Kinktober Day 19: Double Penetration (1 hole)

Story by URBeast on SoFurry

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#15 of Kinktober 2021

Alright! Some more of Cain, and my boy Gregg. Didn't expect to wind up using Gregg so much for these, lol, but he's super fun! I'm hoping to be a bit more definitive with who he is as a character, though if readers feel he's been pretty consistent characterization wise (other then the one time he had a dick, because sometimes he does and sometimes he doesn't lol). Also! There's some pregnancy riskiness in this one, and Cain is on the younger side, so y'know, if you want, you can imagine this is the backstory for Cain's son, Abel's, conception :3 I don't really have a set, canon mom for him. Could be Gregg's his other parent, which could be fun down the line. If I decide to do anything with that, haha.

Also, massage was another prompt I kind-of-sort-of tried to use, but it only showed up briefly so I didn't title it that way. I guess I just wasn't really in a very massage-y mood.


  1. Double Penetration in 1 Hole / Master & slave / Massage

(CW: Intersex male, Pregnancy risk)

Cain dropped onto the couch with a groan. The bare-chested, muscular pitbull sagged back against the soft cushions, sighing and letting his eyes slip shut. His jet-black fur, crisscrossed haphazardly with pink and red scarring all over his body, was dripping with sweat from a long day working in the sun. At his side, a chubby raccoon, similarly shirtless but clearly rounder and softer, also settled onto the couch, glasses askew as he huffed and puffed.

God damn...'' the gray-furred, pudgy man grumbled.Next time Gregg asks me to help him move, I'm telling him to go fuck himself...''

Rude.'' Gregg, a scrawny, furless cat in a button-up shirt, strode in through the doorway behind the couch, carrying two bottles of beer.Guess I'll just give both of these to Cain, then.''

Aw, come on, I was kidding!'' The raccoon, Fides, pleaded, shifting to peer over the back of the couch and offering wide, begging eyes.Don't be mean, Greggy,'' he continued in a slightly higher, silly voice.

``Jesus, you're pathetic,'' Cain teasingly rumbled, rolling his eyes.

Gregg chuckled, coming up to the back of the couch and holding out both beers to his friends, commenting, ``Thanks again for helping with this, you two. I really do appreciate it; anything you need, let me know!''

``I'm fine with beer for now. Maybe pizza or something later,'' the chubby raccoon shrugged, accepting his beer and taking a sip. He sighed contently, settling back in his seat; it was nice and cold, refreshing after all that time moving furniture and gardening supplies.

Cain chuckled, twisted slightly to reach up and take his beer... and hissed sharply, a paw going up to his broad shoulder and wincing. Damn,'' he grunted, taking the bottle gratefully and lowering it, wincing as the muscles of his shoulder ached and stung again.Must have pulled something...''

Oh, well!'' the furless cat chimed, ears perking up.Want a little shoulder-rub? You know I give good ones, hehe.''

Mm, sure,'' the big canine rumbled, smiling a bit and nodding at his friend's suggestion. Gregg settled up against the back of the couch, leaning down slightly to reach his smooth paws down to the larger male's shoulders. He began to rub and massage firmly, thumbs and palms pressing into the pit bull's aching shoulders.Ooh... Mmf, kinda forgot how good you are with your paws...''

Hehe,'' Fides giggled at that.Yeah, you usually get regular reminders of how good he is with his mouth, huh?''

Gregg scowled at that, but Cain let out a laugh. Well, I guess you aren't wrong!'' the pit bull chuckled, shaking his head.Mm, but I really appreciate this, Gregg...''

Still slightly scowling at the raccoon, Gregg sighed, before smiling and returning, ``It's no problem, Cain. I really appreciate you guys coming out and giving me a hand moving all my shit, heh.'' Even as he spoke, he continued rubbing expertly at the larger man's shoulders. Cain leaned forward slightly, giving a bit better access to his upper back; the feline was quick to begin massaging there as well, fingers working along the length of the man's well-sculpted musculature.

Fides took a drink of his beer, watching the cat and dog idly, still a bit giggly as he relaxed topless on the couch. Then, though, his eyes drifted downwards, and he smirked. ``Mm, I think I see something ELSE you might want this big, cute kitty to help you with...'' he chimed, gesturing between the large canine's legs.

Oh.'' Cain blushed, glancing down at his tenting jeans. He could feel Gregg still working at the knots in his muscles, a shudder rattling his body slightly as a particularly aching section was soothed.Mmf... S- Sorry, man...''

Heh, it's no worries, big guy,'' the cat assured, leaning down a bit lower and, still gently massaging the man's shoulders, pressed a kiss to the top of his head.I certainly wouldn't mind taking care of that for you...'' he purred further, one hand continuing to massage the dog's shoulder while the other curled down his front, stroking at his muscular pectoral.

``F- Fuck...'' the canine groaned, feeling those lithe fingers pressing and stroking against his body, soothing touch practically washing away a good deal of the soreness he'd built up over the day. He grunted, feeling his cock throb in his pants.

Well, the cat DID offer...

``Mm, come here,'' Cain growled lowly, reaching a paw up and catching the feline's neck. His muzzle tilted up, and he dragged Gregg down into an abrupt, hungry kiss, teeth scraping at the feline's lips before his tongue was shoved into the furless cat's maw, a moan leaving him. Gregg shuddered as he was kissed by the larger man, groaning softly and blushing as he struggled to kiss back, suckling on the dog's long, slick tongue.

Soon, the kiss broke, and Gregg, purring lustfully, swept around the side of the couch, already unbuttoning his jeans. Cain chuckled, settling back on the couch and licking his lips as the cat approached. In moments, jeans and underwear were on the floor, and Gregg was stepping out of them, smooth legs, ass, and groin exposed now.

Fuck,'' the dog huffed, setting a paw on the feline's hip.I never get tired of seeing your pussy...''

Pfft, dork,'' the cat chuckled back, though he was blushing and unable to help biting his lip. Sure enough, between his legs, rather than a pair of balls and a sheathe or dick, the feline had a pink-lipped slit, just barely standing out against his peach-colored flesh. The dog rumbled happily, setting his other paw on Gregg's hip and holding the feline right in front of him, one hand reaching for that already-dripping wet vagina.F- Fuck...'' Gregg whimpered as Cain began to stroke a dull-clawed digit up the length of his passage.

Fides, relaxing with his beer in hand, watched, soon fishing out his own fully-erect, humanoid cock and giving it a few lazy strokes as he watched his friends go at it. Cain's fingers soon closed on the feline's clitoris, gently tweaking and stroking at the nib of flesh and making Gregg moan sharply, legs trembling as he tried to hold himself up, leaning forward and setting his paws on the dog's shoulders again.

Mmf, c'mon, man,'' the cat whimpered, hairless tail swaying from side to side happily as he was teased and played with.I- I didn't... Ah! Take my pants off so you could finger me...''

``Hehe, needy kitty,'' the dog chuckled, leaning in and pressing his nose under the feline's shirt, which hung down past his bare beltline. Cain lovingly kissed and licked at the cat's belly, right above the dripping slit and achingly sensitive clit, the canine's paws slipping around to grasp at his body; with how much larger the dog was, his paws practically encompassed everything, thumbs hooking around almost to his pussy while the rest of the fingers cupped his smooth, round ass cheeks.

Fuck!'' Gregg whined, arching his hips back into those strong paws, panting sharply.J- Just get your pants off, man...''

Cain murred softly, nodding his head even as he gave the cat's body a few more kisses. One last short, teasing slurp to the feline's clit, and the dog was leaning back, the shuddering cat struggling to stand on his own for a few moments as the larger man reached down to pop open his pants. In no time, fat, furry balls had been tugged out, sheathe pulled back fully to reveal the dog's fully-engorged, throbbing canine cock, knot half-swollen and ten-inch, tapered girth pulsing and dripping precum.

Teasingly, the canine leaned back and waggled his cock enticingly, urging, ``This what you were wanting, kitty-cat?''

``Fuck yes,'' the cat answered easily, licking his lips. If it was possible, his vagina seemed to grow even more wet, sweet-scented fluids dripping down his inner thighs.

``Then get down here, and ride me,'' the dog huffed back, bringing his paws back up to Gregg's hips. This time, instead of holding him up, he dragged the feline down. The cat set his knees up on the couch on either side of Cain, shuffling and letting out a surprised giggle as the two men maneuvered to line up dripping-wet slit with pulsing-hard cock.

``Ooh, fuck,'' Gregg moaned, head tilting back as the tip of that canine prick found his opening. He rocked his hips forward, biting his lip as he took a few inches inside of him in one go, toes curling and tail thrashing as he impaled himself on the canine's dick.

Part of him knew, in the back of his mind, that he should have scrounged around for a condom, or taken the canine up his ass instead. But, they were all tired and needy, and he'd been feeling that desperate ache in his pussy all day watching Cain and Fides work to unload his things from the large moving truck he'd rented. So, he threw caution to the wind, trusting, or hoping, that nothing could come of it.

Cain whimpered, jean-covered legs trembling slightly as tight, hot feline pussy engulfed his shaft. He continued pulling the cat up against him, soon close enough to begin nipping and kissing at the slender man's neck, eliciting more whimpering, happy moans. The dog's cock throbbed inside that slick hole, warm fleshy lips caressing every inch of it. ``Go-o-od, you feel... amazing...'' the canine panted heavily.

In no time, his knot was pressed to the feline's pink vaginal lips, throbbing hotly right against Gregg's clitoris as they nestled together, panting and huffing. As they settled against each other, the cat glanced over at the chubby raccoon, blushing and taking sips of beer and jerking off to the sight beside him.

The cat chuckled, hooking his arms around Cain's neck and holding the topless canine against him as he teased, ``Hey, Fides... Mmf, you want in on this?''

The raccoon raised a bushy eyebrow. ``Uh, I mean... I assumed...''

C'mon, man, I've got space in my pussy for two,'' the feline informed, winking at the chubby man. Now blushing, Fides gulped, then licked his lips, downed the last of his beer, and stood up, dropping his own pants to his ankles and kicking them off.Mm, here, Cain, lets get a bit more comfy for all three of us...''

The big pit bull did most of the heavy lifting yet again, shuffling around so that he was sitting lengthwise on the couch, the small of his back against the armrest and one leg hanging over the edge, paw firmly planted as Gregg settled back into his lap, panting and whimpering with pleasure as the dog's shaft throbbed inside him. Now, though, Fides had space to settle in behind them, knees on the couch as he prodded his cock under the feline's tail.

``Mmf, like I said... go for the pussy, man,'' the cat informed, leaning forward and nestling against Cain's chest, purring happily. His tail flagged upwards, showing off a great deal; the raccoon couldn't help but groan with pleasure, cock throbbing at the sight of the feline's plump, round ass cheeks, winking tailhole, and a little bit of visible slit, nestled around the canine's visibly-throbbing knot, heavy, furry balls nestled down between his legs.

``Goddamn, you two are so fucking hot,'' Fides panted out, setting a paw on the feline's back and stroking up under his shirt, clumsily massaging at the cat's lower back.

Hey, don't sell yourself short, big guy,'' Cain chimed, hooking his arms around the cat, one up around his shoulders, the other down low to grasp his hip. The grinning, scarred pit bull winked up at his chubby companion, adding,I'd be honored to bend you over and plow your fat ass sometime. Or the other way around, I'm not picky!''

The raccoon blushed at that, but smiled and nodded. I'd be down to take you up on that sometime,'' Fides answered,Mm, but right now, we have a kitty to fuck!''

Gregg shuddered, trembling in Cain's grasp as the raccoon now settled in close, grinding his leaking, humanoid cock against the feline's taint. Smearing precum and the cat's own fluids around a bit, before lining up with the other man's leaking pussy, and beginning to press firmly. The three men grunted, panted, and huffed, rocking together lightly until... ``Mmf!'' the cat grunted out, burying his face in Cain's chest and whimpering happily as the raccoon's fat dick spread him open as well. He could feel both fat cocks grinding through his insides, pressing him open wider and wider, deeper and deeper, until both men were settled balls-deep.

``Ooh, fuck,'' Cain grunted, before growling with pleasure.

``God... N- Never felt a dog dick like this...'' Fides rumbled, panting hotly. He could feel every pulse of the pit bull's girth throbbing against his own, their furry nuts settled together as they just enjoyed the tight heat of feline pussy.

Holy shit, I'm so... full...'' the cat whimpered, blushing intensely. His ears were pinned back, furless body trembling. The heat and pleasure radiating from his over-stuffed abdomen was driving him wild, mating instincts thrown into overdrive.I need... Fuck, p- please, breed me, guys... Fuck me, ah...''

The dog and raccoon didn't need to be told twice. Steadily, the three men began to work. Fides was grasping at the cat's hips and slowly thrusting in and out of him, panting and groaning each time he hilted himself inside the feline's slit, the wet blend of precum and vaginal secretions squelching out around his shaft and making a mess of his thick pubic fur. Cain, meanwhile, kissed and nipped at the feline's neck and face, growling lustfully as he manhandled the furless male's lower body, bouncing him on his lap, throbbing cock pounding in and out steadily. It was all Gregg could do not to start riding both of them with reckless abandon, purring and whimpering into the pit bull's assuring kisses and licks, clumsily returning a few of his own as four paws caressed his body, two fat, throbbing dicks barreling into his hole.

God, n- Not...'' Fides whimpered, now thrusting a bit quicker, his heavy nuts slapping against Cain's repeatedly.Not gonna last long back here, boys...''

Me neither,'' Cain grunted back, his hand squeezing at Gregg's smooth thigh, practically gushing precum into the feline's pussy.Shit, you're so tight, Gregg...''

The cat couldn't even answer. He was a writhing, pleasured mess, purring and mewling as he was fucked open by his two friends. His paws clumsily grasped at Cain's bare upper body, soon hooking up around his neck as his naked lower body was bounced in the dog's lap. The new angle had ensured that every thrust on the canine's part was grinding against his clit.

The three friends continued to rock and thrust together, wet squelching, grunting, and moaning filling the air, alongside the smell of sex and sweat. Fides had his eyes clenched shut, head tilted back and groaning openly, his legs starting to ache and tremble but no part of him wanting to stop fucking the cat. Cain growled, dragging the dazed feline's muzzle up to meet him for a deep, lustful kiss, thick canine slobber dripping down their chins as they made out, all of them growing closer and closer by the second.

``Ooh, fuck!''

Fides came first, his cock slipping out from the feline's slit and grinding up between his ass cheeks, smearing fluids up the cat's taint. A second later, he orgasmed, hot spurts of creamy raccoon jizz jetting out all over Gregg's smooth ass, making a gooey mess of his round cheeks, winking hole, and hairless tail. The raccoon whined pitifully, immediately hit by exhaustion and flopping backwards onto the couch, finishing his orgasm while slumped back against the other arm rest, oozing cum down his pulsing shaft and furry balls into a messy puddle on the couch's cushion.

Gregg came second, the feeling of Fides' hot seed on his rump setting him off. He clenched around the dog's shaft, yowling and breaking the kiss between them, head thrown back and eyes pinned shut as he clamped down and orgasmed. Hot fluids spurted out from his slit, rhythmically working at the canine's dick as he squirted all over the canine's groin, painting him with feline juices.

This, of course, set off Cain, who began to thrust vigorously up into the orgasming cat. He growled, nearly howling with ecstasy as he slammed his knot up into the loosened feline vagina with a wet, sloppy pop, easily pushing inside and dumping his load into the other man. That didn't stop him from holding the bottomless feline's hips firmly, pounding upwards into him even as he dumped hot, thick ropes of canine seed into Gregg, who could only whimper and sag against his chest as he was filled up.

Soon, Cain too sagged tiredly, flopping back against the couch and whining pitifully. He couldn't even muster the energy to keep clinging to the cat, arms falling limply to his sides as he panted and groaned, tongue lolling from his maw. Gregg remained panting against his chest, able to feel every pulse and spurt of the dog dick inside him.

He shuddered, partially sitting up and using his legs to pull up off the canine. With another all-too-easy, wet pop, it came free, Cain whining in objection as his pulsing dick was let to flop and ooze cum out in the cold, open air. His legs trembled, poised over the canine's exhausted body and peering down to look at his gaped pussy, still belching out dog jizz like a faucet. It, of course, only got on Cain, who seemed to sexed-out to notice.

``F- Fuck...'' Gregg whimpered, still poised over his friend before flopping back down onto him, this time without a cock inside. He could feel the canine's dick throbbing against his taint, though, now leaking cum to join the mess of raccoon jizz on his ass.

Ah... Th- Thanks...'' Fides barely grumbled out, holding up a thumbs up.That was... holy fuck...''

Cain grunted, and seemed to find a bit more strength, bringing his arms up to wrap around the feline and hug him close. Fuck, man...'' the dog huffed, able to feel his own mess spilling out onto his lap.S- Sorry...''

It's fine,'' the feline dismissed tiredly, yawning.Mmf... We were probably gonna get an insane amount of jizz on this couch anyway...''

``Heh... fair enough,'' Cain agreed, chuckling weakly and nuzzling at the cat.

Fides chimed tiredly, ``Hey, so... Hope it's cool if we crash here tonight. Because... I don't think I can feel my legs right now.''

``Yeah, it's fine... We can just sleep on the couch, or move up to my bedroom when we can all walk again,'' Gregg shrugged, before yawning again and settling on one of Cain's pillowy pectorals, sighing softly. Still leaking virile canine seed, the cat soon passed out, shortly followed by the comfy pit bull and worn-out raccoon.

Cain's now-warm beer continued to sit, almost entirely full, on the nearby coffee table.