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"He's been a real sweetheart, his father still doesn't know."

"Really? Totally Clueless?"

"Oh yes, out with his loser friends most of the time."

The two women laughed, one a gorgeous older vixen and the other a taller female equine. Both were liberally enjoying some wine, and if the necklines or mid-thigh cutoff of their dresses was any indication, planned on some downtown excitement later that night.

"So does your kit suspect anything?" the mare asked with a wiggle of her eyebrows, her impressive bust shifting slightly.

Cathy the vixen smirked as she sipped back her drink, "I may have teased him a little too much Monica, it's too much fun."

"Oh you nasty bitch, what did you do?"

"Well...you know how boys his age are, so after I caught him peeping I may have encouraged that little complex of his..."

"Oh my god you unbelievable bitch, and you were trying so hard to live up the cozy housewife image." The mare giggled again.

"Well don't tell that harpy from the homeowner's association, she wants any excuse to gossip about me."

"So what happened with James?"

"Left him a link to some fox and wolf interracial, a dirty mag, and maybe...a pair of my panties."

Monica was openmouthed in shock, and tossed back the rest of her wine.

"I don't believe you."

"It's true. I get such a rush teasing him, it's adorable how he blushes."

"And he's your son, you just know that's going to give him a massive complex."

Cathy sighed, and swished her glass as she thought.

"I know, but part of me is glad. I love my boy, and he never was a very decisive male. I like having him adore me like this, and I feel safer he's happy like things are rather than getting stuck with some harpy who'll drain him for alimony and give him nothing in return."

"Aww," Monica blushed, and the mare hugged her friend lightly, "Girl, that's adorable."

Catherine giggled and hugged her back, "He's my little sweetheart, and if it makes him happy I don't see the harm. I'm keeping him all to myself."

"You've got your own personal creampie cleaner, don't you?" the mare teased in a singsong voice.

"Monica!" The vixen smiled in mock scandal.

"Oh don't lie, you've thought about it haven't you?"

The vixen huffed and sipped some wine in pretend-offence, only making the mare laugh harder.

"He'd probably love it you know..."

"...maybe...I just-"

At that moment, the two heard the door open and close. From the front of the house, the call "Mom, I'm home!" echoed, and the look on Monica's face darkened into cheeky amusement.

"Well well..."

Cathy hushed her with a smile, and the two turned to look at James as he poked his head in.

"Hey sweetie, how was school?"

"It was alright mom, Hi Miss Lewinsky."

"Oh dear, Monica's fine."

It was clear to the two women that their state was arousing to the kit, since his blush telegraphed those thoughts perfectly. It was with a cruel smirk that Cathy decided to have some fun with Monica there.

"Sweetheart, my feet hurt. Would you mind?" She lifted one elegant footpaw out, and the kit's eyes zeroed in on her long exposed leg.

"S-sure."

As the kit kneeled down, his ears burned as he heard the two women chat in a stage whisper.

"Oh he's so obedient Cathy..."

"I've got him wrapped around my finger, he'd do anything I told him to."

"...anything?"

The taller mare's breast bumped into Cathy's own as she leaned up against the vixen to whisper in her ear. What she said made the fox's eyes go wide and she batted the other's shoulder lightly with a scandalized grin.

"Monica!"

"What? You know he'd do it..."

"But tasting other men's...?"

"I'll prove he's at least interested."

"He'd never do it hun..."

The mare only giggled again, and turned to the young fox massaging his mother's feet.

"James, we have to get going, why don't you kiss your mommy goodbye?"

The 13 year old kit nodded happily and got up, before one of the mare's own elegant legs tapped him in place.

"Oh I didn't mean kiss on the lips dear."

Monica reached over and lifted up one of Cathy's thighs, exposing her round, creamy white and red ass cheeks underneath her cocktail dress. The vixen was wearing a black thong that contrasted wonderfully with her fur.

"Want to give her a good luck kiss before we go have fun on the town?"

Flushing completely, the kit nodded fitfully, and shaking slightly drew closer under the two women's amused stares. His little muzzle inched forward, and he pressed a kiss into his mom's soft ass cheek. The women tittered, amused at his cute embarrassment and eager kiss.

"Good boy, how bout one for me too?"

The mare lifted up her leg, exposing her own creamy beige ass. A sheer red bikini cut hugged her unmentionables.

James turned his head and pressed a hesitant kiss up against the older woman's warm ass too, making a cute noise when his hair was ruffled.

"Nice and obedient. Maybe when we get back mommy will let you help her clean up, hmm?"

"Monica you're incorrigible." James's mother said with a laugh, but not denying the idea.

The two women began getting ready to leave, and it was as Cathy nipped off to her room to grab her purse that Monica turned to James and bent down with her hands on her knees, generous bustline dangling in front of the hyper stimulated kit.

"Just in case you get a little adventurous, here's somewhere you might want to visit downtown." The mare handed the kit a slip of paper with an address, biting her lip as a positively cruel expression crossed her face. "I'd like to get your mommy to come by some time, maybe if you help convince her to go you can have a little fun too, you pathetic little cuck."

James felt his dick twitch at the insult, and noticing his renewed blush, Monica giggled and kissed his cheek.

"Good boy."

Cathy returned and the two slipped on their heels. With a flirty wave and a wink, Catherine left James home alone with the unspoken agreement that his father not find out.

James waited as he heard their car speed off, and feeling his heart race and that familiar twist in his gut of nervousness and arousal, he patted off barefoot to his laptop to find out what the address was that Monica gave him, his little dick twitching in anticipation.

---

The intercity was a scary place.

Downtown past the nightclubs and stores, the seedier parts of the area were home to homeless people, criminals, and all manner of drug trade and prostitution. James knew not to wander around before, but now the idea of being vulnerable down there made his dick twitch.

He'd called the weasel from that one time with his mom, who'd given him his number. The slightly shady character had been amused that the kit wanted to go to that particular address, and agreed to drive him. The only payment was the young fox's mouth on the weasel's smelly dick during the trip, and a quick rough fuck leaving a hot load up the kit's tailhole before he was kicked out of the car with a laugh.

James shivered as he felt strange eyes on him, before hurrying to a brick building in the alleyway.

When he turned the corner, he found himself in a section of alley between the run-down buildings with a steel door on one side and a wolfess smoking outside it.

She had bright purple hair dyed in a sort of gradient, and pierced ears. Her grey fur looked very soft, and her breasts were certainly large, barely covered by a worn t shirt with some band on it, and a pleather miniskirt hugging her wide hips that led to fishnet thigh highs and stiletto heels. It was hardly a guess that the female wolf was a streetwalker.

"Um, hello?" James ventured shyly.

She looked at him, and raised a brow at the 13 year old fox loitering in such a place. "You lost kit?"

"I'm looking for the Tailraiser, someone told me it was here."

"Maybe, why? You look a little young to come looking for this kind of place."

James bit his lip and stared up at the wolf with a tremor in his voice.

"I-I know, but please don't get me in trouble. I just wanna go in..."

The wolfess made an 'aww' sound at the little kit, and snubbed out her cigarette after a drag.

"Alright, I think I can let you in, but you gotta do something for me sport. Still wanna come in?" She asked with her arms crossed under her heavy breasts and her hips cocked.

The kit nodded vigorously.

"Alright cutie, close your eyes..."

James did so, breathing in deeply as he tried to keep his racing heart calm. He was so nervous being alone in the intercity, the filthy and reek of the alleyways scaring him slightly, although the taboo of how wrong it was to be there exciting him. He heard the rustle of fabric, and without warming, a soft warm weight was suddenly placed over his face.

Opening his eyes, James saw the cruelly smirking face of the purple-haired wolfess leering down at him, and a weighty flaccid dick that she's freed from under her skirt and panties now sitting across his muzzle. The musky smell clearly said she's cum a few times that day, and the aroma of not having showered that day either clung to her with a sweaty overtone, rather than a stink. She smelled like a whore, and it was driving the shocked fox crazy.

"Well? You want in, this meat's going down your throat kiddo."

Shaking slightly, the kit feebly reached up, and opened his little maw to accept the large smelly dick.

His paws barely fit around the hefty shaft, and the flared head sat heavily on his tongue. He pursed his lips around the crown, and began to suck in a few more inches, feeling it harden in his mouth. The wolfess murred appreciatively, swishing her hips as her she-cock was fellated by the underage fox.

"Fuuuck...you got such a cute lil mouth..."

James kept suckling, feeling the length fill his mouth until it began to push into his throat. He held his breath as it pushed back, and with one violent thrust felt his nose touch the wolf's pubes as she bottomed out.

Moaning blissfully, the wolfess grabbed the young fox's ears and withdrew her cock dripping with sticky saliva and precum, before pumping her hips forward again, a bulge visible in the kit's throat as he struggled to breath in between being facefucked.

Her tits bounced in her tight black shirt, nipples erect. Her ass jiggled as she tensed up, feeding the vulpine her dick. The red rocket was swelling up at the base, and the grey furred streetwalker tilted her head back as she enjoyed the creep towards release.

"Mmmmm... I'm gonna pump your tummy full, kiddo."

Tail swishing, she sped up her thrusts until her face tensed up, and she gasped as her knot made an audible 'pop' as it stuck inside the kit's maw, and her red canine dick began to twitch and spurt thick ropes of cum down his tight throat.

James was shaking, wide eyed as he patted and grasped at the wolfess's hips in futility. He couldn't breathe, and the thick, syrupy sperm flooding him was blocking his throat, even as the knot kept his maw open too wide to even budge. His eyes were beginning to roll back as he choked to death on the streetwalker's delicious cock, seeing her smirk down at him in sweaty afterglow. Just when he was approaching the edge of consciousness, the knot lessened, and her dick withdrew with a creamy 'plop,' leaving the kit on his knees in the filthy alley, couching up what sperm he hadn't swallowed.

"Thanks kid, you got a sweet mouth-pussy."

Getting up, James wiped tears from his eyes and smiled, the front of his shorts wet with his cock's discharge. The wolf laughed at the sight of him, and ruffled his hair.

"I'm Kayla. Why don't you come on in with me kiddo?"

Following the purple-haired wolf's lead, James padded after her into the dark interior of the filthy brick building.

---

There was muffled music playing, and the sound of a few videos of an adult nature being watched. James found himself trailing the wolfess in a corridor, dim and black, with stalls on one side, and some cushioned doors on the other. A set of larger doors led to some kind of lobby, and another turn led down to what looked like a sex toy shop.

"I got a room here, c'mon."

James followed the sight of the wolf's swaying ass as they passed through a cushioned door. Inside was a round bed with red sheets, scattered clothes and sex toys, and band posters lining the walls. The kit nervously took a seat on the bed as Kayla pulled a pink see-through penis shaped bong from a drawer and began setting things up.

"You ever get high kiddo? What's your name anyway?"

"James...and, no..."

The taller female chuckled and slipped off her heels, and shimmied out of her skirt. She was left in fishnets and her band tee, relaxing on the bed next to the fox as she lit up and took a hit.

Exhaling slowly, a cloud of smoke filled the air, and the wolf held it in front of James. "Just put your mouth on the tip and suck when I tell you, nothing new right cutie?" She said with a wink.

James obediently suckled the end of the glass cock bong, and as it was lit he sucked in when she told him. The first one was too much and sent him into a coughing fit which made her laugh, but Kayla took another hit before coaching him through it again.

Soon the pair were laying next to each other sleepily content.

Kayla flipped a remote and a flatscreen on the wall turned on, a porno playing on the channel. James looked over at the wolfess and her bare bottom, cock hanging out, before slipping off his own shorts and laying bare-assed next to her. The sight made her smile.

"What kind of porn you like, kit?"

She scooted closer to him, her arm around his shoulders as they melted into the soft pillows. Flipping through the adult channels they came to scenes of interspecies, gangbangs, public sex, and then one of a bunnygirl cuckolding her boyfriend with a much larger great dane. At James perking up, she giggled and left it there.

"So you get off on cuck porn?"

"Y-yeah."

"Why, your lil girlfriend left you for a better guy? See your sister fuck some hunk?"

"No, um...I kinda..."

"Whaaat?" Kayla smirked at the shy lil fox.

"...saw my mom..."

The wolf's eyes lit up, "Oh you are a dirty lil perv aren't you? Saw you mommy getting fucked stupid?"

James nodded, huddling closer to the warm tall girl.

"And that gets you hot, huh?" The lewd sounds of the bunny taking it in her ass on-screen filled the room, "You watched your momma get a dick inside her?"

"Mmmhmm..."

"Must have been a real cock, not this little garbage you got here..."

James flushed at the insult, as Kayla turned on her side to measure up her thick she-dick to his little thing.

"Yeah, mine's a lot bigger than yours. How's it feel to be whipped by a girl, loser?" The wolf's smirk was nasty, but she playfully ruffled his ears.

James bit his lip, blushing. He felt good, really good. Turning on his side he pressed his little cock against the wolf's much larger one, and rested his face in her cleavage.

"I like it. Feels good being bullied by girls."

Kayla laughed, stroking the kit's hip. "You're adorable..." She mumbled quietly, before inching forward and planting a kiss on his muzzle, and hugging him close. The two of them rubbed against each other, limbs tangled as they writhed in the feeling of being high and the soft sheets, warm bodies and sexual tension.

"I always wanted a little brother..." Kayla whispered as she felt him all over, nipping his neck and kissing him.

James was punch drunk from the kissing, reveling in the slight taste of men he detected on her tongue, clearly she'd been busy earlier. He murred into her tits as she molested him, feeling his little dick spurt precum.

"Hey, Kayla?"

"Mmm?"

"C-can I...lick your, um...butt?"

The streetwalker looked down at the fox with a sleepy smile, and turned over, sticking out her round ass.

"Enjoy..."

James gripped the two big, soft cheeks, and pressed his muzzle deep into her ass, feeling his maw touch the muscled sphincter of her tailhole. He darted his tongue out, eliciting a hiss from the wolfess, and began to lick and bathe the sensitive hole.

"Oh-hhh...you fuckin' perv..." The wolf moaned, lost in arousal.

James kept licking, even as the whore sat up to smother most of his face, making it hard to breathe as his whole world became the juicy ass planted on his maw. He kept licking away, delving into the ring itself, and tasting sperm in her ass from previous clients. He whined as he felt her fishnet-clad feet playing with his little cock, while Kayla began to jerk off while the underage fox rimmed her.

Her voice climbed an octave cutely, as she bounced lightly on the kit's face, pumping away at her dick. The tempo increased, and the wolf's back arched as she approached her peak again.

James was startled when Kayla abruptly lifted her ass off his face, and flipped him onto his tummy, squawking as he was suddenly held down, and felt the intrusion of her cockhead past his ass cheeks.

"I'm gonna breed you kiddo."

The kit's eyes almost rolled back as he felt the biggest cock in his life enter his butt. He gasped, and above him Kayla gasped too, resting her fat tits on his head. Her hips began a steady motion thrusting into the little fox, her grey fur clashing into the red. Her purple dyed hair flipped as she tossed her head back, smiling in bliss as the vulpine ass kissed her dick.

"Good lil bitch... let big sis cum inside you..."

James began to whimper as he felt the knot pressing against his entrance, and it was with a howl that both of them convulsed when the knot popped into his ass, shuddering as Kayla's sperm began to flood his backdoor. The wolf's ass cheeks tensed up as her cock spurted again and again, her back arched as her climax milked off into the cute kit.

The sweaty pair collapsed to the bedsheets, Kayla smothering James with her larger body, and the kit happily smooshed beneath a hot streetwalker.

"...I love you sis..." James whispered with a quiet smile.

The wolfess bit her lip, a rumor of hot tears just at the edge of her eyes before hugging her little fox toy close. "I love ya cutie, big sis will take care of you."

They lay there, and napped for a little bit, before talking some more as a porno played on the TV.

"So why were you coming here anyway, kiddo?"

"One of my mom's friends said I should, and she wanted me to convince my mom to come."

"Who was it?"

"Miss Monica."

The wolfess blinked, "I know her...oh kiddo...you have no idea what you're leading your pretty little mom into..." The streetwalker grinned.

"...like what?" The young fox asked.

"Kit, there's a room in the basement where we film some stuff you shouldn't, and if Monica's tastes are anything like I know they are, your poor mommy's going to find out what a gangbang feels like. Hell, they'll probably want you on stage next to her taking some too..."

James gulped, yet his little dick twitched.

Kayla smiled, and bent down to suck on his cock till it was free of excess cum, moving up to kiss him with a mouthful of jizz.

"Don't worry kiddo, I'll come with you. You can check out Monica's performance tonight, and if that's something you like, maybe we can get your cute lil mom in here too."

"Okay...hey Kayla?"

"Yeah kiddo?"

"Do you think...y'might want to, come visit us at our house sometime?"

The wolfess looked at him with her maw slightly open, smiling hesitantly.

"You know I work the streets, right kid? I'm not exactly girlfriend material..."

James gulped and hugged the taller girl.

"I want you to come visit. I always wanted a sister...and, you can m-meet my mom if you want."

She smiled nastily, "Oh? And if I fuck your slutty momma?"

"T-then I'll clean you both up."

Kayla giggled, and kissed the kit again.

"You were born to be a lil cuck, weren't you? Alright, big sis will come take care of your mommy so you can jerk your sad little dick, mmkay?"

The kit's face blushed deep red, and he snuggled into the wolfess.

It was then that there was a knock on the door.

"Hey Kayla, we got a drunk mare and a vixen who showed up to do the gangfuck, you want to come supervise?"

The two looked at each other with a grin, and James felt butterflies in his stomach again at the thought of seeing his mom again.