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Paying a Ticklish Debt

Beefed up version of an older story that Tumblr took down at some point (I hate when they do that). Dude buys drugs, dude can't afford drugs, due has to find some way to pay for the drugs. Semi-willing tickle story that is SFW, provided your work is cool with a slight description of something happening in someone's underwear.

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Jay was in trouble.

Since starting college he’d become a regular on the party scene, and with the scene came all sorts of pleasures and vices that the boy had never experienced before leaving home for the first time. Growing up in a small farming town, working hard on the family farm throughout high school, he’d never had the chance to even think about partying and drugs. Now that he was in the big city he was catching up on the major gaps in his partying education. He was spending far more time at the clubs and bars than he was at the library studying, but there was always time to study later. For now, it was time to live up the life that he never knew was even possible.

The trouble began when Jay started working up a sizable debt with his dealer. The man had been happy to keep giving the farm boy drugs... up until the moment he wasn’t. His dealer warned him that he expected payment for everything he’d given the boy, and he expected a fair bit of interest on top of it. Jay had no idea how he was going to pay it all back… the money he owed was more than Jay had ever had in his bank account at any one time. Jay was smart enough to know that you don’t stiff a dealer. He told the man that he didn’t know exactly how or when he’d pay him back, but promised that he would pay it all. To his surprise, his dealer said they could work something out. This brought both relief and anxiety: relief in the sense that he wasn’t going to get his knee caps broken (did people really do that?), but anxiety over whatever this supposed pay back might look like.

The dealer invited Jay over to his home to work something out. The message Jay had been given was clear: he would arrive at the dealer’s house a boy in debt, but would walk back out a free man. Jay had an internal battle between fear and relief. Sure, heading over to some guy’s house who sells you illegal drugs doesn’t sound like the brightest thing to do, especially if you owed them a lot money, but there was also that glimmer of hope that the debt would be cleared. Jay dithered back and forth on whether he would go through with whatever the dealer had in mind, In the end hope ended up winning and Jay agreed.

Jay arrived at the house as instructed, knocked on the door, and was let in by his dealer. The house seemed normal enough, a quiet detached home in a quiet and suburban area, and the fear that he was going to be murdered and melted in a bathtub started to fade. He was led into a room on the second floor and suddenly the worries about not walking out of the house returned. Right in the centre of the room was some sort of bondage set up: there was a set of stocks at the foot of the contraption and hooks that could be used to tie someone’s hands up above their head. It looked a little home made, but sturdy

The nervous guy was ordered to strip down to just his underwear. His dealer told him this was his last chance to back out of their alternative payment arrangement, that if he wanted to talk out the door right now he could, but he’d still owe all of the money. Jay was extremely apprehensive, but secretly part of him was excited to see this set up. He wasn’t into guys, but he’d always had dark thoughts about being tied up, and it looked like he was about to get the real life experience. With shaking hands Jay pulled his shirt up over his head, and let his jeans fall to the floor. The last thing he slipped off were his white sweat socks, which he bundled up and tossed over with the rest of his clothes.

Once he was wearing only his underwear (some tight form fitting black briefs), Jay was ordered to sit down, put his ankles through the holes in the stocks, and raise his wrists above his head. Clearly his dealer had done this once or twice before, because it only took a few minutes to get Jay locked in place. He tried to move, pulling at his wrists and kicking with his feet, but wasn’t able to get anything to even budge. He was stuck in place. The nerves were there, but Jay could feel a certain thrill shudder through his body. He didn’t know what was coming, but he was starting to get excited.

He asked his dealer what would come next, but the man only smiled. He approached, taking in the full sight of the completely helpless farm boy. Without saying a word, Jay’s dealer wiggled his fingers in his exposed armpit, playing with the small tufts of hair. Jay couldn’t contain the laughter that exploded out of his mouth the moment those fingers touched his skin. It was a secret he’d held onto tightly till this very moment… Jay was deathly ticklish. Fear was now starting to overtake hope. Getting tickled for drugs wasn’t a thing, was it?

Once Jay was firmly bound and immobile, his dealer set up a camera on a tripod across the room, pointing right to where Jay was tied. The bound boy asked what the camera was for, but the dealer said to just forget it was even there. If having the camera was going to be a problem, the dealer would untie Jay right now and send him on his way… but he would still owe the money. Paying back all that he owed wasn’t happening, so Jay agreed and tried to pay no attention to the camera recording him.

His dealer moved, now standing behind Jay, and then attacked Jay’s smooth upper body with groping, tickling hands. The fingers ran up and down his sides, paying special attention to each and every single one of Jay’s ribs. Usually it was just the pads of the fingers, but every now and then Jay’s dealer would change his tactics and drag his nails from Jay’s waist all the way up to his arm pits, then back down again. Jay struggled and trashed, pulling heavily on the restraints, but nothing would budge. He was hysterical, cursing and swearing. Those hands explored and tickled every inch of his upper body, from his pits, to his sides, to even his belly button. The dealer lowered himself to a crouched position behind the boy and spent time focusing on digging his fingers into Jay’s tummy. While Jay had always been hard and muscular from working on the family farm growing up, the past several months of eating terrible food and drinking a lot had softened his stomach a bit. Ten fingers took advantage of this, wiggling and squirting into the soft flesh. Jay tried everything he could do to escape the tickling hands, from sucking in his gut to thrashing back and forth, but nothing worked. He couldn’t escape his torment.

Jay lost all sense of time as his upper body was explored, but it felt like the tickling was never ending. He begged and pleaded, swore he’d find some way, ANY WAY, to pay the money back if only his dealer would stop tickling him. The dealer, of course, never relented. After what seemed like an eternity, the torment stopped. Already having worked up a sweat, Jay, breathing heavily, slumped in the chair with his eyes closed and mouth hanging open. He was so tired already that he didn’t even notice as his dealer stepped around him and moved to his exposed bare feet.

Without warning, those squirmy and tickling fingers that had just been assaulting his pits and stomach danced up and down the farm boy’s exposed soles. Jay screamed and tried in vain to pull his feet away from the assaulting fingers, but the stocks, though a little raggedy looking, were strong enough to keep Jay in place. The sweat on his feet caused those fingers to slide effortlessly over the soles. While Jay laughed and kicked, the tips of the fingers explored his soft soles.

While Jay’s upper body had been ticklish, his feet were even worse. Working on the farm and wearing heavy boots all the time took a real toll on your feet. Because of that, Jay took very good care of his feet to keep them soft and smooth. Every night he would slather them with lotion and sleep with a pair of white cotton socks. There was nothing worse than dry, itchy, rough feet, and Jay worked his hardest to keep his feet in as good condition as possible. He didn’t think he had especially nice looking feet, no one had ever really commented on them before, but even though he wasn’t working on the farm anymore he kept up his foot care routine.

The dealer tormented both feet at once for a few minutes before he grabbed the toes of Jay’s left foot and pulled them back. For the brief moment that the tickling stopped, Jay didn’t spare a single second before he screamed and yelled for mercy. He said he was willing to offer anything, ANYTHING if this would all stop. His dealer paused for a moment, winked at the panicked boy, and said that this was exactly what he wanted.

Without a drop of mercy, Jay’s dealer raked his finger nails up and down the stretched sole, causing every never ending in Jay’s foot to go haywire. Even with his eyes shut tight and his teeth clenched, tears were leaking down Jay’s face. He thought he was experiencing the worst of it until the fingers that were tormenting him went right into the gap under his toes. Jay threw his head back and howled as fingers and nails explored the sensitive skin under and between his toes. He tried to curl his toes in defence, but his dealer’s hands were far too strong. He didn’t give up, he continued to try and fight however he could, but Jay knew in his heart there was nothing he could do until his dealer decided that he’d had enough.

As soon as Jay’s reactions started to dim a bit, his left foot getting accustomed to the treatment of those fingers, the dealer switched over to the right foot. Flexing the sole back with strong hands, he attacked the right sole with the same ferocity as he did the left. Jay didn’t even fight back this time. His body was tense as a spring, but he didn’t try to pull his foot away or curl his toes anymore. There was no point. He had to accept that this wasn’t going to be over until his dealer decided it was over. And that… was a little exciting. Terrifying. But also exciting. Jay didn’t need to look down to know his body was reacting to this situation, too. The laughing boy just hoped his dealer didn’t notice that Jay’s underwear was a little tighter than it had been when they first started.

Once his dealer was satisfied that his feet had been given a proper treatment, he moved up the legs to tickle the backs of Jay’s knees and his exposed thighs. The feeling wasn’t as bad as the tickling sensations on the soles of his feet, but when those hands were pinching and groping his thighs, it was tickling mixed with something else. When Jay let out a loud moan between peals of laughter as his dealer’s hands went further up his sensitive inner thighs, his dealer actually joined in the laughter. By this time Jay’s briefs were more than a little tight, and he prayed to God there wasn’t a little wet spot on the tip.

With no clock in the room and the windows blinds pulled shut, Jay had no idea how long he’d been in the room. All he knew was tickling, and that didn’t seem to stop. He’d lost all sense of time, and even felt like he was losing his sense of self, when the tickling finally stopped for good. Jay’s entire body went slack, and he hung there by his wrists while his legs turned to jelly in the stocks. His breath came out in ragged puffs as sweat and tears freely ran down his face.

Once he was able to catch his breath, Jay asked if his debt was now paid off. His dealer smiled at him and said this was a good start, but they weren’t done yet. That, to pay off the tab that Jay had built up, it was going to take a few days. Jay moaned and raised his head, looking at his dealer with blurry eyes. What did he mean… a few days? Like… he couldn’t leave yet? He was going to remain tied up? His dealer smiled and they were going to have a lot of fun the coming days. The dealer said that they hadn’t even gotten to the toys yet. Jay asked what he meant by that, but his dealer said that he’d find out soon enough.

Three days later, a sweaty and broken Jay left his dealer’s home. His skin tingled all over from the nonstop tickle torment of the previous days, and even walking on his sensitive and tender feet was hard. Jay vowed he would never touch drugs again as long as he lived, and he would never step foot back in that house. He was right about the drugs, he remained sober, but he would darken the doorstep of his former dealer’s house a few more times.

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