“C’mon, sugar, gimme some love too…” Jack purred, rolling into the touch of the tentacles as more moved from Timothy to thoroughly explore him as well. Through fluttering eyelids, Timothy watched his lover being groped and stripped by the maroon appendages. They wound over Jack’s legs, popping open the buttons of his pants with odd dexterity, even untucking his worn sweater from his waistband. Timothy breathed out in arousal as the tips pressed into the scarred plump of Jack’s hips and stomach as they pulled his pants and shirt off in tandem. Jack wiggled his legs and put up his arms to help in the process, until the pants were pooled around his knees and his sweater was tossed over the bedpost.

“Mm….that’s more like it…” Jack purred as the tentacles explored his torso, squeezing in loops over his pecs and trailing up and down his belly. Tim could even see him shiver, gritting his teeth in pleasure as the tips even daringly started to rub and pinch at his nipples. Timothy watched, for a moment ignorant of how the tentacles were continuing to explore his own body, licking his lips as his lover spread his legs even further on the bed, inviting the maroon tentacles to trace up his inner thigh and curl about his hardening cock.

Okay. Maybe this wouldn’t be so bad.  

Sequel to the Jack/tentacles fic, this time with Jackothy!! Just a bunch of sloppy tentacles fucking both of them, the usual.

I’m thinking there may be a third installment with Rhackothy, so hang tight for that if that’s your thing!!

Un-beta’d because I have to head to dinner but I wanted to post it….will edit it when I get back

He should have recognized that Jack actually being nice to him was a major red flag.

Jack was almost never genuinely nice to him. Sure, there were days when he was tolerable, and on occasion he did nice things for Tim, but there was almost always some kind of ulterior motive, whether it was to get Tim to go to a meeting with a department he hated, or to weasel the last cookie out of the batch out from under Tim’s nose.

So when Jack helped him shed his various layers, rubbing the double’s shoulder after slinging the clothes over the foot of the bed, Timothy should have been suspicious. But he had been so tired after the stress of another day of being Jack that he had welcomed the tenderness, even letting the other man press him back into the bed. Timothy had sighed softly as he laid back against the thick covers, stretching his arms and legs out pleasurably. He had been all ready to just wrap himself up in the blankets take a quick cat nap, when suddenly the bed started to quake and shiver. Timothy’s eyes had fluttered open, head flicking to the side as his eyebrows creased in confusion. Before he could fully understand what was happening, large, undulating appendages were crawling up from edges of the bed, roping over him even as he let out a shocked scream and tried to thrash about even as he was wrapped up in the slimy, muscular tentacles.

“W-What the hell, Jack!” Tim screeched, writhing around on the bed against the tentacles that were now lapping all over him, weighing him down as the tips wound around his wrists and ankles to hold him firm. He squealed out indignantly as the tentacles started to slip underneath his clothes, licking up and down his well-formed abs and giving them tender squeezes here and there. Tim’s heart leapt in his throat, eyes watering in fear as he fixed Jack with a glance that was both angry and terrified.

“J-Jack, call it off! Get it off me right now!”

“Mmm…” Jack tapped his fingers in faux-thought, “nope!” Jack popped the “p” with a sharklike grin.

“Not gonna happen, Timmy. I mean look, look how much Assmaster already loves you!”

“A-Assmaster?” Timothy stammered, head turning from side to side, trying to get a better look at the monster that was holding him down, but he couldn’t get a good read on it. Jack’s devilish grin shone as he clambered on top of the bed, sitting on his knees between Timothy’s spread legs.

“Heh. Yeah. She’s a good girl, isn’t she? I told her she was going to love you and hoo boy, she already can’t get enough of you, pumpkin.” Jack chuckled as the tentacles pulled up Timothy’s shirt, yanking the fabric all the way up past his chest to hug at his collarbone. Jack’s eyes glittered as his double’s pretty tan torso was exposed to his eyes, soon to be explored by his hands as Jack’s palms smoothed against Tim’s front. The double’s stomach hitched softly at the touch, abdomen rolling and quivering at the tingling warmth of his lover’s hand.

“You’re lucky I haven’t had my fill of these sweet abs, kitten, or else I would’ve made you change ‘em awhile back.” Jack purred, running his hands down the tone of Timothy’s stomach, making the younger double squirm and fuss.

“N-Not my fault you got fat, Jack—“ Tim yelped as Jack tweaked one of his nipples with a pout.

“Shut up. I’m not fat, just…just a lil’ winter weight is all…” Jack pinched a little harder until Tim was hissing, teeth gritted, before returning to softly rubbing his doubles sculpted pecs.

“H-Helios doesn’t even have winter…” Tim mumbled noncommittally, already more focused on the feeling of Jack’s hands on him than on insulting his egotistic lover. The tentacles weren’t helped either, curling and groping over his body in tandem with Jack’s greedy fingers. Trails of glimmering cold slime tracked over his body, making him look like he’d taken a bath in golden glitter. Jack loved smudging the trails over that pretty tan skin, grinning when the tentacles started to lap and curl against his wrists.

“C’mon, sugar, gimme some love too…” Jack purred, rolling into the touch of the tentacles as more moved from Timothy to thoroughly explore him as well. Through fluttering eyelids, Timothy watched his lover being groped and stripped by the maroon appendages. They wound over Jack’s legs, popping open the buttons of his pants with odd dexterity, even untucking his worn sweater from his waistband. Timothy breathed out in arousal as the tips pressed into the scarred plump of Jack’s hips and stomach as they pulled his pants and shirt off in tandem. Jack wiggled his legs and put up his arms to help in the process, until the pants were pooled around his knees and his sweater was tossed over the bedpost.

“Mm….that’s more like it…” Jack purred as the tentacles explored his torso, squeezing in loops over his pecs and trailing up and down his belly. Tim could even see him shiver, gritting his teeth in pleasure as the tips even daringly started to rub and pinch at his nipples. Timothy watched, for a moment ignorant of how the tentacles were continuing to explore his own body, licking his lips as his lover spread his legs even further on the bed, inviting the maroon tentacles to trace up his inner thigh and curl about his hardening cock.

Okay. Maybe this wouldn’t be so bad.  

The tentacles flowed with Jack as he shifted forward on his knees to straddle Timothy’s hips, firm yet yielding as they snaked over his form with an odd familiarity so unlike the restrained and experimental way he was being treated. Jack fiddled with the buttons on Timothy’s pants until the tentacles nudged his fingers out of the way, grasping at the waistband and slipping the unzipped garments down to the double’s ankles. Timothy gasped as the appendages investigated new skin, sliding over his hips before winding around his cock, the glimmering, gold lubricant slicking up his shaft before they prodded gently at the already swollen red head.

Timothy was so distracted, both by the way his cock was being massaged and by the sight of Jack being explored and groped by the tentacles that he didn’t notice the appendage sliding up his cheek until it was prodding at his lips. Tim barely had enough time to take in a breath of surprise before the tentacle was shoved into his mouth, the maroon flesh bulging out and pressing against his tongue as he thrashed about at the sudden intrusion.

“Easy, Timmy, don’t choke…’cause, uh, this would be really weird to explain to a medic.” Jack observed him with a slight humor on his lips, lips that were soon invaded in kind by a far more gentle appendage. Through his watering eyes Timothy could see the way Jack’s cheeks hollowed as he sucked on the tentacle, the way his eyes fluttered and rolled slightly as it slid further down, his throat pulsing and bulging as it forced its way down—

His thoughts were interrupted by a long moan as the tentacle in his mouth did the same, diving past the mouth of his throat and deeper inside of him, swelling up and releasing something thick and heavy that settled like syrup in Timothy’s stomach. The double nearly gagged, dribbles of saliva escaping his stretched lips as warm fluid was pumped inside of him. He felt a warmth starting to build inside of him, gradually spreading outwards until his fingers and toes were tingling with numb pleasure that smoothed out any remaining worries that he may have had about the situation.

Jack was letting out loud, obscene grunts as he continued to suck and lick over the tentacle in his mouth, his eyes opening in half-slits to stare down at Timothy. The tentacles sensed his wordless command and spread out over his asscheeks, giving the plump flesh a firm squeeze before the dove inside. Jack tensed up for only a moment before relaxing, body held up by the appendages as their brethren began to penetrate him, one after another, wiggling up into his ass until three were firmly lodged inside of him, with one more curling anxiously at his stretched hole. Timothy watched through hazy, pleasured eyes as his boyfriend was finally penetrated by the creature, and when two tentacles started to push against his own hole, the double relaxed and let them in.

He knew he was tight, tighter than Jack, and it was a bit more of a chore for him to take the tentacle than it had been for Jack. Timothy’s heels slid against the silky sheets, hands clenching into fists from where they were bound above his head. His teeth bit slightly against the tentacle in his mouth as the ones in his ass pulsed and fluttered around inside of him.

He could see Jack’s stomach bulge and ripple as the tentacles thrusted deep inside of him, moving underneath his flesh as they pushed as far as they could go. His lover was in absolutely ecstatic, completely giving himself up to the tentacles, and Tim could hardly believe how something so alien could be so sexy.  

He whined and shut his eyes as he felt the tentacles pushing further inside of him as well, curling up against his prostate and sending a wave of sensation surging through his body that left him seeing popping colors.

Timothy was utterly lost to his own pleasure when the soft brush of something familiar and human ghosted over the tip of his cock. The double forced his eyes open against the flood of need and gazed down at his groin to see Jack hovering right over his beet red cock, still entwined with one of the smaller tentacles.

Logic pulled at him briefly, telling him there was no way that Jack could fit Timothy’s cock inside him along with the tentacles—four now inside him—but then Jack was lowering himself, or the tentacles were lowering him. It didn’t matter, especially not when the bouquet of tentacles shoved inside of Jack parted around his cock, welcoming him into a slimy, pulsing embrace as Jack’s body steadily engulfed him.

Timothy arched back as far as the tentacles would allow him too, body straining against their grip as he let out a moan that would have surely reverberated throughout the dim room had his mouth not still be stuffed full of tentacle. His eyes nearly crossed as his cock was squeezed between Jack’s slick insides and the writhing tentacles that were already stuck deep inside of him. His whole body spasmed with involuntary pleasure, hips pitching upwards and rocking Jack into the tentacles embracing and supporting him. Timothy could no longer tell whether it was Jack moving his hips to ride him, or the tentacles controlling him, but he didn’t care, obsessed with the overwhelming feeling of the tentacles inside of him and the tight slick warmth of Jack around him. He knew he wasn’t going to last much longer, and after a few more desperate thrusts upwards he was coming, cock flexing against the nest of tentacles sheathing his member.

Jack let out a loud, ugly moan, his eyes rolling lustily in his head as he rammed his hips back down against the cock and appendages inside of him. His cock jerked against his bulging stomach, painting his skin with release as he came all over himself, shuddering body soon going limp in the embrace of the tentacles, which continued to thrust inside of both men for a couple moments longer before the entire mass of appendages quivered, swelling up and releasing torrents of thick fluid into them.  

Jack’s stomach bloomed outwards as it was filled with cum, Timothy’s own belly swelling out slightly as he too was flooded with the creature’s release from both ends. Timothy squeaked at the sudden pressure inside of him, while Jack let out a load, glutinous moan, a drop of glimmering cum trickling from the corner of his mouth as he slouched forward, suspending in the slack grip of the tentacles.

Timothy whimpered dumbly as the appendage inside of his mouth gradually deflated, pulling back out of his mouth and leaving a trail of thick, golden fluid dribbling over his lips and down his chin. He watched from under fluttering eyelids as the tentacle inside of Jack’s mouth pulled out as well, a gush of molten golden flooding over his lips and splattering onto Timothy’s stomach. Jack met him with a sharp grin, teeth stained with glimmering cum as he leaned in close to Tim, until his lips were hovering just above the double’s.

“How….how’s that….huh, Timmy…” Jack panted hoarsely, before leaning in to press a kiss against the young man’s lips.

Tim mewled pathetically back into Jack’s mouth, the golden monster cum sticky and dripping down as they kissed, more glimmering fluid sloppily trickling from between Tim’s lips and trailing down his throat. Jack’s tongue was slick, covered in the monster’s fluid as they messily made out until Jack pulled back, looking dreamily down at the double through hazy eyes.

The tentacles inside of them deflated after a couple more limits, leaving both men empty and leaking besides each other. Jack’s head rested on Timothy’s now slowly rising chest, the double idly tracing his fingers through his lover’s sweater hair as the tentacle lazily curled over them, cuddling them close in the afterglow.

“What do you think of her, pumpkin?” Jack mumbled hoarsely against Timothy’s chest, eye  half open as he snuggled close to the double. Timothy hummed happily, a satisfied smile quirking on his lips.

“I….that really was…wow…”

“Heheh. Thought you would. Nice going, Assmaster.” Jack turned his head to kiss at one of the roving tentacles

Timothy winced.

“Yeah, um, about that…maybe ‘Assmaster’ isn’t the greatest name after all? How about something like….Cuddle Butt…or Squishie…or Fluffy…”

Jack snorted against his chest, lifting his head to look at the double.

“She’s not a cat, Timmy.”

“Okay, she just doesn’t really feel like an ‘Assmaster’ to me at all.”

Jack stared at him incredulously.

“Tim, did you just stroke out during the past half hour or so, cause like—“

“I meant personality-wise, Jack, jeez,” Tim huffed, letting a tentacle nuzzle affectionately against his cheek. “He’s so pissy,” He complained to the appendage.

“Hey! Don’t you go turning her against me.” Jack whined, dropping his head to blow a retaliatory raspberry against Timothy’s chest that had the double squealing and breathless. The tentacles responded with confused petting which had Tim giggling softly as he stroked them, finally starting to feel exhaustion pulling on him.

“Mm….gonna take a nap…don’t do anything too fun while I’m sleeping, ‘kay?” Tim smirked at his lover as Jack lifted himself up on his elbows, kissing the double once on the lips before resting his head in the crook between his neck and shoulder.

“No promises, kiddo.”