tagTranssexuals & CrossdressersTrapped and Trained Ch. 14

Trapped and Trained Ch. 14


It had been thirteen days since my last outing. Thirteen days since I was forced to sit in the middle of a bukkake of dozens and dozens of men, feeling the warmth of their sticky semen drizzling down my cheeks and chin, dripping steadily onto my exposed, and now pierced, breasts before being made to clean it all off, swallowing every last drop. Thirteen days of being trapped in this prison of an apartment, a place I used to call home but now call hell. Thirteen days...

I wish I could say that I'd been left alone, but I was kept on a meticulous schedule. Through the clitty ring that I was still trapped inside as well as the intercom system that could blare obnoxious and near deafening noises, I was being manipulated around the clock. My biological clock was starting to adapt as well, sadly. I felt like a dog being trained. They say that, to truly create a new habit, to perform the same task for seven straight days - try thirteen and everything becomes second nature, even the things I was being made to do. It was all becoming automatic and I hated it.

Every morning at 6 a.m. sharp I was to roll out of bed. I would change out of my lingerie and step into one of my skimpy bikinis, apply tanning lotion all over my body, then lie down in the tanning bed for 15 minutes. Once my time was up, I would step out and return to my room, where I would remove the bikini and take a shower. When the shower was over I would get out, blow dry my hair, straighten it and then put on my lotion and makeup for the day.

Next I would walk to the fetish room and open up my morning message - I wasn't sure if it was from my Master or Vicki or just someone with a very perverted mind, but it was always there waiting for me. Inside of this email was no text, just images of the clothes and jewelry that I was to find in my various closets to wear for the day. It was always something skimpy and revealing... periodically there would be no top pictured, so I would be required to walk around topless, feeling my heavy breasts dangling from my chest, looking down to see the little silver balls peeking out from both sides of my nipples. On those days I actually found myself yearning for a bra to wear before I would come around and tell myself to be thankful that I wasn't wearing more feminine attire. I would try to imagine myself wearing my gym shorts and no shirt, walking around as a normal guy on a normal day... and it could be convincing until I would feel the string of my thong invading the crevice between my ass cheeks, or I would have to pull up my stockings on the days I wasn't made to wear a garter belt.

Once I was showered, made up and dressed, I was required to report to the living room. I go to the kitchen and retrieve my morning protein shake from the fridge in the kitchen. On the kitchen counter would be my assortment of pills for the day, which I was required to swallow and then show my mouth to the camera, lifting my tongue and pulling my cheeks open as it zoomed in to ensure that I had swallowed them. I tried fooling this system on the first day only to receive an immobilizing jolt through my clitty ring for five minutes... that was enough of a warning not to try it again. Such precautions were always taken that it seemed I was always a step or three behind my captors. I hated being in this situation and hated even more that it felt like I was being outsmarted by them at every turn.

After taking my pills and drinking my shake, it's typically around 8 a.m. For the next 3 hours, or for however long the videos are played, I'm to sit on the couch and 'research' whatever content is placed on the TV. For all ten days the first video has been an instructional one on how to perform the perfect striptease and pole dance. I must have had an entire notepad filled with notes on the various moves and tips provided in that video - it was ingrained in my head to the point where I could practically recite the entire thing. After that video ended I would sit through 2 or 3 more, typically porn videos where I was to always place myself in the role of the female (or the bottom male for gay videos) and to take copious notes on how that person performed. What he or she did to enhance the sexual pleasure of the one that he or she was fucking/sucking/seducing. By the time the videos were done my hands were always cramped from all of the writing - if I ever paused for what felt like more than two minutes I would receive a warning shock through my clitty ring, always answered by furious note taking on my part.

Once the videos were over I was to go to the room with the tanning bed. Inside there had been a stripper pole installed, as well as a life-like mannequin with an 8" fully erect strap-on locked to his pelvis, sitting upright in a chair. The first 45 minutes I was in this room I would have to perform various stretches, getting loose and limber. I'd always considered myself a fairly flexible person, but ever since starting this stretching routine I more flexible than I'd ever imagined possible. I couldn't quite fit my feet behind my head, but it sure felt like it was coming soon... a thought that scared me. I was able to bend all the way over at the waist and place my head between my legs, looking up to see my fake pussy and asshole (which it has now become second nature to refer to as my pussy).

After the stretching was done and my muscles had been sufficiently warmed up, the flat screen TV that was mounted on the wall would turn on, signaling that it was time to start my performance. For the next hour I would mimic everything done on the TV. The first half hour was done on the stripper pole. I'd swing around on it, hold myself upside down, slide the pole up and down between my breasts, between my ass cheeks. I'd lean back on my hands, straddling the pole, sliding it up and down between my thick fake pussy lips, all the while tossing my hair around to the beat of the music pounding inside of the room. It was an incredible workout, probably harder than anything I'd done before.

Finally that music would stop and a different video would come on the screen. I always hated this part the most. I'd swallow deep and step off of the mini platform that the pole was up on, moving over towards the realistic looking mannequin with the huge cock bulging out from underneath the jeans he was wearing. Again I'd mimic the video, gyrating my hips up against his cock, pressing my breasts against his face, straddling his legs as I moved up and down, acting as if he were fucking me. Then the worst part of the performance would pick up. I'd unzip his pants and pull out the monster dildo, then go through the seduction moves again, this time feeling the cock sliding up and down my ass crack, occasionally getting caught and almost sliding inside of me before I turned around and worked my way from pressing my breasts against his face on down until I was sliding the dildo in between my breasts, breathing warmly on it as it made its way up near my mouth. I was never made to actually take it in my mouth or pussy, but what I was being made to do was almost more embarrassing as I moaned and ground my ass into the crotch of this mannequin, feeling the dildo press against me, trapped between my body and the rubbery plastic of the mannequin. All the while I could see the red dot emanating from the camera in the corner of the room, a reminder that people all over the world could be watching and that the video was being recorded, now forever existing on a hard drive somewhere.

Once all of my "performing" was done with, the time was usually around 1 p.m. From then until around 4 p.m. I had to go into the fetish room and chat with my "fans" on my site, consisting also of performing for them anytime someone paid a fee, allowing them to send me a request. There was a video chat going on, but they couldn't hear me so all of my responses had to be typed. I found out that this was because they wanted to be able to monitor what I sent. This was found out the hard way when one man requested that I spend the rest of the chat with an 8" vibrator in my pussy that could be controlled by the users in the chat room. I sent a message telling him to go fuck himself and calling him a pervert, but what instead showed up on my screen was a long message about how I had so hoped that someone would allow me to use that plug, that it was my favorite and that I hoped they would really test my limits with the controls. I stared at the message dumbfounded until a private message appeared on my screen in red font, warning me to behave appropriately and to hurry up with accommodating the plug request. The rest of that chat was hell as I spent the next hour with a plug in my pussy that was constantly fluctuating its speed, never allowing me to grow accustomed to its presence inside of me. The users constantly laughed and mocked me as they watched my expression changing with the pace of the vibrations... yet I still had to tell them about how 'good' it felt and how much I 'loved every second of it'. Fucking pricks.

After my chat session on my site was done around 4 in the evening, it was time for another protein shake and another dose of my pills. I'd choke all of that down and then be back on the couch watching more videos, taking more notes, taking part in the participation points of the tutorial videos or re-enacting particular scenes with my pink dildo. I'd be forced into that for a solid two hours, my body completely spent by the end of it around 6 p.m.

Once the videos clicked off for that session, it was back to the tanning bed. I'd gladly kick off the outfit I'd been made to wear, but then begrudgingly slide up another pathetic excuse for a bikini, putting the straps perfectly in line with my now extremely defined tan lines. Most of my body was a perfect bronze tan, but underneath those lines was now a contrasting white that stuck out from all angles, the lines of the thong dipping down between my cheeks from high up on my hips. My breasts were a beautiful tan color aside from the small triangles just over my nipples and my aureoles, small spaghetti straps jumping up over my neck and behind my back. More tanning lotion spread all over my body and fifteen more minutes in the tanning bed.

After tanning I always felt disgusting, but rather than get to take a shower I had to stay in that room and go through an extended stretching routine that lasted over an hour. It was similar to the routine before I had to perform on the pole, but with much longer counts and much further reaches. As it went on I could feel the elasticity in my muscles increasing and hated to say that they felt great once it was completed. Once I was free from this place I thought I might actually continue with these stretching routines. Once I was free...

Around 8 p.m. it was time for a long, hot bubble bath to ease my aching muscles. Like everything else, however, I wasn't allowed to just sit back and enjoy it. At the bottom of the tub was a small pink dildo which I had to slide my fake pussy over, feeling it press up against my imprisoned cock underneath it. The whirlpool of the tub would kick on, forcing the dildo to vibrate uncontrollably and massage my cock through the fleshy interior of my fake pussy. It drove me wild and made it impossible to concentrate, but it was also increasingly frustrated as the ring around the base of my cock made it impossible for me to orgasm - it just took me to the edge and kept me dangling there for the duration of the bath.

As I stepped out of the tub and put lotion all over my body once again, it was back to the fetish room to check for my nightly email. Inside that email again would be pictures of what I was required to wear to bed - usually some kind of elegant lingerie. I'd go through my closets and drawers trying to find the matching items, angrily slide them on and then slip into bed, feeling the silk sheets tickling my soft, silky smooth legs as I moved, sending shivers up my body. If I was lucky I'd immediately fall asleep - but most night I laid there in bed, completely awake, afraid to close my eyes and to see the images burned into my mind of all of the cocks I'd sucked and ridden. Most nights ended with me curled up in a ball in the bed, my face buried in the pillow, rocking myself to sleep before 6 a.m. came the next morning and it started all over again.

6 a.m. on the 14th day came, marking two weeks since I'd been made to do anything with a real cock. I suppose that was good news, though it was hard to accept that good news to me now was making it through two weeks without having a throbbing cock pulsating inside of me until it spewed its load in me or on me. How much times had changed. How much I missed my old life.

No time to think back now. I rolled out of bed and slipped off the pink baby doll I'd worn to bed last night, followed by the crotchless black thong. In its place I slid up a black wicked weasel thong bikini, looking at the tiniest patch of material straining to cover my fake pussy lips before putting the strings and cups in line with my tan lines. I straightened up and spread the slippery tanning lotion all over my body and climbed into the tanning bed for my morning session. Fifteen minutes later I could have sworn I felt the tan lines burning even brighter in contrast to my body as I walked into my bedroom and slipped off the bikini, hopping into the shower to wash off the greasy feeling of the tanning lotion.

Climbing out of the shower I went through my normal routine of drying and straightening my hair. It took me a while to get used to using a hair straightener, but after watching a handy tutorial I was now becoming quite the pro at it, hating the new skill I had picked up as I looked in the mirror at my blond streaks of hair now flowing beautifully over my shoulders and resting over my breasts, the silver balls of my nipple piercings peeking out from the small gaps between the blond and black hairs that my now permanent hairdo was styled with as I fixed a few strays.

I was getting used to my breasts, as much as it surprised me to be saying that - I really never knew how different it could be to have these heavy pieces of flesh hanging from your chest. They got in my way for the first week or so as I would knock items over or hit them on my keyboard as I leaned in on the computer, but now I was growing accustomed to having them there and the pressure on my back that came with them. The stretching and working out seemed to help strengthen my muscles, making carrying them around a bit easier, but I also learned that corsets and bras offered wonderful support to them... so even though I hated wearing those items, I seemed to be much more comfortable when I had them on with my D cup breasts fully supported.

I caught myself from the mesmerizing moment I was in the midst of while staring at my breasts and brought myself back to reality. I sat down at my vanity and began picking through the various makeup items, applying a generous amount of everything just as I had learned. I put on a hot pink shade of lipstick along with the other staples of my routine... I didn't have to go as heavy on the foundation any longer with how my tan was coming along as well as how the pills I was taking were softening up my skin. I could go more with my "natural" skin tone now, but I still put on plenty of blush, mascara, eyeliner and eye shadow. This was probably the most humiliating part of getting ready as it was, essentially, up to me on how I looked in the end, which was always like a prostitute on the busiest night of the year. But I knew that if I didn't do a good enough job that I would be required to do it all over again, so I figured I would just try to go through the humiliation once and then be done with it.

Looking at myself in the mirror I was satisfied with my whore-ish look. Well, I wouldn't say I was 'satisfied' per se, but I knew it would suffice well enough for me to move on to the next step. I stood and walked into the fetish room, sitting down at the computer to see my morning message waiting for me, as always. As I popped open the message and looked through the images, something just seemed different as the outfit was more revealing and intricate than usual, but I thought nothing of it and went on my quest to match everything up.

First was a dress that no woman in her right mind would ever wear, I didn't care who it was. It was labeled as a 'cage dress' and was basically just strips of leather with silver studs in it. It left practically nothing to the imagination as strips of leather were formed to leave large squares open all around the dress. There were no bra cups, so my chest would be completely exposed and unsupported as a thin piece of leather would simply rest on the top of them, meeting a silver o-ring in between them. A loop came up from that o-ring that would go around my neck and hold the dress up. Down from the o-ring a long vertical strip of leather went down to the bottom of the "dress". There were other vertical strips that ran down as well, I counted seven in all, spaced out evenly throughout the dress. There then were six horizontal leather studded strips that ran around the dress. None of the strips could have been more than half an inch wide, so you can imagine that the squares that were left by this pattern were quite large and extremely revealing.

After finding this dress I saw that I was to also wear a black thong underneath. Well, at least part of me would be covered by solid clothing I thought, even though the crotch of the thong would do little more than hug the outside of my fake pussy lips from the look of the photo. My thoughts were confirmed when i found it - the material seemed sheer as I held it up to the light, seeing my fingers behind the thin black cloth. Wonderful.

Once I had those items I was on to find the black leggings that were pictured next. The front and back were a fence-net looking material while the sides sported smaller fishnet openings from my mid thigh down to my ankle. I shuttered as I imagined how it would feel to slide the material up my silky smooth legs before moving on to find the 5" open toed black heels I was to wear to complete my wardrobe. I looked down at my toes, remembering how I was told by one of the fans on my site to paint my fingernails and toenails a bright pink shade and cursing whoever that person was.

I brought all of the items back to the bedroom and began the process of putting everything on. The final result made me feel ridiculous, but looking in the mirror all I saw staring back at me was one of the hottest pieces of ass I'd ever seen. This outfit screamed sex appeal and, as I suspected, left very little to the imagination. My massive breasts perkily hung free with the strips of leather all around, providing no purpose but to drive men and women alike wild with out kinky it appeared. The tan lines of my breasts seemed to contrast even more now that the black leather was surrounding them. I turned around and saw the black string of my thong disappearing between my ass cheeks, the square openings the leather strips formed doing nothing to hide every last detail. I looked closer to see my fake pussy lips bulging against the tight sheer cloth trying to contain them. The leggings definitely added a sexual effect to the outfit with my bronze legs peeking through the various holes in them down to my heels with my pink toes standing out through the opening. I hated to admit it, but fuck I looked hot.

It was becoming harder to snap myself out of those trances, but once I did I cursed myself for letting my mind wander once again and forced myself to think about my poor cock caged up, unable to get out. I gulped and my face was on fire as I angrily walked out of the bedroom and into the kitchen. For a moment I thought about rebelling, about stripping the clothes off and just allowing them to send enough electricity through me to just end everything... but I was still hanging on to the belief that better days were ahead. Days where I would be free, where I could get all of this work reversed and probably go through some kind of drastic psychotherapy to forget that it had all happened. Those thoughts may seem foolish, but they were getting me through each day as I continuously went through the various possibilities of escaping in my head, wishing that some brilliant idea would come to me and that I could just vanish from this life.

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bySissyIndy© 10 comments/ 102215 views/ 27 favorites

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