Trapped and Trained Ch. 11

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SissyIndy
SissyIndy
988 Followers

I found myself blushing as Alice spoke of me as if I were some item for sale, and actually found myself a bit hurt when I heard her say that my figure could use some work. I thought I was in wonderful shape. I looked at myself in a mirror to my left and found myself picking at my body, looking at a small bit of fat on my stomach and thighs, but I was certainly in great condition from my athletic background. Finally I snapped myself out of this thinking - what was I doing? Was I actually offended that this woman didn't completely approve of my body dressed in this female attire? What was wrong with me?

After apparently getting the approval from Alice, this Miss Vicki woman slammed her binder shut and placed it in one of the drawers of the desk. She leaned on the desk, giving me a wonderful view of her cleavage down the front of her gown, as she looked me up and down. She twirled her fingers, signaling for me to turn around and made me do that a few times. She gave a hesitant nod and then turned to Alice.

"Well, it's better than what he's done in the past, I'll say that much. We still need to see what we're working with though. Set her up in room one with the usual first analysis configuration."

Alice came around the desk again and grabbed me firmly by the hand, leading me behind the desk and down one of the hallways. She led me to a room with a large "1" printed on the front and we walked inside. Before turning on the lights, Alice stripped my dress off of me, leaving the boots and the thong on. When she then turned on the lights I saw that it was a fairly empty room with some large items covered with sheets along the walls and then some kind of a frame in the middle. It was on top of a black pentagon shaped bottom, there were two sturdy metal poles leading up to a crossbar connecting them. At each corner there were two separate chains hanging down leading to cuffs at the bottom of each. On both sides of the frame I saw a crank with a spool, apparently for retracting some of the slack in the chains. There was a bench in the middle of the pentagon which Alice led me to and had me lie down on. Once I was laying down she took the cuffs at the end of each of the four chains and secured them to my wrists and ankles, putting small padlocks on each lock to ensure that I wouldn't be able to remove them. She then alternated between each of the cranks, slowly lifting my arms and legs up until the small of my back was just barely resting on the bench. I then felt Alice begin to wheel it out from under me, leaving me hanging in the frame, completely helpless.

Alice walked to a desk on the side of the room and pulled out a clipboard with a piece of paper attached to it. She walked over to me and made sure the chains were nice and tight, then began to speak to me, but not ever pausing to ensure I understood or leaving any time for me to ask questions.

"Now, Candi - you have passed the sight inspection by Miss Vicki, which you should take as the highest of compliments. She is very selective with those who she selects to train and mold into her vision of perfection. This is the initial analysis phase, where you will be graded on a scale of 1 to 10 on a variety of different categories through the tests that I will be performing on you. It is imperative that you try your absolute best in all phases of this analysis, since your performance will have a direct impact in the intensity of your training from this day forth. The time of all of the tests will typically span roughly four hours, so you are in for quite a long session. Over the next four hours you will experience pain, humiliation, exhaustion, and, perhaps, pleasure - but that depends on what gets you off, sweetie! Let's get started! Your first series of tests are to establish a pain threshold for you. As I perform each test, you will endure as much as you can, and then when you can no longer continue, you will say the words 'Please, Miss Alice, no more.' Upon saying those words, that particular pain test will end and you will be graded before we move on to the next test. Ready? Ok."

She didn't wait for any kind of approval from me when she asked if I was ready - given how she had me set up, it didn't really matter if I was ready or not, she could do as she pleased to me and knew it. I craned my neck to the left and watched her as she went to a closet in the room. She came back out with a large pink paddle and immediately I began to struggle against the chains, trying to break them loose. She smacked it in her hands a few times and then gently rubbed it against my exposed butt cheeks.

"Just a little spanking, Candi. Nothing to worry about. Remember to say please when you've had enough and then it will be all over - but remember that there will be consequences later, with their severity dependent upon how long you make it."

She stopped rubbing the paddle against my ass and moved it away. I squirmed with anticipation, desperately looking around the room, trying to find something, anything to distract her and prolong this. But there was nothing and I felt the first strike land flush against my cheeks, causing me to pull my arms up against the chains, trying foolishly to get away. Alice just laughed and struck again and again. As each strike came I bit my lip and groaned in pain - after twelve strokes it felt like my cheeks were lit on fire and I couldn't take any more. I screamed the words for her to stop, stopping her in mid swing. To my temporary delight I saw her take the paddle back to the closet. She picked up her clipboard, shaking her head with what seemed like disappointment and wrote down a few notes. She walked back over to me.

"That's a new low, sweetie. Your cheeks are barely even as pink as your pretty little thong and you already stopped me. Miss Vicki will not be pleased, but it's your decision. Now on to the next test."

She again disappeared into the closet to my left, this time coming out with nipple clamps and a small cloth bag. She quickly snapped each of the clips onto the nipples of my fake breasts, causing the metal teeth connecting them with my actual nipples to pinch down just as hard. There were chains hanging down from each of the nipple clamps, which I understood the purpose of as soon as Alice started laying out the different weights on my stomach in front of me to see. There must have been ten different sizes of weights in pairs. She took the smallest weights and clipped them on to the chain of each clamp, causing me to yelp in pain and grind my teeth together. She stepped back and allowed the weights to rest for a few minutes before coming forward and attaching the second set of weights to each chain, causing tears to start to form in my eyes and my nipples to scream at me to tell her to stop. Another few minutes passed before she applied the third set of weights, pushing me into a realm of pain that was just too much for me to handle so I quickly pleaded with her to stop, saying the magic phrase. Quickly she released the clamps and allowed them to fall to the floor. She again went to her clipboard with the same look of disapproval on her face.

"You just don't do well with pain, do you hun? That's certainly going to be a point of emphasis in your training - Miss Vicki requires a very high pain threshold. Before I moved up to be her assistant I had to take all ten of those weights for one hour. Okay - one more pain test and then we're on to the next category."

I couldn't even imagine the pain involved in having all ten of those weights hooked onto my nipples - it was unbearable. One more time she went to the closet and again came out with a cloth bag. She emptied the contents out on the desk to my left and I saw that it was dozens of clothespins. Again I began to plead with her to just let me go, but it was on deaf ears. She picked up a handful and walked over to me. I guess since I had a fake pussy and fake breasts her options were limited, but it seemed like she had dealt with that before. She pinched up a small piece of skin on my upper thigh, just above where my boots ended and attached the clothespin, causing me to squeal and shake my leg, trying to get it to release its hold on me, but it stubbornly kept its teeth sunken into my flesh. Without a delay, Alice had hooked on five more clothespins, leaving me with three apiece on each of my thighs. She then moved onto my stomach with the same routine and the pain was searing through my body. When she attached the fourteenth clothespin I again folded, asking her for no more and then exhaling in relief as each of the pins were removed. Again to the clipboard, again with the disappointment.

"Well, I'd say that was a colossal fail in that category. You have a huge amount of improvement to do there before you pass Miss Vicki's standards. But anyways, on to your next category. This will test you in different areas concerning your ability to please men and women - from how big of a cock you can take in that cute little pussy of yours to how long of one you can take in your mouth, and also how good you are at eating pussy. So here we go."

She walked over to one of the items that had been covered by a sheet and slid it off, revealing a machine with a drill atop of it, currently hooked into a medium sized dildo, perhaps 6" in length and a normal girth. She wheeled the machine over towards me and then I felt a coolness in the opening of my pussy, then her fingers sliding in and out of me as she lubed up my hole. She was so business like in the process that I knew she had done it plenty of times before. She then lined up the dildo with my pussy and flipped a switch on the machine, bringing it to life as I felt the pressure of the head of the dildo pushing inside of me. She allowed it to slide in and out of me for a few minutes before shutting the machine down and wheeling it back a few steps. She then took a larger dildo, about 8" in length and much thicker and placed it on the end of the drill. She again moved the machine into place and turned it on. The thickness of this dildo felt like it was going to split me in half, the edges of my pussy straining to accommodate it as it thrust in and out. Once more she clicked off the machine and took out another 8" dildo, but this was thicker yet again. She slid that dildo onto the drill and moved the machine back into place, but before she could turn it on I folded and pleaded with her to stop. A smile crept across her face, dripping with evil as she turned the machine on and then went to her clipboard. The head of the dildo felt wider than anything I'd taken before as it unrelentingly pushed against me, swaying me backwards against the chains until finally it broke through. I screamed in pain as it slid all the way inside of me as Alice came back and shut the machine off, leaving me impaled on it. She looked angry.

"Candi, you really need to focus. You see, I knew you could take that cock and now look at you. There were plenty more to go through but you just aren't even trying. Since you stopped me before you took that one I can't give you credit for it, I was just proving a point for you. To help that point sink in, I'll keep that in place as we go through the other tests."

I was dripping in sweat as I watched her return to the closet in the room, returning with a handful of black dildos of varying lengths. They were all normal girth, but they looked like they ranged from 4" all the way up to what must have been over a foot. She took a tube of pink lipstick and painted it on my lips, telling me that it would be used as a marker for how far down I made it on each cock. She then took the smallest dildo and placed it at my lips, applying a bit of pressure as I took it all the way in. Alice then had me clamp down my lips, leaving a thick pink O at the base of the cock before she removed it. She repainted the lipstick on my lips and repeated this process through the 8" cock. She picked up the 9" cock and I knew there was no way I was going to be able to take it all the way, so I stopped the torture before it could start and asked her to stop. The 8" cock had nearly caused me to vomit from my gag reflex, but I had made the pink O at the bottom, being completely out of breath as it was removed. Again I saw the evil smirk across Alice's face as she still continued to apply the lipstick to my lips. I said the magic phrase again, but before I could finish it the next dildo had been stuffed in my mouth, continuous force from Alice forcing it further and further down my throat. As it started to trigger my gag reflex I started to panic against my restraints until I finally resigned and tried to relax my throat, watching in a combination of shock and sadness as it continued to slide down my throat until I pressed my pink lips against the base. Alice held it there for a moment before sliding it back out.

"I see you're the kind of slut that just needs a little force. That'll be fun - we haven't had a resistant one in a while. Miss Vicki loves those the best and they typically wind up making the best whores in the end. Anyways, again you don't get credit for that last one. You're really ranking low in each stat so far - maybe you'll make up for it with your pussy eating. I mean, you have to be good at something, right?"

I watched as Alice hiked up the bottom of her white dress, showing that she wasn't wearing any panties underneath. She released a bit of the tension in the chains, lowering me down to just below her waist, eye level with her shaven pussy. It was glistening as she had obviously become turned on during this analysis procedure. She came over to me and swung one of her curvaceous legs over my head, now straddling me as she was on her tip toes. She slowly lowered her feet down to be completely flat, causing her pussy to completely sink down onto my mouth. She gripped the chains and started to slowly sway me back and forth, causing my nose and mouth to slide along her pussy and occasionally touch her asshole. This was also causing the massive dildo still deep inside of me to start fucking me as I swung front to back, eliciting groans from me as I was reminded of its thickness testing the boundaries of my hole. Breathing was difficult like this, but I noticed that I could periodically grab a breath as she slid me away from her. Finally she stopped and kept me centered on her pussy, taking my nipples in her hands and twisting them. I went to work on her pussy, licking like never before, sucking in her clit and thick lips, shoving my tongue as deep into her pussy as it would go. She seemed to be getting turned on as she twisted my nipples harder. I licked faster and deeper inside of her pussy as she started to lower her weight onto my face, grinding her pussy against me now. Finally she shuttered and I felt the rush of her cum release from her pussy. She apparently was a squirter as the juices streamed against my face, some going up my nose causing me to cough and spasm underneath her. She climbed off of me, pulled her dress back down and walked over to her clipboard again as if nothing had just happened.

"Plenty of room for improvement, but overall, not the worst I've ever had. Okay sweetie, that does it for your initial testing for today, let's get you down from there."

She walked over to the machine with the dildo in my ass and turned it to life for a moment, causing it to fuck me. She giggled as it went to work on me, but I was too exhausted at this point to protest - I was at her mercy. After a few minutes she turned it off and wheeled it back to the wall. She then wheeled the bench back underneath me and released the cranks to let me down on top of it before unlocking the cuffs holding me in place. I collapsed back on the bench, but Alice was wasting no time and pulled me to my feet. She tossed me my dress as I clumsily put it on with the combination of the 6" heels I was wearing and the workout I had just been put through. All I could smell was the scent of Alice's pussy as it was deep inside my nose and I was sure it was also in my wig at this point. Once my dress was on Alice led me back out of the room and into an office across the hallway where Miss Vicki was waiting in an executive style chair behind a massive desk. I was led to a small chair across the desk and sat as Alice handed Miss Vicki the clipboard and then disappeared back into the store.

Miss Vicki put on her glasses and panned over my testing results. She shot me a stern look and then went to her computer, apparently logging my results into some kind of a program. She flipped through a few different screens, entering values and then switching to the next for what went on for roughly fifteen minutes as I just sat there attempting to recover my energy. Finally she spun her chair around to face me.

"Okay, Candi. Here's the deal - your Master has paid me good money to put you through my training course, which will transform you from this shemale bimbo wannabe that is sitting before me into a top of the line pleasure inducing machine by the end of it. I understand that you are here against your will, so to speak, but that is here nor there and is of no concern to me. I am only interested in results, I don't care why you're here or how you got here or who you were before you came to me - right now, you will do exactly as I say or you will suffer dire consequences. To give you an idea - the last one who disobeyed me to the point of no return was sold into sexual slavery overseas, where it is my understanding that, a 'girl' such as yourself would have her testicles removed and be drugged up, locked in a room and have several John's come in to be pleased however they wish multiple times per day. That would be your life. So, as bad as this sound, I assure you that what I offer is much better than the alternative. Do you understand?"

My head was spinning - how had my life come to the point where being trained to be a model slut was the best alternative I had available to me? I collected my senses enough to nod a shock induced 'yes', so Miss Vicki continued.

"Good - we'll work on your manners as we go, but for now you are to return home the same way you got here. You will report back to me tomorrow evening at 7pm sharp where we will begin your official training. Before that time, you will have the following assignments. On your way home, while you are on the subway, you are to initiate a sexual act with at least two men. An associate that you don't know will be following you from a distance to ensure both your safety as well as your cooperation. Once you have completed that task you may leave the subway and return to your apartment. Once inside, you are to watch the instructional video of how to give the perfect blowjob as well as two of the male on female pornography films. During all of these films you are to take copious notes. When you report to me tomorrow I want you to be able to tell me, from memory, what makes a perfect blowjob. I also will ask you various questions about the other films - how the female moves as she is being penetrated, what does she do and say to help her partner experience the most pleasure possible, how does she seduce him prior to intercourse. You will be required to answer all questions to perfection in order to avoid a punishment, and from what I can see on your chart, you would not do well with my punishments, so I suggest you watch the movies more than once to ensure that you have a complete understanding of them. Now, off you go."

Alice again appeared at the door and guided me by the arm out of Miss Vicki's office. She walked me through the store and out the front door, closing it behind me. I had reported to the store at roughly noon and here I was leaving at 5pm, the middle of rush hour. The subway would be packed. I made my way through the three blocks of walking to the subway station, again picking up a ticket under the name of "Candi" at the ticket station, again walking down the stairs and feeling everyone's eyes on me as I waited for the train to arrive. I looked nervously around the strangers waiting for the train, wondering which of them was Miss Vicki's associate that was to ensure I did the unthinkable and initiated a "sexual act" with at least two men on this ride home. So many of the people were undressing me with their eyes, though, that it was hard to discern who the spy was. Before I could examine any further, the train pulled into the station, packed to the brim with people as I made my way on, sliding in between people until I finally found a small opening to stand. The doors shut and the train pulled off.

SissyIndy
SissyIndy
988 Followers