tagTranssexuals & CrossdressersTrapped and Trained Ch. 02

Trapped and Trained Ch. 02


I drifted in and out of consciousness over the next hour, periodically snapped back into reality when the dildo assaulting my mouth would pause deep in my throat and eject a fresh deposit of cum into my bowels. Looking up at the television display of my abuse I would normally have been turned on by the sight of this brunette in a pink corset and black stockings leading down to her pink high heels being pounded by this horrid machine from both sides. Knowing that the slut in the video was me, a man forced to wear these whorish clothes and caked on makeup with a brunette wig bouncing up and down as I was seesaw fucked was unimagineable... yet there it was in HD, happening in front of my face. In and out the dildos pulsed, having no mercy on my sore holes, just repeatedly pounding them hard and deep.

I heard the door to the basement open and out of the corner of my eye saw my new Master coming down the stairs with a big grin on his face. I hated him, but was glad to finally see him reappear as it meant that I could possibly be out of this ordeal soon.

"Well then, how's my sissy fuck slut doing with her first round of training?" he sarcastically asked, coming into view. "Enjoying the video? I sure was enjoying it upstairs while I put together the next month of your training. If we stick to my schedule, you should be the best little slut this town has ever seen. Men from all around will travel here, responding to your online ads, paying for a chance to have you to themselves for an hour so that they can fuck you silly and drop load after load deep inside you."

He moved behind me to check the progress the six inch dildo was making on opening up my asshole... which I now have to refer to as my pussy. The dildo had been pounding away with no let up for the better part of an hour. The first half an hour was pure hell as my virgin hole was assaulted without abandon. The last half hour was a bit better, but I was still certainly a long ways off from accepting this new role from my demented Master on becoming some kind of sissy fuck doll for his amusement. Once he let me out of this thing and sent me on my way I planned on heading straight to the police department and suing him for everything he would ever be worth and sending him to jail for the rest of his life. You just can't do this sort of thing to people.

"Looking good back here" my Master said with a bit of self satisfaction, ending it with a smack on my ass as I screamed into the dildo that was currently paused in my mouth, awaiting the freshest deposit to be sent down my throat. He was obviously happy with himself for designing these machines to open up my holes against my will. "A few more go rounds with this machine and a few other training tactics and we should be up to some thick monster dildos opening you up. Around that time you'll likely be begging me to strap you on this thing and to fire up these machines with the biggest dildos I can find. A pure slut in the making is what we have here. I can't wait to see you being a party slut for a group of sex starved men. They'll rip those clothes right off you and fuck that pussy of yours from dusk til dawn."

With that he made some adjustments on the machine that was pounding in and out of my sissy pussy. I felt it start to slow and then, thankfully, it came to a stop. The only problem was that it stopped while completely impaled inside me, but as long as it had stopped, that was a mini victory for me. I felt that I was one step closer to getting out of this hell hole and trying to get back to my normal life. Yet still I was gagged with my mouth wide open and a five inch ejaculating dildo was having its way with my throat. I saw my Master check the bag of his cum that was supplying the dildo with its ammunition, appearing to be satisfied with the amount that had been deposited inside of me. The bag was nearly empty, meaning that nearly half of a gallon of cum was now sitting inside of me. With how the machine worked I really had no choice on whether to swallow the cum or not as it sat inside me for a few minutes, not allowing me to breathe unless I swallowed the contents, then it would come back to life once again. Such an awful contraption, yet ingenious at the same time.

"Very nice - I'm sure you're getting a great feeling for how a man's cum tastes and feels while inside your mouth. That is essential to your training. Eventually you'll crave that taste. You'll pass a man on the streets and immediately wonder what his cock looks like, how it would feel pulsing in your mouth and pussy, and how his cum would taste when he explodes inside your mouth. That's when you'll know you're the sissy fuck doll that I envision you becoming. That's when there will be no turning back."

What the hell was he talking about? There was no way I could ever pass a man on the street and have those thoughts. I'm the kind of guy that passes a hot girl on the street and imagines pumping my cock into her, not having one pumped into me while dressed up like some hooker as I was at the current time.

He again played with the settings on the other machine, and I again felt the pace start to decrease. The machine came to a stop with the dildo just outside of my opened mouth. Smirking, I saw my Master punch in a few more keys, then adjust the tilt on the dildo just a bit to aim a bit higher. I was curious as to what was going on when he punched one more button and I watched as the dildo began emptying the content of the bag, shooting huge streams of cum all over my face. There was more cum left in the bag than I had originally thought as, by the time it stopped, my face was covered in a thick coat of cum. I felt it slowly run down my face while some of it leaked inside my mouth.

"Everyone loves a good facial as the ending to a porno" my Master said as I saw him switch off the video cameras. A porno... this was all a video production for him, and I was the star of this flick.

He wheeled the machine away from my face, then gave me a final warning before removing my gag.

"Now, I'm assuming you've learned to obey me. So when I take this gag off, I know you'll be a good sissy and not say one word unless asked a direct question. Otherwise I'll just fire these machines back up and then head out for a nice long dinner after I've hooked up an even larger cum bag to both of these dildos. By the time I'd get home you'd be overflowing with cum. Moan like a whore if you understand me."

Not liking that option, I did my best to force out a whorish moan, the kind I'm used to hearing come from one of my dates, not from my own cum covered mouth.

"Good sissy. I knew you'd be trainable." I felt him unbuckle the gag from behind my head and slip the cum covered device off of my face. My jaw was unbelievably sore and it was still incredibly difficult to shut my mouth after it had been forced open for over an hour. Now if I could just get off of this horse I could be free and start exacting my revenge, I thought to myself. Those thoughts were quickly eliminated by what I heard next.

"Now" my Master started, "I've been upstairs going through your personal belongings. Very irresponsible of you not to password protect your cell phone. But very convenient that you went through the extra steps of inserting home and email addresses for the majority of your contacts. Now that I have all of this personal information, I feel I have sufficient control over you to do as I command. Any objection or unacceptable conduct from you will result in this nice video I've compiled of your first training session to be sent off to them, from your transformation into being a sissy all the way through to the facial you received there at the end. Your family, friends, work associates... everyone will then know that you're a cum craving whore. I imagine that would go a long way towards ruining your life. Now, if you don't want that done, it's easy - all of your decision making rights will be removed. You will live your normal day to day life as you used to, but whenever you get a message or call from me, you will do exactly as I say, exactly when and how I say to do it. If you understand, then, in your best sissy voice, ask me to turn you into the sissy slut you've always dreamt of becoming."

I was speechless. Here I thought I was so close to getting out of this mess, and now I find out that I'm basically this demented man's slave until he decides otherwise. Hell, in just meeting him he had already drugged me, dressed me up like some extravagent whore, then strapped me up to these machines and deposited nearly half a gallon of cum in and on me. What would the next request be like? What would be happening to me a month from now?

"I'm waiting, sissy" my Master stated, interrupting these terrible thoughts. "I already have a scheduled email set up to send this video every night at 11pm on the dot. It will send unless I am here to enter the password and stop it. It's 10:30 now, so I'd suggest you get on with any question you'd like to ask me..."

Swallowing hard and tasting the remnants of cum that were still coating my mouth, I pitched my voice as high as I could and squeaked out: "Master... will you please train me to be the cum sucking sissy whore that I've always dreamt of being?"

Smiling now, my Master said "Well, if you insist, I would be glad to use my expertise to train you to use that mouth and tight pussy the way they've always been meant to be used. They're excellent tools for draining cocks, and over the next few months and possibly beyond, I'll teach you exactly how to make the best use of those tools. Now, if you'll excuse me, I have to go stop an email from being sent. You've passed your first day of training, Candi - you should be happy!"

With that he smacked me on the ass and removed the dildo from my pussy. He then unbuckled my arms and legs from their cuffs and walked back up the stairs. "Come on upstairs when you're ready and we'll see what you can do to earn the keys to those heels and that collar. Then maybe I'll give you your clothes back and let you take a shower before you head on home for the night. Or if I'm not satisfied with your behavior, maybe I'll make you walk back home with those clothes on and the dried up cum on your face. Quite a few shady neighborhoods to walk through to get back to your neck of the woods. Someone dressed up like that would just be inviting some of those characters to take advantage of you and start up some impromptu training sessions for you!"

He closed the door behind him, leaving me laying down unbound on the sawhorse. I slowly stood up, feeling the soreness in my joints from being stuck in one position for such a long period of time. Standing, I felt myself wobbling and cursed these pink heels my feet were imprisoned in. I tried playing with the black padlocks that secured them to my feet, but it was no use as I had no way to unlock them. I felt the lock on my amped up dog collar and came to the same conclusion. I could remove the clothes I was wearing, but I imagined that would only anger this strange man and, given everything he currently had on me, I decided I should try to play along until I could at least get out of this place. Once outside maybe I could figure something out. I just had to get out of here.

I started walking towards the steps and felt out truly sore my ass... my pussy... now was. It had been fucked raw and was extremely sensitive to the touch. My breasts bounced with every step as I remembered having the gels glued to my chest. Hopefully I could not only get the keys to the devices locked on me, but also some kind of solution to take the god awful breasts off of me. Slowly up the stairs I went, opening the door to the living room.

There my Master sat, smiling as he faced the door. In front of him was a wide variety of sex toys, arranged from smallest to largest, and also a few glasses arranged in size with what looked like the familiar contents of cum sitting inside them. As I approached, he spoke.

"Well Candi, I see you made it up the stairs. That's your name now, Candi, which is short for Candi the Cock Slut. Now we get to play a game. You can see all of these toys and the glasses full of your new favorite source of calories sitting in front of you. Well, there's a reason for that. You see, each toy and glass earns you something. This smallest dildo - if you get that all the way down your throat and hold it there for ten seconds, well that earns you one of the four keys you need to get the heels off. It's only about four inches and you've already taken more than that downstairs. The five incher will get you another key, as will the six incher and then the seven incher will earn you the last key."

I couldn't believe what I was hearing. After everything I had endured downstairs, at least those acts were out of my control as I was tied down and forced to take those dildos in each hole. Now I was going to have to do it to myself just to get out of these heels? My Master continued...

"Now, these dildos over here work a little differently. You can see they have some suction on the bottom of them to secure them to your chair over here. If you bounce up and down on them for five minutes, they will also earn you a reward. This small one here will get you your shoes back, and as you go up in size, all the way up to this eight incher, you'll get all of your clothes back."

My clothes... finally, I would be able to get out of these slutty clothes and back into my comfortable jeans and hooded sweatshirt. No more thong riding up my ass and rubbing against my chafed pussy, but my boxers. No more pink high heels but my comfortable nike cross trainers. Eyeing the glasses of cum, I awaited to hear what they would earn me.

"Yes, these are glasses of my cum that I see you looking at. I'm sure you're craving their taste. These will earn you back your personal belongings. This little shot glass gets you your phone back. This slightly larger glass gets your your house key back. The medium sized glass earns you your car key back. And this large glass gets you back your wallet and all of its contents back."

I obviously needed all of these things if I were ever going to leave this place. But there was so much of this man's cum already sitting in my stomach, I didn't know how much more I could take. Finally, he said one last thing:

"Now, if you want the key to that collar and a chance for a shower before you leave, then you need to accomplish every last one of these tasks. One drop of cum left, then you get to wear that collar home with the cum and makeup still on your face. One cock that you can't deepthroat or take balls deep, then you get to go on home with all that lube dripping out of your pussy and running down your legs."

I had forgotten about the collar. I had to get that off, there would be no way to explain it. I could get away with wearing a scarf while outside, but what about my job? I couldn't go sit at my cubicle with a scarf on and I didn't have any turtlenecks. I had been planning on skipping over some of the tasks to just get the bare essentials, then replacing the rest, but now I had no choice but to get through everything and get that damn key for this collar. This nightmare just kept getting worse and worse as it unfolded, and I feared this was just the beginning. Deep down I knew that this was the easy part and that the worst was still far ahead of me.

Wanting to get everything over with, I decided I would try to tackle multiple tasks at once. I took the five inch dildo and suctioned it to the chair. I lubed it up as much as I could, then picked up the small dildo and the shot glass of cum. I eased myself down on the dildo, finally feeling my cheeks touch the chair. Once fully impaled, I downed the shot glass, licking the leftover cum from the bottom to make sure no drop was missed, then began to bounce up and down on the dildo. Since I was already stretched out, this was fairly easy to accomplish and I started to work the other dildo in my mouth while bouncing. I was used to a larger one, so I was able to take this one to the back of my throat and count off the ten second requirement before removing it and focusing on keeping a steady rhythm on the dildo in my pussy. After five minutes, I was given my rewards and moved on to the next sizes up.

The tasks became continually harder to accomplish, but eventually I had made it all the way up to the largest for each set. These were too large to be able to do simultaneously, so I approached each individually.

I took the large glass of cum and placed it to my lips, watching it slowly start to ooze forward. Trying to hold my breath, I tilted my head back and took in a mouthful. It was so revolting that I nearly gagged and spit it all out, but I was able to keep it in. Over and over I went through this until it was nearly empty, but the rest just would not come out and I couldn't reach my hand all the way down to get the rest out. I was forced to take the thin four inch dildo and use it to scoop the rest of the cum out of the glass and then suck the cum off of it. My Master was very pleased when he watched this and laughed hard while it happened.

That task complete, I moved on to the seven inch dildo that I would have to deepthroat. I struggled mightily with the six inch dildo, repeatedly gagging and having to remove it to stop myself from throwing up as my gag reflex was invoked. I decided it might be easier if it was wet first, so I licked up and down the shaft, coating it with saliva. Again I heard my Master chuckle as he watched this, but my dignity was lost long ago, probably after taking my third or fouth load of cum from the ejaculating dildo. This theory worked pretty well, but it was still difficult to accomplish. I finally was able to force the massive cock down my throat and hold it there for the required ten count, but not even a millisecond longer.

Gasping for breath, I picked up the monster eight inch dildo and just couldn't possibly imagine how I would fit it inside me. It just didn't seem possible - the sheer thickness looked like it would split me in two. I had to do this to get my jeans back as well as to complete all of the tasks and to remove this collar, so I took it over to the chair. Suctioning it to the chair, the weight of it made it tilt off to the side, so I had to steady it with one hand and guide it into my now gaping pussy. I groaned as the head forced its way inside, feeling it fill me up and as the pain started to settle in. Slowly I worked my way down on it, a tiny bit further with each bounce, until I finally felt the fake set of balls resting against my ass. I sat there for a moment as I gathered myself, then slowly worked my way back up. It took me another fifteen minutes until I was able to go all the way down and all the way back up, then I slowly started to bounce as my Master started his timer. Those five minutes felt like a lifetime, but once they were up, my Master stood and threw me my jeans and the key for the collar.

"Very good, Candi. I'm impressed - but sadly I don't feel you deserve a shower. You can enjoy the drive home with that cum caked on your face over your makeup. I wouldn't pause for too long as the stop lights, you never know who you might attract with those inviting lips of yours. Plus anyone with their windows down will be able to smell that cum on you due to the sheer quantity. Now, off you go - I'll be in touch."

Quickly removing the collar from my neck and throwing on my jeans, I hastily grabbed my belongings and rushed out the door. Once I felt the cool night wind I felt free, then rushed to my car and locked the door behind me. I fired up the engine and tore out of the neighborhood, convinced I would never head back to the place again. Surely he was joking and wouldn't be serious about sending those pictures and videos out to my family and friends. As I was thinking that, I saw my phone light up. I had received a video message.

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bySissyIndy© 17 comments/ 266250 views/ 69 favorites

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