Chapter 0 - Dexter's Mom

Naruto sat at his desk continuing his mundane work. Gazing over the countless papers hoping for something, anything to jump through his office. For some excitement to enter his life after all this time of dull work. And his wish was granted as a knock at the door interrupted his thought. “Excuse me sir. Mr. Hokage? I found this wanted poster that said you are hiring for a maid.” The soft voice called out.

The young Uzumaki looked up only for him to gasp and his eyes grow wide. Never in his life had he been in the presence of such a perfect bombshell. The voluptuous redheaded MILF, clad in a tight green blouse revealing huge breasts with skin-tight blue jeans that nicely showed off her superb shapely hips and that amazing fat bubble ass. Sitting at the top of her tall and smooth legs, were two massive lobes that formed an insanely huge bubble-butt. The sheer mass of the two fat cheeks couldn't simply be called a butt. It was a ridiculously gigantic, mammoth-sized curvy ass. Just past the first curve of her ass was her tiny waist. Her torso was so tight and skinny it made the proportion of her hips look preposterous. Continuing up her figure carried on her chest, the two most obscene big breasts. The Uzumaki was completely transfixed by the woman. “Ah yeah. I mean, yes of course please come in.” Naruto told with his body leaping with lust.

Dexter’s Mom smiled as she closed the distance, swinging her huge hips side to side sexily. “Perfect. I’m from out of town and my family just moved here recently. So I was hoping to find a job and this would be perfect for me.” She explained with her sweet as honey voice as she sat down on that juicy booty.

The young Uzumaki nodded, taking note of how big her rump was. “That’s sound great. Although there have been many applicants recently.” Naruto told, hoping to get another view of that rounded backside. 

Dexter’s mom simply smiled assuredly. “I can clean, wash and make everything look spotless. Don’t you worry young man, I am the best when it comes to being a maid.” The red-headed MILF told with confidence.

“Hmmm, that sounds perfect but you’ll need to prove it to me first.” The devious Uzumaki assured.

“Whatever it may be, I’m ready.” She assertively told.

The young horny Uzumaki knew he couldn’t mess up his chance with this bubble-butt bombshell. “Fantastic. First, I will need to perform a physical before we can proceed any further.” He explained plainly.

Dexter’s Mom was taken aback. “Oh, a physical? Is that really necessary?”

The Uzumaki was desperate, with sweat running down his body just to see a glimpse. “Uh yes. This is standard procedure for all applicants. I will need you to strip down for me.” He clarified. 

“Um, are you sure? I’m a bit cautious, but I really need this job. The pay is just so good.” She tried to contest. 

“Yes, ma’am. No one can gain employment unless I know they can perform at the highest standard.” Naruto explained hoping to see that rump.

She had her reservations, however the salary was too good to pass up. “Oh ok. If you say so.” She stood up from the chair and pulled up her blouse, releasing her d-cup tits to bounce in the open. 

“Now turn around for me and get those pants off.” She stood there for a moment with a blush considering how wrong all of this is. With the thoughts of the salary she slowly turned around and dug her fingers into her behind, with apprehension she slipped her tight jeans down. Free of the restrictive material causing him to gasp, her booty now revealed to be even larger than previously thought. The Uzumaki’s thick penis grew rigid at the sight of her ass coming free of its prison, swaying in the air. 

This booty was two humongous lobes of pliant flesh. This ass was two watermelons, swaying when it moved, daring to be squeezed. This was a gigantic ass of mammoth proportions.  Naruto was salivating as he closed the distance. “I will need a closer look.” He walked around his desk, then dropped to his knees gazing over the massive rounded dumper. Without a word he grasped the huge ass causing her to yelp. “Please calm down miss, this is part of the process.” He explained as he gripped the giant butt. His fingers aggressively clutching the giant soft cheeks, pulling them apart and letting the cheeks bounce. 

She blushed madly as this stranger worked her naked body, nervously trembling under his grip. “Ohhhh. I don’t know if this is right.” She softly told with a moan, feeling his rough hands grasp and squeeze. 

“You want to make a good impression, don’t you?”

“Of course.” 

“Then allow me to get a good look.” Naruto told as he continued to grip and shake the big bubble butt. “I can’t help it. As my maid I will need to study your strengths. Starting with your endurance. I will need you to bend over my desk.” He commented as stood up and pulled open a drawer from his desk, grabbing a bottle of lube.

Dexter’s mom watched, not sure what to do. “I shouldn’t. This is all too much, to fast, sweetie.” She softly spoke hesitant of her next action.

“You don’t want to mess up this chance. You’re so close to getting this job.” The blonde told as he dropped his pants. Dexter’s mom jolted back at what she saw, her eyes wide in shock and unable to hide her emotions as her mouth gaped opened. Standing from between his legs was a massive fat eighteen inch mega cock. Her whole body frozen in shock and awe at what she saw. His huge head stared menacingly at her, with delightful broad girth. The immensity of his pillar was like nothing she had ever seen, its length and thickness unmatched. Already rock hard, and with a set of heavy balls to match. The sight made her stare with those wide eyes.

In complete astonishment she didn’t speak a word as he gently moved her to his desk. Dexter’s mom still paralyzed as she allowed the young Uzumaki to lead her, being forced over his desk with her giant ass raised up. Naruto then poured a bit of lube down onto her asshole. She moaned as he used a finger to pump in and out of that tight hole, now working in the lubricant as far as he could with a little extra poured out for good measure to get that big booty ready for a pounding he desired to give. 

Naruto used his hands as he spread her full huge cheeks apart with one and used the other to line up his arm thick rod with her entrance, testing her butt-hole with a couple of prods. He then pressed the fat crown of his thick monster manmeat against the entrance to her little back passage. Her tiny hole resisted his mass penetration as he pushed. “OOOOHHH young man you might be too big for me.” Dexter’s mom told as she felt the big log trying to gain access to her tightest of holes.

“Nonsense!” Naruto furrowed his brow as he renewed the force behind her butt. Meeting expected resistance considering his vast size. Before she could speak, he brought his hips back then launched forward and used power forcing his way with the herculean penis into her butthole, her little asshole parted, his obese cock pushing in deep. Causing them both to yell in delight as he forced his thick log in her stunning, fat ass. 
 
“AHHHHH! SWEETIE THIS IS TOO MUCH!” Dexter’s mom met agony as her little butthole was stretched several sizes, her eyes growing into giant bulges, fingers unbearably clawing at the desk. Meeting immeasurable agony as an excruciating scream left her throat. The pain dominant, once a little ass now gaped around the tree size thickness, making her screech throatily out.
 
“AHHHHH! OH... OH GOSH! OH! YOURE SO BIG!” The sexy MILF now with overwhelming tears of pain, her discomfort impossible as her butthole was ripped open. The snug hole enveloped his obese manmeat inch by inch, as her face contorted. "UUUUHHHH! IT HURTS SO MUCH!” Dexter’s mom screamed back, grimacing as ache overwhelmed her, unlike anything she had experienced before. Feeling a wicked burn of torture from the thick invasion and sinful pleasure from being stretched out by the dick. Never before had she been so packed up her booty and it wasn't even close. 

At the same time the Uzumaki couldn’t help but groan, his massive manmeat deep in the MILF. "Holy shit! MMMMM fuck so damn good." It was the best and tightest ass, let alone hole he'd ever been in before in all his days, feeling like a fucking vice all around his shaft, even with all the lube he'd applied to himself and to her. The Uzumaki felt nothing but elation as his dick was encased in her tight cavity. Her butt was warm and hugged him snuggly. He reached out to grab her gigantic bubble ass cheeks and palmed them vigorously, deep in desire for Dexter’s mom as her moans only got more frantic.

Her perfect tight, round asshole was painfully forced to accommodate the shoving of a thick eighteen inch monster. Her breathing erratic as her hips were spasming in throbbing pain. The mix of agony and ecstatic pleasure made her head spin as he thrusted into her. "AHHHHH! You're... UHHHHH! GONNA RIP ME APART! AHHHHH!" Dexter’s mom howled already with wide eyes. Looking back at that smug, handsomely smiling face then down to her rump to see that huge arm-thick dick stuffed into her from behind. Already feeling like this monster-meat was splitting her in half and he was barely a quarter of his total length inside of her. 

"MMMM Oh, I think you've got the potential to handle all of me." The hunk behind her claimed as he held onto the MILF’s ass. Making sure she was positioned right in front of him so he could smoothly thrust into her stunning, tight backside. Staring down to admire the sight of his fat pillar pushing into her asshole before drawing back. Never leaving Dexter’s mom juicy rump so the head and a few inches were always inside of her. Showing his talents as he knew her back passage would need to adjust to being excruciatingly stretched out. Which in a way, made it perhaps worse in her case as her whines indicated as he made this butt fucking a long, drawn out process. 

Dexter’s mom knew she needed to endure and survive though the torment. "AHHHHH OH GOSH! I’ve never had something so big in my butt! OH MY GOODNESS AHHHHH!" The redhead hissed out. One hand slamming on the desk for a moment like a cage fighter giving up a match as she felt his obese dick burrowing a home for itself inside her tight, rounded ass. Her cheeks bouncing back and forth from that harsh motion of his thrusts. "OH... IT H-HURTS! UUUUHHHH! HURTS!" She yelled, both loving and hating how thrilling it was to have her anal passage rammed by such a vast slab of man-meat. Even all the lubing done before wasn’t easing off the pain completely as her walls continued to be spread widely apart. Her red haired head lowering down as she tried anything to keep her focus and not lose her mind to the first time getting her ass fucked by a huge dick.

“Come on, just endure it. Earn this damn job! MMMMMM!” Naruto told as there was no way he was wasting this chance to put this bubble-butt MILF through the works. Not limiting his sinful strategy to thrusting his fat pillar in and out of her backside as he managed to fit in over half his eighteen inch length into her rump. Lifting a hand up to deliver a sharp slap onto her fat shaking cheeks. The crack ringing out before her head snapped up with a new howl. The sound of a mix of outrage, pain and the hint of pleasure as she panted out with a glare back at him. Squeezing the struck cheek afterwards as he pumped in with a firm motion, stuffing another fat inch in to make her moan and stare back with that conflicted look like she wanted to slap him back in return.

"You’re a naughty boy for doing this! AHHHHHH!" Dexter’s mom panted out as sweat rolled down her pretty face. Fitting nicely with her eyes watering up from the pain of her back passage getting split wide in a way that she couldn’t handle. Another spank onto her cheek jolting her body back to life, keeping her in that classic doggy style position to get ass banged from the back. "AHHHHH MMMMMM YOU B-BASTARD! AHHHHH! YOU'RE GONNA RUIN MY BUTT!" She screamed again as her body shifted as his fat log got further into her tightness from the fiercer pumps. All the while her pussy was dripping with juices without even being touched since her hands were still so busy trying to tear chucks out of the desk she was bent over.

"Mmmmmm! Yes! Moan for me! Take this big dick!" The smirk on Naruto’s face showed that he was happy getting to fuck the MILF up her tight, near virgin if not completely fat backside. Keeping a hold on her waist so she was straight and in-line with his obese shaft as he violently pumped away. Groaning out and starting to get his own healthy shine of moisture across his toned body as he powerfully thrust into those tight and rounded cheeks. His filthy desire about her ability to not just handle this kind of deep and firm anal sex, but the sheer size of his pillar from length to thickness, looking more and more true with each pump she took. 

Dexter’s mom tried to handle this fierce booty banging but leaving her screaming out as she had to handle the pressure of his obese dick stretching her as he fucked. "AHHHHH! OH Gosh! H-HOW IS IT FITTING IN? HOW ARE YOU GOING SO DEEEEEEP!" Dexter’s mom screamed out in discomfort as she was drooling onto the desk trying not to lose her mind to all this lustful fucking. Her eyes looking glazed over as she stared ahead and her brain tried to keep from being destroyed from the supreme mix of pleasure and pain from this kind of rough butt fucking. 

Suddenly, a loud yell exited her mouth, followed by a deluge of incoherent cries and screams. "UUUHHHHH! Fuck! Fuck! Fuck!" the busty MILF shrieked at the top of her lungs as an intense orgasm ran through her. Her chant grew more intense, reverberating through the room with the constant slaps being heard. "AHHHHHH!" She screamed, juices dripping down her legs as her cunt spasmed in a sweet climax. Her rounded tits swinging back and forth underneath her as she jolted from the stiff pumps entering into her ass from behind. Her hair a wild, bush-like mess all over the place with a few strands stuck to her cheeks. Her make-up already wrecked with lipstick being smudged with rolling tears of black eye-liner down her face. With the pleasure making her moan out as her body reacted to the stretching out of her back passage.

“MMMMM I knew your big butt could take my giant cock. Fucking TAKE IT.” Naruto was still pounding away into her with the classic filthy position. Driving his fat pillar in and out of her asshole, leaving her tunnel spread out but left naughtily snug around his shaft as he pumped away. Groaning himself with that wide smile as he stared down. Finally seeing her rounded cheeks meeting his body to make her butt go from merely jiggling to full on clapping off of him as he filled her up beyond a point she ever dreamed she could handle. That slapping noise mixing perfectly with her moans as he gave her backside the pounding of a lifetime as many men would give an arm and a leg to attempt.

“UUUUHHHHH! OH GOODNESS! Your big dick is too much!” Dexter’s mom body jolted harder now as she struggled to stay up in position, never mind keep her wits about her as her ass was fully stuffed and claimed by a man she still didn't know the true identity of. His crotch hitting off of her booty with powerful pumps to make her shift forward while her breasts swung as sweat coated her already stunning frame. Screaming out between moans as her head lowered again and her arms buckled, leaving her dumper raised up thanks to his hold on her. Naruto saw this, and tried the old trick of delivering a spank to her rump as he fucked it to spring her back upward. 

“Uuuuhhhh!” The redheaded MILF was too far gone at this point for it to work, leaving her just gasping from the mix of harm and stimulation from the slap. So it just resulted in the red mark of his hand print starting to form on her cheek from the repeated shots she's taken during this sex. Rather than showing concern, and perhaps hoping for this all along, he just smiled as he groaned and carried on spanking her huge jiggling cheeks once in a while to leave her branded even more than the state of her asshole would be by the end of this all.

"AHHHHHH... F-FUCK... FUCK!" Dexter’s mom panted as her face rested against the desk as the giant eighteen inch manmeat slammed deep into her bowels. Stains of make-up from her cheek along with the eyeliner tears and smudged lipstick covered the desk while her hair was sprawled about. Face down, booty up like a common whore while her pussy continued to drip with arousal. As if a part of her had always wanted to be dominated and ravaged like this. "FUCK! FUCK! AHHHHH... FUUUUUUUUUUCK!" She screamed away as her eyes stared blankly ahead while the Uzumaki never stopped his brutal attack. Tits pressed into the desk while her hips stayed raised up so her rump could jiggle away. The clap of her cheeks hitting off the stud behind her so loud and constant that likely the rooms above, below and to the sides could figure out some filthy action was going on. 

"MMMMM... I won’t get tired of fucking your fat ass like this! MMMMM." The Uzumaki thrusting away into her back passage with that wide, shameless smile on. Another slap to her booty to make it shake and show off the tattoo-like mark of his palm now on her soft skin. Acting like they've been regular fuck buddies for years instead of this being just a first time encounter between them both. 

The MILF looking like a defeated broken prize as she laid passed out while he hammered away into her booty with a blur. "MMMM. I'd say you clearly earned yourself the job." Naruto added to mock her. Knowing she was drunk in pleasure unable to form the words to reply. A far cry from the loving wife, just to be tamed by his huge dick stuffing into her butt-hole. His massive manmeat pounding away into her rear like he's drilling for oil. And not having to hold back now that he was repeatedly going balls deep into her backside like it was built for this single purpose to take his fat third leg.

“UUUUH! Naughty bastard.” The only response from the MILF was more loud moans and pained mewls as her back passage might have given up the fight to resist his length driving in, but it didn't make the burning of being spread wide go away. Her frame shifting on the desk as she had to move every time a new pump drove down into her asshole. Her face rubbing away to leave the evidence of her make-up and drool onto the desk. Perhaps wishing now she'd asked to just get mouth pounded instead as now she was looking far from the nice, confident beauty. Looking like she'd be more fitting to be an alley-whore as the sweat rolled off her body as she moaned out while her rump got stuffed again and again. The sort of fucking that would leave most women, even those far more experienced with anal than her, with a quite profound limp in their step for the upcoming week and beyond.

"You’re ruining me!" The next sound out of her was a loud moan of delight as Naruto bottomed out hard into her bowels. The clapping ringing out like a machine stuck on overdrive as he drilled her with a somehow even more merciless pace than before. The primal position making him look like a caveman claiming her as he pounded her while she lay in her own juices and sweat on the soaked desk. 

“AHHHHH!” The busty MILF screamed at the top of her lungs as an intense orgasm ran through her. Her nipples spiked as the spasms of the orgasm electrified her senses. The pleasure erupted from places deeper than where any orgasm had ever come from. Her pounding heart thudded in her ears until she felt like her head would blow up. Bursts of light exploded directly in front of her eyes. As she writhed under his spell, he maintained a sure and steady rhythm pounding her. 

“Ohhhh UUUHHHHH! SO MUCH!" Dexter’s mom let out an earsplitting cries as he penetrated her nonstop with eighteen inches of meat sinking into her ripped booty, pressing hard deep up into her bowels. Mind frazzled as she stared blankly while time seemed to break for her as she remained in place, with the constant powerful thrusting from the dick forcing her to be split in two. Her tongue hanging out of her mouth in delight as her eyes stayed rolled up to gaze at the ceiling as she got railed. 

Her lower legs angled back and toes curled in the high heels she still had on as her fingers held onto the desk like her life depended on it. Being held like a defeated prize as her make-up dripped down her features along with the sweat. It seemed hard to believe she was only slightly less of a winner in all of this than the man ravaging her. Still able to moan out as her snatch, despite having not been touched this entire time, dripped away to add to the soaking on the desk.

“Damn you’re really gripping my cock, slut! God I can’t stop fucking you!” Of course at this point the Uzumaki was getting his own stamina tested as he found a new high gear to give the stunning woman the sort of pounding she and her lovely body deserved. His hips crashing into hers over and over with the generous cushion provided by her rounded cheeks as he slammed his obese log into her asshole. Her back passage spread apart with just the perfect amount of tightness left that if she ever let anyone else tap this ass in the next month she wouldn't feel them. 

Naruto grunting out as his own sweat dripped off his body, hitting onto hers and the desk they've been fucking on. The clapping of her booty into him along with both their moans masking the creaking of the desk which would only further let anyone in any adjacent room know some wild action was going on.

His level of tiredness was nothing to the state of the redhead MILF underneath. Her arms falling to her sides as she panted out with mumbled, cock-drunk words in between her moans. Eyes half-open but still glazed over like the thrill of deep, rough anal sex would be something that would stick in her from this day onward. Her head fully slumped on the desk. The saliva leaking from her mouth dripping over the desk along with the trails of her black eyeliner tears as the other smears of make-up. All as her asshole got hammered hard and deep like her sole purpose in life was just to take his huge long cock like this instead of being the beautiful loving mother she's supposed to be.

"AHHHHH AHHHHH! MMMMMM! FUCK. FUCK FUCK FUUUUUUCK!" Dexter’s mom was only brought back to reality when his free hand gripped her sweat-soaked hair to make her face tilt up a bit more. Just a prelude as he buried his cock into her rump one more time and kept it buried in. 

"Gonna blow a huge load up your ass!" A deluge of cum fired out and roared deep into her abused bowels. The woman herself cumming and sprayed the desk as Naruto erupted into her with his climax. The hot thick and virile seed pumped directly into her helpless bowels. She moaned again, another shattering climax roaring through her. The sensation of hot spunk splattering deep into her already well fucked tunnel being the trigger she needed as she howled in delight again. He kept thrusting into her as his cock kept shooting abundant sperm deep inside her. She was thrashing about like a ragdoll while his blistering cock spewed out blast after wad of milky jizz at the apex of her stomach.

Grunting into her ear as he unloaded into her back passage, treating her ass like a cum-dump. A wide, sex-drunk smile across that ruined face as her pussy dripped juices and her body shuddered. Only adding to the mess on the desk she was pinned down on as her folds let out more of her arousal to soak down.

Finishing inside of her ass, Naruto emptied himself and didn't pull out until he was spent. His hips bucking once in a while as a shot fired out and he groaned. Releasing her head as she, as expected, slumped down into her own mess as he shifted back. Her asshole gaping wide in a state that usually was only reserved for whores taking a triple penetration. Admiring that and the sight of his cum leaking back out of that pummeled hole of the MILF. Her passage having no resistance left to prevent his load seeping to drip all the way down her already soaked with juices and sweat body, to add to evidence all over the desk as Dexter’s mom remained slumped, defeated and pounded.

 Author’s note- Any help would be greatly appreciated. https://www.patreon.com/Wolftheswordsman 