Cuffed by the TaskMaster

By Padlocked Slave

I never set out to be a long-distance captive doing humiliation tasks for a strict disciplinarian. For a whole fucking weekend no less. It just sort of happened all of a sudden. And like getting stuck in quicksand, I found after a very short while that I could not escape.

It all started in a rather unexpected way. You see, my big fetish is locking metal bondage — handcuffs especially. But anything that locks really. I’ve spent many weekend hours looking at tumblr feeds and flickr accounts featuring handcuffs and prisoners, often fantasizing of being locked inescapably in a particular set of bracelets. Along the way I joined the CuffClub, a handcuff collectors online discussion group, which is where I first encountered the guy. The site was mostly collectors and law enforcement types. But some kinky people were on there as well.

This guy had posted some pictures of a set of high-security cuffs that were unlike any I had ever seen. They had this special locking mechanism with what looked like a unique key. Sort of like a house key, but for handcuffs. I just had to message the guy about them, and he chatted me up. We seemed to hit it off, and after a while I could not believe my luck when he agreed to ship the cuffs to me so that I could try them on.

But there was a catch.

He said that I would have to lock the cuffs on via webcam while he watched. I thought it was an odd request but hey, his cuffs his rules. He said something like, “sure buddy I will be glad to let you try on my cuffs — but I will keep you busy in them, too.”

I was excited to try on his unique pair of cuffs, and I really didn’t think too much about that comment at the time. I should have. Maybe subconsciously I was turned on somehow. I was also intrigued a bit by his screen name (TaskMaster) but I did not think too much about it before sending the guy my full name and home address. He said I would receive the cuffs this coming Friday and to keep my whole weekend free. What am I getting myself into, I thought. But I did not have any plans that weekend anyway, just some leisure reading and probably wasting too much time online.

He told me to add him on skype, which I did, and he told me I would receive the cuffs via FedEx before the end of the day Friday and that I should meet him online at 9 p.m. local time. That Thursday after work I did not see him online so I poked around on some other sites. For the heck of it, I went over to FetishWorld, where I have a profile but don’t do much there, and I typed in his name. And that’s when I realized that I might have bitten off a bit more than I can chew with this guy. Turns out his screen name matches what he is into — namely giving others tasks to perform! For his amusement. Oh fuck. And not just any ordinary tasks, but time-wasting tasks, humiliating tasks of all sorts. Some involving bets and dares, or games of chance. There were pictures and stories from many of his followers. This was a guy with a huge online following, well known in this particular fetish, which I did not know much about until now.

I thought of messaging him right away to back out of the whole deal, but after entering in the tracking number for the shipment he had given me, it said the package was “out for delivery” and I figured it was too late. Then late that night before I went to bed I saw him log on to CuffClub, and I messaged him there.

“Hey fella,” he wrote, “ready to get cuffed by the TaskMaster?”

I was nervous as hell having discovered his kink side and I told him so, and confessed that I had looked him up on FetishWorld and had some idea of what I might be up for. He told me that I was wise to be scared but that I did not have anything to fear really because all I had to do was follow his instructions and that everything would turn out OK for me. He was friendly and laughing a bit at my uncomfortable-ness. Also he said that I could still back out, by refusing the delivery, and he would get the cuffs back with no hard feelings but then I would lose out on my chance to wear those cuffs. If I accepted delivery, though, I was agreeing to his terms. He told me I was not allowed to open the package until told to do so on cam the next night.

So, with my head spinning in excitement and confusion I agreed to play along with his game. He made me write it out, that I was agreeing to follow instructions as ordered. (I figured if things got too out of hand, I could unlock the cuffs at any time and ship them back to him. He would probably get mad, but I would have my weekend back.)

That night I could not sleep very well, but the next day (Friday) I managed to get home from work a bit early. The package arrived, and it was heavier than I was expecting. I set it aside and had an early dinner, took a shower and turned off the ringer on my phone so that at the appointed time I would be ready.

I logged on promptly at 9 p.m. to the CuffClub site and he asked again if I was ready. He made me repeat our understanding again, that I was agreeing to follow his instructions and that I was doing this willingly and that I agreed to abide by the consequences. I was really nervous, yet excited.

He had me log on to skype and open up a one-way video chat. He could see and hear me, but I could not see him. He had me open the box on cam and I took out the cuffs — an amazing pair of high-security specialty cuffs with an intricate lock. But there were no keys I the box! Instead, there was a small key safe box with a four-digit combination code. The kind of box that realtors use when showing houses. He had me place the key safe on a shelf behind me and told me I was not allowed to touch it without his permission. And then he had me lock the cuffs on. Hands in front.

“There,” he said, “how do you like the cuffs? Are they as fun to wear as you thought they would be?” I told him (truthfully) that the cuffs were awesome and that I liked having them locked on very much. “Well, we will see how you feel about them next Friday after you have been wearing them for a whole week,” he laughed. I did not think that was funny and he could tell by the expression on my face.

“OK, prisoner,” he typed. “The rules for tonight are simple. Do what I say, when I say and how I say, and I will let you out of those cuffs. Fuck up and you stay in them.” I noticed that he was no longer calling me “buddy” or “fella” but “prisoner” now. My heart was pounding fast and I had a big knot in my stomach.

“If you are a good prisoner and follow orders, you might get those cuffs off tonight before bed,” he typed. “But if you fuck up, you stay cuffed.”

“Oh, and you might want to check your CuffClub email right away, because your first task starts in just a few minutes.” With that he terminated the video conference, and I was left, handcuffed, with the key in my possession but out of my control. Back at the CuffClub email page, I got a chill up my spine. There were seven unopened emails from him, all queued up in order with the following subject lines:

Task 1 – Open at 9:30 pm

Task 2 – Open at 10:30 pm

Task 3 – Open at 11:00 pm

Task 4 – Open at 11:30 pm

Task 5 – Open at midnight

Task 6 – Open at 1 am

Open at 2 am

And I knew immediately that I was in for a long night and that whatever he was going to make me do, I had to do so with handcuffs on. At exactly 9:30 p.m. on the dot, I opened his first email to find this simple message:

“Starting immediately, on skype, type my name (TaskMaster) every 10 minutes. Do not be late or miss even by one minute. I want to see an IM from you with just my name, exactly at 9:30, 9:40, 9:50, etc. Go!”

I was still on skype and typed his name as instructed just in the nick of time. Then, exactly 10 minutes later, and while looking closely at my computer clock to be absolutely sure, I typed his name again and hit the return key at 9:40 exactly. Planning ahead to the next interval, I typed his name again planning to hit return when the time came up again. But just to be safe, I opened up the clock with the second hand and waited until 15 seconds after 9:50 to hit return again. I figured the skype clock and my computer clock might not be calibrated exactly, and I did not want to accidentally have it show 9:49. Between the 9:50 send and the 10:00 I went to the bathroom to take a quick leak, but I was back at the computer to hit send at 10 seconds after the top of the hour. I wondered what was in those other emails. I typed and sent his name again at exactly 10:10 and again at 10:20 and looking at the IM chat window I noticed how precise I had been and I felt a bit of pride, but also a dose of humiliation. Here I am typing some guy’s name I never met before, while handcuffed.

After hitting send on the 10:30 message, I opened up the Task 2 email to read this message from him:

“Right now, prisoner, you are hopefully getting the hang of it. But it’s time to increase the pressure a little bit. Starting exactly five minutes from now, you are to type my name every five minutes on Skype — at 10:35, 10:40, 10:45, etc. Go!”

And so I obeyed. Every five minutes, at exactly 15 seconds after 10:35 and 10:40 and 10:45 and 10:50 and 10:55 and again at 11:00 I had typed and entered his name, and there was quite a pattern to it all. The “Task 3” email at 11 p.m. was a bit different:

“OK, prisoner, by this time you are most likely starting to feel the pressure. It’s time to give you a rest. You may go and turn on the TV and watch a program. Any program will do. For the next 30 minutes, just go watch a show on TV.”

I turned on the TV and started watching what happened to be on. (It was a show called “Tattoo Nightmares,” about people who got bad, embarrassing tattoos and who were looking to have their tattoos “covered up” by expert tattoo artists who tattooed new tattoos over the old embarrassing ones.)

Immediately after the show, I opened the “Task 4” email, exactly as instructed at 11:30 p.m.

“How was the show?” he wrote. “What did you decide to watch? Now I want you to write me a summary of the show. At least 300 words. Tell me what happened. Send it to me via return email before midnight. Go!”

So I proceeded to write my report — still wearing the handcuffs it was hard to type — about the guy with the nike swoosh tattoo on his chest which was backwards, who got them to turn it into a tattoo of a computer circuit board. And the woman who had the “born to sin” tattoo around her belly button who got it covered by a tattoo of flowers and butterflies. And there was a third guy who had a big sword tattooed vertically on his back, but the handle of the sword came up onto his neck making it look like a penis on the back of his neck with his shirt on. He got his corrected with a tattoo of a bigger sword but this one had swooshes on the handle so the neck part no longer made him look like a dork. I managed to send my 300-word “book report” on the TV show just before midnight, and just in time to read the next task.

“Starting now (exactly at midnight) and every 10 minutes, you are to type “Thank you TaskMaster for giving me tasks,” which I did every 10 minutes as instructed. I used “copy and paste” for this, but I waited until the exact moment at 12:10, 12:20, etc., before hitting the return key, figuring that would probably be OK to do it that way.

At exactly 1 a.m. I opened the next one.

“Continue to type the same message but every 15 minutes,” and while this was easier it was also harder because it was now after my normal bedtime and I was tired and trying not to fall asleep. I had been handcuffed and “chained” to my computer for more than four hours now and not really sure what to expect with the next email, whose subject line said “open at 2 am” but did not say “task” on it. Maybe this will be an email with the combination to the keysafe? And I will be able to take these cuffs off and get a good night’s sleep? Or? Maybe he is going to fuck with me more. At 2 a.m. exactly I opened the last of the emails.

“OK, prisoner, you have hopefully completed your tasks for tonight. But I will need to check your work when I come back online tomorrow morning.” He had apparently been offline all this time. Maybe at the movies? Or out to dinner with friends? Meanwhile I had been doing all this stupid typing for his amusement, to be checked later. “So you get to sleep wearing those handcuffs,” his final email of the night continued. “Get some rest, as good as you can with those cuffs locked on. Meet me on Skype again at 9 am.”

I was happy to finally have a break. And I was very much hoping that he would be pleased with my work come morning, and that he would let me out of these cuffs by then. Having not slept the night before, I managed pretty well for myself overnight Friday and after taking a bit longer than usual to get comfortable I managed to sleep soundly through the night.

I had set my alarm and was back at the computer, logged on to skype, exactly at 9 a.m. as instructed. But he was not online! At 9:05 a.m., I sent him an IM saying, “Good morning, TaskMaster, your prisoner is here.” And then I realized that was probably a stupid thing to type but it was too late so I just sat by the computer and waited. And waited. I did not turn on the TV or anything, but I did heat up some oatmeal in the microwave and ate that while sitting there. Finally at just after 11 am, he came online and messaged me: “I see you completed your tasks, but before releasing you from those cuffs I will need to check your work. Wait.”

And so I waited for what seemed like eternity but was only about 10 minutes. He wrote back: “Excellent job, prisoner. Much better than I expected. Your report on the TV show was excellent, it felt like I was right there!”

My heart raced and I was so glad that I had performed well. I could just taste the freedom from the cuffs, which was surely imminent, having done as instructed by this strict TaskMaster. After all, he had agreed to release me if I followed his instructions. I was eager to go take a shower and check my mail and go out to lunch.

What happened next, though, made my heart sink.

“But…” his next IM said.

I waited.

“You were five minutes late this morning, and I therefore must punish you.”

Reading this filled me with frustration, fear and dread.

“Stand by for further instructions.”

I tried to explain that I actually was online exactly at 9 a.m. as ordered expecting to meet him, but that I had IM’ed him at 9:05 seeing he was not online yet. He said he believed me, and that it was just too unfortunate anyway and I was really in no position to argue and that it was really best to accept my fate, and that I should thank him and stop complaining.

I thanked him.

About an hour later, he told me to go back to CuffClub, and check my email. More tasks. Seven more! But these were just numbered and not time stamped. The instructions were beyond anything I had contemplated. In the first task, he had me go back into the 300-word report, and count all the times I used the letters e, f and k. In the next I had to count the number of periods and commas. Then I had to go back in and highlight all the e’s in yellow, the f’s in blue and the k’s in red. There were more of these tasks that were even more tedious and it took me until after 5 p.m. Finally, I got to the last task, which was simple yet deadly:

“At exactly 3 a.m., you are to send me an IM on skype saying, “Thank you TaskMaster for letting me try on your cuffs.”

So after dinner with the cuffs still locked on (cold cereal out of a bowl) I went to bed early, setting my alarm for 2:45 a.m. so I could thank the guy for letting me try on his cuffs. He hadn’t given me instructions for Sunday morning, so I got up exactly at 9 am again and IM’ed him exactly at 9 am on he dot this time.

“Good morning, TaskMaster, your prisoner is here.” And finally just before noon he came on and this time, he emailed me the code. I had spent all of Friday night and all day Saturday cuffed and controlled and was finally free again on Sunday afternoon. I took a much-needed shower and went to the diner for some food and then for a walk. It felt weird to be outside. I felt that everybody was staring at me.

 

Metal would like to thank the author, Padlocked Slave, for this story!

 

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