Bound By Blackmail Ch. 24

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Brady sat at the head of the table, hips turned outwards and completely bare, while he consumed his delicious-smelling meal. Meanwhile, my mouth bobbed up and down on his cock while he smacked away above me. He inched forward and let his sagging sac hang over the edge. My hand instinctively reached up and gently fondled them until yet another disgusting load was shot into my mouth.

"That was great, Sissy; the food and the head," he clarified with a pat to the top of my head. "I want you to get this kitchen cleaned up. I'll be back down in just a bit. There are some things we need to discuss."

With that, Brady left me there wondering what fresh hell was he going to be bestowed on me. As I cleared the table and washed up the dishes, I tried to think of just what would he would want to discuss with me; as if there was ever a discussion as opposed to simply orders. Did he have some other means for me to embarrassingly and painfully make him more money? What further hell could he put me through to pad his wallet just a little bit more?

It was about twenty minutes later when Brady came down looking only a tad bit more modest than before. He was in a pair of his ratty boxers and an old, stained t-shirt that probably should have been thrown out a long time ago. That wasn't everything he had with him. Besides his cigarettes, he carried a manila folder along with a yellow envelope that had a decent bulge to it. Both were placed at the head of the table where he stopped and turned to look at me.

"On your knees, bitch," he ordered. Considering I'd sucked him off not even a half-hour prior, it seemed like an odd demand. Still, I complied as normal.

"You have turned into a mighty fine sissy-slave for me. Those few, short months ago, I never would have envisioned you coming this far. You went from a very timid, sort-of guy to the stunning sissy-girl on her knees; ready to latch on to any cock that comes close enough to you."

If I was ready to do anything close to that, it was because I had been ordered; which I only obeyed through self-preservation.

"Thank you, Master," I said almost automatically.

"You've made me a little bit of money with that body. I wish you could have made me a whole lot more, but we can only do what we can with the time we are given."

The way he was talking, I started to get a small, glimmer of hope. That was something that I'd abandoned weeks earlier. Was he getting at what I thought he was getting at?

"We both knew that our employers coming back would put a wrench in our relationship and it looks like that time is upon us."

"What are you saying, Master?"

With a smirk, seeing the elated expression on my face, he responded, "The Brother's are back in town."

A wave of emotions came over me. The dominant one was excitement. I knew with them back, Brady's little blackmail deal was going to have to come to an end. It had to! If they found their money missing, sure I'd have to come clean about what happened but I'd take that bastard down with me. I'd have to tell them about being blackmailed so that their janitor could make some money off of me. That wouldn't be good for either of us. Of course, there was no way for either of us to get out of this mess without cold, hard cash to pay the safe back.

"Master Brady, please tell me you've got the money for me to put back in the safe."

His grin widened. He clearly liked the panic that began to burn in my eyes. The excitement of getting away from Brady was trumped by the thought that he would somehow screw me over and I'd become ever much like Clint and Daniel. As much as I hated my sissy-slave life, I really didn't want my face pounded in followed by a stint in prison.

"Do you think you've earned enough money, Sissy?"

"I have sucked and fucked enough people to pay that safe back a hundred times!" I shouted. Brady wasn't too pleased with that. He promptly stepped over and I received a sharp slap across the face for it.

"You watch your little cunt mouth. You're still my property, you know."

"Please, sir," I started, rubbing my assaulted cheek in the process. "We'll both be in big trouble if I don't put that money back."

"Oh, I see you've thought about this. So, you plan on taking me down with you?" He asked in an amused tone. I was in no position to threaten him.

"Sir, I thought that was the whole point of this; you make a little money off me and I make the money to pay the safe back."

"Well, you got one thing right; I've made a little money off your ass." I knew what he was getting at. He wanted to act like I hadn't made him enough money. I had whored my body out for months; or more like I had been whored out. Was he expecting a small fortune out of my sucking cock? Did he expect to retire from my hole getting fucked time and time again?

"Master, that isn't fai..," I started to protest. He put his hand up and cut me off.

"Calm down, Sissy. Don't get your panties in a twist," he told me.

Brady picked up the envelope and opened it up. From it, he plucked out an impressive wad of cash. It all looked to be one-hundred dollar bills. While I couldn't be certain, it looked to be close to the size stack I'd helped myself to.

Was he truly going to honor our deal?

"I've got the ten grand you need to get your cute, little butt out of trouble," he chuckled. I wished I could say that he simply passed me the money to make it official, but our deal wasn't going to be simple. He tucked the cash back in the envelope and set it back down. "Before you get this money, we have to discuss a few things. Get up and take a seat right there," he told me, pointing to the other end of the kitchen table.

I collected myself off the floor. My eyes kept shifting to the envelope of cash. Part of me just wanted to dash for it. That was literally my ticket to freedom. However, Brady stood way too close to it and the look on his face seemed to dare me to try something. Keeping calm, I took the few steps over and sat down in one of my kitchen chairs; something that I wasn't used to doing anymore.

"As I've just established, I have made some money off you these past few months, but I really thought that I would have made a decent bit more. You know, it also wasn't fucking cheap keeping you in clothes and makeup along with your training and toys," he said; as if I actually wanted any of that shit! "Perhaps I should have whored you out more, but I did enjoy having my own personal maid that served me in more ways than one." The rubbing of his crotch told me just exactly what he meant.

"Anyways, getting back on topic," he started, releasing himself. "Being the clever guy that I am, I've come up with a solution to make the investment in you worthwhile."

His hand reached out and I thought that he was again going for the envelope of cash I desperately needed. It was passed over and his five fingertips landed on the Manila folder. He didn't open it up. Using the pressure of his hand, he slid the folder across the table. I tensed up as he maneuvered around me with his arm extended over my left shoulder, bringing the folder to rest directly in front of me.

"Have a look in there, Sissy, at what I have to offer," he whispered into my ear. He then raised back up and corrected himself with, "We'll, more like what you've got to offer."

Brady stepped away and I flipped the folder open. There was a small stack of papers held together by a large paperclip. Just from the looks of it, I assumed it was a contract of sorts. I picked up the packet and flipped through its pages; more skimming the material than actually reading it word for word. I didn't really need to do so since the cover page gave me a good indication as to what it was for.

My eyes scanned through the words, picking up key ones along the way. There was Brady's name, and my name; my actual, real name. There was also my address and the information of my current mortgage holder. Then I saw the word 'Transfer' in multitude.

"Are you expecting me to sign over my house!"

With a snicker, he replied, "I was worried all that legal jargon was going to be simply too much for your ditzy mind, but that's basically the gist of it."

Was he out of his fucking mind! The man had taken so much from me, even control of my home. Yet, it was still legally mine! I had envisioned many nights trapped in my small room of the day I could tell him to get his shit and get the fuck out! That this was my home, my domain and he was no longer going to rule it or me.

Now even that hung in the balance.

"It's quite simple, Sissy. I've grown quite comfortable here and the value of the house and property exceeds what is left on the note. I think that would help to make up the difference in what I expected to make off of you."

"I know you've gotten comfortable. You smoke anywhere you please in it and let anyone you want to come in and treat it any which way they want," I said bitterly.

"This is my house!" He said with authority. Just to prove his point, he took one of his cigarettes from his pack and promptly lit it. Using the two fingers holding the sick-smelling thing, he pointed to the folder and said, "That's just strictly to formalize it."

"You're crazy. I'm not signing this!" I said stubbornly. For a brief moment, I felt like I had a little bit of control, and then I folded my arms over my faux chest and felt the tits I was forced to wear under my ridiculous dress that I had no say in wearing.

"Well, Dafni, I can honestly say I'm not surprised. I mean, you feel like you've done your end of the deal. I, unfortunately for you, don't see it that way at all." Brady gave a sigh and continued with, "So, the only thing I can do is take this ten-grand and go about my business."

Brady picked up the envelope and held it up for me to see; taunting me with it.

"I, of course, will feel an obligation to our employers to let them know how a little weaseling sissy took money from them like it was nothing. I think once they see how you like to doll yourself up, they'll know you took it to buy yourself pretty outfits, probably a new pair of actual tits, and maybe even an operation to get that silly clit between your legs lopped off."

That last part made me cringe!

"They wouldn't think that!" I said with a churning in my stomach.

"Oh, they wouldn't? Just look how far you've come into this slutty persona. You're living it better than even you imagined. Plus, all those ads of yours online along with the photos and video you've taken to admire yourself, you vain bitch. Who wouldn't think that."

This mother fucker really had thought this whole thing through.

"And just so you know at this point, with them back in town, there will be little place that you can run before they find you. Maybe you want to go have a look at your pictures on your wall to remember how you'll end up when they catch up with you."

More fucking blackmail!

"Don't forget too that when you start your prison sentence for embezzlement, the banks going to take the fucking house anyways. I could probably get it pretty cheap that way as well."

"You're insane!" I said in a determined but hushed tone.

"No, I know what I want and further more what I'm owed." Brady grabbed a pen and clicked it open. He laid it on top of the contract and stepped away. "The choice is yours. Sign it and get the money you need to save your neck, or refuse and see what may happen in the coming days."

There was an ominousness to his tone. I hadn't thought he was fooling when all of this started; the whole reason I ever went along with any of this disgusting, humiliating blackmail. My gut was telling me the same thing while sitting at that kitchen table. A house would do me no good if I were beaten to a pulp and then tossed in prison for a few years. I had to at least get the money back into the safe and get the fear of the Brothers off my back. Then I could focus on the problem at hand.

"You know this will never stick," I tried to say convincingly as I shakily picked up the pen.

"If you really think so, then you should have no fear in signing it," he told me, easily seeing the pen quake with my nervous tremors.

My breathing was heavy and my heart was pounding away as my anger grew. Did I actually believe it? I mean, he was only a fucking janitor; and a creepy, disturbed one at that. There was no way he would actually, legally take my home from me. Right?

Putting pen to paper, I quickly scribbled my name on the dotted line. While it felt good to actually use my real name, I hated the circumstances in doing so.

"You're not going to get away with this," I told him again as he closed up the folder and took it away from me.

"I guess time will tell," he said in a confident tone.

"I want my money," I said, cutting my eyes up to him. He smiled but didn't move to pass me the envelope he still held in his tar-stained hands. He rather set it back down on the table, well out of reach.

"First off, we both know this isn't your money. And secondly, we have one other thing to discuss."

What the hell was it this time?

"Seeing as how you've just become homeless in a matter of seconds, I would like to make you a very generous offer."

"What?"

"Now, before you get your panties in a twist, just hear me out. You don't have a roof over your head anymore and you barely have any money. Two very important things for anyone to have. I would be willing to remedy one of those issues very easily."

Brady stepped closer to me. Whatever he had in mind was exciting him. Cutting my eyes down, I could see the bulge growing beneath the tattered boxers; all the way to the point that I could just see the tip of his member trying to peek out from the opening in front. He was enjoying the position he was putting me in and the power it gave him.

"If you ask me very nicely and promise to be a good sissy, I'll allow you to remain my property and you can go on staying here as my permanent sissy-slave."

Did he say what I thought he just said?

"What!" I said, flabbergasted.

"You heard me. If you want to stay here in this house, under my roof, I want you to beg me to stay my sissy-slave permanently and pledge your loyalty and obedience."

Alyssa, to an extent, had been right. He wasn't prepared to let me go. Brady wanted me to stay and continue the same humiliating and demeaning services I'd done since meeting him.

"Before you say anything, let me lay it out for you."

He apparently had a whole plan. First, after returning the money and getting everything squared away at work, I was to put in my resignation. Apparently, I just wouldn't have time to continue to work outside the home. I would become homebound unless Brady took me somewhere, most likely to be whored out, or I was given permission to go someplace myself. Most of my time, at first, would be the same; cleaning his house, cooking his dinners, tending to his needs and desires, all while prancing around in my ridiculous maid uniform.

"I know you're used to all that, and I'm sure rather enjoy it," he told me with a garbled chuckle. "And as much as you like your area downstairs, becoming my obedient, permanent slave does afford you the ability for advancement. Especially with the acquisition of fresh blood."

It was an analogy I'd heard before, but still it seemed grim and foreboding. He let me know that he didn't plan for me to become his one and only slave. Brady had plans to expand his little money-making operation by training yet another guy-turned-girl into becoming his little whore; well partly. That's where I was to come in. I was supposed to use my own training and my own experiences and impart that knowledge onto what would be my protégé and probably a less-than-willing participant in Brady's little sissy-slave endeavor.

"My next slut would move into your little piece of paradise downstairs and I would fix up one of the spare rooms upstairs as your new quarters. Obviously something pink and girly that a sissy would simply love! Plus, as my top sissy, you would earn the privilege of getting to be so close to your owner."

It would be my responsibility to work with this new sissy and train them and to oversee their progress. They would also take on the brunt of making our master money by all the means I used to do; although he made it clear that I would never be fully off the hook with using my body for his financial gain.

"You want me to be like Alyssa?" I said.

"Exactly! I want you to be just like your little girlfriend. Train up whoever I bring home and the more money they make me, the easier your life will be."

Was Brady actually serious. Did he really want me to voluntarily stay his sissy-slave? Where I would be starved, mistreated, and whored out at his whim?

"Think it over carefully, Dafni. You may think that you are undeserving of such an offer, but you may find that becoming my top sissy isn't the worst thing out there for you."

The smile on his face, along with his impending erection, continued to grow. He was excited at the offer he'd just made me and the decision I was going to have to come to. Did he really believe that I'd seriously consider it? It was laughable that he would think that I would find any allure in it. Despite that thought, there was a lingering feeling that perhaps I shouldn't be so quick to cast it aside. That perhaps there were some pros to it and that I could maybe find some comfort in such a fucked up situation. What in the hell had this man done to my mind?

"So Dafni," he started in a gravely tone, lighting himself yet another cigarette with the head of his cock peeking out as if to hear my answer. "What's it going to be?"

To be continued.....

Dafni seems to be so close to finding her way out of this predicament. Will she take her leave of him and try to claw her way back to being Evan or fully submit and forever call herself Dafni? Let me know what you think. Again, thanks for those who follow and still enjoy reading this series.

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AnonymousAnonymousabout 2 months ago

Hoping for part 25 soon! One of the best stories on literotica.

AnonymousAnonymousabout 2 months ago

I like the story. I want to hear more about the effects of Dafni's transition. Are her breasts developing so that she can't hid them? Is her face fuller and softer so that she appears more feminine to those at work? Is she getting hips? What about her emotional state with all that estrogen flowing through her brain. Is she more emotional now? Does Brady have her on her period? As Dafni becomes more fem, sweeter, and docile, does Brady act nicer to her? I can see Dafni asking for help from Brady doing men's work like killing a spider or doing something so that Dafni doesn't break a nail that she just used her allowance on getting done up. I can see Dafni asking Brady to hold an umbrella for her so that the rain doesn't ruin her hair that she worked so hard on.

AnonymousAnonymous2 months ago

I agree with @ChloeMai

sgoliveirrasgoliveirra3 months ago

Would have liked to be the sexual parts more detailed, but all-in-all it's a pretty good story.

BJGoodheadBJGoodhead3 months ago

One more thought...if Dafni decides to remain with Brady I hope she uses her sissy feminine wiles to develop him into a less slovenly character. Her “devotion” to him as her master and protector could lead to Brady developing into a better man. Furthermore, “Brady’s” house won’t last long if he continues to let “renters” destroy the place and punch holes in the walls...maybe he will start to take pride in his home once he owns it...under Dafni gentle influence.

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