Bound By Blackmail Ch. 14

Hello readers. Here is the fourteenth chapter in the series. I'm steadily working on new chapters. Sorry if it seems like it takes a while; I just try to make each part as good as I can and hope that some of you like it. As always, I would love to hear your thoughts if you would like to leave a comment. Also if you would like to rate as well. Thanks for reading.

We pulled into the parking lot of the shady motel where my hell first began almost a week prior. While driving across the parking lot, my eyes cut up to the second floor where the pass-through was located. I could see myself running from those three guys; jetting out of there, around the corner, down the stairs, across the parking lot, and to my car that had been sitting just a few spots down from where Brady was parking; all while in that skimpy nightie with the hood and gag locked on my head.

Those items were now gone but I felt like I was much worse off. At least under that delicate nightie and the tawdry, leather sex apparel, I was still a guy. With my wig pinned in place, and the makeup, and the tits glued to my chest, I looked even more like an actual female.

Brady stopped the car and I was told to get out. I didn't see anyone nearby, thankfully, but I was still worried. The sun had already set, but there was still too much daylight for my liking. I stuck out in my pink dress like a sore thumb. My feet carried me quickly across the parking lot. Miss Eve, along with Alyssa's training, had gotten me to where I could walking fairly well in a pair of heels. However, I still stumbled a bit. The dilapidated lot and my haste didn't help and I was forced to slow myself down to keep from falling. Of course Brady had to crack a joke.

"I knew you were anxious, but calm down before you fall and fuck up your dress." I grumbled a little under my breath but didn't say anything else.

We didn't head straight for a room. Before, Brady had it all planned and laid out; having sent me the key to the room where he'd placed the instructions and the items for me to use and wear. This time, we headed for the front of the building towards the double doors of the lobby. I got quite nervous as there was always the potential for guests, or creeps in this instance, to be hanging around inside.

"You wait here for me," Brady instructed me just as we passed through the doors. That order I didn't have to be told twice. I cowered in the corner and tried to somehow become invisible.

The lobby, surprisingly enough in such a lavish establishment, looked tarnished and run down. The tiled floor was cracked up and the carpeted area had stains that I didn't even want to guess what caused them. There was an odor that smelled party of cigarettes, drugs, and just plain filth. I noticed a janitor sweeping up a hallway and wondered to myself, 'what was the point'? When his head popped up and caught sight of me, I turned crimson and looked away as if I'd never noticed him.

Brady went up to the front desk where a pudgy, balding man sat behind the counter. I peered over to see them having a short, seemingly light-hearted discussion. The clerk looked to have a smug disposition about him until Brady nodded my direction. He turned his head to see me standing there, cracked half a smile, shook his head, and then turned back to Brady. A few moments later and the pudgy clerk passed off what looked like a couple of card keys. I had a feeling the clerk knew I wasn't there for some cooperate business meeting in my skimpy, pink ensemble. It made me wonder just how many 'working girls' made their way through there.

"All set, slut," Brady said, steadily typing something out on his phone as he passed me. I looked back at the clerk who gave me a wink and an amused smirk. I quickly turned heel and darted back out the door.

Last week, I had been up in room two-eighteen. As if to keep with or start some tradition, Brady had requested the same room. Before ascending upstairs to my awful accommodations, we stopped at the car and got my bags. I use the term 'we' loosely as Brady made sure I toted all of it. The wheels on my bag were having the same difficulty rolling on the poor surface as my heels had walking. The two bags plus my purse over my shoulders didn't help with my control of it. I could see Brady peering back over his shoulder and heard him having a chuckle to himself at my hardship. As much as he wanted to turn me into a girl, chivalry wasn't part of that deal.

"Welcome back," he said as he opened the door and moved aside for me to enter. I stepped into the dark, gloomy hell I was in not even a week prior. "Brings back some fond memories, doesn't it?" He asked with a gleeful grin.

It was hard not to replay the events of the previous weekend in my head. First was the filthy floor that I'd been forced to worm across when I was left alone still shackled and helpless. That lead all the way back to the bathroom where I'd both had my body hair chemically burned off and Brady had chained me to the shower while he cleaned my so-called pussy. Then there was the awful queen bed with the saggy, lumpy mattress. I looked upon it and remembered laying there bound and gagged; having to do that all to myself or face dreadful consequences. Then having my self-proclaimed master fucking me like some cheap whore. All of it gave me a deflated, depressed feeling.

"No," I replied. "There's nothing fond about this."

"There's those cold feet again. Don't get nervous. Once those guys start coming," he said before stopping to chuckle at another lame pun, then continued with, "They'll be cumming in you in no time."

I dreaded to think of that hell. Just who would these guys be and where would they come from? Did he really expect a bunch of men to really want basically some dude in drag to make them cum? Or did he think this motel contained nothing more than sick guests like the three drunk guys?

I tried to tell myself not to worry. No way there would be enough guys to make this worthwhile for him. Once he would see that putting me in a dress with some new hair and makeup wouldn't bring in many clients, he'd just drop this whole thing; maybe even to the point that he'd exit my life for good. It was at least a warm, hopeful feeling and that's all I was trying to be; hopeful.

And then there was a knock at the door.

"Oh, sounds like we've got a visitor," Brady said matter-of-factly and then moving to answer it.

Who, or more like what, stood on the other side was a very hulking guy to say the least. He looked like he should be standing in front of a club or something as a bouncer. The man was a tad taller than Brady but quite a bit bulkier. His head was shaved and his neck was massive, leading down to his impressive torso. His shirt conformed to his very muscular body to the point that it looked like a mild flex from either of his massive biceps would begin ripping it in two.

"You Brady?" He asked in an anticipated low register.

"That would be me," he said as he stepped aside for the man to enter. I swear the guy had to turn slightly to get through the doorway. "And you're.....Dimitri, right?" Brady hesitated. "I think that's the name Roger gave to me."

Roger? What did he have to do with this guy?

"That's right," Dimitri said. "I assume that Roger went over my role here for the weekend and my cut?"

"Oh yes! Everything is laid out and in order. I think this will be a very prosperous weekend all the way around."

Brady shut the door and Dimitri began looking around the room. It didn't take him long to spot me; after all, I did look like a walking neon sign. Our eyes locked and I could almost feel that hulking intensity. It made me quite uneasy.

"I'm assuming that's your slut?" His arm lifted and his pudgy finger pointed me out.

"That's her, alright. That's my Dafni!"

"Does she know why I'm here?"

"No. I haven't gone over that with her. She's so airheaded that I try to keep things simple."

I shot Brady a look. Not that I really cared what Mr. Muscles in front of me thought, but he was making it sound like I was actually some ditzy blond. The guy just smirked as if the sheer sight of me told that story.

"Dafni, is it?" He addressed me directly. That caused my throat to go dry, but I managed to choke out a response.

"Ye.....yes, sir," I stuttered a bit. He gave a muffled chuckle; clearly amused at my intimidated reaction.

"I'm Dimitri, in case that wasn't obvious enough to you," he said; like my ditzy brain couldn't comprehend one name used just moments before. "I'm an associate of Roger and Eve who I believe you know."

I didn't have much to say, so I meekly nodded my head in acknowledgement.

"Let's go over what I'm doing here and what I expect. Take a seat so that you can listen and understand everything."

I did as he asked, or really commanded, and sat on the edge of the bed. His presence was much more massive and intimidating that way, considering I barley came up to his shoulders standing up.

"I'm here for three reasons; to keep you here, to keep you safe, and to make sure you're not letting your clients down. Not necessarily in that order."

Dimitri elaborated a little more; telling me he specialized in security and control. His physique helped to paint that picture. Either Brady or Eve had enlisted his services In making sure my clients were well behaved and most importantly paid before being allowed in to see me. Though he wouldn't be in the room for obvious reasons, he would be close enough in the event that one of them may get a little bit too rough.

"Of course Dafni doesn't mind when guys get a little handsy. It really gets her motor running," Brady made sure to chime in.

"Master, I..," I started to object. Dimitri saw the look on my face but abruptly cut me off.

"I have no doubt she loves it, but I'm here to make sure that her clients don't get too handsy. After all, there can be too much of a good thing," Dimitri said with a smirk. Then he got serious and looked dead at me. "I'm here for your safety, but not to pull a guy out of here because you don't like what he's doing to you. You're a working girl and those guys better get what they paid for."

"Very well said, Mr. Dimitri," Brady applauded. Dimitri stepped out of the way and it was Brady's turn to give me a little pep-talk.

"I know you're quite nervous, but I think you'll get over that pretty quickly once you start plowing through clients; or more like the clients plowing you." He snickered at his joke. I was getting sick of them!

"I expect you to be courteous, hospitable, and gracious to any guy that comes through here. Remember the training you've received this week on just how to do that. They've paid a pretty penny to come have their fun with you and you're going to make sure they leave here satisfied. After all, this is the first stepping stone to building up your clientele."

"What are you going to expect me to do?" I asked with my stomach doing flips. Brady gave a smile and elaborated.

There were going to be two different types of sessions; the quickie sessions and the playtime sessions. They were as they sounded, only I wasn't planning on having fun with either. The quickie session were fifteen minutes with a client where I would either suck or fuck a guy; maybe even half-and-half as Brady put it. These would be the guys who just wanted to get their nut off real quick on someone.

The playtime session was set at forty-five minutes. Like the quickie session, there was a good chance I'd be taking a cock, along with its load, in one of my holes. However, the client would have a range of toys at their disposal. Things like; gags, shackles, whips, floggers, dildos, and all sorts of other fetish gear for them to use on me at their whim.

It didn't stop there. Some of the clients with the longer session could request me dressed up in a certain outfit that Brady was sure to pack. They may even request that I already be restrained. The one charged with that particular duty was Dimitri. I could see a smirk at the mention of that.

"You'll have anywhere from ten to thirty minutes to prepare yourself between appointments," he told me; like it was a fucking doctor's office or something. "That'll include fixing your makeup and cleaning out your pussy if it's been fucked."

I was starting to get lightheaded just at the thought of any of that happening to me. Just who would these guys be? There was no way there could be enough depraved men out there who would pay money to have time with a guy in women's clothes and I decided to share that theory with Brady in the slight hope he may agree.

"Master, please, there is no way this could be worth your time. Surely these guys you think will want to rent me would rather seek out an actual girl instead of someone like me. You'll never make enough money for all your efforts."

Brady, thankfully not angry at my outspoken opinion, gave a hardy chuckle. "Oh, Dafni, don't sell yourself short. First, you are a girl; a sissy girl, but a girl nonetheless. No one can hold that silly, enlarged clitty against you. Even you know you look killer once your hair and makeup is done and you fit that petite body into a tight, little dress."

I had no doubt the two saw my face in agreeance. With all my girly clothes and accessories on, I looked incredibly feminine, and it was only going to get worse. Those hormones were going to help further shape my body. Alyssa, aside from her own caged male appendage, looked to be all girl. There wasn't a trace of masculinity about her. Still, would all that yield clients who would want to use me as their sex-doll?

"But still, sir..," I started.

"And don't you go to fretting that there won't be any gentleman callers," as he put it. That was just a churched-up way of saying disgusting, vile men. "The response I've gotten from your ad says it all."

A lump caught In my throat. "Guys are actually responding to you?"

"Of course they are!" Brady exclaimed happily. Then he added, "Well, more like they're responding to you! I've been taking pictures and video of you all week and posting them to your ad. I'm sure you're quite curious; would you care to see for yourself?"

That was a rhetorical question as he already had his phone out and opened to it. The ad looked like some raunchy, shady site that only demented creeps would search; basically the demographic that would want to use me as their sex toy. My page opened up to a pink background with large, purple cocks silhouetted in. I was in shock to see me standing there in the pink dress from Roger's. Eve had definitely done her job. I really looked like a smoking hot, yet slutty girl. There was no hint of my caged cock contained just beneath that short skirt.

That's not to say my crotch was purposefully left out. It was made quite clear in the ad that I was a 'Sissy Girl' and there were plenty of photos to show that. I had photos in my maids uniform where I was in mid-curtsy with my chastity quite clear and visible. My mouth went dry at the thought of people seeing me like that. Brady also had photos of me in my schoolgirl uniform, my nightie, some in nothing but lingerie, and even some of me naked with my wig, makeup, and breasts still on. Brady had been snapping pictures of me while I had been distracted during my training sessions or chores. They weren't all from his phone as most looked to be stills pulled from his security cameras. If there was any sense of relief, it was that I was done up so well that it was quite difficult to tell it was me under all that femininity.

That didn't stop the pictures from getting far worse.

As bad as it was to see me in drag and naked for the whole internet to see, the last few pictures were the worst! There were photos of me sucking cock and having cum either on my face or in my mouth. I felt such embarrassment at the one in my maids uniform on the floor of my own bedroom with a mouthful of Brady's cum cupped on my tongue.

"You put those online!" I said; shocked and highly pissed off.

"I sure did," he said; ending with a sharp slap across my left cheek. It wasn't overly hard, but enough to get the message across. "Don't you use that kind of fucking tone with me, slut. How else are guys going to know what kind of a sissy-whore you are if they don't have a visual?"

I know I had to be crimson and not from Brady's slap. My face burned from embarrassment at the sight of those photos. If those weren't already bad enough, the page also had a little ad supposedly written by none other that Dafni the sissy-slut.

'HI boys! My name is Dafni and I would love for you to come spend a little time with me. I absolutely love having a big, hard, throbbing cock to play with. Either take my pussy for a ride or shove it deep down my throat till it explodes. I just love cum anywhere on or in me! It seriously turns me on to become someone's cum dumpster. Want to have a little playtime beforehand? I'll gladly be your sex-toy for you to use and abuse. I can be your naughty girl that needs to be straightened out. Come teach me a lesson and then have your way with me. I can't wait to see you!'

"Cum dumpster!" I said, unable to stop myself.

"It's quite catchy and it describes you to a T."

I couldn't believe how he was portraying me. My ad definitely looked inviting to someone depraved enough to come treat me like a piece of trash. Still, I had my doubts that it would draw enough attention to be worth his time. There was also another aspect that I wasn't sure he'd even considered and felt I needed to bring it up.

"Master, you can't do that!" I started to get frantic. "What about the police. What if they see that ad and then come to arrest me for solicitation?"

"Are you worried they may come and spoil your fun?" He asked, giving a fake, hardy laugh that ended in one of his disgusting smokers coughs. "I wouldn't worry about anything like that, especially in this shady area. Why else do you think I chose this dump; other than the fact that it reflects what a cheap, cum-hungry whore you are? Hell, there may even be a few cops who come to a shit-hole like this to get some release."

I honestly didn't know whether I should be devastated or relieved at that notion. Police showing up may save me in the very short-term, but there would be a price. Brady made sure to put that in perspective.

"Of course, if you were to get into trouble, I know you wouldn't do anything foolish like trying to tell some outlandish story about being forced into all of this. You'd have to tell them why someone would be doing all this to you. I know you're airheaded, but even you have to see how that wouldn't end well. Then, I'm afraid they discover that tell-tale footage of your little safe-raid and you'd find yourself in quite the pickle. I'm sure they'd realize real quick that you were just simply trying to whore your way out of trouble."

I was terribly worried that Brady actually had a point. He had me in so deep that I doubted I could talk my way out of it; at least not easily and not without incriminating myself. There was one other aspect that he wanted me to consider.

"You probably wouldn't have to sit in jail too long though; maybe just long enough to suck a cock or two. By that time, the Brothers will get you bailed out and I'm sure you would get very well taken care of."

He didn't have to elaborate any further. I was getting the picture he was painting for me. It seemed like any avenue away from this hell I was in would only lead to more trouble.

"So, if you have any sense in that ditzy brain of yours, you're best to act like your true, sissy self."

"Yes, Master," I said in a defeated tone.

"Wonderful! Now we need to get down to business," he said. I didn't really hear him since my mind was whizzing with all the notions of all those possibilities. Brady snapped his fingers in front of my face a few times to get my attention back. "Dafni! Stop fantasizing about a bunch of jail thugs having their way with you and focus."