Bound By Blackmail Ch. 09

This is the ninth installment in the series. If you're not aware of what this series is about, please start at the beginning and read the summaries. Sorry if these stories are taking a little time between chapters. I'm trying to work on them as I can and make them as good as I can. I would really appreciate hearing thoughts and opinions on how you think the story has shaped up thus far and how you think it is progressing. A comment and a rate would be very much appreciated. Hope you like this next chapter.

Brady's hand rested on my ass as I stood there staring at the dildoed seat. He began applying pressure on my bottom to urge me to take a step towards it. I was less than receptive.

"Come on, sweetie. Don't be a bad girl. Your ass really isn't going to feel well if I have to spank it red before you sit. Do you want that?"

"No," I said with a shaky voice. "But please don't make me sit on that. Can't I just sit on the chair without it?"

"Stop playing hard-to-get," he said in an amused tone. He stepped directly behind me and I felt his hands slip beneath my skirt and travel upwards. His thumbs hooked into the waistband of my thong and began to tug them downwards.

Leaning over my shoulder to whisper in my ear, he said, "I know the thought of sitting on that while you learn the ins and outs of being a good little whore simply excites you." With my thong pulled down almost to my knees, he reached up with one hand and jiggled my chastity. "I bet your clitty is just straining in its cage thinking about it."

Brady released me and I defeatedly teetered the few steps with my underwear barely hanging on. Brady produced a tube of lube, applying a bit to the tip of the dildo and then a bit on the end of his finger. Reaching back under my skirt, his finger slid between my crack and the lube was dabbed on my hole.

"Not that your pussy isn't already wet from excitement, but just to help you along," he joked. I was told to take my seat and if I couldn't do it myself, or more like wouldn't do it myself, he would gladly assist me. Figuring it would be better in many ways to do it on my own accord; I slid into the desk and began to sit.

Brady stood back with his arms crossed. He was quite content watching me ease myself down on it. I reached around with both hands and spread my cheeks. At that point, the only things supporting me were my captive feet in the heeled boots. It was quite exhausting trying to balance myself in such a manner. Had my legs given way, I would have fell full force on the dildo and I didn't want to think of the potential pain and injury that would come from that.

I got myself lined up and felt the tip make contact. It reminded me of the man standing just in front of me as he'd teased me with his own member before fucking me hard. My legs burned and I just wanted to get it over with. More and more weight fell upon the rigid dildo until it began to part my hole and make its way in. Even with the lube, there was quite a bit of discomfort. I winced as my bottom continued to drop. Relief, if that was the correct word, came as my cheeks finally settled on the seat.

"Comfy?" Brady asked me with a sideways grin. I didn't amuse him with a response. Brady stepped over to the storage cabinet, took an item from inside, and shut it. What he brought over was an elegant looking present. "As promised, I've got a little surprise for you. I've got a feeling you're going to love it."

It was about the size of a narrow shoebox, wrapped in a vibrant, shimmering pink paper with a white ribbon holding the top on. Brady set it down atop the desk.

"This is just a little present to get you started on becoming a top-notch sissy-whore."

I didn't make a move to open it. The wrapping looked amazing, but that had no bearing behind my hesitation. Whatever lay just under the fancy top couldn't be anything I was going to be thrilled about.

"Don't be bashful about your gift. Open it!" Brady demanded.

Looking like a little girl on her birthday, I untied the long ribbon, freeing the top of the box, and set it to the side. What I found within was horrible enough, but I couldn't honestly say I was surprised considering what I'd been through.

"Go ahead and pick it up, girl. I want to see how it looks in your hands."

What I reached in and lifted out was a rather large dildo. Though it was translucent in a vibrant, pink shade, there was a realness to it. It reminded me of the hellish hand-job I'd given for a tip. The shaft was long with faux veins all down it. Though it wasn't exactly rock-hard like the smaller one I was sitting on, it was still quite hefty.

Towards the back, there was a realistic ball-sac attached that actually swayed a bit with the movement of the dildo. To add a some-what bit of more realism, tiny purple hairs protruded from it as if they were some neon-laced pubes. I found myself reaching out with my free hand to touch them. The hairs were quite thick and curly like you'd expect pubes to be. I looked up to see Brady with a very pleased look on his face. He seemed elated that I was genuinely curious about the item I'd just received. That quickly made me stop touching them.

Attached at the base of the cock and balls looked to be a control panel. Clearly this was more than just some fake dick; which is why I figured it had a hefty weight to it. I turned it around to see that there was a compartment on the back that I assumed held batteries.

"What you're holding in your cute little hand there is a state-of-the-art training device. That is going to be your new best friend next to the real thing," he told me. "It has been in the works for a few years now and gone through a few different versions and upgrades. It's one of the best training aids out there."

"Training for what?" I asked; already knowing the answer.

"It's going to train you to be the best little cocksucker around these parts. See, it works a little something like this..."

Brady went on to tell me more than I ever wanted to know about my new gift. Apparently, it had an on board computer connected to a vast multitude of sensors that detect various stimuli and thus simulated whether the oral job being performed was pleasurable to the average man. It was supposed to be sensitive enough to pick up on temperature, saliva, tongue massaging, teeth grazing, applied pressure, and even the fake balls were apart of it. Just as I'd done to Roger and Brady, the user could fondle the scrotum in a manner it was programmed to deem pleasurable or painful. All of these factors would cause the faux cock to stiffen or soften as well as have its own climax if the job was done to its satisfaction.

"This little guy here," Brady said, holding up an odd looking container that looked frighteningly familiar, "Is the best part about your new toy."

He was holding the container that Roger jizzed in after my hand-job. I was ordered to turn the dildo around so that he could access the back. He pushed a button on the top of the control panel and the back flipped open. The cum-filled cartridge was slid into the cavity that I'd assumed would be for batteries. I heard it docking with a noticeable click and then Brady closed the back up again.

"Now we just hit this button," Brady said as he pushed one atop the control panel. A little red-light illuminated and I was told I could put it down.

"That's a fresh batch from your visit to Roger's earlier today, so it shouldn't take long for it to become ready. The cartridge I just put in isn't one of a kind. Your new mini-fridge has a small freezer section that holds a whole tray of these little wonders. You'll be in sissy heaven when you see all the cum waiting for you!"

What! Did I actually have multiple containers of cum to use for blowjob training? I had barely gotten Brady's load down without losing everything in my stomach. How was I going to contend with more?

"You'll be using at least one of these a day. Each one should give you a heaping mouthful of cum; and yes it is the real deal. Roger and Eve have not only supplied your new toy, but the ammunition that comes with it." He began to chuckle and said one more time, "Comes with it!"

Another terrible pun. What a sick fuck!

"When the light on top changes from red to green the cum has thawed and you'll be ready for your lesson. There will be different settings and difficulty levels you'll go through as you progress. Just think of it as an interactive sissy-slut video game. Your goal will be to get the goods before time runs out. If you don't make it cum in the time allotted, the trainer cock will shut down and you will fail; and just like in school, a failing grade is grounds for punishment. So I suggest you study, learn, and keep that cum-hungry appetite," he ended with a wink.

What a horribly, wicked innovation. Who the hell had spent their time to develop such a device? I dreaded to think of having to endure making it cum day after day. At the same time, I also couldn't help but be fearful of what may happen if I failed to.

"As your training progresses, you'll learn different hand and mouth techniques that will utterly drive men wild. Your new toy won't always be free like it is. That's what the mount on the wall in your room is for."

It made sense now why it was crotch-height and was over the groin of wallpaper Brady.

"This mount will act as a docking station to charge it as well as to give you a bit more realism while you get down on your knees to suck it off. I've obviously offered my image to give you the illusion of sucking off a real cock."

It sounded like I'd be tasked with sucking off both real Brady and fake Brady. That was going to be too much. Everything was quickly becoming too much!

"This will be a daily part of your training. Think of it like slutty homework." Brady pressed a few buttons on the dildo. "I've set it to the standard, introduction level. Just by putting your mouth on it basically guarantees you'll make it cum."

Brady retrieved a remote and turned on the TV. He flipped through an array of videos that all looked like they had the same title. When he selected one, the title screen popped up showing a busty blonde smiling with a dildo in her hand. Above her head were the words, 'Sassi's Sissy Studies.'

"These are training videos that Eve keyed me in on. We'll start with the introduction video that will include using your new toy. I want you to pay attention and be sure to take plenty of notes."

Brady produced a writing pad and pencil for me to use to take slut notes. He then walked around the desk and used straps to secure me in place. Each ankle was secured to the chair legs and a waist strap secured me to the seat. Both of them were locked so I couldn't get up.

"I've got to step away for a little bit," he said, double-checking the tightness of the straps. I was given a stern eye and he continued with, "And I know you're going to be a good girl and do as the video instructor tells you, right? That is unless you're just yearning to be taken over my knee and spanked."

That I damn sure didn't want and shook my head. He cracked one of his sly smiles. I was told he'd be back to get me when my lessons were done. Brady started the video and walked off; ascending the stairs to my kitchen. I heard the door close followed by the sound of the bolt sliding in place. Even if I wasn't strapped in, it looked as if I would still be trapped in my own basement-turned-dungeon.

On screen, the episode title appeared below the busty blonde that read, 'The male anatomy: Getting acquainted with the male appendage.' I couldn't believe it; I was about to be given a lesson in the anatomy of something I already possessed! I didn't give a damn how much my cock had been teased or that it had been locked away. It was still a cock!

The video was of very cheesy quality; like ones that used to play in school. The difference was the instructor appearing as a slutty girl. She stood in what looked like a classroom in front of a teacher's desk. Her clothing was very business-attire; a dark blue jacket and skirt with a white blouse underneath. Only her tits were practically busting out of her opened top and her skirt was quite skimpy. Her makeup was thickly applied and she had on a pair of thick-framed black glasses that looked to not even have lenses in them. Her hair was pulled into pigtails, much like the hood I'd been locked in at the motel.

"Hey there, girls!" She started in a most chipper tone. She hopped up on the desk and expertly crossed her legs. "Welcome to my little classroom. My name is Sassi and I'll be your teacher. We're going to have some fun today!"

Sassi looked and had a name more like a stripper than a teacher. From one of the desk drawers, she pulled out a huge dildo, much like the one I'd just received, and let it balance on her petite, manicured hand.

"We're going to have a little lesson on the gorgeous male anatomy and end by using our new friend here as a physical aid. Through my various videos, we'll dive down the whore rabbit-hole and I'll be showing you some sensual secrets to giving a man a mind-numbing blowjob."

To give a little preview, Sassi turned her head, kissed the tip of her dildo, and opened her mouth to allow it in. The faux cock slid in her mouth with ease. She didn't look uncomfortable in the slightest; a true slut in her natural state. I, for just a fraction of a second, forgot who I was supposed to be and what I was there for. My own cock twitched as I watched her take it like an expert. The pink, metal cage beneath my skirt brought me back to reality as my cock strained against its bondage. I was reminded that I wasn't supposed to find her attractive, but instead become her!

It was fucking frustrating!

"We have to remember, girls," she started after removing the cock from her mouth, "That you have to remain focused so that his desires and expectations are met. Some men love a slut that will go wild and suck it like it contains an antidote while others prefer a girl to take her time and toy with it, edging him on and on. We'll discuss tips and tricks for those different scenarios along the way."

Sassi hopped off the desk and rolled a board over. It was complete with an anatomical diagram of male genitalia that she pointed to with a ruler. It was almost like I was back in biology; with the exception that she wanted to point out what turned a guy on and how to get him erect as opposed to actual, general knowledge.

I'd neglected to jot down any notes the first few minutes of her lesson and hadn't considered Brady's array of cameras. There was little doubt I was being spied on when I felt a jolt come through my chastity. The video then backed up and began to play again. Brady had to be controlling it remotely. It was all a message to do as ordered and take notes.

I began writing what I could, even if I wasn't taking any of it to heart. By the time the anatomy lesson was complete, I had close to two pages of, what I viewed as, worthless notes. Hopefully they would appease Brady.

Sassi pushed the board away and retrieved her dildo. It looked as if it were time for the hands-on portion of the lesson. I was given an overview of this technological wonder that, according to her, every slut should have in her arsenal. She toyed with it and again fondled it with her mouth.

Once she was done, I was given simple instructions; which was basically to just put my mouth on it. This first lesson was clearly to get the dildo to its end result. The introduction code for the training cock flashed on screen. Brady had already set it to this level and it was my turn to raise it to my mouth. I wanted to just skip that part, but I could almost feel the presence of my master from his cameras. He'd already zapped me for not taking notes. I had a feeling not sucking on the trainer cock would yield something similar.

Brady had been right; it didn't take much to get it to completion. About a minute of it just being in my mouth was enough to get it to fully stiffen and climax; filling my mouth with Roger's cum.

"Remember girls, you mustn't be wasteful with what you're given."

Sassi made her own dildo climax and she showed the camera the load of cum swimming in her mouth. She let it swirl on her tongue a few moments before she tilted her head back and let the load slide down her throat. To give the effect of how satisfied she was, her tongue came out and she licked her lusciously painted lips.

Fearful of what would happen if I spat the load on the floor, I started to down it. I was nowhere near as elegant with swallowing as Sassi. Roger's cum, just like Brady's, was thick and awful. I had to choke it down as opposed to letting it lovingly glide down my throat like the teacher-whore. The only advancement I made was I somehow kept myself from dry-heaving it back up.

When the video ended, the TV went dark. I could only sit there quite uncomfortably with my ass still impaled. Not only that, but a bitter chill had started to set in. I was frigid with no means to keep warm other than the tiny dress and my hands to rub my extremities. Roughly fifteen minutes passed before I heard Brady open the basement door and descend down the stairs. He had a smug, gleeful smile across his face. I wanted desperately to smack it off of him!

"My, you're positively glowing in this dim light," he mocked; standing on the bottom step. "You look like you thoroughly enjoyed your new toy!"

"No," I couldn't help but blurt out; fighting against chattering teeth. "I hate this thing just like I hate everything else!"

Brady didn't seem overly irritated at my outburst. In fact, it caused him to give another chuckle.

"Doubtful. I see that gleam in your eye that doesn't lie." He was full of shit! Then he said, "But I do hope your attitude is better for tomorrow when your formal training starts."

"Tomorrow?"

"Oh yes, we've only got a small window to get you out there so that mouth and sissy fuck-hole can make some money."

My stomach did a flip! "You can't be serious!"

He'd mentioned multiple times about basically turning me into some sissy prostitute. I'd hoped it was all just a laugh for him and he never intended to actually go through with it. It appeared like that hope was dashed.

"I think you know me well enough now to know I'm dead serious. How the fuck else will you pay back what you stole?" He started to move towards me and said, "I've got a tutor of sorts coming out to help train you apart from Sassi's videos. You can expect to fill about three hours of your afternoon with that. You've also got an adorable uniform to wear during that time. I know you're going to love it."

I sure as shit wouldn't love it; and I hadn't even seen it. I already knew it would be something ridiculous and impractical. Brady walked past me and into my room. For just a second I thought I was about to be released from my hellish chair. I was able to turn enough though to see him rooting around in my armoire.

"Your school uniform won't be your only uniform, you know," he called out while sifting through the sissy clothes provided for me. I was puzzled by what that meant.

"While you'll be a cum-hungry sissy whore most of the time; well all the time really," he corrected. "I mean, when doesn't a sissy want to be swimming in cum?" He laughed at his own joke. "But you are also my own personal sissy-slave, and with that comes a certain amount of domestic duties."

Brady exited my room with an item while saying, "And this is the uniform you'll be performing those domestic duties in."

Dangling on his extended finger was the wire hanger that held the silliest looking French maids dress I'd ever seen. First off, it wasn't even black like most I'd seen in shows and movies. This one was satin pink with white lace and a frilly, skimpy skirt. A dainty little apron was loosely tied around it; clearly for sheer ascetics rather than function. The sleeves were short and poofy and the bust was low cut; I'm sure to generously show off the wearer's endowment.