The spiritual successor of my tentacle monster series
Jared hefted his toolbox and banged on the door to Apartment 316. He'd stolen a look at the board downstairs, and the name was "Miriam". At some point, someone had taken pink pen, scratched that out, and written "Mimi" over top of it. It was a nice name, so he'd done her the favor of going downstairs with his fake telephone company ID and cutting her phone line.
One of two things could happen now. Mimi could open the door and he would tell her about the unfortunate mix up with her phone line, do some technical looking things in her apartment and then head downstairs and fix what he'd done. There was the possibility of also hitting on her a little if she was hot, and maybe lifting some small change or knick knacks while he was at it.
The other was that she wouldn't be home.
"Phone repair man!"
In which case he would help himself to some new electronics and jewelry.
After three minutes, when it was obvious that no one was home, Jared smiled to himself and dropped the toolbox onto the floor. Kneeling down he cracked it open and pulled out something that looked like a generic piece of technical equipment and which was very good at picking locks.
He scanned the hallway to be sure that no one was watching, then went about getting inside. The tool buzzed and whirred and after a moment or two the deadbolt made a 'snick-snick' noise and released. Another moment and the handle unlocked. Jared smiled to himself, stuck his tool back in his toolbox and went inside.
"Nice." He took the time to remove his shoes at the entrance and admire the apartment inside. It was fairly generic, but all over had little touches of the person who lived there. Stuffed animals dotted the available open spaces, the walls were painted a nice cheery blue, and everywhere were small mementos of the owner's travels. Jared left those alone as he wandered through the house, they were too difficult to resell and not worth the money anyway.
Next he headed to the bedroom. It was hit or miss in downtown apartments whether someone had jewelry which was worth anything or not, but he thought he should check anyway. Mimi's room was much like the hallways, with stuffed animals and knick knacks wherever they could be crammed.
No jewelry case was evident, though, so he went to the chest of drawers instead. Sometimes people kept valuables in their underwear drawer, which was (as usual) Mim's top drawer.
"Hmmm..." He grinned as he rooted through her underwear and found mostly thongs, along with one or two crotchless panties. "Dirty girl... hey, what's this?"
Buried amidst the panties was a picture which made Jared's eyes open wide. It was obviously of Mimi, she'd signed it with some lipstick, and she wasn't wearing a single thing.
"That's hot." She was looking over her shoulder back at the camera and bent over a little so that he could just see the tiniest hint of a shaved, pink pussy under the perfect curves of her ass. She was blowing a kiss at the camera with one hand and spanking herself with the other, and Jared felt immediate tension between his legs at the sight of her. "I think I'll keep this for later..."
She was hot, and he regretted a little that he couldn't just wait around and see what would happen when she came home and found him naked and masturbating to her picture on the bed. Common sense told him she would probably call the cops, so he just stuck her picture in his pocket for later.
Although he was curious about what else he'd find in the room, he didn't want to rifle with her things too much. If she had any expensive jewelry it was well hidden, and there were other, easier, things for him to grab. So he headed back out and made for the living room.
"Ah, there we are." Jackpot! Jared went back outside for a moment and grabbed the dolly he'd brought with him, then wheeled it back in to go to work.
He was on his way back inside when he peered into the kitchen and noticed something on the counter. It was the middle of the day and he very much doubted she would be home any time soon, so he parked the dolly and went to check it out. He was always interested in the little aspects of the lives of people he robbed, it kept him from thinking he was a good person, and besides, after that picture who knew what else he would find?
"What's this?" There was just a single tin can on the counter with a label he'd never seen. Picking it up and turning it around, his eyes widened in surprise.
SEX IN A CAN
"Whoah." Jared chuckled and shook his head, always surprised by what he found in people's personal space. "You really are a little slut, aren't you Mimi? Let's see..." Turning the can around, his face fell as he reached the nutrition information. "Calories? Damn, it's just some chocolate or something."
That was a disappointment. Considering what else he'd found, he'd been half-expecting a sex toy or something. He'd never taken anyone's sex toys, of course, but he'd usually learned something he hadn't known before. Not that he had to rely on toys that often. At six foot two, with muscles that he kept firm at the gym and a face that had once been described as "ruggedly handsome", he had very little trouble with women. When they found out what he did, that little extra 'bad-boy' element usually had them begging for a little Jared-action.
"Hmm... I guess I can have a little chocolate break." He laughed to himself and popped the tab on top of the can. There was a hiss of escaping air, but when he looked inside...
"What the fuck?" Nothing! "Ha... poor Mimi, you get stiffed at the store and robbed in the same day."
Laughing and shaking his head, Jared tossed the empty can back onto the counter and went over to the living room to actually get to work. The first order of business was disconnecting the tangled mass of cables Mimi had behind her TV.
"Where the hell...?"
Over the noise of his swearing and grunting as he looked for wires and sorted through what could only be considered a mess, Jared didn't even hear the sound of a can spinning against the counter top. He didn't want to accidentally break anything when he pulled the TV out, so it was crucial that he got everything disconnected before he tried to move any part of it.
He didn't hear the spinning noise, but he did notice when something warm and firm bumped tentatively up against his leg.
"Huh?" Jared twisted his head around so he could see what was there. "Green? I don't remember a green wire..." Which was true, all of the wires were either black or grey. No green.
He realized it wasn't a wire, though, when he felt it wrap around his ankle and start to drag him out from under the entertainment center.
"What the fuck?" Jared twisted around again, thrashing as he was dragged along the carpet, and managed to hit his head on a solid piece of wood shelf.
For a long moment the world spun and was focused around the shooting pain in his forehead. That moment was cut rather short when he was pulled out into the middle of the living room and found himself getting a good look at the thing which had dragged him across the floor.
"Geeze! What the Hell is that?" He kicked out with his foot to no avail, and then sat up and tried to pry it off his leg. There were two or three other, relatively thin, tentacles that ended in what looked like mouths hovering in the room and he didn't want to know what they were up to. The one wrapped around his leg was enough, thanks.
"Fucking security systems..." Jared managed to pry the thing off his leg and scrabble to his feet within a moment or two, immediately looking to the exit. When he stood up, all three tentacles focused their attention on him, and he wondered just how fast they could move.
He bolted, but they were faster. Jared managed about four steps before the first tentacle got him by the leg and gave him a vicious tug.
After which there was welcome blackness as he struck the hardwood.
Jared didn't know how long he was unconscious, but it couldn't have been more than a minute or two because he was still in the custody of only one of those crazy green... tentacle things. It was wrapped around his leg and had a firm grip on him.
"This isn't going any farther." Swaying from the recent bout with being knocked out, Jared made another grab for his ankle. One of the other tentacles came to its fellow's rescue, though, and grabbed his wrist.
He started to realize he might be in trouble when he found that he couldn't move his arm anymore, the grip that the tentacle thing had was just too strong. He was wondering how he could possibly get out of this when the tentacles dragged him back into the living room, and the third latched onto his free wrist, leaving him with only one leg that he could sort of kick with.
"So now what...?" He sort of expected to be just held there until Mimi, the crazy lady with the crazy security system, got back and called the cops. Instead a fourth tentacle came in from the kitchen, but it was different.
"Oh, you're not serious..." It was thicker and end in what was clearly supposed to resemble the head of a cock. It glistened wetly, and was accompanied by two of the smaller tentacles. "This isn't fucking anime!"
Despite Jared's disbelief, the two new, small tentacles went immediately for his jeans. He had a moment to be impressed by how well managed his button and fly before he was sitting in the living room with his pants around his ankles.
"Get the fuck away from me!" He tried to kick at the tentacles but couldn't get a clear shot. Instead, his boxers ended up around his ankles too, exposing Little Jared to the air. "Stop that!"
While none of this made any sense, he wasn't prepared for one of the smaller tentacles to come forward and start to... nuzzle him. He blinked in surprise as the warm, almost pliant tentacle tentatively caressed him. It started by running along the soft length of his cock, then made little circles on his balls, sending... well, sending little ripples of pleasure through his body.
"What the Hell?"
Then the mouth on the end of the tentacle opened and started to suck on his balls. Despite the strange situation, it actually felt really good, and Jared felt himself swelling in response to the stimulation. A little tongue inside of the tentacle's 'mouth' teased his balls while it sucked on them, bringing pleasure without being too rough. Jared actually found himself groaning in pleasure and his cock stiffening almost of its own accord.
When another tentacle opened up and slid itself down onto his cock, Jared shuddered in ecstasy. The sensation was similar to feeling himself inside a tight, warm pussy, except this one contracted and swelled around him like it was trying to milk him. That, combined with the stimulation of his balls, made him forget about the situation entirely and just enjoy the sensations.
He protested a little when the tentacles lifted him off the ground, but it wasn't until he felt the thicker, wetter tentacle pressing up against his ass that he started to protest again.
"Oh, Hell no!"
The thing didn't pay any attention to him, though, and he felt the warm head of it press insistently up against his asshole. It felt slick and actually kind of good, but he really didn't like the idea of where it was going. Still, the way it was... sucking on his dick made it hard for him to concentrate on any one thing.
The tentacles spent another few moments pleasuring him, working on his cock like they were an expert, and then he felt what he'd been worried about. The thicker tentacle pressed hard up against his sphincter, and in the midst of all this pleasure he felt himself opening a little in response. Then the thing slid inside, causing him to shout in mingled pain and ecstasy.
The feeling of it sliding into him, filling his ass with its warm bulk, was a questionable one until it bumped up against the little knot of nerves that was his prostate and sent a new, strange wave of pleasure through him. He'd never felt something quite like that, but it was incredible.
So incredible that he couldn't stop the orgasm that almost immediately followed. It was swift and thunderous, overtaking his body in one fell swoop and then pumping his hot cum into the tentacle that was clamped onto his cock. He blinked in surprise when the tentacle detached, shaking itself a little very much like someone faced with a bad taste, but then another one took its place.
Although he normally wasn't one to become hard immediately after an orgasm, the combined sensations of having his balls sucked, his ass slowly fucked and his cock teased again caused him to stir and rise almost before he'd become completely soft.
"Hey, take it easy there..."
Still not listening to him, the new tentacle engulfed his cock and started to work on it again, rippling along the entire length and filling him with a kind of ecstatic tension which begged to be released.
He wasn't prepared when another of the thick tentacles came at his mouth, and he gasped in surprise. He didn't have time to close his mouth before the thing came inside, and he found himself with the thick, warm and slightly... sweet thing filling his mouth. He swallowed convulsively, then blinked at the surprising tastiness of whatever this was. Eagerly he starts to lick at the tentacle's shaft and work his lips, trying to get as much of the tasty goo as possible.
It seemed like he was there forever, with one of the tentacles filling his ass, the other deep in his mouth, and two others massaging his cock and balls. It was probably only another few minutes, though, when he felt himself thrusting in time with the rhythm of the thing in his ass. He could feel his orgasm coming, and bucking his hips against the tentacle on his cock made it feel so good.
"Mmmhp blmpph!" He cried out around the thick mass of tentacle-flesh in his mouth as he reached his second orgasm, his entire body convulsing from the force of it. His legs trembles, his back arched violently, and he really got into the sensation of pumping his hot cum into the tentacle.
The thing's orgasm wasn't far behind, either. It was preceded by the strange feeling of the two thicker tentacles swelling inside him, filling him up even more and becoming almost uncomfortable, and then he gasped as he felt thick, hot wads of tentacle cum shooting inside him. It was a weird feeling in his ass, but he found himself gulping at it as it streamed inside his mouth, trying to taste and enjoy as much of it as possible.
After the tentacles shot their load into him, they started to retract one by one until he was lying on the ground, tentacle goo leaking out of his ass and his pants still down around his ankles.
"What the fuck was that?"
After he came to his senses, which took a while since he was in a kind of daze after those two amazing orgasms, he leaped to his feet and started to fumble with getting his pants and boxers back on.
"Fuck, I gotta get out of here!" He didn't know how he felt about how much he'd liked the whole experience, but he knew for sure that he had to leave. Now. Whatever that thing was, it had taken up a lot of his time... and besides, he didn't want to fuck with a woman who kept that on her counter.
He was only halfway through buttoning up his pants when he bolted into the hallway with his toolbox and dolly, and hadn't fully done himself up until he reached the elevator and was hammering on the 'down' button.