Itachi looked coolly at his leader once he was finished with his explanation of Kisame's unfortunately timed illness. Leader looked at him silently a moment, twirling his pen in his hand as he leaned back into his chair. Then he said, "This will not hamper you in any way. This is an easy mission; you are more than capable to do this one on your own." Itachi nodded silently and went to pack his things.
Itachi paused, stopping completely. He could just barely see something in the distance through the heavy mist that he knew had to be the tiny town where his mission was. He slipped behind a tree, changing quickly out of his Akatsuki garb to put on a deep blue shirt and black slacks, each embroidered with a small blue flower to signal him as being from the Aoihana, the false name that Akatsuki worked under when doing acts of good for money. He tucked his clothes safely into a nook in the tree roots to hide them, made a quick kunai mark on the trunk to be able to find it again later, and set back off towards the little town.
The moment he stepped within the gate, he could see that this place was in shambles. The little ramshackle huts were falling apart, pathetic scraps of cloth serving as doors. In the heavy mist, it looked like a ghost town. Except, of course, for the one jolly fat man jiggling up to Itachi with a dainty handkerchief clutched in his large hand. "Oh, oh!" he blubbered with a strange, nervous smile, "Hello, you must be from the Aoihana!" Itachi only nodded. "Oh, hello, hello! I'm the mayor here. I'm afraid there aren't many people here- the thing in the tunnels scares them off, you know-"
"Sir," Itachi interrupted him, "could you please lead me to these tunnels?" he wanted to get this over with and go back home. The mayor jolted, but nodded vigorously, wiping his forehead with his hanky.
"Of course, of course!" he said. "This way, please." Itachi followed him around, making his way through the broken down town, following the man as he skittered and darted nervously around in annoying ways. Itachi could tell that he wanted to speak, but kept up his cold, forbidding aura. This man annoyed him, and he enjoyed his suffering.
Abruptly, his guide stopped a few yards away from a shack that appeared to have had all of its surrounding partners torn down, as if no one wanted to be near it. Fools. "I-I…I can't go any farther," the coward mayor said, glancing at Itachi. "Can- can you go on without me?" Itachi deigned not give that an answer, just turning and walking forward, closer to that odd-looking, leaning and patchy building. He walked in and closed the door behind him, hoping darkly that the mayor would feel bad for letting a teenage boy who looked like a girl who looked like she couldn't defend herself walk in on some 'monster' all alone.
Inside the hut, there was what looked like a hole. As Itachi looked closer, it was a staircase down into the tunnels, and it reminded him of an entrance to a subway. He waited a moment to allow his eyes to adjust to the darkness before delving into the tunnels, scoffing at people's idiocy. The most likely reason that people were disappearing underground was something far more benign than a supernatural being. It was probably something absolutely stupid, like colorless, odorless gas or hidden potholes that went too far down or a simple lack of air. And then, the foolish people left alive made up some crazy story to explain it. Idiots. Itachi went farther down into the tunnels.
It was even darker down there than it had appeared from above. Itachi forged ahead, keeping his eyes out for fissures in the walls that gas could leak through. His footsteps echoed oddly in the caverns around him, bouncing off the concrete, and he subconsciously flicked on his sharingan. He flicked it off again when his eyes burned. He'd needed to get more soothing balm from Madara for a while now and simply hadn't; he could still use the sharingan, but he tried to do so minimally. And there wasn't anything down here that could hurt him anyway.
He felt something tangle around his foot, and looked down, expecting to see a weed. Instead, it was a strange thing that looked like a large worm with an exoskeleton. He raised his eyebrow, bending down to untangle himself, and heard a forbidding rustling all around him. his head snapped up, sharingan blaring despite the pain, but already his wrists and ankles had been yanked up by the odd worm-things that blended into the shadows on every side. He was suspended, spread-eagled and perpendicular to the ground. His eyes widened. How had they moved so fast?
He felt one cold tentacle slip up his shirt, winding sensually over his nipples and making him shiver. What? What the-…? Suddenly, a dozen of the chords on either side opened up their heads and clamped onto his shirt, tearing it to shreds. The scraps of cloth fell to the floor. Itachi gasped at the sudden cold; what were they doing to him?! They came back again, showing him their dozens of tiny, wriggling anemone-like tongues inside their heads. He tried to squirm away as those tongues touched themselves to various parts of his torso and back, wiggling against his skin. Several took to teasing his hardened pink nipples, and he tried to buck out of their grasp as he was assaulted with pleasure that he didn't want. Against his will, he felt h8imself hardening, and cursed it.
He shrieked loudly in surprise as one tentacle slipped into his pants, its smooth, hard body stimulating his hard-on. He tried desperately to thrash away, but it only made more friction. He jerked hard on his living restrains, but they didn't give; and that thing kept scraping torturously against his need in ways he didn't want. He knew what was going on now. Then, without warning, his pants were around his ankles, then gone. How did that happen?! Itachi hissed when he felt the cold underground air hit his erection, and saw his boxers inside his pants on the ground.
He gasped and started struggling anew as he felt many tongues against many places on his cock and balls. No! no, he didn't want this pleasure! He didn't want the feeling of all those tongues against his vein and head, licking up the precum he didn't want to be leaking! But the harder he fought, the harder they held him, and the harder he became. This wasn't fair! Itachi sent his burning red gaze around, looking for the origin of these things, hoping for eyes to catch in the Tsukiyomi, but he saw nothing.
Something poked against his entrance, virginal and pure, and Itachi screamed at the top of his lungs, "NO!" but it was too late. The thing entered him painfully, ripping him, making him scream in pain. He felt a trickle of blood leak out, and it burned. He screwed his eyes shut, trying to squeeze the thing out of him, but it only brought a stab of shooting pain. It hurt. It hurt so bad, and still everything was teasing him. His mind was caught between the pleasure and pain, and that only made it so much worse.
And they plundered him, moving roughly into his deflowered ass and over his cock, scraping his raw wherever they went. After a particularly hard thrust, he cried out loudly and one of the tentacles took the opportunity to shove itself down his throat. He choked on it, trying to cough around it as it pummeled into him. He felt a ridiculous spike of pleasure in his ass, and involuntarily jerked into it. He felt warm tears prick his eyes, and for the first time in so long he let himself cry. He sobbed roughly, feeling the tears course over his cheeks in searing trails.
And he cried and cried and cried, the pain fogging his mind as he, for the first time, cried solely for himself. He cried for his own pain and suffering, for the blood coming out of his abused h0ole as he was roughly pounded, for his throat aching around the intrusion, for the coil that was continually tightening in his stomach. He didn't want it to be, but it was. There just wasn't any way for him to stop his traitor body. He felt the flash of pleasure again, and blew that frothy white liquid everywhere.
At the same time, every tentacle opened its head and spewed that same liquid all over Itachi's body. He choked on it, trying to spit it out, but he was forced to swallow thickly or stop breathing. It stung him as it entered his hole, leaking out in salty rivulets. It hurt, but he felt the restraints loosen and saw his opening.
He twisted harshly, ignoring the shooting pain, and activated his Mangekyo. There was the sensation of having a white-hot poker shoved through his eyes to the back of his skull as he blew out scorching black flames that would never stop burning, catching quickly to the tentacles. There was a satisfying roar of pain, and Itachi turned and ran. By the time he made it to the staircase, he was sure that they were either dead or in eternal pain.
He almost crawled up the stairs, his sharingan dropping away. Every movement brought pain from his sore backside, and made Itachi remember that he was covered in cunt. It smelled. He imagined the look of the mayor's face when he heard about this…
Then he crawled up against the wall and slipped into sleep.