Bound By Blackmail Ch. 01

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Guy gets blackmailed after an ill-fated decision.
5.6k words
4.44
98.4k
154

Part 1 of the 27 part series

Updated 05/10/2024
Created 08/30/2022
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*Hello readers! Just a quick heads up that this story contains aspects of Forced Feminization, Sissification, BDSM, and enslavement. If that doesn't sound like something you're in to, you may want to exit back and find another story. Please let me know how you think the story is progressing. Your feedback is appreciated.

There I sat in the parking lot of a shady motel a few towns over from my own. Clenched in my hands was the envelope that had brought me there. I had made an error in judgment that I thought I'd been clever enough and careful enough to keep anyone from finding out. The fact was I was in dire need of money and with no other real options decided to borrow it from my employers. That, in itself, doesn't seem like such a bad thing. The problem was I'd decided to borrow the money while completely skipping the step of asking for permission.

At the company I worked for, I'd been hired to run the books and finances at their downtown office. It was a job I'd applied for after seeing an ad and took after a very brief and subtle interview. The salary wasn't half bad and I accepted the job immediately when it was offered to me. The position, after a short trial period, ultimately gave me exclusive access to a safe that contained a fair amount of cash; enough to make any normal person nervous.

A few months in and I'd settled in good at the job. Things were going great! Then I made a foolish decision that got me in some serious hot water. What had gotten me there, like many others, was gambling. I'd made a wager that I was sure would pay off. Ever heard a gambler say that before? After that shockingly didn't work out, I had to find means of paying my debt or suffering at the wrath of the bookie and his goons. These guys were not known to be understanding about not being able to pay. I had to come up with all the money and I had to do it fast!

My options were limited. While I did have a mortgage, getting any cold, hard cash out of it quickly was out of the question. Nothing else I owned would get me the kind of money I needed. Therefore, I got it the only other way I could think of; I took a fairly substantial amount out of the safe at work. Now, I don't consider myself a thief by any means. It is not in my nature to steal and I had every intention of returning what money I took.

Before committing to such a decision, I did sit back to reflect on consequences and repercussions that I might incur should I be found out. I knew that audits of the cash were only done by The Brothers, the company owners, and were not done regularly. Plus, I knew I was going to have a relatively large window of time before they would be back in the office due to an overseas business venture. With that knowledge, I thought I could take it, use it, then return it little by little until it was all back without anyone taking notice. At least that's what I hoped.

Someone took notice!

I received the following note a few days after taking the money. It was left in my mailbox at home. I knew it wasn't by any postal worker as there were no stamps and no return address. It had to have been placed there by the writer of it.

'Hello Evan! You've been caught with your hand in the cookie jar,'

That's how it started, which caused my heart to skip a beat.

'As you'll see by the provided memory card, I've got all the evidence I'll need to give your employers. I'm not sure if you know entirely who they are, but I can assure you they are ones not to be trifled with. To say they would be quite upset at one of their employees, who is in a most trusted position, stealing such a large amount from them would be putting it mildly. Rest assured though that your secret is safe...for now.'

That last part tied a knot in my gut. I quickly got my laptop and played the video file. Sure enough, there had been a secret camera, behind some ventilation, that was angled perfectly at the safe. There was no denying who took money from it; money that I could no longer account for.

'I know you are nowhere close to paying it back, so you've got a couple of options; you can run and hope you're never found. You could come clean and hope they take mercy on you (though I very much caution against this as it has practically a zero percent chance of working), or you will do what I instruct you to do. If you don't, then I'm afraid that this little file will find its way to those people and I really don't think you want that. So, let's just see how far you're willing to go to cover up what you've done.'

The note had an address for the motel and I was instructed to go there the next evening, Saturday, and show up at six o'clock sharp. Inside the envelope was a motel key card with a sticky note attached to it. Written on it were three numbers, '218'. The note also informed me that once inside, I'd have further instructions to follow.

I had been a nervous wreck since receiving that package. My mind was frantic with trying to figure out who would deliver me such a note. Who had access to that secret camera and why were they putting me through this? What could they possibly want from me? How did they know me or where I lived? Should I really give into this threat? Could I possibly think of some way to put the money back before the next evening? Each of those question, I struck out on. I quickly ran out of time and out of options. The only thing I could safely do was go see what this person wanted.

It kept my gut churning for those twenty-four hours all the way up to getting to that motel. Even then I felt nervous; just on the verge of puking. My mind continued to wonder who was exactly was doing this and why? Could it possibly be for money? I hadn't taken from that safe for the benefit of my health. Did they want a cut of it? I had little left after paying off my gambling debt. Surely they had to have some idea of that. So, what was going to be their plan?

At the motel room's door, I timidly knocked, thinking perhaps my blackmailer would answer. There was no sound from inside. Why else would I be given a key card, I thought. When I checked my phone, it read one minute to six. It was now or never. I slipped the card into the slot and opened the door.

The room was empty and eerily quiet. The only lights were from the small lamp on the bedside table and the TV. When I saw what was playing, it made my stomach drop. It was the video of me removing the money from the safe. The video wasn't long but continued to loop. I noticed in front of the TV was a note that was folded so that it stood up. Written on the outside was the message 'Read Me Immediately'. Shutting the door, I walked over and collected the note.

'Hello, Evan. You have taken the first step in self-preservation. Now, it's time to go further; much further! I won't tell you what all I have in store for you right away. I think you'll have more fun finding out the hard way. I have set certain tasks that I want you to do exactly as ordered. These different tasks are separated into five parts as noted on certain drawers.

Read this next part carefully!

You are not to skip ahead or rummage through any drawers. You take each task one at a time and make sure it is done fully before moving on. If you notice, I've got measures in place to keep an eye on you to make sure you're not cheating or disobeying'.

It didn't take long to figure out what the note writer had meant by that. I noticed on the wall that there were cameras held on by suction cups; something I doubted the motel had installed on their own. I spotted three of them in the main room; one of which was basically pointed at me. I was being monitored!

'Now, your first task starts with envelope number one and ends with number five. I'll give you one hour to get all of this accomplished which is ample time as long as you don't doddle. If at any point you decided to leave for any reason, I'll send this video out immediately. If you fail to be done in the time frame I've allotted you, I'll send this video immediately. If you do anything other than what you're ordered to do, well I think you get the picture. Now, each task will become a little bit more extreme than the last. If you begin feeling squeamish, just ask yourself if this is worse than your employers finding out. Now, not to take up any more of your time, I suggest you get started. Step one is in the envelope that was under this note. Make sure you follow them in order, unless you want you-know-what to happen. See you soon.'

The note ended with a winking smiley face. My palms started to sweat and I began trembling. What the hell was I supposed to do? What game was this person playing and why were they putting me through this? If I didn't go through these tasks, I would likely never find out and have to deal with the consequences of my employers finding out; whatever those may be. I wasn't ready for that option, which only left one option. I looked over to see the clock on the night table read four minutes past six. If the note was right, I'd have to be done by seven. There was no way for me to know what all the tasks entailed or how long they'd take since I couldn't just start snooping. I'd just have to dive in.

Grabbing the first envelope, I ripped it open and took the note out.

'Your first task is simple. There is a box under the window and you'll find a padlock lying inside. Leaving everything in your pockets, you are to strip naked and place all items inside; pants, shirt, shoes, everything! Once complete, you are to attach and close the lock so that everything will be inaccessible and sealed away. After this, move to step 2.'

I was in shock. I had to quickly read that over again to make sure I'd read it right. My eyes had not deceived me. I had been told to strip naked! There was one last note at the end to spur me on.

'You may have some hesitancy. Let me reiterate that you are under a time constraint and take another peak at the TV and think about your employer and what may happen if they see this.'

This bastard had me. If I left and that tape was turned over to them, I had no idea what they may do to me. My best bet would be to run. But how long could I do that for? Eventually, my problem was sure to catch up to me sooner or later. I really didn't want to be looking over my shoulder for the rest of my life. Maybe this demented fuck just wanted to embarrass me and be on his way. That was the best I could hope for, even if I didn't fully believe it.

Timidly, I began removing all my clothes. With each article lost, I could almost feel those tiny camera lenses watching me. My body trembled, both from nerves and the chill in the room. I deposited everything in the box as directed but hesitated on the last part. I didn't want to lock it, sealing away all my things where I had no access to them. That included my phone and my car keys. However, that would be going against the note's orders. Even one little disobeyed order could cause the blackmailer to take action and expose me. Doing it quickly so as not to second guess myself, I snapped the lock shut.

Next was step two which happened to be the top drawer of the dresser. I opened it to find two bottles; one labeled 'A' and the other 'B'. There was also one of those kitchen timers with a twist knob along with the envelope containing my next orders. I grabbed the envelope and removed the note.

'Take bottle A with you to the shower. Do not turn on the water! Stand inside and cover yourself from the neck down. Leave no skin uncovered. Make sure you spread it into crevasses and other areas that are not quite that open. When done, stand and wait twenty minutes. Use the timer to make sure you don't short it. You may feel some discomfort, but this is normal. After twenty minutes, wash and dry off. Then make sure to apply a generous dosing of Bottle B to your body. When these tasks are complete, you may move to step 3'.

Whoever was doing this had removed the labels from the bottles, so I couldn't see exactly what each one held. Bottle A was much larger and was pressure filled. I took it to the bathroom where I found a couple more cameras stuck to the walls. There was one devoted to the tub where I could be watched as I followed the orders of the note.

Once in the shower, I began coating myself with the white foam from the canister. It reminded me of shaving cream. I did my best to do as the note ordered and applied the stuff everywhere. I had to spread my cheeks and lift my sac to make sure those areas were thoroughly coated. I then twisted the timer to the twenty minute mark and placed it on the tubs edge.

Only a few minutes passed by before I felt an intense burning sensation all over. After about ten minutes and I felt like my skin was on fire! At one point, I didn't think I would make it to the twenty minute mark. Shorting it though would be going against the instructions. I gritted my teeth in an effort to endure the agony. When the timer finally rang out, I immediately turned the water on and let cool water cascade down over me. It caused me to shiver but it felt so soothing. The thinning foam rinsed off and circled the drain; though that wasn't all that circled it. There were wads of hair collecting at the base of the tub. As the foam washed away and my skin became exposed, I knew where it all was coming from. By the time I was done, I was as bare as the day I was born.

"What the fuck!" I exclaimed out loud. I got out of the tub, dried off, and inspected myself in the mirror. My skin had become a pasty pink; I'm sure from the solution that had burned my hair off. It felt incredibly tender and still had a stinging sensation. I looked so bizarre standing there with no body hair. Not like I'd ever been overly hairy, but at least I had some. The foam had taken all of it from me!

Shocked, but realizing I was still being timed, I went and grabbed bottle B as the note said. What was in the bottle was a cool, creamy substance that I was pretty sure was lotion. This kind had a peppermint scent to it. Not something that I'd normally want to smell like, but thinking it may help take the sting out of my skin, I quickly lathered it on. I applied the stuff all over my body; as much as I could get of it that is. The lotion did help null the burning sensation a bit. Feeling just a smidge of relief, I carefully checked the note to make sure everything was done before moving on to the next task.

Step three was the next drawer below the one for step two. I was a bit shocked and puzzled when I opened the drawer to see what was inside. Reaching in, I picked up a flimsy, delicate piece of women's lingerie. It was a nightie and a very sexy one at that. The item was a vibrant pink that was mostly a fine, see-through netting. That is to say except for the cups that were covered in a fuzzy purple, long-haired material that had a bow tied between them. Small, silky straps would go over the wearer's shoulders to keep it on. There would be little mystery, regardless of its see-through nature, as the garment looked incredibly short.

There was one other article of clothing held within the drawer; a pair of white, cotton panties trimmed in pink. There was a tiny bow on the very front along with some writing. In a similar shade of pink, there were the words 'sissy girl' written in elegant cursive, one on top of the other.

I picked up the supplied note and began reading.

'Pretty clothing, don't you think? I'm sure you've taken a few precious moments to admire them. I feel bad for having taken your clothes and now you having nothing to cover yourself with; so I figured I'd give you something a little more fitting for you to wear. Especially with that now bare body of yours. You will put the panties on and then slip into the sexy little nightie. Once they are on, I want you to go to the mirror and do a couple of little twirls for me. Make sure to note how pretty you look and give an adoring smile! After that, you may move to step 4'.

I couldn't believe it! First this sick bastard made me lose most of my body's hair and now he planned to make me wear this provocative looking piece of lingerie; not to mention the ridiculous looking panties with the humiliating message on the front. What the hell was their game?

I considered not doing it. Then my eyes landed on the TV that was still looping my tape. Then I noticed that it was twenty minutes to seven. I had no idea how many more things this bastard was going to make me do and if I ran out of time, then everything I'd done thus far would be for nothing. With that in mind, I scrambled to pull the panties into place. The fit was snug at best. Not that I knew much about wearing ladies underwear, but these seemed very juvenile. I then grabbed ahold of the nightie and raised it over my head. The delicate garment felt so bizarre as it gently glided down my body. I continued to tug even after I felt the straps touch my shoulders. Just as I had figured, the skirt of it was so short that it barely covered my crotch.

I walked over to the mirror above the sink. My cheeks burned with embarrassment as I stared back at myself. The bust line lay limp from my lack of female endowment. The rest of my body had a pink hew from the see-through material. However, the white panties were almost on full display. The top of them were visible through the material, but the bottom part was completely exposed from the extremely short skirt. I read the word 'sissy' across the front of the panties backwards in the mirror and indeed felt like one.

Following the instructions of the note, I did a couple of twirls. The action caused the light skirt to easily raise upwards. The panties quickly came into full view from this action. My eyes found the camera in the mirror and I smiled, making sure to rub and touch the garment as I said, "This makes me look so pretty!" I turned crimson at what I'd just said.

After about four of those twirls and my little proclamation, I decided that was sufficient enough. The note only told me a couple of times and not necessarily a time limit. I was ready to move on to step four. I walked over and pulled open the drawer. My jaw had dropped when I'd opened the one with the women's night clothing in it. As bizarre as that was, at least it seemed somewhat normal and any other person opening such a drawer wouldn't have thought anything of it. The contents inside drawer four were definitely of the odd and bizarre type.

Just as the others, there was the white envelope with a set of instructions. Along with it was something I first took to be a blonde wig. I could just barely make out the long, golden locks. In the rooms dim lighting, I couldn't see that there was something else attached to it until I removed it from the drawer. What I discovered was that it wasn't just merely a wig, but rather an actual full-faced hood!

Holding it up, it reminded me of a batman mask. It was made of tight, black leather with a couple of eye holes and an opening where the mouth would be. However, roughly where the pointy ears would go were long strands of blonde hair. There was a set of them that jetted out into a pair of pigtails. The back of the hood had a zipper running from the crown down to the collar below it. A strap would wrap around the neck line and secure it to the wearer's head. Held in a small hoop by the buckle was a tiny padlock that was already opened.

I took the note from the envelope and read it:

'Don't you think these pigtails are just adorable? I think they'll suit you well. After all, they make great handle bars.'

I was lost on that part, but I had a bad feeling in the pit of my stomach.

'The hood is fairly straight forward; unbuckle the neck strap, unzip it, slide your head in, and then reverse these steps. Make sure you've got the neck strap secured tightly. I wouldn't want it coming off. Once you've got that done, make sure to slide the supplied padlock into place and close it. This will alleviate any desire you may have of removing it before you're given permission'.

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