relationship. However when Max saw her with her hands chained behind her back, of course the first thing the human does is ask her if she wants to be freed from the uncomfortable looking attire. Sure he took more glances at her ass than necessary and was pitching a massive tent in her face, but she was still touched that his first instinct was to help and make sure she was comfortable. Strangely though, this also made her mad. He had her on a silver platter and instead of immediately fucking her face like a whore, he shows pity on her? Well she wasn't gonna just sit back and take such an insult!

Slurp Gulp Pop

"Stupid Angel insisted he give Charlie and I lessons." She explains after momentarily pulling herself off of spider demon may irritate her often, but damn was he a surprisingly good teacher. "Now stand still and let me suck your dick!" She could just imagine the rage and disgust her past self would have if she saw her now, but she could care less. Charlie was having lots of fun, now she is too. And if their fun happens to sexually please their human friend, then so be it.

She dives her head back in, taking every inch of his cock inside her warm wet mouth as she furiously sucks him off. Her fists clench as they struggle against her bindings, something about the restraints only encouraging her to use her mouth to its fullest as if to compensate.

"Oh god!" Max cries out as Vaggie's incredible head brings him closer to his orgasm. It doesn't help that whenever he looks down, he gets double the viewing pleasure since he can see both her gorgeous face repeatedly slamming into his crotch, and see that massive shelf of thick gray moth demon booty wobbling from her intense movements.

"I'm gonna cum, gonna cum so hard.~" Max groans out to warn Vaggie, his hands on her head to make sure she receives the message even while she's practically facefucking herself with his dick. Vaggie's eye glances up at him for a moment before she shuts it tight and slams her face deep into his lap, his cock completely buried down her throat.

"Vaggie!" Max yells out as a sudden burst of adrenaline courses through him, his hands firmly grabbing the back of her head and further shoving his cock deeper in her mouth, as if for one moment he was no longer treating her as one of his beloved friends, but now a cocksleeve for him to use as much as he wants. Vaggie feels her body quiver in a strange mix of lust and slight fear, the area between her thighs becoming slick with her juices.

With his teeth clenched and hands grabbing fistfuls of her hair, Max finally cums. A thick blast of his strangely tasty seed filling her mouth to the brim with no signs of slowing down. Vaggie felt her arms struggle in the straps, instinctively trying to move and push away the object currently stuffed down her throat and keeping her from breathing properly. A part of her is thankful for the bindings though, as her pride wouldn't be satisfied if she just pushed him away and coughed up the cum in her mouth. With no other choice and a fierce fire in her eye, she began chugging down all the sticky cream Max was giving her.

Gulp Slurp Gulp

Vaggie noisily continued to suck and swallow every drop of semen Max was producing, intent on showing she was no slouch in the bedroom and could take this dick better than a certain slutty spider. Soon enough Maxwell's orgasm began to end, and his grip on her hair was released. With his head clear, he immediately remembers what he just did to Vaggie and quickly pulls away, albeit with great difficulty as those soft lips of hers dragged so nicely along his shaft, almost as if she was trying to keep him inside.

"Gah! I'm so sorry Vaggie, I don't know what came over me!" He quickly apologizes as Vaggie takes the opportunity to gasp for air, a couple coughs escaping her as her throat can relax now after being so stretched out. She looks up at him with a glare but a hint of red on her face.

"Just because I'm tied up like this doesn't mean you can just use my mouth so roughly! God, I can already tell my throat's gonna be sore." She huffs before turning her head away as if to not look at him.

"Oh Vaggie, I promise I'll make it up to you, a pal of mine taught me how to make lemon tea, maybe I can whip up a cup with some honey for you to soothe your throat?" Max offers.

Vaggie was still looking away before taking a small glance at him. "…tea would be nice. And you have to promise me something."

"Of course, anything!" Max was quick to accept.

"…anytime I'm wearing this outfit, I want you to be rough like that again." She says, looking at Max to see his confused but blushing face and quickly scowls at him with an embarrassed look on her face. "Not because I like it! It's just, this way you're less likely to take out any pent up aggression on Charlie, I'm willing to take it for her. And this outfit just so happens to make it so I can't hurt you in retaliation." She quickly explains, although Max felt like she wasn't being completely honest, but was in no state to question her.

"Uh, okay I promise!" He nods his head before quickly bending down and unlocking her cuffs. "You relax here and I'll get you your tea." He gives her forehead a little smooch for good measure before leaving.

"HEY!" She yells out, face even redder from the little kiss. However as soon as Max us out of sight, a small smile grows on her face. "…I liked that…"

After sharing some tea with Vaggie and getting more confirmation that he didn't go too far, Max went to his room to look over the grimoire. Charlie has tried teaching him how to read the book, but it was still quite difficult. Funny enough, they learned that when he uses his anger to access his wrathful forms, the text becomes easier for him to understand. Max just feels like he's missing one key component to help him comprehend the language.

Aside from studying, his thoughts went again to Charlie, Vaggie, and Angel. So far the three had helped him so much in developing this sex positive side for himself. He already had an idea of how to thank Angel, but for Charlie and Vaggie, he couldn't help but wonder if maybe it was time to take another step. His face grows hot at the idea, the human incredibly flustered just considering the idea. Thankfully he didn't have to ponder on it any longer as he felt his phone vibrate and begin ringing. Looking at the caller ID, he sees it was the number for I.M.P.

"Hello? Maxwell speaking!" He answers into the phone.

"Heeey Maxxie, buddy ol pal of mine!" Blitzo responds in a suspiciously jolly attitude.

"First of all, you don't get to call me that. Second of all, what's up? Does Stolas need the book already?"

"No no nothing like that. This isn't a business call kid, I just wanted to invite you for a fun time with me and my little family!"

"…this isn't a booty call right?" Max asks worriedly.

"What!? No! It's wrestling!"

"You're not convincing me that this isn't sexual."

"Oh for fuck's same, you're doing this on purpose aren't you?"

"Dude, I don't fucking know, here in hell things are weird, I'm learning things I've never knew. Just the other day Angel ordered for something called a 'Sex on the Beach', apparently that's a type of alcoholic drink." Max explains only to hear the imp facepalm.

"Look, its nothing sexual. It's just two or more men grappling each other. And yes I regret phrasing it that way."

"This is getting stupid. Okay, you're inviting me to watch a fight, correct?"

"Yes! I got tickets okay?" Blitzo says exasperated.

"Okay now we finally have it clear. Fuck it, I'll join you guys, as a way to apologize for all these double entendres and because I'm curious as to how wrestling in hell works."

"Perfect! We'll pick you up in half an hour."

Other than the awkward glances between Max and Loona, the ride in the company van to the wrestling stadium thankfully wasn't too bad. Moxxie and Millie were more than happy to chat, the human learning that the couple were married. He wasn't sure how you could get married in hell, but he had to admit that they were absolutely adorable together. Despite the relaxed atmosphere, Max still couldn't get rid of the suspicion he felt whenever Blitzo acted so friendly, but decided to go along with it for now.

The stadium seats were filled with plenty of bloodthirsty audience members as the fights were announced. Max wasn't one for wrestling, but even he had to admit it was fun watching these different demons throw each other around with so much flash and drama surrounding them. It helped that the demons with their many shapes and sizes allowed for a bigger diversity of showy fighting techniques from using tails to bind opponents, four arms to grab and pummel, and even one demon breathing out fire.

The crowd favorite, and apparently Blitzo's favorite too, were the twin brothers, the tag team champions known as 'Beastmonster' and 'The Cyborg'. They were notorious for being incredibly obnoxious heels who showed no shame when it came to playing dirty, whether it was attacking with folding chairs, pranking their opponents in the locker rooms with stink bombs and fresh paint on their seats, or even both jumping into the ring to attack their opponent 2 on 1.

Beastmonster was a green skinned 8 feet tall demon wearing a skinned tiger as a cloak, he apparently had a backstory where he was the twin who embraced his nature as an animal and hunted beasts of all shapes and sizes. The Cyborg though was a purple skinned demon who was the same height as his brother and looked nearly identical except for the cybernetics adorning his face and body, his backstory being he was the twin who believed the body can be improved via technology.

Max couldn't see the appeal for them though, they reminded him too much of bullies, the way they mercilessly tormented their opponents with humiliating pranks and defeats, and apparently even harassed them online afterwards. "Well, it just goes to show that Hell has all types of sinners." Max mumbles as the tag team duo celebrate their latest victory, standing over the broken body of their latest opponent who seemed to just be a tiny imp waaaay out of his weight class.

"There you have it ladies and gentlemen, our 4 time champions are now 5 time! Is there nobody who can stop this powerful duo!?" The announcer questions only for the brothers to snag the mic out of the announcer's hand.

"Why even bother asking? We're the best of the best!" Beastmonster boasted while flexing and lifting up his gold champion belt.

"The odds of anyone besting us are an absolute zero with no margin of error!" The Cyborg adds before the brothers grab each other's shoulders and headbutt each other while laughing loudly. The announcer quickly retrieves his mic before speaking into it again.

"Well today's the day where someone gets to try and prove you two wrong! As a five year anniversary celebration, we will offer the chance for one lucky demon in the audience to battle this deadly duo for a chance to win the champion belt!" This certainly hyped up the audience, many cheering and raising their hands, eager to get the chance to be on the wrestling ring.

"Damn, I'd hate to be the poor bastard who gets in the ring with those two." Max comments with a chuckle as he turns his head, only for his eyes to meet Loona's and the two immediately blush and look away.

"Oh I hope it's me! I'd love to be a wrestler!" Millie yells out excitedly. "Me and my siblings would wrestle all the time!" She informs before putting her beloved husband in a headlock.

"M-Millie! Millie! Choking me!" Moxxie cries out, turning a little purple only for Millie to let go.

"Sorry honey!"

"I-it's okay…I just hope that didn't awaken something in me."

"Oh I can only wonder who's going to get picked." Blitzo says in an innocent voice, smirking on the inside. It wasn't cheap getting it, but Blitzo knew it was a small price to pay in order to get a specific seating ticket. He's been in the circus long enough to know that the so-called 'randomly chosen audience member' was actually rigged to choose whoever sat in a specific seat. In fact, he gave that specific seat to someone he's been wanting some payback for a kick to the face not too long ago.

"Round and round the spotlight goes, where it stops, nobody knows!" The stadium darkened as two spotlights scan the crowd before slowly settling together on one seated human.

"WAIT WHAT?!" Max cries out as the imps and hellhound next to him look at him in surprise.

"Well what have we here? It's the semi-redeemed himself! Come on down kiddo! You're our lucky new challenger!" The announcer beckons the human down.

"Oh hell no I'm not-" Before Max could protest, Blitzo was already dragging him along.

"Well come on Max, let's not keep the crowd waiting!"

"Blitzo you motherfucker, you knew I'd get picked didn't you!?" He accuses with a scowl.

"Who me? Oh I'd never.~" He flutters his eyelashes innocently while Max growls. "Not like it matters, you got a belt to win!"

"Wait, you think I can win?"

"Of course I do! Why do you think I picked you of all people?" Before Max could ask anymore, Blitzo pushes the human toward the ring. "Good luck Maxxie!"

"I said don't call me that!" Max yells before looking at the wrestling ring and sighs before climbing up past the ropes. Meanwhile Blitzo quickly scampers to the betting booth.

"Put down everything on the twins!" Blitzo eagerly bets tons of money, eager to get a big easy payout.

"Are you ready to rumble!?" The announcer asks to hype up the crowd before exiting the ring, leaving Max alone with the tag team duo.

"Fucking hell, guess we're doing this." Max sighs before looking at the two tall demons. "So uh, who do I fight first?"

To answer that, the two demons both pick up Max before throwing him high into the air, the human yelling out as he reaches the apex only to yell again as he falls back down.

"I got him, I got him!" The Cyborg calls out as he catches the human, then tosses him to his brother, the two having a friendly game of catch.

"Stop! This! I'm! Getting! Dizzy!" Maxwell yells as they toss him back and forth.

"Blitzo, did you know he would get picked?" Loona asks her adoptive father suspiciously.

"So what if I did? It just means we get a fun show, and you get your payback for whatever he did to make you mad. What did he do by the way?" Blitzo asks as he chomps down on some popcorn, Loona just looking away before focusing on the fight.

"Come on Max! Fight back!" Moxxie yells to the stadium, worried over the human.

"Show them what you're made of!" Millie adds on.

Now in Beastmonster's grasp and being choked like a chicken, the human takes the words of encouragement and decides to bite the demon's hand.

"Ow! He bit me!" The demon cries out as Max tries to escape, but is instead grabbed by legs and left to hang upside down while The Cyborg comes closer.

"Is that? It is! Ladies and Gentlemen, our champions are preparing for their ultimate tag team attack, the Emasculator!" The announcer calls out as the audience except for a certain three cheer wildly.

The Cyborg puts a hand to his cybernetic eye looking as if he's scanning the human before grinning maliciously. "Weakness identified!"

"Hey wait what are you-" Max questions before The Cyborg reels his metallic arm back and shamelessly punches Maxwell square between the legs, sending him flying to the other side of the ring while the audience cheers at the below the belt attack.

"HAHAHA! He got punched in the noodle!" Blitzo laughs heartily, nearly choking on his popcorn and not realizing his team's less than happy reactions. Moxxie instinctively put his hands over his crotch, feeling sympathetic for the other male. Millie winced as could only imagine what the human was suffering. Loona lastly hissed as she could hear Max's high pitch voice in agony, for some reason hoping there was no permanent damage.

Max was on the floor of the ring, cradling his family jewels as Beastmonster and The Cyborg raised their fists, welcoming the cheers of the adoring crowd. What they failed to notice was Max slowly climbing back up in his feet, a familiar glow running through his veins and a fire burning deep inside him. "That does it."

With the pain fueling his rage, he walks over to the prematurely celebrating wrestlers. "Excuse me." He says in a calm voice, the wrestlers looking at the human in surprise as he jumps onto a nearby post so he can stand taller than the demons. Then with one hand with an iron grip on each of their shoulders, he brings their heads closer to his so they can look at the pure fury in his eyes. "YOU'RE GOING DOWN!" His voice boomed, audible to every spectator and dripping with his signature wrath.

Before the two professional wrestlers can attempt to comprehend what was happening, Max slams both of their heads together, recreating their brotherly headbutt with far more power and pain than their hard heads have ever felt before. With the two of them dazed, he jumps and delivers a swift spin kick to The Cyborg, the purple demon getting knocked down to the opposite corner of the ring. With one brother out of the way, Max lands on the padding before turning to Beastmonster and throws a devastating punch directly into the green demon's stomach, his fist nearly penetrating through the demon's hardy flesh.

"Did I just see his fucking fist from the other side?" Blitzo says in disbelief, many onlookers shocked at the human's power. Not willing to lose his bet, Blitzo quickly scampers down from the stands to the ring, not seeing the rest of I.M.P cheering loudly for Max.

"RIP HIS HEAD OFF!" Millie shouts enthusiastically.

Beastmonster yells out in pain as Max twists his fist. "Stop fisting me!" He yells out, only for Max to shrug and rip his fist out of the demon's abdomen. "GAH! Not all at once!"

On the other side of the ring, Blitzo is reaching through the ropes smacking The Cyborg's face. "Come on you big bastard, I paid good money to watch you win!" He reaches under the wrestling ring to pull out a metal folding chair before handing it to the semi lucid wrestler. "Here you go big guy! Show him what you're made of!" Finally snapping out of it, The Cyborg lifts the folding chair and sneaks up behind Max.

"Max! Behind you!" Moxxie shouts out, Max hearing his shout and turns his head just in time to see the chair wielding demon coming. Deciding to use his smaller size to his advantage, he climbs up on top of Beastmonster. Just as The Cyborg swings the chair down, he jumps off the head of Beastmonster and dodges just in time for the chair to smack the brother instead and knock him onto the ground.

"No! Not him you team killing fucktard!" Blitzo shouts in aggravation as The Cyborg holds a hand up to his mouth, shocked to see the one he hit was his brother.

"Hey!" Max yells, getting the wrestler's attention. "I got a punchline for you, The Cyborg. What's 10 + 9 fingers across the face?"

"Um…uh…what?" The wrestler asks, unsure if he took too much brain damage or if the question makes any sense.

"HEAVY!" Max answers as he jumps up into the air, his head reeled back only to then slam his forehead directly into The Cyborg's face, the impact sounding similar to a pan hitting someone on the head. The heavy attack had so much power behind it that the demon's cybernetics crumple off his face, revealing a perfectly good eye underneath.

"Wait, they were fake!?" Blitzo asks, feeling so hurt that a wrestler would lie.

With the two wrestling demons flat on their back, Maxwell quickly arranges their bodies next to each other before climbing on the ropes.

"Oh shit he's going for it, FUCK THEM UP MAX!" Moxxie and Millie are surprised to see Loona is the one getting invested in this.

With a rage fueled roar to the sky, the crowd cheers as Max jumps off with his elbows in the air. The brother demons are only awake enough to scream in fear as the wrathful human falls toward them and slams his elbows into both of their abdomens. The force behind the gravity and fury fueled attack being enough to cause a shockwave strong enough to knock Blitzo off his feet, strong enough to reach the spectators and knock them out of their seats, strong enough to AUGH!….strong enough to knock the narrator out of their chair!

As the audience climb back into their seats, they see the semi-redeemed demon standing on top of the demons with their champion belt held high above his head before he yells. "WHO ELSE WANTS SOME!?" He yells out challengingly. At first everyone is quiet until the announcer snaps out of it.

"LADIES AND GENTLEMEN, OUR NEW WRESTLING CHAMPION!" He points toward Max, the audience now cheering wildly as they look at the vicious semi redeemed demon standing tall and proud.

Back in the van, Moxxie is driving as Blitzo is ugly sobbing in the back. "I lost my bet, all that money!"

"Wait, you lost? But I thought…you son of a whore, you bet against me?!" Max yells out, a lot calmer now as he sat in his seat with the champion belt over his shoulder.

"Yes! How was I supposed to know you'd win!?" Blitzo cries out before returning to his sobbing.

"I had a feeling something like this would happen, so that's why I bet on Maxwell. The odds were heavily against him so when he won I got a big payout, so thankfully we're not penniless." Moxxie informs, only to get choked out again as Blitzo hugs him tightly.

"Moxxie! You saved our business! Oh if you weren't married I'd kiss you!"

"Only with my permission." Millie adds with a little smile on her face.

"Ugh, you're all so embarrassing." Loona scoffs before looking at Max. "…nice work back there."

"Oh uh, thanks." He smiles at her, getting another blush out of the hellhound.

Soon enough they all reached the Hazbin Hotel, Blitzo deciding to take Moxxie and Millie out to celebrate not being bankrupt due to his poor gambling skills, Loona though saying she wanted to stay behind and talk to Max about something. While a tad worried for his little Loonie, Blitzo figured she'd be safe at the hotel all about redemption and being good. Figuring it's better to get this over with, Max escorts Loona to his bedroom.

She steps inside his room and he closes the door, not locking it though just in case he needs to escape or someone can come in and rescue him if things do get violent. "I guess you've been wanting to talk to me?"

"What was your first guess?" She snaps at him with a glare, slightly red in the face as she lightly snuffs the air, recognizing the human's scent but also something else.

"Alright I deserve that, but come on, isn't there a better way we can go about this? You don't have to rip me to shreds, if it's an apology you want, I'll say sorry as many times as you want."

"Not good enough!" She growls out. "Not only did you pet me like I was some kind of domesticated bitch, but you fucking bit me on the neck!" She reminds him, the human looking away embarrassed.

"Okay for the first thing, we were up to our necks in angels and I figured getting you angry would help thin out their numbers. It worked, but I still touched you without permission, and I'm sorry, I'll try everything necessary to make it up to you. But for the second one, I was defending myself, you were about to bite me first!"

"Because I'm a hellhound dumbass! I do the biting! You're not allowed to bite!" She yells out, looking slightly flustered as she rubs the spot he bit on her neck those many days ago.

"Says who!?" Max asks in a mix of embarrassment and frustration. "If you're gonna try and maim me, then I will claw, kick, and bite as much as necessary if it means staying alive and unharmed! I won't apologize for trying to stay alive, heck I'll bite you again if I have to!"

"You don't have the balls!" She challenges as she steps closer to him, even going as far as to pull off her choker and tossing it aside, baring her neck to him.

"Want me to prove it?!" Max growls out, baring his teeth at her as he doesn't back down and steps closer to her, not letting himself be intimidated.

"Just go ahead and try, pussy!" She insults only to find her shoulders grabbed as Max suddenly pushes her down on his bed. She lets out a growl but any attempt to scare him proves useless as Max is already moving his head to her neck, this time aiming for the opposite side as he sinks his teeth into her exposed neck.

"AH!~" Max's eyes widen as he hears the unmistakable sound of a pleasured moan escape the hellhound, pulling his mouth off of her neck as he looks at Loona who's panting softly, face flushed red and eyes lidded.

"W-what are you looking at?" She angrily asks, trying to glare at him only for Max to rub his hand against the spot he just bit, causing her to make cute whimper.

"Y-you…are you getting off to this?" He asks incredulously, feeling incredibly embarrassed and thinking he may have been bamboozled.

"S-Shut up! Of course nOT!~" Her voice rises in pitch as he rubs the area he bit again, looking closely he sees his teeth left a mark this time.

Max looks at the hellhound under him, watching her chest rise and fall as she breathes steadily, looking at him so frustrated yet also with something in her eyes that he's only seen from Charlie, Vaggie, and Angel. Deciding to take a gamble, he moves his head back to her neck.

"What? Gonna bite again?" She asks challengingly but with a bit of hope in her voice too. The human stays silent though as he just closes in before pressing his lips to the spot he bit, giving the tender flesh a sweet kiss and mashing the hellhound gasp. "W-what was that?!" She asks in disbelief.

"I've already proved my point. I think it's time I show you what else I can do to you." Max says as he returns his focus to sweetly kissing her neck while giving it small nibbles every now and then, Loona squirming under his oral assault.

"K-knock it off.~" She moans out. Much to her disappointment, he listens to her and moves his head away from her neck. Thankfully the disappointment doesn't last long as he then moves a hand to the top of her head, her eyes widening and tail wagging at the familiar sensation. "You wouldn't dare…" She looks at him in disbelief, only for Max to mischievously smile before he begins petting her.

Loona lets out a pleased "Woof~" as Max lets his hands caress and rub the top of her head. "Y-you evil bastard." She insults weakly, unable to fight back against the wonderful ministrations.

Just when she thought it couldn't get any better worse, he began to whisper in her twitching ear. It was only four words, but that was all it took to completely break her. What four words could he possibly say that could ruin such a strong hellhound like her? It was simply,"Who's a good girl?~"

"WOOF!~" She barks out, eyes filled with lust and more embarrassing noises escaping her as he just keeps going, petting her head, scratching behind her ear, kissing her neck, the evil human even going as far as to use his other hand to rub her exposed navel with those cursed dexterous fingers of his.

"Come on, who is it? Who's a good girl? Who's such a good girl?~" He asks again, driving the hellhound wild as he continues teasing her, even going as far as to gently nibble on the tip of her ears. She then noticed the familiar gear building between her legs, the still lucid part of her mind screaming at herself to try and tell him to stop before it's too late, but before she can finally get her mouth to start working, he whispers in her ear one more time. "It's you isn't it? You're my good girl.~"

And with that, the dam broke. Loona lets out a noise that seems like a mix between a moan, scream, and howl as she orgasms, ruining her shorts and the panties underneath, likely making a mess of the sheets of Max's bed too. "I-I'm a good girl!~" She moans out before panting softly as he tries to come down from the intense pleasure.

Max was certainly surprised to see his ministrations had such a big effect on her, definitely not expecting her to cum when he hadn't even touched her pussy. It was an incredible shock, but not an unpleasant one. "Y-yeah, you're such a good girl." He confirms as he kisses the top of her head, making her whimper and her body tremble.

When she finally calms down, she turns her head toward him, feeling a bit of clarity now and feeling quite embarrassed after cumming so hard in front of him, but not sure what to say or how she would even say it. Should she threaten him, bargain with him, she even considered if she would have to beg?

"I just want you to know," He began before she could speak. "That whatever happens here, no one has to know. It can all stay just between you and me. My lips are sealed on the matter." Max explains with a smile, much to Loona's confusion.

"W-why? Most guys would try to hold this kind of stuff over my head if they found out. I threatened you time and time again…and you're just gonna keep it a secret?"

"I'm not the kind of guy to kiss and tell, I just think that bragging about this kind of thing or taking someone's vulnerabilities hostage is a real asshole thing to do. While some people don't think sex is that big a deal, I still think of it as a pretty private thing. What happens between two, or more, people in a private setting should stay private, at least as private as the people involved both agree to." The human explains, Loona studying his face carefully for any clue that he might be telling her what she wants to hear.

"…so, you're not gonna say anything?"

"I mean, I'm likely gonna need to explain the stain on my bed if anyone catches me trying to wash it, but I swear to keep it to the bare minimum. I promise your reputation is not at risk, as far as everyone will know, you're still a major badass."

"…take off your pants." She suddenly says as she begins stripping, Max stunned and blushing as the full extent of her curvy body is revealed to him, he really needed to ask someone how these clothes keep such big breasts or bubblebutts hidden.

"W-wait what?" Max asks instead as he felt his boner from the heavy petting session throb excitedly.

"Jeez, do I have to spell it out for you? We're gonna fuck!" She states confidently, practically all signs of the previous whimpering good girl suddenly gone.

"Y-yeah I got that much, I'm just trying to understand why!"

"Because you got me all riled up you moron! Whispering all that shit in my ear, kissing my neck the whole time, and it turns out you're a real decent guy? One way or another, I'm taking that stupid monkey dick of yours inside me!"

Max gulps as he tries to think things through. On one hand, Loona seems like a great girl/hellhound, and he's gotten a lot of experience these last couple of weeks, but is he ready to give his virginity?

"…you're not gonna say you don't want this, right?" She meant to ask that sarcastically, but a bit of her fear that he'd say 'no' slipped out in her voice.

"I-it's not that I don't want to, I'm just kinda unsure since I'm a virgin." He admits, much to her surprise.

"B-bullshit! No way you're telling me a virgin made me cum that hard!" She yells in denial, only to cover her mouth, worried she might have yelled too loudly.

"I mean, I have some experience. A couple friends here at the hotel have been trying to help me get more in tune with my sexual side. So far the most we've done penetration wise are just blowjobs, I've yet to actually…do the real deal." He tries to explain somewhat flustered.

"What, you're gonna tell me you have the princess of hell sucking your dick? And you somehow got her girlfriend involved too?" She jokes in a snarky tone, only for Max to look away embarrassed while Loona connects the dots. "No fucking way. Next you're gonna tell me you got that pornstar bending over backwards for you too."

"Actually he's my neighbor, thankfully he's out watching a movie with Cherri. And I wouldn't say bending over backwards, but he has tried tempting me by bending over." He admits, only to realize he may have said too much considering the stare of disbelief she had in her eyes.

"…how the fuck?"

"I-I don't know! I'm still trying to come to terms with it myself! Sometimes I wonder if I died fighting Kushiel and I'm in some kind of strange personal heaven."

"Makes more sense than what I'm hearing." She mutters before looking away. "So…they never went the whole way?"

"It's mostly my fault, a part of me is still nervous about that. A blowjob is one thing, but full on sex means leaving me fully exposed, completely vulnerable both physically and emotionally. I'm just worried I'll slip up in some way and ruin things beyond repair." He explains his fears, looking down at the floor.

Loona looks at him with some sympathy in her eyes before noticing something sticking out of a drawer near his bed. Her curiosity overriding any morals saying that snooping is wrong, she looks inside to see many different condoms and a note. "Holy shit you weren't kidding."

"Huh? H-hey don't look through my stuff!…wait a minute I don't remember putting anything in there. At least nothing other than my spare chapstick." She looks at him with a raised eyebrow. "Don't judge me! I live in California, the dry weather leaves my lips super dried up, and I'd rather not kiss someone with crusty raisins for lips." She rolls her eyes, a small chuckle leaving her as she looks at the note.

"Dear Max, I know you're still nervous about your first time, but I figured a good next step in your sexual education would be an explanation in safe sex and a demonstration of how to put on a condom. Simply present one to me and we can begin your lesson. From, Charlie." Loona reads as Max walks over and examines one of the wrapped up condoms.

"Huh, she sure chose a big variety, premium lubrication, ribbed, extra thin," He lists off as he looks at the different colored packages. "Wait, there are flavored condoms? Would cum mix well with it?"

"Wait there's something else." Loona says as she looks at the bottom of the letter. "P.S, I borrowed your lip balm because the weather report said today was gonna be dry, I'm sorry and I owe you one."

"Sneaky little thief, it's not lip balm it's chapstick, it's different! She's lucky I can't stay mad at her." Max huffs as he tosses the condom he was inspecting back in the drawer.

"…you said you're nervous about your first time right?" Loona asks, getting a nod from Max. "Well, did you know doing it with a condom doesn't count?"

"…I wanna say bullshit, but considering the loopy rules surrounding sex, I could also believe that to be true. It took me forever to find out what getting to 'second base' or 'third base' means, doesn't help that everyone has different definitions of them."

"Everyone has their own rules. And I say, condoms don't count. You can think of it as like, advanced practice kissing." Loona explains.

"Advanced practice kissing? Wouldn't that just be real kissing?"

"J-just stop overthinking it!" She huffs at him, Max holding up his hands in surrender before the hellhound calms down. "…it's just an offer, you don't have to if you don't want to."

Max was still nervous, but Loona seemed to be taking this somewhat seriously. He figured she may just want to pay him back for promising to stay quiet, either that or what's him in a vulnerable state so then they both have something to keep secret.

"…one condition." He suddenly says, grabbing Loona's attention. "If I say 'stop', we stop immediately. No safe words, we stop when I say stop. Promise me." Loona was astounded by the absolute seriousness in Max's voice. A part of her wanted to be offended that he thought she wouldn't take this seriously, but looking closely she could see little twitches and shakes from his body. He was incredibly scared, but wished to push forward and overcome this.

"I promise. You say the word and we stop immediately." She confirms, Max seeming to ease up a little before beginning to strip, Loona taking in the sight of the human naked in front of him. Sure she's seen some human's try to get lucky with her while she was disguised, but they never got as far as this. It was certainly strange seeing a real naked human like this in front of her, but the big throbbing boner was flattering.

"Okay, so how do we start?" Max asks, trying to not let the jitters get to him. Loona just shows him one of the standard condoms. "Oh right, duh…how do we put it on?"

"Are you kidding?"

"They never showed us the condom on the banana stuff in high school, they only did the sciency stuff about the sperm reaching the egg and showed a video about how a teenager cumming from a dream is natural and common, yet I've never had that once." Max explains, going a bit off topic while Loona just shakes her head.

"Just take a seat, I got this." Max nods and sits on the side of his bed, spreading his legs so she can have easier access to his phallus. With a practiced movement, she tears open the wrapper with her teeth and reveals the thin piece of latex. She contemplated showing off and teasing him, but thought it'd be best to just do this part quickly, so she simply rolls the rubber down the tip and properly wraps up his package. "There we go, it's not too tight is it?"

"No, I mean it's a little snug but kinda like putting on a pair of gloves, not like gardening gloves but like the form fitting gloves from a hospital or in science class. Am I over-explaining?"

"Relax, you're fine." She pats his thigh gently. "Just lay on your back on the bed and I'll take the lead. Is that okay?"

"I-I guess, being the bottom of this kind of thing seems kinda scary."

"Don't worry about labels of tops or bottoms right now, you just focus on enjoying yourself." Max was certainly happy to have Loona show this side of herself as it's really helping him relax as he moves to lay on his back. Loona climbs on top of him, the hellhound looking down at him as she adjusts herself so she's positioned with her naked sex right above his shaft.

"You ready?" She asks, giving him one more chance to back out, even if he could tell her to stop at any time.

"As ready as I'll ever be." And with that, Loona slowly lowers her hips, the covered tip pressing against her folds, Max gasping softly from the heat of her pussy, not expecting to feel so much with the condom on. Little by little Loona lowers herself on top of him, Max's hands gripping the sheets as inch after inch of his cock disappears inside her.

"D-damn it, you feel so big.~" Loona moans out, a whimper escaping her as Max's cock throbs in response.

"I-it's so warm, so tight.~" Max whispers, the strange but pleasurable sensation making him worry about being overwhelmed, but not wanting to stop in the slightest, soon enough Loona has Max's cock fully sheathed inside her, the two panting softly as they both get used to the sensations.

"Fuck, even without a knot you're still spreading my insides.~" She states as she rotates her hips in a circle, making Max gasp in pleasure. "Oh?~ Did you like that?~" She asks teasingly.

"I-I've never felt anything like this. I can't imagine how it's supposed to feel better without a condom."

"Well you don't have to worry about that, we have plenty to practice with, assuming you don't go limp on me after cumming once." The smug look on her face ignites something in Max.

"You'd be surprised, I have a lot of stamina in me." He mentions as he moves his hands to her hips, gently rubbing them.

"I dunno, you sure you're not gonna cum too fast when I do this?" She then raises her hips, making Max gasp a little before she suddenly drops them down, her fat ass smacking against his thighs. "Or this?" She asks as she raises herself a little higher just to slam down once more, biting her lower lip as Max grunts from the pleasurable sensations.

"Still think you can handle me?~" Even if a part of her knew she'd still stop if he said so, there was something so fun in teasing him like this. When he doesn't respond, the human just closing his eyes and breathing in and out, she raises herself higher, his condom covered dick slowly reappearing out of her tight pussy until only the tip is left inside her. "Or are you gonna just blow your load like a cute little quick shot?~" She playfully mocks only to feel the grip on her hips tighten.

"Pretty big talk from my 'good girl'." Loona raises an eyebrow at that only to suddenly feel Max's hands pull her down and his hips thrust upward, meeting her halfway as his cock is once more buried inside her. "Tell me, are you a 'good girl' or a 'bad bitch'?" He asks with a sudden dangerous gleam in his eyes.

"…I-is it too late to say sorry?" Loona asks with a whimper while Max just grins.

"FUCK!~ H-how did you learn to do this?~" Loona asks in between moans, the hellhound currently being lifted off her feet, her legs hooked over Max's shoulders as the human continues thrusting in and out of sensitive pussy.

"Oh you know, some late night reading." He wasn't gonna say he got these ideas from reading smut.

"Y-you think you're being cute?" She questions him as she tries to find some way to fight back despite getting her insides rearranged by human dick.

"Bitch," He leans his head toward her ear to whisper. "I'm adorable.~" He grins before nibbling on her ear, earning some cute moans from Loona as he continues thrusting deep inside her.

"N-no fair.~" She whines as she struggles to think straight, not wanting to be consumed by the pleasure so easily. "T-take it easy already, you're gonna make me cum.~"

"Oh? Is someone getting close?~" He teases, his minor grudge satisfied as he kisses the hellhound's cheek. "Go ahead and cum, you made such a cute face last time, I wanna see it again.~"

"Y-you big sexy jerk.~ I-it's not fair, I'm gonna-" She whimpers as she tries to hold it back, only for Max to whisper again.

"Be a good pup and cum for me.~" With that said, Loona can't hold it back anymore as she holds Max tight before moaning in pleasure, her pussy squeezing tighter around Max's dick as she climaxes. Thankfully for her, Max was reaching his limit too. With a few more thrusts inside her, he reaches his own orgasm, releasing a fat deluge of his semen directly into the rubber, Loona shuddering as she feels the heat of his seed despite the latex protecting her from any possible impregnation, albeit human and hellhound procreation couldn't be possible, then again the only humans to be in hell are already dead sinners, questions for another time.

Once the two began to recover from their orgasms, Maxwell gently laid down Loona on the bed, both catching their breaths as he slowly pulls out of her, dragging the cum filled condom out of her.

"F-fuck, you let out a lot didn't you?" She asks playfully.

"It's your fault for being so gorgeous." Max states as he seems to revert back to his usual self. "Uh, how do I…"

Loona chuckles at that before beckoning him closer. "Here, let me." She carefully pulls the condom off of him, a bit of cum still oozing out of the tip of the cock before dripping onto her face. Curiously she licks it up, her eyes widening as she looks at the condom.

"I wanna apologize for getting so rough back there, and say thanks for going this far with me." Max began only to watch as Loona opens her mouth and pours out the creamy contents of the condom into her mouth, greedily swallowing the human's semen.

"Mmm~ so thick and warm~" She mumbles in between swallows. "What were you talking about?" She asks absentmindedly as Max states at her, his cock rock hard and ready for another round.

With another condom on, Max now has Loona bent over as he fucks her pussy once again, the room filled with the lewd sound of his hips smacking against her fat ass.

"God!~ What's gotten into you!?~" She moans out as Max just grunts and keeps thrusting, the condom doing little to stop Max from fucking the hellhound as if he was trying to breed her.

"I-it's your fault for teasing me, I'm not gonna stop until we use all of these condoms!"

"Y-you can't be serious!" She yells out only to gasp as he bites down on her neck, another orgasm making her body shudder as Max fills the condom inside her.

"Such a good girl.~" Max praises as he pets Loona's head as she bobs her mouth up and down his shaft, her tongue swirling around the flavored condom.

"Mmm, I wonder what's causing the different sensation, wearing a condom, or how your mouth is just different from the others." The human wonders out loud as Loona looks up at him, her eyes rolled up as his cock hits the back of her throat.

"That's it, good girls get to have a big treat!~" Max smiles before releasing his next load into her mouth. One of his hands moves to pull off the condom as he pulls his cock out of her mouth, just to quickly put on a new one, ready for the next round.

"T-too much.~" Loona whines as she lays flat on her back as Max thrusts into her from on top, his mouth biting her neck once again, adding to her collection of bite marks.

"It's okay, this is the last condom, just hang in there. You're doing so good.~" He praises as he kisses one of the spots he bit, making her shudder as he slams his hips into her.

"A-almost there.~" He grunts out, gritting his teeth before releasing the last load inside her, the condom filling to the brim. The two lay there panting heavily as their fun came to an end. Max slowly pulls out of Loona, the hellhound whimpering softly as his warmth leaves her aching pussy. He pulls off the condom before tying it and putting it with the other used condoms. "Jeez, I didn't think I could produce that much. Now I just gotta figure out what to do with these."

"Fuck if I know, sell them or something, your cum doesn't taste half bad." Loona idly comments, blushing softly as she looks at the several used pieces of rubber filled with human cum.

"You can have some of them if you want.~" Max teasingly offers.

"Really!?" She asks excitedly much to Max's surprise. Realizing her outward expression of enthusiasm, she reels it back and nonchalantly plays with her hair. "I mean, sure whatever."

Max just chuckles at her cute embarrassment. "…thanks again for this, I think I took a big step."

"It was nothing…just don't go thinking you can start calling me for sex though!"

"Oh of course not, I'd need to take you out to dinner first. I'd like to think I got some class.~" He playfully winked at her, earning an eye roll and amused scoff. The two look at each other for a bit, their heads still muddled from the many rounds together. Ever so slowly they began moving their faces closer, feeling each other's breath, taking in their scents, their lips centimeters away.

"Hey Max! I came to return your lip balm." The two suddenly backed away from each other, Loona grabbing a pillow to cover her lower half, as the door opened to reveal Charlotte Morningstar with a smile on her face, just for that smile to fade as she takes in what she's seeing.

"D-don't stare!" Max yells out, Charlie quickly covering her eyes, albeit peeking more than necessary as Max quickly puts in some underwear, tossing Loona her clothes too.

"What's going on here! Who is this?…Wait, aren't you the hellhound from I.M.P?" Charlie asks as Loona gets dressed.

"I'm a hellhound, I work for Blitzo, it's not that hard to put together." She answers with a hint of bitterness.

"W-wait, are those the condoms I gave you?" The princess dashes across the room and looks at the pile of cum filled latex. "Y-you used them all. Does that mean…" A dawning horror makes its way onto Charlie's face.

"Okay I admit it." Max began with an embarrassed look on his face. "I was still nervous about the idea of giving my first time, so I told Loona after she found the condoms and your note, and she said she'd help me practice. I didn't know that using a condom meant the sex didn't count as your first time." Max explained, Charlie's eyes widening as she looks at the human, seeing nothing but honesty in his eyes.

"Y-yeah exactly, that's what other demons say anyways." Loona adds, Charlie looking at the hellhound who seemed not only embarrassed but a tad disappointed.

"So that means…you're still a virgin?" Charlie asks slowly while Max nods his head.

"Yep. I think that was technically third base? Ugh that stuff is still so confusing, doesn't help that it's baseball terminology, never was a fan of that sport, or any sorts in general really."

Charlie is silent at first before letting out a relieved sigh. "Good, uh I mean, I'm glad you were able to take such a big step, I'm proud of you Max!"

"Oh thanks Charlie. Still, I'm sorry for using up all the condoms you gave me, I had no idea I'd use them all so fast."

"Don't worry about it. In fact, it gives me the perfect idea of what we can do next time!" Charlie said with a big smile.

"Well, it looks like you two have everything sorted out, I'll leave you to it." Loona says as she begins to leave only for Charlie to suddenly appear at her side and grab her shoulder.

"Not so fast." Charlie says with a menacing tone in her voice. "I believe you and I need to have a little talk."

"…oh fuck me." Loona hisses.

"Oh I think you got enough of that already." Charlie states, her smile looking quite forced as she escorts the hellhound somewhere more private.

"Hmm, I got a good feeling the two of them will be great friends!" Max smiles, oblivious to the danger the hellhound may be in.

Wtf nearly 10k words! But yeah we got a fight scene and lots of lovin for Max! No need to worry about Loona, Charlie is just gonna interrogate the hellhound about how she managed to use every last condom, she wants all the details. I considered separating this into two chapters but I couldn't find a good way to separate it without making both chapters too short. I hope you all enjoyed it! But wait, what about Max pranking Alastor? Oh wait it's down here!

Semi Canon Omake

"3…2…1…now!"

The sudden sound of an air horn causes Alastor's eyes to snap wide open. Feeling naturally upset at the loud noise waking him up, he snaps upward only to feel he's not in his bed, but on a large raft in the middle of a lake.

"Good morning sleeping beauty!" Alastor looks toward the source of the voice to find Angel Dust holding an air horn, Maxwell laughing his heart out while holding a video camera, and Niffty giggling while holding a strange case.

"Oh this is just gold. Say hi to the camera, Alastor!" Maxwell calls out with a grin.

"I never knew pranking could be so fun! The best part, this is harmless…unless he can't swim."

"I'll carry him out if necessary." Max reassures the little maid.

"Ah I believe I'm beginning to understand, this is just a jape! For a second there I was sure I was gonna have to kill all of you." Alastor chuckles, before looking at the three with a dark grin. "Though I could still punish you for interrupting my sleep."

"Don't threaten me with a good time!" Angel quips with a cackle.

"I know you're trying to be scary Alastor, but trust me it's not working with how ridiculous you look." Max explains, still grinning as he keeps filming.

"I suppose that's fair, a gentleman in his nightwear on a raft in the middle of a large body of water is quite humorous." Alastor conceded.

"Not as funny as your face though. Niffty did some great work!" Alastor raises an eyebrow before seeing the little cyclops maid pull something out of the case and hand it to Max. "Here! The water isn't very reflective, but this is!" Max throws the object at Alastor who manages to catch it, looking at it now he can see it's a compact mirror.

He opens it up to see not his regular demonic smiling face, but his face decorated with white grease paint, a red nose, a big painted smile, and on top of his head was a big rainbow wig.

"HAHAHA! Please tell me you're still filming, I need a copy of the look on his face right now!" Angel pleads, gently shaking Max's shoulder.

"Don't worry I got it all!" Max confirms as he struggles to not let his laughing shake the camera too much, already believing this video will be perfect collateral for Vox. "Great work on the makeup Niffty!"

"Oh I can't take all the credit, Angel helped by offering his makeup kit in the first place."

"Really? Where'd you get the rainbow wig?" The human asks Angel.

"Let's just say some customers of mine had some interesting tastes, and leave it at that."

Max just shrugs at that, not needing to know anymore, only for his eyes to widen at the sight of Alastor crushing the mirror in his hands. "Okay, I think it's time to run!"

"Yes. Let's." Niffty quickly agrees as the three dash with the human, trying to get as far away as possible while Alastor transform into a far more terrifying demonic form and began floating over the water in pursuit, the trio unsure if the clown makeup makes him less scary or even scarier.

"It's just a prank bro! Just a prank!" Angel Dust yells out as they run for their lives from the clown faced radio demon.