The Assessment
It was Friday afternoon. I arrived at Boss's house all excited. My big test was this weekend and if I passed I would be allowed to cum. Just the thought of that focused my attention on the chastity device encasing my genitals in unyielding steel. I grabbed my gear bag and headed into the garage of Boss's house via a side door. His black jeep was parked in the driveway, leaving plenty of room for me to prep myself in there as I was expected to. My test was not till tomorrow, but Boss wanted me to be in the right headspace for it to give myself the highest chance for success. I entered the garage and locked the door behind me and then quickly stripped, pulled out my rubber suit and quickly went about getting myself into it. The tight black shiny suit clung to me as I slid into it. It felt so good and smelled great and my poor denied cock strained hard in its prison. I really hoped I passed my test tomorrow; it was so long since Boss had allowed me to cum!!
Once I was suited up I strapped my gag on. It was an inflatable butterfly gag with a tube that would allow Boss to feed me liquids through it. As directed, I had switched to protein shakes the day before so that my liquid diet would not require me to pass solid waste. I quickly inflated the gag. I wanted to stop once my mouth was full but I knew better than that and especially knew better than that on assessment weekends, so I kept pumping until my cheeks where bulged out and uncomfortably full of the gag. Once this was done I went over to a corner of the room where there was a drain and some o-rings attached to the walls. I quickly attached some leather restraints around my wrist and locked them with the small padlocks that where left there for me-- locks that I did not have the key to. I attached one wrist to one of the o-rings on the wall and then pulled a blindfold over my eyes and felt around until I located the other o-ring and then attached the other restraint to that. Then I waited. I guess Boss was as excited about this weekend as I was because I didn't have to wait long. I heard the door open and not too long after that, smelled His cigar smoke. I concentrated on keeping my breathing steady, forcing myself to show no discomfort as His stogie smoke filled my nose. I heard the slight creak of leather and could only imagine how He must be dressed. My cock twitched again thinking about how close He would be standing to me, that leather clad god of a man with His cigar.
I felt Him move behind me and spread my legs to assist with what was to come. The Bardex enema nozzle was well lubed and I had lubed myself up a little before coming, so the insertion of it caused me no discomfort. I felt the bump of the first bulb pass my sphincter and then not long after I felt it swell. Boss inflated the first balloon and then the second one. Now whatever He pumped into the enema nozzle would be trapped in me for as long as He saw fit. I felt His hand on the back of my head and then he removed the blindfold. I blinked a few times in the fresh light. He was dressed as I had imagined, but the actual sight of it always outdid my imagination. Starting at the bottom where His black Sendra boots, the toes coming to a nice point, the heel nice and high. The leather of His jeans was tucked into the boots so I could admire the pattern on the sides of them that hugged His lower body. The pants were held up with a Sam Brown belt. He was wearing a leather shirt tucked into the jeans and a leather tie with a nice neat knot rested under the collar. Over the top of this a heavy leather motorcycle jacket made Him look hot as hell and made my cock strain even harder. He was grinning, which usually meant I was not going to enjoy what came next. I looked to my left and suppressed the urge to groan. Three bulging enema bags were hung next to me. Boss walked over to the small bar fridge He kept in the garage, opened it and pulled out a 2 liter Coke bottle a little over two thirds full of golden liquid--His piss saved up for me. I then knew this was going to be a really hard assessment weekend. I really hated cold piss and I knew those enema bags where going to stretch my gut to busting, but that's what Boss loved. Having a tied up, helpless boy hanging there with a bulging gut full of water and His piss. He hung the bottle upside down near my head and the tubing that He had attached to the neck of it attached to my gag. It was pinched shut with a clip just like the bags. Not hurrying at all, and with a deliberateness that only caused my dread to grow, Boss unclipped the clips on the three bags and then finally on the tube to the bottle of His piss. Immediately, His cold piss filled my mouth, the coldness making the taste of it nearly unbearable, but I knew my torment would not end till that bottle was empty so I dutifully began to swallow.
Soon I was in agony. The water in the bags had filled my gut quickly and the cramps had started not long after that. Boss obviously loved it. My gut was swollen and distended and the rubber stretched over it. Boss was running His gloved hands all over it, feeling the solidness of it as the water trapped in me pushed it out; laughing at my occasional burp as I also filled myself with His piss. It took like what seemed forever till I finished all the cold sour piss in that bottle. The whole time cramps wracked my body, till my legs where shaking and tears where running out my eyes. Boss had a massive bulge in His jeans as he continued to rub His big leathered hands over my gut, feeling the change to my body He had caused by filling me at both ends with so much liquid. Mercifully, the last of the piss finally left the bottle that hung near my head and traveled down the tube as I kept swallowing. I let out a grunt to signal that I had finished. Boss nodded that He understood and kept rubbing my belly with His gloved hands some more. I tried not to whimper too much but the cramps and the discomfort of holding so much liquid in was starting to take its toll. I concentrated on the fact that I was being assessed and tried to keep as calm as I could, breathing in through my nose in deep measured breaths. Of course with Boss and His cigar so close this didn't help calm me too much, since then I had to also concentrate on not reacting as I breathed in deep lungfuls of His cigar smoke.
Soon however the torment ended as Boss disconnected the enema nozzle and then deflated the balloons, allowing the nozzle to slip out and the water to gush out of me and disappear down the drain. It ran perfectly clear; I had rinsed myself out well before coming over.
Boss unclipped my hands and led me, trembling slightly still, inside. He walked me into the play room and I looked straight over to the loader to see what I was in for. It looked like this assessment wasn't going to get any easier anytime soon. The loader was His name for a stool that sat over a winch on the floor and under an exposed beam in the roof. On the stool sat a large metal plug, one of the largest I knew He had in His collection. I walked over and stood above the stool; Boss walked over to the shelves in the corner and returned with a handful of items. He stood in front of me grinning as He smoked the last of His cigar, looped a piece of rope back on itself and then slowly started to wind the tail end around and around the doubled section. Soon He had a noose ready and waiting for me. I bowed my head and He slipped it over my neck and then with the flick of His wrist threw the other end over the beam and tied the trailing end of it with a half hitch. I looked down at the noose to see how much slack I had. Many times I had been loaded so I was able to gauge how long it would be till the noose tightened and started to cut off my air. From the looks of things I would actually be seated fully by the time this happened. Boss pulled my arms behind me and up and clipped the restraints together, and then He attached some chains to some o-rings in the floor and looped them around my ankles. My feet were far enough apart that once I was seated on the stool it would be very difficult for me to stand up again since my arms would be useless.
Boss then held up THE KEY. I couldn't help but groan this time. Oh how I wish I could reach out and take the key, but only Boss had it and that's the way it looked like it would stay for a while. He unzipped the front of my catsuit and then used the magical key to remove my chastity device. My free cock immediately sprang straight up in the air and I groaned at how good it felt to be able to get an erection again. Of course with the good came the bad. My balls also now hung down exposed and Boss waited no time looping a thin chord around them a few times and then tying it off at the other end to the loop at the end of the hoist cable. He then went and sat in His chair and pulled out His big fat cock. He was hard as a rock and I felt the drool in my mouth gather as I looked at that tasty piece of meat he wrapped His gloved hand around. He sat back and grinned at me, then as he worked His cock he pressed the button he held in His free hand and the hoist started up.
I will spare you the obvious description of what happened from there, it was not too long later that the tugging on my balls had me hovering above the top of the plug and the noose around my neck had tightened and would soon have me struggling for air. My thighs where burning as I tried to maintain the stance above the plug. I really believed I wasn't ready for that monster yet, but I didn't want to fail my assessment weekend so I kept my eyes focused on a spot in front of me and tried not to think about what was coming next. The noose was pretty much helping me maintain my balance at the moment. Soon however I would be forced to sit onto the plug and that's when it would start to choke me. I heard the whir as the motor on the winch started turning again and tried not to panic as I felt the cold metal tip of the plug make contact with my skin and at the same time the noose around my neck began to tighten and I had to struggle a bit to take a breath in.
The agony of the plug forcing its way into my guts was only mitigated by the fact that I barely had enough air to think about it. Black spots where swimming across my vision and I had lost the battle with composure and was thrashing around trying desperately to stand so I could not only get air but free myself from the invasion in my ass. But the cord around my balls forced me to lower myself more and more. The echoing started in my ears and my frantic snorting for air through the noose was getting me less and less results. I locked eyes with Boss standing in front of me, His gaze intense. I tried to plead through my gag but of course that was helpless. My legs shook and trembled and I desperately tried to fight off the welling blackness in front of me, but in the end it got me. My eyes rolled up in my head and I passed out.
It was really a blessing in disguise and I know Boss did it to help me because He cares. He pulled the half hitch free the second I passed out and my body would have simply slumped down. He would have steadied me with His hand, and while I was unconscious my relaxed muscles allowed the giant plug to slip into me and then the base would be grasped by my ass and it would be locked into place. He must have also reached orgasm at that point since when the room spun hazily back into view, He was panting and the front of my catsuit was covered in His cum. I groaned one long deep agonized groan at the feeling in my ass, I was REALLY full. All I wanted was for it to be out of me right then. But Boss had His hand on my shoulder steadying me on the stool and my balls were still anchored to the floor. He stood there and kept me steady as the shakes that follow regaining consciousness finished wracking my body and kept firmly pressed down on my shoulder. I couldn't help it, tears sprung to my eyes and I wept as the agony in my ass overcame me. Boss pulled me forward and patted me on the back as I sat on the stool weeping from pain, my head resting against His chest. It was not the first time He had hurt me so bad I had cried, and it wouldn't be the last. He was molding me to be a better person and that would require some discomfort on my part.
Not long after that I was on the footrest, well that's what I called it anyway, It was like a long low coffee table, but with a leather padded top and thick leather straps every 20cm. Boss had helped me stand up with my new giant plug inside me and then had given me a leather cuddle, in the form of a leather straight jacket. I was now wrapped up nice and tight in its strong leather hug; the crotch straps between my legs had been done up nice and tight to ensure that the plug would not shift from its place deep in my gut, and honestly I was not sure I could actually shit the damn thing out anyway, I had then been led into the living room and laid down on the footstool, then Boss had carefully buckled up all the leather straps with the last one going across my forehead. Once they were all done up tight, (and Boss made sure that they were TIGHT), I couldn't move at all. The table was solid wood, so even if I struggled it wouldn't be going anywhere. Boss had left the room and when he walked back in with a bucket I winced inside-- this assessment weekend was obviously going to be a very trying one. Boss placed the bucket down and pulled two items out of it and I knew exactly what they were going to be. The first was an icepack which He wrapped around my cock. It was not long till the freezing cold contact caused me to lose my hard on and that's when the next item was put to use. I hated sounding and so I hated catheters even more, the feeling of the tube sliding down the inside of my cock was unpleasant and just wrong, and the constant burning 'I have to pee' sensation once it was inside me was not at all fun. The end of the catheter was placed in the bucket, and then Boss sat back, lit a big cigar and rested His booted feet on me while He enjoyed TV. Now was quiet time. I had fulfilled my purpose to make Boss cum, and He had no need of me at the moment so I just lay there quietly and enjoyed the fact that I had been rewarded with being His footstool. There were plenty of other out of the way places He could have stored me.
Before he went to bed Boss fetched a cold protein shake from the fridge. It was half full and He topped the other half off with a steady stream of His hot piss and then fed a tube from it to my gag so I could suck it down throughout the night. (If I knew what was good for me I would make sure it was empty by morning or at least empty enough to take Boss's morning piss). Then He went to bed. Laying there with the pain of the giant plug in me still throbbing though my body, I concentrated on the small noises of the room to take my mind off my situation. I was like this to get into the right mindset for tomorrow when I was to be assessed, so I needed to take in the lessons Boss was teaching me and get in my sub space.
The next morning after Boss had fed me His morning piss and then had His own breakfast. He unstrapped me from the footrest and took me into the bedroom where my uniform was laid out. First were the jeans which had been pre-prepared. I had found a pair that were pretty tight and had been wearing them and then they were hosed down by Boss and then He staked me out in the yard, so that when they dried on me they were nice and skin tight. Before he had me put on the jeans, Boss added a ball stretcher to my balls, and I felt Him press against the base of the plug and then He passed a small box with wires attached between my legs. I realized that the metal plug was an electro plug and this was the unit for it. I struggled into the jeans; it involved me having to hop and lie on the bed and tug and all sorts of uncomfortable positions to do while wearing a butt plug. Eventually the jeans where on and then Boss handed me a belt with a GIANT buckle on it. The thing covered all of my hand and then some. I threaded the belt around and did it up with the buckle covering a good portion of my crotch. Boss then slipped the electro unit behind the buckles and used some duct tape to keep it in place.
Now it was time for the boots. Until now I had only been allowed to wear lace up boots in Boss's presence and today was the assessment for whether I would be allowed to wear cowboy boots like Boss so for the test I was to be put in a hybrid pair. The heel and the toe of the boots looked like traditional cowboy boots but they were actually laced up, with 20 eyelets. Boss rolled up the bottom of my jeans and had me stand in them, although like I said they were lace up boots and instead of laces through each hole Boss threaded a zip tie and zipped it closed, and then on the top of each of the boots he threaded a chain around the tops of the boots and locked it through the loopholes of the boots. This took some time so I guessed I would probably be spending the night like this. Once the boots were done, Boss tugged my jeans back down over the boots. The outline of the chain at the top of the boots was visible through the jeans but unless you knew what it was or you where looking for it you would not exactly think something was amiss. I had to keep reminding myself that part of the assessment was that I had to appear comfortable in public. I was wearing clothing that would draw a little attention but not much for the area we were heading to. However, the clothes couldn't have been further from what I would usually wear but this was what the test was all about. Next came a simple plaid shirt that I buttoned up to the top. It would hide the neck seal of my rubber catsuit. However it was cold enough outside that I would need a jacket which is what would be doing most of the work for me. Boss then cuffed one of my wrists with a shackle and then handed me a plain black leather jacket. I pulled it on and then put my hands in the pockets of the jacket. I felt the hole in it and reached through and grabbed the other cuff and cuffed it around my wrist on the other hand and now I was trapped with my hands in the pockets. Boss left me standing like that and went to change.
It wasn't long before Boss returned and He looked hot as fuck. He had swapped His leather for denim; denim jeans and jacket, and the high black boots He put on would definitely draw some attention, since they stopped above His knees. The buckle he wore was just as big as mine. He wore His jacket collar popped up and He had a white Stetson on His head. He was hands down the hottest goddamn cowboy I have ever clapped eyes on. He had a black Stetson in His hands which he placed on my head. Since we where now both dressed it was time to leave and He led me by the arm outside and helped me into the jeep. Before we stepped outside He popped the collar of my jacket up. I bowed my head and with the collar and the brim of the hat, my tilted down head hid the gag still in my mouth. Once in the jeep, Boss buckled me in good and tight since my hands were locked in the pockets of my jacket. Then we were off. I swear He swerved on purpose to hit every bump He could find on the drive there, each vibration in the road sending waves of intense sensation through the plug in my ass.
We rolled into the area where the test would be carried out, a local rodeo that was on. Boss parked the jeep and then reached behind my head and unbuckled the gag and I finally was able to spit it out. I said nothing but flexed and stretched my mouth a few times. It felt great to have the gag out. Boss hopped out and came round and helped me out of the car. I took a step and then stumbled as an electro shock wracked through my guts. I gasped but managed to not make any noise aside from that. I quickly looked around. No one else was around thank goodness. The shock was probably Boss giving me a peek at the exam to come. I said nothing and continued to walk. Boss walked along beside me. The next shock through my ass barely caused a pause in my step, though my jaw clenched a little. We walked along. Boss's boots got some looks but not that many, and I didn't seem to attract any looks, which was fine by me since part of the test was that I draw no attention. We made a few loops around the area and went and found some stands to watch the main ring of the rodeo. Boss got up and left to head to the bar. This was a nerve wracking moment for me as I was left sitting in the stands by myself, the plug deep in my ass getting occasional electro shocks-- the only signal I had that He was still in the area. Soon He returned with a beer. He continued to ignore me and I continued to act as though nothing was amiss, that we were just two guys sitting and watching the rodeo. The day was cool, but we were sitting in the sun and unlike Boss I was wearing a few layers, which included a rubber cat suit underneath, so I started to sweat a little. Boss got up again and returned after a fearful 15 minutes with two beers, or at least two beer bottles. Boss casually dropped a key in my jacket pocket and I quietly uncuffed my hands and then accepted the beer bottle Boss passed me. I took a swig making sure to keep my face neutral, since, as I had expected, the bottle was actually full of Boss's warm piss. Boss then made the move I had been dreading. He opened His jacket and pulled out two cigars and offered me one.
So here was the final part of the assessment. Boss had respected my decision that I was a non smoker, though he still tormented me a lot with His cigar smoke. But if I accepted this gar off Him now and smoked it here that would mean I was accepting that I would be trained as His new cigar slave. There would be no turning back. And it really was an offer; there was no punishment for not accepting the offered stogie. The rewards however would be considerable. I managed to keep my hands steady as I accepted the gar from Him. I noticed a satisfied smile play across His face. He had me where He wanted me now, sitting in a public place dressed as He wished, with complete control over me. I relied on Him totally, and now I was accepting a new level of training. He held a light up for me and I put the end of my gar to it and puffed to get it lit. As he had lectured me on the methods, I tried to remember everything He said like not drawing the smoke into my lungs and managed to not cough too much to draw attention. The taste was so strong.
Once I had finished Boss gave me a nod of a job well done. I casually placed the key down on the bench we were sitting on and then slipped my hands in my jacket, and if anyone had been sitting close enough they may have heard the slight click as I refastened the cuffs around my wrist. Boss sat back and smiled as he swigged on His beer and turned up the voltage in my ass and watched me struggle not to give any signs of discomfort, no doubt planning all the scenes he could now put me through, now that I had accepted His offer to be trained as His cigar slave. No doubt some interesting times where ahead for me.
I was just happy that I had passed my assessment.