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The bar was dead that night. Jeremy looked around the at the empty chairs arranged in the smoky back booths, seeing the only other people making out just in sight, not bothering to hide with the lack of people. Jeremy rolled his eyes and turned back to the bartender, Tiffany. The woman raised an eyebrow at him, and held up one finger. Once she had given him his last drink, he paid and took his time, sipping the whiskey as he just stared at the wood grain of the table top.
Tiffany leaned over next to him, her phone in her hand. "You look like shit."
Jeremy snorted. "Thanks for that," he said, taking another sip. He cleared his throat of the burn before he continued. "I was just hoping to see someone today. Maybe get lucky."
Tiffany chuckled, tapping lightly at the screen. "Why don't you do on Grindr like everyone else?"
Jeremy shrugged. "It just feels cheap, ya know. Plus just because they're gay doesn't mean they're into, ya know, me."
"Well," Tiffany drawled out. "If you're looking for a good time I know a place."
Jeremy gave her a hard look. "If there is one rule of a bar, it's to never fuck the bartender, Tif."
She only laughed harder. "No, no, idiot. That would be a disaster waiting to happen." She put her phone down and looked at him with a serious gaze. "I've got.... something that will give you all the good feelings you could ask for. I know for sure you would like it, kinky bastard like you."
Jeremy balked at the description, his eyes darting around in case there was anyone within hearing distance. "Say that louder, why don't ya?" he sniped. "I don't want your used dildos."
"Ew gross," she said. "No, hear me out. I got this weird underwear off this site, and... let's just say it's got some surprise features." She turned her phone over so he could look at the screen. It was on a website for a store not three blocks down the street. There were pictures scrolling through different types of underwear. All with lace and see through crotches. "I know this sounds weird, but I literally can't do it justice, you'll just have to see it for yourself."
"Tif, you sound crazy. You married to the underwear?"
"I'll give you the money to pay for them, and if you don't like it you can keep it, pay me back if you do."
Well, that was an interesting wager. Jeremy took a moment to think about it. "All right, sure. If you've got 50 bucks to just toss around, why should I stop you."
******
The underwear that came a few days later were not the ones that he had been thinking of. When he had ordered them in front of Tiffany, he had hidden the screen when it had asked for a selection, and he was relieved to see that they were the bright blue ones that he had chosen, close fitting and revealing, barely enough material to cover his crack. What could he say? He liked the look.
The box they came in was needlessly big. He looked at the instructions which seemed to be a bunch of ways to not wash them, but also had instructions like 'Don't leave in direct sunlight' and 'make sure they have room to breathe when not in use.' Jeremy wasn't a big fashionista, so maybe those weren't weird things to put on a tag, but to have them as an instruction book? A little weird.
Jeremy was skeptical by this point, but he was determined to see this through, if only for the absolute tirade he would give Tiffany when this didn't live up to her promises. He made sure all the doors were locked and the lights in his apartment were off except for the ones in his bedroom, he even got a glass of water and a midnight snack, just in case. He left the curtains open, because no one would be able to see in, and he liked looking at the night sky. He slid the panties on, expecting something to happen at any moment, but other than the nice feeling of lace on his balls, nothing happened.
He admired himself in the mirror on his dresser for a few moments, idly playing around with his balls and loving the way it gripped him. After a while though, it got boring, so he went over to the bed and sighed, picking up his laptop from under the bed frame. Once it had booted up he clicked around on some porn sites, determined to at least have one normal jerk off session before hitting the hay.
He was halfway through one of his classics when he felt something... moving. He pressed the spacebar and moved the computer off his lap. The underwear was still where it should be, but Jeremy was looking closely at it, and it seemed to be tighter than it was before. The whole outline of his cock was detailed into the fabric, and it seemed to be twitching on its own. He reached out to try and pull it away, only to find that it was stuck to him. A shiver of fear lanced through him and he frantically tugged at all angles to get the panties off, to no avail. It didn't hurt exactly, but this wasn't normal and he didn't know what was going on. The only thing it seemed to succeed on was making them cling tighter, the fabric over his ass digging into his crack. And something was... sucking on him? He tried to twist to see what was going on, but before he could, he felt a cold something poking at his lower back. Jeremy would have screamed if he had any breath at that point. It slithered up his spine as he tried desperately to grab hold of it.
When he finally wrapped his hand around it, he couldn't figure out what he was holding. It was squishy, and the coldness was what he had mistaken for slime. It wrapped around his hand, and as he tried to pull away, it trapped his wrist in an iron embrace. Jeremy flipped onto his stomach, pushing against the mattress in a mad attempt at getting leverage. Two more slimy things poked at his ass, somehow under the fabric, and now they were getting soaked. He wouldn't even be able to get a refund for these.
The things were now wiggling around in the front of the underwear. He could see it happening as he looked down the length of his body, the lace moving. Two small, fleshy looking... tentacles? Jeremy didn't want to call them that, this wasn't a hentai after all, but what else could they be? He watched as one of them emerged from the underwear, feeling along his stomach, pausing on places where the muscles jumped under the skin. The little guys seemed to have a goal in mind, and along the way they were finding all of his sweet spots. The one behind him was still going up his back while keeping his arm pinned securely, making Jeremy have some very confusing sensations going on, in both his mind and his body. They still weren't hurting him, but this was so weird. His cock, for better or worse, didn't seem to have his own hangups, slowly coming to attention as the tentacles moved on to his chest. His arm was getting tired, but he couldn't roll over at the risk of hurting the other. He lowered himself gently onto his side, freeing his hand, but there was nothing to do with it.
More tentacles were making their presence known, some joining the ones behind him, some staying inside the confines of the underwear to poke and prod at his cock. He could see them through the sheer fabric, wrapping around his cock and squeezing at it, making Jeremy see stars at regular intervals. It was hard to remember why he needed to get out of this, and as the tentacles started swirling around his nipples, he forgot entirely. The tentacles seemed to recognize that he had relaxed, and let his arm go. Jeremy instantly clutched at the sheets under him, biting his lip to keep the sounds he was making at bay. He didn't know how to handle all of these sensations, it was like having five hands touching him all at once, and in all the right places.
The slick in the underwear was soaking into his crack. The newest development was that there were more tentacles poking at his crack, sliding down and focusing on his hole. He didn't know if he should fight it or help them, they didn't seem to care if they were under his weight or not, so he twisted and turned as he pleased, writhing as they breached him. They all seemed to be connected, working in tandem with each other. As the ones in the fabric pushed further into his ass, the ones attached to his front creeped up around his neck and up toward his face. Just as the other ones thrust in, the ones by his lips pushed into his mouth. Jeremy didn't even think to bite. They tasted sweet, and the more he licked them, the more slime they produced. Jeremy had no idea why they wanted to do this, but fuck if he was going to stop them.
He got lost in the motions, his body moving with their rhythm, pushing his ass back into its thrusts and sucking down the two that were determined to get down his throat. They were so small that Jeremy didn't gag on them, and the smooth texture just made him want to twirl his tongue swiveled them as they wiggled around. The talented tentacles were also diligent in their exploration, easily finding his prostate once they were deep enough and relentlessly teased the area, making him see stars and moan around his mouthful.
He got so distracted by the pleasant sensations that he wasn't aware of their growing size until it was too late. The tentacles became huge, as big as a cock and just kept going, like they were going to burst with something. He then felt the pace pick up, the tentacles in his face and ass somehow pulled all the way back before slamming into him again, over and over shaking him to his core. He tried to brace himself on the mattress, but more tentacles sprung out to tangle around his arms, holding him flush against the sheets. He got the hint that he should hold still. The exuberance of the tentacles seemed to be fueling his own lust, spurring him on. He could barely move his hips fast enough, moaning so loudly that he was sure his neighbors would call in a noise complaint. His muscles were so tense, so covered in slick that he felt at any moment he would just melt, or snap into a thousand pieces, something. He had no idea what was on the other side, but he was climbing higher and higher.
He swore that he felt something suck on his neck, and that was the final straw, he practically vibrated with his orgasm. The tentacles didn't stop moving, almost mechanical in their dedication, not easing up even when his dick was completely soft. It still felt like he was coming, his body occasionally shuddering as his mind struggled to catch up.
His prostate became oversensitive, and he whined in pain. The tentacles seemed to understand this at least, and stilled. He felt the ones in his mouth stroke his tongue before slowly sliding out of him. He watched dazedly as they shrank back into the underwear, the fabric shifting with the movement, before disappearing altogether, the only bulge under the fabric left was his cock, wet and spent.
His bed was a mess. He was literally soaked from all the slick that they left behind, not to mention the puddle of come just next to him. He made a valiant effort to roll off the bed, but his limbs just weren't cooperating. He collapsed back onto the bed in a heap, and he convinced himself that it wasn't so bad, that he could clean up later, before he passed out.
******
He woke up with the blankets covering him.
The next day Jeremy stuffed a hundred dollars in Tiffany's tip jar.