1 comments/ 59671 views/ 26 favorites He Creatively Escalates My Torment By: sydneydom Author's note: This story is set in Sydney, Australia, where it's the middle of summer during Christmas, and the sun stays up until 9 P.M at this time of the year. * I awoke to the sound of a heavy metallic click, immediately feeling the uncomfortable and unnatural stretching of my asshole that can only be the result of a widely spread speculum. He must have drugged me at our Christmas party. The last thing I remembered was feeling very tired after dinner, wanting nothing more than to go home to my soft bed. I shifted in my bonds, realising that my arms were bound behind my back and I was forcibly bent forward over some kind of hard surface. I could feel something strapped to my face, which felt a bit heavy for a conventional blindfold. "Oh good, you're awake." He clicked a button on the device, which whirred into action. My vision was still blurry, but I could see that he had put a set of "virtual reality" goggles on me. The image de-focused and refocused, and I could hazily see a girl in secretary's work clothes bent forward over a table with her arms handcuffed behind her back and her legs forcibly spread apart. It took me a few seconds to recognise myself in this awkward and unique third person perspective, realising that he had concocted a new scheme to push the envelope on how worthless and humiliated I could feel while he tortured me. Picking up a mirror, he revealed what he had done. He was wearing a device strapped to his forehead with cameras positioned just above each of his eyes. "I thought you'd like to really see yourself being abused. I've wired up the feed from these cameras to your goggles, so your eyes see what I see. Naturally, I want you to have a full stereoscopic 3d experience. " He slowly toured around my body, taking care to show me his meticulous handiwork. My vision was returning to normal and I felt a little impressed by how immersive and lifelike my hijacked vision was. I was strapped to a table in a room nicely lit by the summer evening sun. It couldn't have been long since the party. My tight grey office skirt was hiked up above my ass, and my black stockings were pulled down just below my ass cheeks. My legs were spread and firmly taped to the table's legs, stretching the crotch area of my stockings tightly between my thighs. Moving closer to my asshole, I could see that he had inserted a large metal speculum into my rear, which had already stretched my asshole an inch and a half wide. "I thought it would be fun to see how long it would take you to wake up." Observing myself like this was humiliating yet strangely exciting, giving me a new perspective on how helpless and exposed I am when bound in this fashion. Grabbing the handle, he playfully twisted the speculum. I could tell he hadn't used any lube, as he had decided a while ago that minimising my comfort whilst maximising his pleasure was the priority of these sessions. The warm metal stubbornly clung to my asshole, twisting and distorting my skin whilst refusing to slide relative to my sphincter. Applying pressure to the handle, he widened my asshole out another half an inch, clicking the speculum into place. I felt violated and so very horny. I could feel the wetness trickling from my cunt down my thighs, as I felt the cool breeze of the air conditioning unconventionally lapping against the inside of my open canal and damp legs. Seeing myself being manipulated in first person while immediately feeling the result of those actions felt incredible, like he had managed to find a perfect coupling between my shame and stimulation, reaching some sick new pinnacle in my debauched ass slavery career. It was almost as if it were my hands twisting and abusing my own asshole, with an uncompromising mind of their own that was completely unresponsive to my internal monologue's silent cries for mercy. "Today, your ass will literally be my canvas." I wasn't sure what this meant, but I'd surely find out soon enough. He peered into my asshole, using a torch to see more clearly. "I see you've kept yourself nice and clean like a good slave should." Daily enemas had become part of my routine now, as I was subject to this sort of abduction and treatment at any time without warning. Using both palms, he applied strong pressure to the speculum again, clicking it twice and stretching me out to a full three inches. My sphincter started to ache deeply as my skin felt like it was going to tear. He reassuringly inspected my asshole closely, calming me a little as I saw no signs of bleeding or long term damage. "Sometimes I grow tired of your puckered clamp of an asshole," he derided. "I think I need to experience your tender and fleshy rectum more intimately." He picked up what looked like a sizeable rubber inflatable plug from under the table and slipped it into my cunt with relative ease. Positioning himself with his torch so that he (and I) were peering deep into my asshole, he began to inflate the plug. I could see the lower surface of my asshole begin to bulge upwards towards its upper surface and the entrance of my ass. He mercilessly pumped away until my canal was fully pinched closed and he was uniquely presented with the lower surface of the inside of my asshole, which was now unnaturally pressed against the inside of the speculum. I had already habituated the piercing pain in my sphincter and this additional pressure presented a new and dull ache deeper in my anal tract. He unceremoniously prodded my newly exposed flesh. "My canvas is ready. Now it needs some art," he mockingly remarked. He pulled out a permanent marker from his pocket and began to draw concentric circles on my exposed rectal wall. The tip was sharp and rough and each stroke produced a piercing stinging sensation, leaving behind a burning trail as the alcoholic ink seeped into my tender flesh. I could see him drawing a target symbol on my canal wall, which strangely offended me as I realised what was coming. Sensing my realisation, he prodded and twisted the marker hard in the centre of the target, pushing my flesh against the unmoving inflated plug in my cunt and eliciting a sharp, focused and acute pain analogous to a needle's penetration. I could see that he had done a remarkably good job of drawing a neat, black target sign on my dry and exposed inner wall's flesh. He capped the marker with a click. "That's right, my art isn't for admiring. It's for fucking," he proudly proclaimed. His pants and belt hit the floor with a clank as his vision shifted while he positioned himself above me behind the table. This was going to hurt, a fucking lot. He stuffed a hard rubber cylinder between my teeth for me to bite down on during my impending ass rape. The build-up and unique perspective on my preparation had my heart racing as fast as possible, building a panicked excitement in me like I had never felt before. Breathing was becoming more difficult as I began to hyperventilate. I had never felt so scared and aroused before in my life. "It's going to take you months to get over this. Every time you climax, you'll be reminded of how it pales in comparison to this moment." He was right. This experience was going to set the bar pretty high. I felt tears well up as I reflected on the steadily escalating desire for debasement and torture that he had fostered in me over the last year. Over a short time he had turned this young and innocent fresh graduate into a deviant that craved nothing more than dry, painful and vicious ass rape. He had managed to retrain my once conventional desires so successfully that this fresh bout of shame only added to my already indescribable arousal. He began to shove his thick cock into my ass, ignoring the sides of my sphincter and pushing straight into my tender and exposed rectal flesh. Suddenly without warning, he thrust as hard as he possibly could, displacing the inflatable plug slightly downward and mostly pushing his cock upwards into the upper wall of my ass, searing deep into my colon's dry and raw flesh. My eyes shut involuntarily as I winced in pain, mentally retaining the last image of him fiercely grabbing my hair as he straddled me. It was a piercing and shocking agony like I had never felt before that could only come from this kind of calculated mistreatment. He began to violently rape my dry rectum as hard as he could, grunting satisfyingly with each thrust. Each penetration hit me like a piston, pounding my head with an indescribable torment, like a shock wave emanating from deep inside my ass and exploding upward into my head. The severe magnitude of the pain was quickly transforming, as I submitted completely to my sexual torture and felt my orgasm steadily build. Each successive thrust muted more of my anguish, adding more arousal and pleasure to my steadily filling reservoir of brain chemicals. The pain now felt like a distant memory as the scraped insides of my asshole gave off waves of pure, blinding ecstasy with each brutal thrust. I began to involuntarily visualise my vagina throbbing and ejaculating as my crotch area filled with an overwhelming rush of warmth and pressure. I wasn't sure whether the mechanics of my torture were causing me to piss myself, nor did I care. He smacked my ass hard with a cold and metallic object. Momentarily opening my eyes, I saw him holding a file in his left hand, whilst rhythmically tugging my head back with a fistful of my hair in his right hand. He reached underneath my pelvis and aggressively began to draw the long file across the head of my clit, slowly bowing it across my body like a violin. He pushed down hard and took care to punish my clit in one rough and continuous unrelenting stroke, bursting my reservoir violently with his commensurately violent action. The back of my eyelids turned a bright red, and my hearing was overcome by a blasting high pitched tinnitus as my brain began to be completely overloaded by my orgasm, causing me to uncontrollably scream as loud as I could. It felt like a dam had ruptured in my brain, completely saturating every sense and surpassing every sensory process I had ever experienced in one brief moment. As every pore and synapse simultaneously exploded in pleasure, my whole body started spasming in sync with my throbbing and collapsing asshole, which rhythmically clutched his cock and started to extract his cum. I could feel the throbbing action pulling on the rigid unrelenting speculum, generating more pain in my stretched sphincter which was constrained to a mild quiver as the adjacent walls of my canal pulsated rapidly. He mustered all of his energy, ploughing himself deep into my ass while pushing down hard on the speculum with his pelvis, cumming deep into my raw and abused channel. Finally spent, he lay on top of me as my orgasm continued to convulse my asshole and suck the remaining drops of cum from his now more slowly spasming cock. He withdrew his cock and backed away from me. He hit my ass hard with the file, "Open your eyes, fuckbag." He was peering deep into my ass with the torch. I could see the target symbol had completely disappeared, replaced by pink gooey traces of his cum mixed with my blood. My asshole was still mildly spasming, beating like a heart and uncontrollably compressing the inflated plug in my cunt. He shoved a finger into the lower wall of my asshole which had re-presented itself to the world by virtue of the inflated plug in my cunt that remained pressed against the speculum. Tracing out an impermanent target symbol delicately with the fluid mixture, he mockingly proclaimed, "Now THAT, is art."