Tentacle Adventure!

Jem's walk home from work is derailed. To clarify, it's derailed by tentacles. Tentacle sex. Eggs? What else can I say, it's tentacle sex, eggs, man gets his pussy wrecked, the typical stuff.

Jem frequently walked to and from work. His apartment was only a few blocks away, and he didn't own a car anyway. He had a bike, and utilized public transportation.

He enjoyed the walk, as he usually made in the daytime. He worked opening and day shifts at Crow's Grill and Bar, before the bar aspect really kicked in. Jem was fine with this. He hated drunk people.

He was also, unfortunately, a pushover, so when a new coworker--Mariah--asked to swap shifts, and she asked so nicely, and she was just so cool, how could he say now And that became a habit, and he found himself walking home at night once a week.

Jem was aware of his privilege as a man; were he a woman, this walk would be much more dangerous. As it was, the first few times he had to make the journey, he found his heart beating out of his chest by the time he reached home, only to race up the stairs to his apartment and gratefully greet his cat.

Jem wasn't a physically imposing kind of dude. He was 5'11, lanky and knock-kneed. He wasn't weak, persay--the biking certainly helped, and left him with defined muscles in his thighs and calves, and he had broadish shoulders, if his arms were a little squishy. He was strong enough to those huge bags of flour here and there at work and that was good enough for him.

All things considered, it should round out to a safe walk. And, as time would prove, it was! After the third round, his nerves steadied, and he began to enjoy it--the sounds of the nightlife around him, the clear night air, and-- most wonderfully--the last alley before his apartment.

Between a dive bar and a building of indeterminate use, there was an alley filled with broken glass. Not large shards; whatever happened here, it happened a long time ago, and all the glass had become powder since. What little streetlight made it through the alley caught the glass as though it were crushed diamonds, leaving a spectacular road of starlight.

Jem's lucky streak would break in that alley.

Jem was exhausted. Well and truly. This is was why he hated night shifts. Drunk assholes and noise everywhere and endless work with no room for breaks-- the food industry was unforgiving. He clocked out as quickly as soon as his cutwork was done and ducked out the door before anyone could ask if he had time for one last little favor. He did not have time, thank you very much! He had a cat to feed and Netflix to watch.

Jem was too tired to even feel afraid tonight. He went through the route on sore feet, fumbling with his apron ties. They were tangled and wouldn't come undone.

He swore and stopped, violently wrenching at one end. The string snapped. He swore again, and yanked it off, balled it up and threw it behind him in a rare display of temper.

Jem sighed. "No, you need that, dumbass," he muttered, and turned.

He realized he was in the alley of broken glass. Jem looked at the glittering asphalt under him, and felt his anger cooling.

"Lovely evening, isn't it?" he told the pavement. He meant it genuinely. The air was cool and dry, and soothed his sweaty... everywhere.

Calmed, he went to retrieve his apron. It had just fallen against one side of the alley, next to a pile of cardboard boxes. As he grabbed it, he heard some sort of sound, something wet. He stepped back warily, squinting at the boxes. They were soggy. It had rained earlier, hadn't it?

Water seeped from them, hitting the edges of his shoes. It must have rained.

As he stared, a sound caught his ears--something wet, moving. He cautiously approached. Most of the boxes were broken and stacked up inside of each other, but a large box near the front was open. He heard another sound, slightly louder, and-- he heard this small, barely there mewl.

He inhaled sharply and opened the box, expecting to see waterlogged kittens or puppies or something equally heartbreaking.

It was too dark inside to make out what it was, but he saw slight movement. That mewling sound, again, louder. Jem dug around in his pocket for his phone. He turned on the flashlight, and peered in.

The nest of tentacles froze.

Jem froze.

They stared at each other for a moment.

Jem reeled back at the same time a tentacle whipped out of the box and wrapped around his wrist. It wasn't strong enough to pull him back so Jem kept backpedaling, hyperventilating--should he scream? He should probably scream--but it wound up his wrist as he pulled it out, almost like spaghetti.

There was a moment of resistance, when it had pulled as far as it could, and he was yanked at it. It was held to whatever else was in the box, like it was an appendage to an organism, and it just kept winding up his arm. It was just strong enough to fight him as they played a bizarre game of tug-of-war.

He'd dropped his phone like an idiot; it had clattered to the ground, flashlight vaguely illuminating the area.

Two more tentacles rose from the box, swaying like serpents. One swayed forward slowly, almost hypnotically. The other wrapped around his wrist and yanked.

"That's cheating," Jem accused, heels skidding on the asphalt as it pulled him closer. The first tentacle was wrapped up to his shoulder by now, strange, undulating pressure against his shirt. "That's two on one, c'mon, guys--"

He heard voices outside the alley. Cheerful, yelling voice. People coming home from the bars!

He began to scream for help, and the third tentacle shoved into his mouth.

Jem was stunned, attention ripped back to the tentacles. Was this karmic retribution for watching hentai as a teenager?

He crossed his eyes down at the thing in his mouth--at its deep violet, shimmering skin, how it was about as thick as a cucumber and his mouth stretched around it--and the way it felt, sitting heavy on his tongue, heavy and warm and with a pulse.

And wet. So, so, so, wet! It was almost as though it were salivating, and it filled his mouth with that moisture, forcing him to swallow, rapidly. He tried to scream, anyway; muffled, pointless, pathetic.

It didn't move itself; the tentacles on his arm pulled him in closer, the second one abandoning his wrist to wrap loosely around his waist. Not tugging, more like gentle nudging. The movement brought it slowly further into his mouth.

Jem shook his head, making a base, animal sound of panic in the back of his throat and tried to wrench back--he knocked off the tentacle around his waist--the tentacle in his mouth suddenly thrust further, knocking against the back of his throat. Jem gagged. That moisture was filling his mouth, god, he felt like he was going to drown--

Distantly, he noted that it had a pleasant, light taste. Like pineapple.

It spilled out around the corners and dripped down his chin. The sound of his choking was absolutely disgusting. He swallowed desperately.

The tentacle in his mouth vibrated, like a growl, and shifted somehow. Hot, thick liquid started to drip down his throat. Jem groaned helplessly.

The thick liquid dripped into his stomach. It reminded him-- the memory seemed absurd in this context-- of drinking hot chocolate after coming in from the snow as a kid, and the way it was so hot he could feel it down his throat to his stomach.

That was what it felt like now; hot cupcake batter, sliding down his esophagus. It lit up his stomach, and something strange happened.

His arms went lax, and the tentacle wound sweetly around his waist again, like the arm of a lover. The tentacle around his arm undulated comfortingly, and the tentacle in his mouth shifted, keeping up the trickle of liquid. It vibrated again, but more like a purr. Jem... whined.

He didn't feel his feet moving as the tentacles guided him back to the box. He was only thinking about that heat in his belly, about how it was beginning to warm up the rest of him. The tentacle around his arm retreated. He reached after it on instinct.

That startled him half out of his trance. He should be running! He jerked back, and the tentacle returned in a flash, but this time, it slipped up his sleeve, wrapping around his bare skin like a boa. He shuddered and flinched away from that awful, slimy sensation, from the painful pressure. It was like the worlds wettest blood-pressure machine.

Fear beat its way back through the haze. The tentacle on his arm squeezed and Jem yelped. It was producing that moisture, too, steadily coating his arm like grease. He could smell it. Yeah, it was like pineapples!

HIs skin tingled where the moisture touched, and Jem's pulse started to calm, again. The tentacle in his mouth shifted further forward, down his throat, and he gagged, but it didn't stop, just nestled further. The pain faded from his arm, like the tentacle's mucus was numbing it. Or, not numbing it. He could still feel. God, he could feel more, like his nerve endings were on fire, and every movement of the tentacles sent sparks flying to his gut.

The heat from his belly had filled his body. He was overheating. He realized he was right against the box, now, leaning over it. He stared into it, at the nest of tentacles that were moving, now, slithering over each other like snakes. The tentacle lifted his arm and dangled it into the box.

The tentacle around his waist slipped beneath his shirt, curling around his abdomen. The cool slickness was a balm against his sudden, prickling heat. Jem moaned quietly.

The panic came back again, full force. Moaning? No, no, no, no--

His fingers curled around the nest and it purred.

His eyelashes fluttered.

Another tentacle slid forward, and slipped under his waist band. Wasting no further time, it wrapped around his cock, which he belatedly realized was fully hard and painfully sensitive. When had that happened?

Unimportant. More important was that delicious pressure.

He cried out around the tentacle, and bucked his hips. It stroked his cock slowly, the tip of the tentacle lined up agains the head of his cock. Trapped in the confines of both his boxers and black jeans, the tentacle's wetness was soaking through his pants. He realized it was dripping down from his crotch, like he was a girl. The thought shouldn't have been as hot as it was, but it sent this awful wave of arousal crashing through him. His legs went weak and he crashed to the ground, knees hitting the asphalt.

He was bent over the cardboard box now, head just inches above the mass of tentacles. The tentacles down his throat began to retreat, sliding up his throat again. Jem made a noise he didn't know he could make, and as it slipped out, he found himself chasing it. He licked his lips, panting. The tentacle had left a trail of that thick liquid on it's way back, and though he couldn't taste it before, he could now. It wasn't sweet. No, it was musky, and musty, and almost disgustingly masculine. Reminded him of visiting the gym, of the particular smell of fresh sweat, before it went stale and gross. Or, no, it reminded him of gravy, perhaps, of something thick and savory to be enjoyed--he did just that; working it over his tongue and swallowing slowly.

He leaned in and licked at the tentacles. They purred and sweetly caressed his cheeks and head.

The tip of the tentacle by his cock opened like a flower, and closed around the head and his cock. Jem inhaled sharply. It gave a firm, upward twist around his cock and sucked and Jem came immediately, crying out into the tentacle and grinding his hips against nothing.

The tentacle fucking milked his come--clamped around his head, it swallowed every drop. The tentacles shuddered, and sprang to strength.

The cardboard box was shredded as they exploded outward, twisting up like a flower of tentacles. Jem shouted in shock as he was yanked into the air, the tentacle around his waist suddenly strong and firm. The tentacle around his arm leapt forward and grabbed his other wrist, binding them together above his head. Two new tentacles grabbed his ankles and held them out-- they worked together, twisted him into a pose they liked; held aloft, knees half bent and spread, spine arched out and ass in the air, wrists crossed over his head.

He felt ridiculous.

He held there, bound and panting, staring at the light of his phone. Guess it was still going. He stared down at the broken glass, and found that, really, they looked like the night sky. Like he was being held by this otherworldly creature, octopus or flower or none of the above, in a sea of stars.

Jem smiled.

A tentacle bobbed in front of his face. He stared at it, and it was all smooth, slightly tapered at the end, with a little hole like a cock. The ones holding him were entirely smooth, too; below him, more were rising, and these were differently shaped; the one that retreated from his pants was thinner than the others, and had that bell shaped end that could open. Some were thin as hair, some were thick as his thigh, some were ribbed and ridged and two, curled around the base, were glistening and translucent.

Jem felt like the one staring at him must've been the one that had been recently acquainted with his uvulae. Vibes, mostly.

They looked at each other.

Jem shrugged, as much as he could, anyway. Adult life was already so goddamn weird. This might as well happen.

He licked his lips and opened his mouth.

With a happy, trilling sound, it leapt forward.

He moaned as it entered his mouth, sitting on his tongue, and shifted, releasing warm liquid into his mouth. This was thinner, and, he thought, sweeter? Like strawberry milk.

He swallowed, and the tentacle slithered forward into his throat, wiggling to get comfortable. He gagged again, then moaned.

It kept releasing that milk, straight down his esophagus.

Jem wondered if it had noticed his tasting it earlier, and had stopped to let him taste it first as a result. That would be oddly sweet. He laughed absurdly.

The milk settled sweet in his stomach, and there was a lot of it. Like, a lot of it. After just a few moments, he found himself uncomfortably full. On instinct, he tried to pull back, but he was held fast. His stomach cramped around the milk, and then he felt something truly fucking strange.

It began to drain, and he worried he'd peed himself, but there was none of that. Instead, the warmth that had flooded his body earlier intensified, and he felt like he was on fire all over. The tentacle that held his cock earlier returned, wrapping around it, and a pair of tiny, thin tentacles slipped down his waistband as well, circling his ass. Slick as they were, they poked inside, and he twitched, surprised.

He twitched in his bindings, not really to get away but just to move as they entered him. The intrusion was foreign and he wasn't sure how to feel about it.

They slowly worked in and out, adjusting themselves, and wound around each other. Another pair of thin tentacles join them, and by the time those had meshed, they'd worked his ass into a buzz of pleasure. The strange feeling has melted and became a haze of hood. They found finally hit on his prostate, and pressed up to it in delight.

Jem moaned. Loudly.


Embarrassing.

The tentacles found it encouraging. They wrapped around his chest, massaging his slowly growing breasts through his shirt.

His slowly growing breasts.

Astonished, Jem jerked back, realizing that--the heat the milk was sending through him-- it was causing him to... change. He thought back to his dripping crotch, and giggled around his tentacle, hysterical.

The tentacles wrapped around those breasts, working them like playdough. The layers of fat built on them slowly; they started at as just little handfuls, then no larger than oranges, then straining against his shirt.

God, it looked hot--the fabric tightening, barely able to contain them, the buttons pulling apart, little peeks of skin poking through. His breasts began to feel painfully constrained by his shirt, and he shifted uncomfortabley, as they just kept growing until the buttons popped, one by one, raining across the alley. The tentacles tore off the remnants of his shirt. They could've just done that earlier, he thought exasperatedly.

His breasts hung below him, a D cup by now, he thought. They were threaded through with blue veins and capped in pretty pink nipples. A tentacle wrapped around one, squeezing it and Jem moaned. It wrapped around the nipple, tweaked it, and he squealed in surprised delight.

Distracted by this, he noticed quite late that it wasn't just there he was changing. His pants were uncomfortable tight around the ass-- and though his thighs hadn't changed much, muscled as they'd already been, they filled out the rest of the jean. But layers of fat kept stacking over his ass and hips, bringing out a curve like--like he was a goddamn woman! A hot woman, yes, but--

The tentacles in his ass kept teasing his prostate and the tentacle on his dick kept milking it even as it shrunk. Jem's panic briefly returned, and he almost struggled, as it twisted his dick as it shrank, and shrank, and balls disappeared into his body. Soon his dick was just a nub-- a clit, he though distantly-- that a tiny tentacle wrapped around and twisted.

He cried out in a sharp shock of pleasure.

His pussy swelled.

The tentacles ripped away his jeans and boxers, freeing his fat ass and jiggling hips. Juice splattered from his new cunt to the pavement.

His breasts had now grown beyond normal sizes. He'd need a custom bra, he thought in wild humor.

The tentacles squeezed those breasts and suckled at his nipples, and he writhed and whined in delight.

A tentacle wounded back and slapped his ass, the fat rippling. He cried out and threw his head back. It slapped him again and he groaned, rough and so horny it hurt. His cunt fucking wept.

A tentacle was pressing against it. He ground down and back against it. It was ribbed and ridged and felt fantastic. He felt this strange empty feeling. He needed it in him. Now.

He looked down at it. It was thicker than his forearm. His eyes widened. Without further ado, it lined up, and began pressing in.

Behind him, another tentacle of similar size started to press into his sopping ass. Jem made this low sound like a wounded animal as they pushed in together. There was no escape; lean away from one, you just leaned into the other. So they moved inexorably forward, until they were pressed against his cervix and prostate. Another tentacle crept into his mouth, twining around the first, and Jem gurgled.

The tentacle in his cunt began to fuck him. Slowly, as first, every drag of it against his insides like fireworks, and then it built up speed, until it was jolting him with every move, and he was making this high "Ah! Ah!" every time it slammed in. It hig what must be a g-spot, and though it wasn't instant electric pleasure, the accuracy had this slow-building, full, intense pleasure, this coiling in his gut that he could only anticipate the climax off.

The tentacle in his ass began to move now, too, fucking him slowly but surely. He thought that one must be larger than the one in his pussy. It dragged in and out, and those smaller tentacles that had remained milked his prostate all the while.

It was too much. He orgasmed with a muffled scream, nearly blacking out from the force of it. The fluttering of his walls around their unyielding pressure only made it worse, and he came a second time on the heels of the first, wailing around the tentacles.

In a flash, like vultures, three smaller tentacles dove for his cunt and clamped around his clit and folds. They milked as much of his cum as they could. It only spurred them on-- they fucked him harder, and harder, and harder--

Two tentacles twisted into his cunt around the first. One sat against his g-spot and fucked in and out, finding it over and over, and the other entered shallowly press against his a-spot, curling in with a come-hither gesture that was going to drive him insane. A tentacle sucked at his clit like it was still a dick, and those tentacles on his tits unfurled and attacked his nipples, sucking, too. He whined and whined, feeling something strange in them, watching milk dribble down one of the tentacles. Messy eater. Was he just lactating the same milk they'd given him? Questions.