Date: Fri, 24 Jan 2014 12:07:55 +0800 From: Matt Loh Subject: The Headmaster (scat) This story involves caning, spanking, breback anal sex and scat action. Feedback and emails are welcome! matt.loh.83@gmail.com *The Headmaster* I stared at the door in front of my Headmaster's door, feeling a lump in my throat. My heart was pounding in my chest, not knowing what to expect, and my cock was rock hard by now, straining against the gym shorts that I was wearing, in anticipation of what I hoped was to come.... Thinking back on what led up to today, my mind drifted back to my younger days; when I was in high school and in my early teens. Caning was a very common occurrence in schools and homes here, and there were strict rules for boys that we had to follow. Serious offences in school were punishable by public canings, and these were commonplace. I remember clearly watching the first public caning when I was 12 or 13 or so, being slightly in awe and fearful, at the same time being strangely aroused. Watching a bigger boy spread his legs and bend over, and crying out in pain as the strokes landed deliberately, slowly and painfully on his barely protected buttocks had a very dramatic effect on my groin and cock. I remember going off to the toilet after and jerking off vigorously with the image of the boy and the sound of the rattan cane on his buttocks fresh in my mind. Being that young and horny, I blew not one, not two, but three loads over the toilet seat till my cock was dry. I had gotten my first caning when I was 13 or 14. Back then, school canings were all no-nonsense, serious affairs. I remember being marched down to the Headmaster's office for an offence that I don't remember anymore now. That same feeling was there again; the lump in my throat, the pounding in my chest as I stood there in my shorts. The Headmaster's words were a fuzz in my brain as I struggled between the fear and how outrageously horned up I was. I was sure I was stiff as a rod in my shorts, and it already started to hurt. Then all of a sudden, I was made to bend over, over his large wooden desk. I spread my legs apart in a bid to give my cock more room to expand, and pushed my bum out; it felt good, sticking out like that. I remember him tapping my buttocks with the cane for aim, and then the first loud swich and thwack. The sting and pain was tremendous, it felt like my whole backside was on fire, I cried out once but didn't straighten up, and I could literally feel the welt form, my heartbeat throbbing along it. My hardon immediately vanished, but was not slow to reappear as I squirmed against his desk. The caning was slow and deliberate, as they often are, so the punished boy has time to think upon his wrongdoings (or so they say) and for the full sting of the strokes to set in. I was originally supposed to receive 6 strokes, but for straightening up and rubbing my buttocks, I received 2 extras. This was followed by corner time with my legs open and hands behind my head, humiliating, but extremely arousing as both my cock and the welts on my buttocks throbbed in unison. Following that first caning, I remember hurrying off to the toilet, locking myself in one of the cubicles and stripping off my shorts, getting naked waist down as my steel hard cock sprang free. I spread my legs wide and squatted down, vigorously pumping my cock with my fist. I came within 2 strokes, blowing a huge load against the toilet bowl in front of me and also onto the floor. I was still insanely horny even after, thankfully it was after school hours by then, and I remained squatting there, my asshole spasming as my orgasm came down, and I continued stroking my still hard cock. I placed a finger from my other hand back against my own asshole, which was by now lubed from the cum running down my asscrack. Opening my legs wider, I pushed my finger deep in, feeling my cock twitch in pleasure as I anally penetrated myself. Instinctively, I started fingering my asshole, feeling how the penetration intensified the sensations as I jerked off. I pulled my finger out intermittently as I fisted my cock, and ran it along the fresh welts on my buttocks, feeling the warmth. I contiinued jerking off furiously, cumming hard another 2 times before I grew tired and my legs started to really ache. Not bothering to clean up the cum, I got dressed and got home. Once home, in the privacy of my own room, I stripped off again after a bath, and admired the thick red welts in the mirror, getting hard once again. The welts were livid and thick, running nearly perfectly parellel across my buttocks, even through my shorts, I could see that the Headmaster's aim was nearly perfect, nearly placing all the strokes directly on top of each other, maximising the sting and pain for the boy. As I admired the welts, I stroked my rapidly hardening cock, which was by now, aching quite a bit from the constant arousal. From them on, caning became quite an obsession. The internet was readily available, and porn with caning, particularly on males, became an addiction. After school, I would spend hours scouring the web and downloading videos, keeping them stored away, masturbating while watching them countless times over. It was quite mesmerising, watching teenage looking guys to grown buff men taking canings. Some were quite severe, in particular I remember watching one with a very buff bottom guy with a shaved head bending over without restraints, taking a really severe caning by an even more buff, bigger black guy. He trembled and moaned, and took in excess of 100 strokes, getting and losing his erection a few times through the caning. He was bleeding quite a bit by the end of it, but he looked far from being spent yet. The black guy cleaned him up and the bottom quickly spread open his asscheeks as his Dom jerked his cock to full hardness. I had never seen a bigger cock than that, and I was extremely turned on, and jerked myself off, as I watched the black man lube his cock up lightly, then push his entire length up the bottom's asshole. The fucking was hard and relentless. Without even touching his own cock, then bottom spewed a load of cum, as the black guy kept up his fucking, only blowing his load over the other guy's face after a further 10 minutes or so. In school, I was in a way, sometimes fixated on getting caned. Like earlier mentioned, canings remained very commonplace even for minor offences sometimes, and were dished out fairly liberally. For recalcitrant offenders, expecially, the canings would get progressively more severe. I would often find myself on the receiving end of canings, for offences done on purpose, and without fail, was already extremely turned on. However, canings in school were always no-nonsense affairs, and they were not delivered bare bottomed, which I so craved after awhile, nowhere near as explicit as what I would watch online and jerk off to, and fantasise about having done on myself. Regardless, they were always quite severe, and the Headmaster, after awhile I think, got rather annoyed at having to see me repeatedly for punishments. He caned even harder and did not have any qualms increasing the number of strokes or giving me extra through the canings. Little did he know that after awhile, I guess I too developed a higher tolerance for the pain and sting, and progressively, I could stay aroused and hard throughout the whole caning without even losing my hardon. Near the end of high school, when I was about 16 or so, I remember vividly one encounter with the Headmaster. I was just caned the day before, a good number of strokes, and the welts were still very fresh. Working myself up into a frenzy later at home with a good round of porn and numerous jerking offs, I got into trouble again (on purpose) the day after and was promptly marched back to the Headmaster's office. I could see he was visibly annoyed at having to see me again so soon, and I was hard by then. Bending over again, I opened my legs, my cock straining against my shorts. He said in a business like tone, cane in hand, "Matt, I'm sick and tired of having to deal with your nonsense, 24 strokes today." I gulped in anticipation, I had never received this many strokes before. My cock throbbed as he lined up the cane against my buttocks. He stepped back so he would have more room to swing the cane, tilting back slightly then swinging his arm down hard, his first stroke showed me he really meant business this time. The thwack was one of the loudest and the sting was immense, upon my already welted buttocks, I started squirming immediately, crying out once (rare on the first stroke since by then I was a very seasoned recipient of canings). He gave time in between strokes for the burning and pain to build up until it was at its climax, which he timed perfectly, before he lay another vicious stroke down. The pain built up immensely, but I guess the masochist and submissive in me got the better of me. I was squirming in both immense pain and that same strange arousal as well, my cock remained hard and strained, and I got extremely close to cumming by the time he was at 15 strokes. I kept my legs apart, they were quivering somewhat, both in pain and the heightened arousal was in. My cock was still straining and it was starting to hurt. I could feel the Headmaster rap my buttocks with the cane a few times in warning for the next stroke. "Keep your buttocks out Matt," he said in a matter of fact voice. A loud swing, smack, and and excruciating sting followed almost imemdiately. The stroke landed probably perfectly right over some of my existing welts, really causing the pain to reach a peak. Coupled my extremely aoursed state, and my exposed, embarrassing position with my buttocks stuck out, I came immediately in my shorts. I moaned and cried out loudly, shuddering, my legs immediately turned to jelly and I thrust my hips out a bit as my cock and asshole spasmed in unison as I came probably with the hardest orgasm of my life. The Headmaster could probably not differentiate it between the reaction from a boy in a lot of pain, but I was cumming harder than I could ever imagine. I could feel the cum flood my undies and I'm sure a big wet spot formed immediately on my shorts. My legs continued trembling as the Headmaster paused in between strokes. Meanwhile I was trying to ride out my orgasm, as I was sure I pumped a gallon of spunk in my shorts. My orgasm slowly came down, and so did my hardon. I was still breathing heavy but the intense orgasm took to edge off my horniness. "I don't want to tell you again Matt, buttocks out, legs apart." the Headmaster's voice boomed from behind. The cane came up again and the sting from the next stroke was a million times worse now that I had cum. I immediately straightened up and cried out, reaching behind and clutching my buttocks with both hands. The Headmaster did not say anything till I bent over again, clutching the edge of his table. "That just earned you another 2 strokes, I advise you to stay bent over until I tell you to straighten up. Now buttocks out," he said again. There were 8 or 9 strokes to follow, each of which were pure agony. I was quivering in fear as each one passed, my legs were jelly, and my buttocks were on fire. The pleasure and arousal had completely gone now and my knuckles were white from gripping the table edge so hard and also from sheer terror. I was sobbing slightly now, deeply regretting getting into this situation, as the sting of each stroke brought my attention back to my badly bruised and welted buttocks. I breathed heavily as I rode out the pain from the last stroke. I stayed bent over, not daring to move till I was told to do so. I could feel the cum running down the inside of my thighs now, hoping that the Headmaster would not notice. "Now straighten up and get out of my office Matt," the Headmaster said in a stern voice behind me. Not daring to turn around immediately lest he noticed the big wet patch in front of my shorts, I waited till he had moved to return his cane to the cabinet before I straightened up and walked quickly towards the door. I left his office and quickly made my way to the toilet. I was lucky it was already after class hours and there weren't many teachers or students around. I managed to get to the toilet without any incident and quickly locked the door behind me. Stripping off my shorts and undies quickly, I stood with my buttocks facing the mirror and turned around. I was slightly aghast at what I saw. The caning was surely the most severe I had up till this point, and coupled with yesterday's, had left my entire buttocks covered with livid welts. I had already started to bleed a bit from at least 5 to 6 different areas. Looking at the inside of my shorts, I was filled with a large pool of cum, it was a bit of a mess. The entire situation started to arouse the horniness in me again. I felt my cock quickly rise, imagining bending over again for the Headmaster, and submitting my buttocks to another good caning with a raging hardon. Stroking myself off again, I spread my legs apart, as I admired the angry red welts, and slipped a finger that I had dipped in my own cum, right up my tight asshole. My cock twitched in my fist as I felt my finger go in and I moaned a bit in pleasure. I couldn't squat as I normally liked to do when I masturbated and fingered my ass (squatting always really opens my hole up), because I wanted a good view of the welts as I jerked off. So I remained standing as I bent my knees slightly so my finger could get in deeper. Then started thrusting hard and jerking off feverishly till I spunked hard and satisfyingly again, all over the floor. Following that day, I grew a bit frustrated. I still throughly enjoyed the deeply erotic feelings from a school caning, but I yearned for the absolute nastiness and outright kink that I watched on my regular daily porn sessions. I guess there was always that slut in me. Canings in school were always pretty no-nonsense and delivered on a covered ass. This always left me intensely horny after, and to my own devices to finish myself off with a good wank in private after. I then started joining porn sites with gay / bi guys who were into kink and caning or spanking, and visited chat channels with a similar profile of guys. In my area, well, as I have mentioned before, caning is pretty common, both in schools and at home. And as a direct result, I think, it turns out that there are many (if not a whole lot) of guys that are into this exact kind of kink. It was easy finding guys who were into caning. I started with chatting and exchanging emails, and it wasn't long before I plucked up the courage to meet one. I remember the first time meeting some random guy off the net to be caned. I felt the same way as I did during canings, the excitement and anticipation in my chest. He claimed to be an experienced older guy and he had delivered numerous canings to other subs. I made it clear what I wanted and that I wanted to be fucked, or basically, do whatever he wanted sexually. I met him at his own home, and he opened the door bare chested, with a long, medium thickness cane in his hand. He was a pretty big guy, and I could see that he liked what he saw.I was pretty active in sports in school, I swam, did gym and basically was pretty fit and had a bit of a tan. The sports and workouts basically kept my testosterone levels pretty high all the time I think, and kept me constantly horny. My buttocks were definitely a good target I thought, not flabby at all, but definitely a good, pert, toned set. He groped a bit at my buttocks and I did not object at all, standing still for him. I got horny quickly and started getting a raging hard on, and so did he, judging by how he tented his shorts. We didn't speak much but knew what each other wanted. I quickly stripped off my shorts. I was wearing a feminine slutty yellow thong as he had wanted, and it was quickly shucked off, my cock springing free immediately. I was already rock hard, as I removed my shirt, now totally naked. Wordlessly, I walked into the living room and bent over his sofa fully. I pressed my chest down against the seat of the sofa, keeping my stomach down low and this had the effect of really sticking my buttocks out for him. I'm sure it was quite a sight. I had "saved up" for him, also at his request. Meaning that I hadn't gotten a caning in at least 2 weeks now and had not masturbated for an equally long time. As a result, you can imagine I was pretty darn horny and needing release now. He picked up the thong from the floor and brought it up to my mouth. I knew what he wanted and opened my mouth as he gagged me with my own slutty thong, keeping my position. I could hear him remove his own shorts and could imagine he was jerking off now. I spread my legs apart now, and bent my knees slightly, feeling my asscheeks start to pull open and expose my asshole to him. This was really getting me hot now. I couldn't take it anymore, and reached into my mouth, ungagging myself for a short while, my cock still throbbing. I looked back at him, my eyes glazed with pure lust . "You like this position? Want me to spread a bit wider for you? I want you to cane my buttocks as hard as you can, any number of strokes till you are satisfied," I pleaded. "Fuck, that's hot. Yes, open up some more for me," he replied, stroking his cock. I spread even wider for him, keeping my buttocks as high up and out for him as possible. My asshole seemed to twitch as I readied myself for him. I put the thong gag back in my mouth and waited in anticipation. He didn't waste much time as he lined the cane up, pulled his arm back and took a good swing. The cane landed squarely across my bared buttocks with a sharp thwack. This was the first stroke I received on my bare buttocks and the sting was much more pronounced. It was much more painful but I had been on the receiving end numerous times and I had no problem with maintaining position. The intense sexual energy of the entire situation, the fact that I was naked, my legs apart and in such a lewd position, getting a stinging caning on my bared buttocks by a hot muscular guy, and the fact that I was starved of a caning and a good wank for the past 2 weeks made me mad and absolutely pent up with pure horniness. I practically moaned in pleasure through the gag as I felt the sting in my buttocks start to build up. Opening up my legs even wider, I made sure he got a good view of my shithole, and my muscular toned thighs strained a bit, I kept my chest pushed down into his sofa so my buttocks remained way up and out to give him a good target. He groped my right asscheek after the first stroke, feeling the warmth his first stroke generated. His pulled my asscheek hard to the side, exposing my hole further and making me even harder, and I felt his thumb press right up against my tight shitter. I bet he could feel it twitch. He moved back again and followed up with an equally vicious swipe with his cane upon my unprotected buttocks. I could literally feel the welts start to form now, and I was rightly impressed with his accuracy and skill as a caner as the strokes were really painful and stinging. He took his time, like the school Headmaster does. probably enjoying the view in between strokes and masturbating himself. I moaned into the thong gag in my mouth, which was probably soaked by now from my drool. I counted the strokes in my head, keeping still and making sure my position was satisfactory, spread open, like a slut. When he got to 12 strokes he walked back up to me, cane still in hand, as my buttocks pretty much trembled. I was definitely in a lot of pain, my backside felt like it was on fire, and I was still horny as fuck, my cock was throbbing and harder than ever before. He reached into my mouth and pulled out the gag, leaving me free to talk and moan out loud now. I knew what he wanted me to do without even him asking. I turned my head to the side so I could look back at him as he stood behind me. "Cane me harder, please, more, give me another 24 at least," I pleaded and begged him. I was literally drooling in lust He smirked at me as he stroked his own cock, and I could see that he was definitely fully hard by now. I kept my buttocks out high as he raised the cane again. The strokes came steadily, the pace very much controlled by him. I continued moaning loudly with each stroke. Though the pain was immense, I felt immeasurably pleasured and aroused, and I remained fully hard throughout. "17 sir, thank you Sir," I would moan. Each stroke would be clearly counted. "Harder Sir, I want to learn my lesson well Sir," I would beg and plead in between strokes. I could tell that he was turned on by me asking for harder strokes and he did his best by progressively taking harder swipes with the cane. "Keep your legs wide apart and your buttocks out boy, make sure you keep that hole open," he said as he tapped my buttocks with his cane. I wasn't sure I could hold out much longer, being in a constant state of arousal. My cock was throbbing and my balls were aching to bust a load. My buttocks were, I'm sure, properly welted up by then and he was standing behind me with his caning arm drawn back. He swung foward forcefully with really good aim and landed perfectly squarely over the centre of my buttocks over a series of other welts, and the sting pushed me over the edge. "Oh fuck, I'm cumming!" I yelled out. My cock spasmed and so did my asshole as I erupted in a huge orgasm. I blew thick ropes of cum over my own stomach, all over the sofa and on the floor as I shuddered hard. I struggled to keep my position as I involuntarily thrust my hips forward a bit, my cock cumming without even being touched. I tried to keep my legs wide apart as I orgasmed, so he could get a view of my spasming asshole. My thighs were starting to wobble from the sheer force of the orgasm and I gripped onto the sofa. "Fuck, that's hot boy. You never told me you could cum from being caned," he said lustily behind me. I continued cumming for what seemed to be at least a minute, my chest heaving and my eyes closed, until I started to cool down somewhat as I rode off the remaining of my orgasm. He stook behind me, continuing to jerk off, till I bent over and pulled me by the hair. "Fuckkk, I'm cumming too," he growled. "Open that mouth, I'm going to cum on your face" He yanked my head up slightly by the hair as I opened my mouth, closing my eyes. He quickly erupted in his own orgasm and I could feel the warm cum splatter over my face and into my mouth. He came a really huge load and I was sure it made a hell of a mess over my face, till he finally stopped and let go of my hair. Wordlessly, he walked back to where he was standing and picked up his cane again. "Now, I don't think I even gave you permission to cum, and you've really dirtied my sofa and my floor," he said matter of factly. "Keep your buttocks out, open up your legs, you're getting another 24" I was still recovering a bit from my orgasm, but was aware enough to know what was coming up. Though spent, and having most of the edge of my horniness taken off after that huge cum, I was still ready for more. I already felt my cock getting hard again at the thought of getting even more strokes of the cane from this hot caner. I pushed my chest and stomach down low again, presenting my buttocks lewdly to my caner and kept my legs spread wide open, bracing myself. "Cane me, harder...." I could barely mouth the words, heavy with lust. He was as good as his word, and he resumed the caning. The first few strokes directly after my orgasm were truly agonising, as I felt a trickle of blood now. The sting was incredible but it didn't take long for me to really get super horny again. I wanted even more, and he delivered. I moaned into the sofa like a bitch in heat as he slowly took his time, giving my buttocks probably the heaviest punishment I'd ever experienced up till then. Each smack from the cane rang out loudly through the room, even louder than my cries and moans. He reached 24 eventually, finally putting down his cane. I was insanely aroused again by then, again very close to cumming, my asshole, cock and balls throbbing in unison as I breathed hard from the pain and arousal. He was probably as steel hard as I was and quickly came up behind me and squeezed one of my severely welted buttcheeks. I held still as he groped me, then heard and felt him spit squarely on my asshole. His saliva ran down my asscrack and over my asshole, and he ran 2 of his fingers down as well, rubbing his spit around my tight, as of then virginal fuckhole. I knew naturally what he wanted, and reached back with both hands and held on to each asscheek. I could feel the welts and the intense heat from my buttocks as I held onto them and stretched them apart as wide as I could, giving him full access to my shithole. I obediently flexed and pouted my hole open to show him I wanted him inside me. He pushed both his fingers in firmly and I opened up easily for him, taking both fingers knucke deep. I moaned loudly as his fingers brushed and pressed against my prostate. He knew how close I was to the edge from how hard I was panting. He thrust his fingers in and out in a rough anal fingerfuck and I did my best to loosen up, as my asshole had tightened up quite a bit from the stinging caning. It didn't take very much at all. Within 10 strokes of his fingers or so, I felt my cock spasm and jerk again as I bit my lip and came like a firehose. I moaned out loudly and told him I was cumming again, for the second time, without even touching my cock. I spewed a huge load of cum, dirtying his sofa even more as my asshole spasmed hard around his fingers. He continued roughly and firmly fingerfucking my asshole, not even bothering to give me a reacharound because he knew I didn't even need one. He roughly stretched my asshole open with his fingers as I continued oragasming, before abruptly pulling out as my cock was still spasming. I was overcome by the strength of the orgasm and kept my legs open and squatted down to ride it out. I could literally feel how my asshole was contracting in time with my spurts as well and I reached down to pump my cock for a few strokes with my hand. He pulled me up by the hair and pushed me roughly onto the sofa as I was trying to pump the last few drops of cum out my cock. I lay back, knowing what was going to come now. I was in quite a mess, drying cum over my face and hair from his earlier load and a fresh load I spewed on my own stomach. I could also feel the warmth of my own cum I just spurted all over the sofa against my back as I lay down. He cock was hard as he roughly yanked one of my legs back and pushed it way back beside my ears. I am pretty flexible from my exercise and sports so that was no problem for me. I used a free hand to pull my other leg back and open wide as he pumped his own cock, getting it ready. I was still hard, keeping my legs wide apart as he squat down a bit and placed his cockhead at the entrance to my shithole. He didn't bother with a condom and neither did I. He was at least a good thick 7 inches and he definitely was stretching my virginal asshole open. I relaxed and flexed open my asshole as he pushed and he quickly popped his head in, filling me up nicely. I quickly grew accustomed to the sensation and started jerking myself off, keeping my other hand holding my legs apart. I moaned in pure lust as he started pushing, and he was quickly buried in balls deep, officially taking my anal virginity, using only his own spit for lube. I was in total ecstacy by then, not knowing that getting my ass fucked could feel so good. He started thrusting quickly, turned out that he was a pretty good assfucker as well as caner. He gave deep, solid thrusts that lodged his entire cock up my ass with every stroke, and he would pull out till only just his head was gripped by my sphincter before thrusting in hard again. His cock rubbed up against my prostate and I knew that coupled with my jacking off, I wouldn't last very long. The fucking was hard, wet and really really good. He started leaning over me after awhile, using his bodyweight and stretching my legs even wider apart with his hand, thrusting his hips at the same time to try to get in deeper. From the way he was breathing and sweating, I knew he was close too. "Oh fuck, I'm going to cum," he groaned out loud, keeping up a good and fast pace of assfucking. I then felt him pause and tense up. He then used both hands to spread my legs apart and pressed all the way down till both my thighs were pushed down hard into the sofa and my ankles near my head. I felt like I was speared into two, as he thrust his hips inwards and started shuddering. I could hear his loud moan and could feel his large cock start to spasm and shoot his big load directly in my shit tunnel. I could literally feel the warm jets of cum along the insides of my shit chute. He panted a bit, his orgasm lasting at least a good long minutre, before he finally pulled out his softening cock. I felt used, abused, and loved every single second of it. It seemed like my randiness knew no bounds. It was pretty late by then, a Friday night I remember. Good thing there wasn't any school the next day, and my parents were used to me staying out late on Fridays. Little did they know their boy was being an anal slut for this hunk. We stayed naked like that for a bit, but I felt horny again almost immediately. I still hadn't released my thrid load. I stayed till about 4am that day, not wearing an inch of clothing, and had anal sex at least another 5 or 6 times, all bareback, and it seemed I just couldn't get enough. I sucked him, rimmed him (my first time rimming someone), did ass to mouth, and he had an equally insatiable appetite for sex. He came another 3 or 4 times in my asshole, and had a couple more loads blown over my face and mouth. He was nearly dry orgasming by that time. I came an equal number of times at least and I knew that from then on I would be hooked on nasty man to man sex. After that incident, I was totally addicted. The internet chat rooms and hoopup sites served as a convenient portal to meet guys who had similar interests, and as I had mentioned earlier, that is a lot of guys over here. The new top I had hooked up with became a regular as well, since that first encounter, as I knew he could deliver really stinging canings and a good bareback buttfuck after. I started regularly meeting other tops for caning and fuck sessions in random hotels, at their houses, and even ended up in a few group fucks with other bottoms and tops present. It was like after I started, I couldn't stop. I was pretty reckless as well, I hardly, in fact never, even cared if the tops used rubbers at all. After a caning, all I wanted to do was get fucked. I must have taken countless loads in my ass, down my throat and wherever else on my body the top wanted to cum. There are some guys who are top, some who are flex, but I was a totally and completely a 100% bottom slut. I knew it deep down and I couldn't get enough. I met guys very regularly and apart from getting caned at school I would regularly get it from random guys off the net. Gradually it became a weekly affair, sometimes even a few times a week. High school went by like that over the next 2 years or so, I'm not exactly sure how many but I must have met over 50 to 60 different guys for caning / sex sessions. I must say the appeal of a fit, athletic teenager who is a total slut for the cane and bareback fucking got me many tops who wanted to meet me again and again. They would introduce other tops, and I sometimes didn't even need to look for tops over the net, since I also repeatedly went back to those that I found were really good caners or really good fucks. One thing that I really wished for though, was that school canings could mirror what happened in my private sex life. School canings remained very no-nonsense, pants on, and it grew quite frustrating with my hardon always raging in my shorts. Though the sexual canings I got from my tops satisfied me in a lot of ways, the arousal and sexual energy I felt getting caned in school was really quite different, and in many ways, even though the canings were very business-like, the sexual tension I felt was always tremendous. I went on to college soon enough, and the caning culture there did continue. though as young adults, corporal punishment was not dished out as often. But when it was, it was really severe. Minor offences were not dealth with by canings anymore like it was in high school, but offences like cheating in an exam, smoking, fighting in school, were all still punishable by caning, and very severely at that. The headmaster in my college always had a stern look, and he had a reputation for being really harsh as a caner. He was a white man, fairly tall and looked very buff for a guy in his late 40s or 50s. He played squash and tennis a lot, apparently, and this must have contributed to the ferocity of his cane strokes. I was still fairly new in college and hadn't got caned by him yet, though I had received a few canings from other teachers. They were fairly severe and well delivered but I was very keen to experience one by the headmaster himself. I had heard rumours that he was gay, but I thought it was all just idle talk among the boys. Outside of school, I continued hooking up with new tops and meeting up my old ones very regularly for canings, if not just for sex. I started developing a taste for orgies and group fucks and I especially enjoyed those where I was the only bottom guy and there were 4 or 5 other tops just taking turns having their way with me. I guess I just enjoyed being very submissive to these guys and please them sexually. There was one particular day that I remember, that I was surfing online gay personal sites, one in particular I used a lot where I knew a lot of hardcore tops frequented and were especially into fetish and kink. I had come across a personal of a white guy that I was interested in. He showed only body photos and mostly did not include the face except for one shot where the lower half of his face and jaw were visible. He was really buff and well built, and it looked like he certainly had a fetish for caning as he had a very wide variety of canes, according to what I could see in his pictures. He looked uncannily like my current headmaster though I brushed it aside. His profile name was "SternCaner" and it read as such: "Middle aged dominant white male into corporal punishment and especially caning. Into sports and fitness. Extremely well-practised with the cane, has a wide assortment of paddles, straps. Only serious bottom boys to apply, place available. Fit asian bottoms a big plus." I eventually messaged him over the site and sent some pictures of myself without face pics, but strangely never received any reply. I went on with meeting my other tops and soon forgot about him. Soon after, I got into trouble at school again. I was a bit of a problem student on and off, and usually would be up to some form of misbehaviour. This time, I had been caught cheating in a mid-term exam (I did that sometimes as I really didn't enjoy the books). Needless to say, punishment was usually swift in coming. Since it wasn't the first time and the exam was a fairly major one I was marched to the Headmaster's office promptly. I wasn't too bothered at that time since I was in a way, pretty used to it. I remember standing with my hands behind my back, looking at the Headmaster from across the desk. He looked stern as always and very no-nonsense. He gave me a dressing down the usual spiel about how serious an offence cheating was. The punishment, he announced, would be the cane, and that I would be required to report back to his office after school hours the day after in my gym attire (this was the norm). I guess making the boy wait for a day before punishment served to make him dread and fear it more and reflect upon what he did, making the punishment all the more dramatic. It had that effect on me too, in addition to making my cock extrememly hard. The day passed agonizingly slowly. I went to school the next day and the day too, passed slowly. I could literally feel my heart beating along my buttcheeks as I anticipated what was to come. Given his reputation for really severe canings, I wondered how I would fare. The corridors were pretty much deserted by the time I started walking to his office. I could hear my footsteps down the cold floor, till I stopped in front of his office. Now, let's get back to where we left off at the start.... I stared at the door in front of my Headmaster's door, feeling a lump in my throat. My heart was pounding in my chest, not knowing what to expect, and my cock was rock hard by now, straining against the gym shorts that I was wearing, in anticipation of what I hoped was to come. I knocked on the door, hearing it echo down the corridor, and I heard his voice clearly through the layer of wood separating us. "Come in," he said. I opened the door, walked into his office, and then went up to him, standing in front of his table, hands behind my back. He continued writing busily at this desk, appearing to be quite oblivious of me standing there. My eyes quickly fell upon the cane resting of the front of his desk. This was a mid thickness cane, and I knew how these felt. Too thick and they thud hard but don't sting, too thin and they sting a lot but don't leave very thick welts and they don't give off much of a dramatic sound. Medium ones however, are used by the ones who truly know about caning, they can sting like hell and really hurt, and the sound it makes on vulnerable buttock flesh is loud and emphatic. My heartbeat definitely picked up as I realised what I was dealing with. I also noticed that he left his cabinet open, and it showed off a hell of a selection of rattan canes, I estimated at least 12 to 15 canes. This was a man who knew how to dish out punishment I was sure. Now he looked up at me, removing his glasses and placing them on the table. "Now, Matt, I hope you have reflected on what you have done and how serious it is." "Yes Sir," I replied, looking at him. I couldn't help but feel how closely he resembled that guy from the caning website, now that I was so close to him. My cock continued throbbing, at full attention now. I though, this could be a chance to take a school caning "to the next level" so to speak. "Cheating has and will always be a serious offence, and the punishment has to reflect that. You will be caned today, Matt" "Yes Sir, I'm sorry Sir." I was insanely worked up and horny now. "You will receive 36 strokes of the cane on the buttocks." My heart leaped, this was a pretty large number for a school caning. I gulped, not knowing how to reply, but just nodded my head. He slowly got up off his chair and picked up the cane, walking towards and then behind me. He swished it in the air swiftly and sharply a few times, and the force in his hand was unimistakable. I could hear the swoosh of the cane as he stood at the side of me now. I thought to myself, should I try to "seduce" this guy, and how? "I want you to bend over and put your elbows on the table. Buttocks tight and push them out." he said sternly. It was customary that canings were delivered on covered skin. We kept our shorts on, and the caners, and those receiving, all knew this. I decided that it was now or never. I gulped, and hooked both thumbs over the waistband of my shorts and underwear, and pulled them all the way down in a single motion down to my ankles. My head was spinning and I couldn't notice how he reacted to this. All I knew what that my cock sprang free, and was so hard that it immediately sprang back flush against my stomach, pointing straight up. I looked down, it was visibly throbbing, and I could see my cock head was shiny from my pre-cum leaking out. It had to be obvious to him how insanely aroused I was. Apart from that, I had fading but still very obvious welts on my buttocks from an earlier session I had with a top a few days ago. If he noticed them, he didn't say anything. I did not turn around to face him, instead looking forward, pretending nothing happened. I waited awhile, letting him take this in, and then as he instructed earlier, I bent over slowly. I was familiar with this position, I placed both elbows on the desk and put my head down. I spread my legs a bit and pushed my stomach down a bit lower. I pushed my buttocks as I was told. He said nothing for awhile, I'm sure he was processing things and seing what he should do. "Spread your legs wider Matt," I heard him say as he stepped behind me. He tapped the inside of both my thighs as he said so, adding more empahsis. I spread my legs apart wider, I could feel my asscheeks pull apart now, as my cock continued to throb. He tapped my buttocks with the cane now. "Buttocks out." I pushed them out for him. From the corner of my eye, I saw him step slightly back, cocking his right arm fully back, then unleashing a full blooded stroke. I knew immediately I was in for a serious caning. The crack of the cane was tremendous, it must have been heard through all the empty hallways. The pain was immediate and incredible and I cried out once, trying immediately to stifle it. My buttocks felt like they were on fire and I straightened up immediately, going up on my tiptoes, my hands shot back and I clutched at my buttocks in pain. I knew I could take a lot of punishment from all the canings I took over time but this was on a completely different level entirely. I kept my mouth shut, biting my lower lip as the pain reached its crescendo. My breathing was ragged and heavy, and this was stroke one. "Now you will get back into position. You just earned yourself an extra 3 strokes for that." the Headmaster said. "I'm sorry Sir, I will do better." I bent back over the table and tried to regain composure as he once again positioned my buttocks with the cane. The next stroke was just as painful, for each stroke he would lean back and use body weight, momentum and his formidable arm strengh to really lay it across my buttocks. The pain was even worse now but I managed to maintain position, even as I squirmed and my buttocks quivered. "Two Sir, thank you Sir," He knew exactly what he was doing. His strokes were "followed through", as if he were caning "through" my buttocks. This gave each stroke more power, instead of caners who would lift the cane off the buttocks after impact. His technique and aim, I could tell painfully, was extremely polished. He could deliver each stroke nearly one on top of the other if he wanted, and he knew exactly how long to wait in between strokes, allowing the pain to reach it's peak before immediately unleashing the next vicious stroke Even though I was a seasoned recipient, I whimpered quite a bit. My cock would normally stay steel hard through a caning but the pain killed off my erection after the fourth stroke. I squirmed as I could barely count now. "Four Sir, thank you Sir." I said as I bit my lower lip. The fifth stroke definitely drew blood as he laid on a really hard one across my already welted flesh. This was the fastest anyone had ever drawn blood from caning me. He stopped awhile and let the pain sink in. I was breathing hard as I struggled hard to keep my position. It must have been quite a sight for him. I knew I was in good shape, and my tops mostly comment I have a great set of buttocks for caning, toned, muscular and yet just enough of a bubble butt to give the caner a good target. And here I was, naked from waist down, bent over, my legs spread open and my buttocks pushed out and presented for this tough disciplinarian. Now having put livid welts on my flesh, and him having a view of my asshole as well, must have been extremely satisfying for him. And inside, I started feeling, that's what I wanted to do, to satisfy this guy, sexually. Despite the pain that he reminded me of with each stroke, I started feeling horny once again. I could feel my cock start to stiffen again, getting hard pretty quickly as I remained bent over, feeling much like a 2 dollar whore, naked from waist down and my cock throbbing. He reminded me of the pain with another stroke that quickly followed, and my buttocks were once again, lit on fire. This time though, I remained absolutely hard. I kept my elbows and palms on the desk and turned my head to the side, pressing my cheek against the desk, so I could actually watch him give me the caning. I pushed my stomach down low and spread my legs apart some more, as he waited in between strokes. He could see me adjust and I'm sure he got a better view from it. I started to sweat a bit from the exertion, pain and also from the mounting sexual excitement and I could feel a drop of sweat flow down my lower back, down my asscrack and deliciously over my asshole. He lifted up his arm and followed up with another stinging stroke. This time I moaned audibly as the pain seared through my bum, and I got up on my tiptoes. My cock throbbed and my asshole twitched as I worked felt my mind absolutely clouded by lust. My first bare bum caning in school was turning out to be an absolutely erotic and painful experience. He reached 12 strokes, and there were 27 more to go. By now I was sure my buttocks were already a mess of welts but I was even hornier now than when I started. I gulped as he cocked his arm again, the next stroke landed just above the crease between my buttocks and upper thigh. This one stung a lot and I cried out, both in pain and pleasure. "Thirteen Sir, thank you Sir." He continued with 2 well placed strokes just above this one that nearly had me hopping. The loud, crisp smack of the cane on my bared buttocks continued to ring very loudly. I moaned again after the next stroke, and deliberately pushed out my buttocks even more as my lust grew. He must have gotten the sense that I had started to enjoy the caning a bit too much now. I thought I saw what was a bulge on the front of his pants, as I looked at him from the side, in my near nakedness. His next stroke showed me he continued to mean business, as I clenched my teeth in pain as my buttcheeks continued to burn. "Seventeen Sir, thank you Sir." my breathing was ragged now. He paused a bit, before placing another stroke squarely in the centre of my quivering buttocks. This one hurt especially bad as my buttocks were already badly welted in this area. I immediately straightened up, and clutched at my buttocks again. "OOOWWWWWW!!!" I yelled, squeezing my buttcheeks hard, I could feel the welts, and where skin had been broken and I was cut. The pain was really intense this time. I took awhile to regain composure as the Headmaster waited. "And that, young man, has earned you yet another 3." he announced. I could sense he was really starting to enjoy this caning. Suprisingly, my cock didn't really show signs of letting up as I quickly regained my erection, displaying it proudly as I was clutching my buttcheeks. This was really quite lewd, though he didn't make any comment at all. I was somewhere in between insanely horny and insanely in pain, but as the sting died down I just wanted more. "Please Sir, may I bend over your sofa for the rest of my caning?" I asked. There was a wide leather sofa in the corner of his room that had a pretty low seat. I imagined bending over it and pressing my chest down on the seat would stick my buttocks out nicely and give him an even better view and target. He seemed to know what this request meant, and he nodded his head, motioning to the sofa with his cane. I walked over to the sofa, my heart beating hard against my chest, and my cock was visibly erect still, which I am sure he had totally noticed. I bent over and pressed my chest down against the seat, keeping my elbows close together, this served to stick my rump out, and I bent my knees a bit, pushing out some more, keeping my buttocks tight, though opening up my thighs to give him a good view. This must have drove him wild, because he very quickly lined the cane up against my welted cheeks, tapping lightly for aim, then unleashing a mind-numbingly painful stroke. I grit my teeth down hard. "Yearrrrghhhh," I cried out, but still managing to keep my position. My thighs trembled in pain as I tried to ignore the pain from my 20th stroke. I still had not even reached the halfway mark taking into account the 6 extras I had earned. "Twenty Sir, thank you Sir,' I could barely even manage. The next 6 strokes were slow, deliberate and found their mark excellently, leaving my buttocks an even more heavily welted, quivering mess. He landed them low initially, starting over the lower buttocks just above my thighs then worked his way up, eventually hitting just above centre on the 6th stroke. I was in absolute agony, constantly shifting my feet and squirming, but kept my buttocks pushed out at all times, I was definitely breaking a sweat, and I think so was he. It couldn't have been too easy delivering every stroke like that, though I'm sure he enjoyed it. The scene could probably have been in a porno. Fit, toned, horny boy in his late teens naked from waist down, covered in a sheen of sweat, bent over with his bum stuck all the way out, covered in welts, his cock hard and dripping pre-cum, and a middle aged, muscular, white male standing behind him, a hardon tenting his business trousers, and wielding a nasty looking cane in his arm. He continued his slow, painful, yet insanely hot caning. Each stroke really stung like hell, but through the pain the sexual energy of the whole situation kept me horny and on edge. "Thwack!" My buttocks quivered as a new welt formed right smack across the centre. "Thwack!" This stroke fell diagonally across. The pain was tremendous and had my knees shaking. "Thwack!" This one striped the upper part. I kept my bum pushed out, waiting for the next one. My cock was steel hard, throbbing and oozing precum relentlessly. "Crackkk!" The cane marked me deepy just between my upper thighs and buttocks. As the strokes came slowly and consistently, I felt my balls swell up as if till bursting, my cock straining and ready to spew. Though my asscheeks were positively on fire, welted up and bleeding, I never felt hornier, and I was sure I was going to bust a huge load. I stayed bent over, presenting myself lewdly to this man, opening my thighs to show him my eager fuckhole. He lined his cane up against my buttocks again, tapping lightly a few times, steadying his stance, then leaning back a good bit, then lashing out full strength with his powerful arm. This stroke cracked viciously with the loudest smack up till that point, possibly drawing some blood as well. The sting and burn was increadible as I cried out loudly, partly moaning as well, then I felt my cock spasm and finally explode in a huge orgasm. "Oh fuckkkk.... I'm cumminggg!!" I moaned out. I felt the warm cum splatter against my stomach as I started spewing my load. Ropes of cum landed over his sofa as well as I exploded in an orgasm larger than I had ever felt before. My thighs and legs were shaking from the intensity of the orgasm as the Headmaster moved beside me so he could watch my cock spew its load. I was moaning loudly as the waves of my powerful orgasm raced through my body. Feeling incredibly horny still I squatted down as I continued cumming, spreading my legs wide apart and leaning back, thrusting my hips forward and I started openly masturbating and jerking my cock further as it continued pumping an immense cum-load. My cock was slick with precum and cum and i slid my hand easily over its shaft. I could feel my asshole twitch and spasm in time with my cock as well, as I closed my eyes and swallowed, trying to ride out my orgasm. I was still spurting hard, ropes of cum messing up the Headmaster's sofa and the floor. All the while, he watched wordlessly, and I'm sure all the concealed sexual undertones this caning had up till now, were by this act, completely out in the open. I shuddered as I came down from the really hard orgasm, still pumping my twitching cock, squeezing it dry as the last few drops of cum oozed out. I realised that I had been holding my breath up till this point, finally exhaling, and breathing a bit more regularly now. "Now, I didn't give you permission to cum now did I, look at the mess you made." I heard him say, standing beside me now, watching me fist my cock. I suddenly felt sheepish and realised how inappropriate this looked if he seriously meant business and wasn't interested at all in the sexual part of this whole situation, though unlikely. I quickly pulled my hand away from my cock, leaving it still throbbing and at attention, and got up from my lewd, open legged squat. "I'm sorry Sir, I will bend over again." I said softly. I kept my legs open and once again pressed my chest down low, this time feeling my warm cum against my own body, this was hot. I was still hard and throbbing, still feeling horny and not satisfied yet though I had cum hard. The edge had been taken off by the intense orgasm but I think I was used to being fucked after canings and that was what I wanted now. "For that shameless display, I am adding another 12 strokes to your punishment. That means there are another 23 strokes to go boy," the Headmaster said. I remained bent over, getting myself ready for the next stroke, trying hard to compose myself. The Headmaster didn't show any signs of letting up with the next stroke. The sting was incredible as he lashed my buttocks, and having just orgasmed, the pain was much harder to bear. I quivered as I waited for him to continue. Surprisingly, the next stroke did not come when I expected it to. The Headmaster walked up behind me, and I felt one of his hands grab my heavily welted right buttcheek. He squeezed firmly, and I half wainced in pain, half moaned in pleasure. I knew now that at this point, the caning has crossed the line between strictly business and pure sexual lust. I remained still and did not protest as he no doubt admired his handiwork with the cane and kneaded one asscheek. I practically felt my asshole twitch in anticipation. "You enjoy this more than you feel the pain don't you boy?" he said. There was a noticeable change in the tone of his voice. "Yes Sir," I shamefully, my voice choked up with lust. "We're going to have to do something about that now don't we then?" I could hear his footsteps as he walked away. I heard him opening a drawer, and I turned my head to the side to look behind me, my bum still thrust up and out for him. I saw him pull out what looked like a paddle. I got a closer look as he walked back, turned it that was a leather paddle, and apprently quite well worn. I had been on the business end of leather paddles before. The flexibility of the leather made for a much more painful smack and a good loud satisfying sound for the top, and for those who really were experiences, they would know that it was much more painful than plastic paddles. "Buttocks out boy, open up your legs further." I eagerly obeyed him, sticking out some more and even getting up on my tiptoes, bracing myself as I spread my thighs apart. "Thwack!" the pain was excruciating on my already thoroughly punished buttocks. Instead of a sharp sting, I felt the pain like a deep aching bruise, and subsequently like my whole buttcheek was set on fire. It was a sharp contrast to the cane but given how hard it was delivered by the Headmaster's strong arm, the pain was equally bad. What followed was a relentless assault on my buttocks with the paddle. He followed each whack very soon with another, punishing my asscheeks severely, alternating each smack on both my buttcheeks, giving them an equal number of smacks. They were delivered with such force I felt my face and chest being pushed down into the worn leather of his sofa. I moaned out loud and then started cyring out in pain after about 12 to 15 smacks. The pain was incredible as I squirmed and struggled to maintain position, my erection vanished quickly and my cries became louder, though I was determined not to cry. The smacks rang loudly through the room, mixed in with my cries of pain. After about 30 vicious smacks, he lay the paddle down beside me and bent down to pick up my underwear from the ground beside his table. He walked back to me and roughly opened my mouth, forcing my own underwear in and effectively gagging me. He then picked up the paddle again and continued his punishment, giving me another 12 to 15 resounding smacks. My cried were muffled by the gag as my backside screamed out in pain. He was nearly bringing me to the brink of tears, before he put down the paddle and walked up behind me again. My mind was spinning and numb with the pain I felt in my buttocks, I could almost feel my heartbeat throb all over both my buttcheeks and I was sure they were completely red and angry from the paddling, and not to mention with a mess of welts covering it from the earlier caning. This was by far one of the most intense caning / paddling sessions I'd ever had, and I had the feeling it was far from over. He stood beside me now, and pulled out the underwear gag from my mouth. My chest heaved with relief as I breathed heavily, trying to focus on something apart from the pain. He grabbed my asscheek again roughly and I immediately winced, this was much worse after the paddling, and I could feel the heat coming off the surface of my punished buttock. He loosened his grip, then I felt his thumb come up right beside my pouting asshole, and the rest of his fingers gripping my asscheek, before he tightened his grip, effectively pulling my asscheek wider apart. No doubt he wanted a good look at my tight teen fuckhole, and I wanted him to see it. I could hear him unbuckle his belt now, and I watched him as I lay bent over, my head turned to the side. He pulled his zipper down, as I gulped in anticipation. He must have been in a whole lot of discomfort I realised, when I saw the huge erection that immediately tented his boxers as his pants dropped to his ankles and he stepped out of them. His other hand remained firmly planted on my asscheek as I remained submissively in my position. He shrugged off his boxers and my jaw nearly dropped as I saw his cock spring free. I had been used to the size of other Asian guys and though I'd been fucked by white guys before, this guy was huge. His cock was steel hard, and it curved upwards slighty, his cockhead was swollen and shiny, also glistening with precum and by far the biggest I'd seen (and I'd spread my asscheeks for plenty of guys by then). What impressed me most was his length and girth, he was thick as hell and the veins ran along his entire shaft. I'd never been fucked by anything that thick, even when taking toys and dildos into account, and his length was equally impressive, I'd estimated 9 inches easily, given that he must be at full hardness now. I watched him as he spread his legs slightly, his hips slightly thrusted out, and he slowly fisted his hard cock. coating it with the abundant precum seeping from his cockhead. He then let go, his cock throbbing as he gripped my arsecheek harder, then giving it a firm spank with his hand, which gave me a jolt of pain not far inferior to a smack of his paddle. I knew he wanted to take my hole, and I reached back now with my own hands, one hand on each asscheek, feeling how intensely warm they were from the caning / paddling. Spreading my legs some more, I stuck out my bum as far as I could and stretched my asscheeks apart as wide as I could get them, till it actually started to hurt a bit. My hole now lewdly exposed, I proceeded to relax my shitter, then flex and pout it open, as he watched me intently, still fisting his cock. My hardon returned quickly, in full force, and I felt my arousal more intensely than ever before. I kept my asscheeks sluttishly apart for him, waiting for his next move. He moved his hand and I could feel him pressing against my pouting asshole with his thumb, I relaxed and opened it up further for him. He could feel my shitter open up and he started rubbing it, applying a bit of pressure. I moaned and pushed my bum out some more, keeping my asscheeks wide apart. He removed his thumb, and I heard him spit once, and soon after felt his spit squarely over my asshole. "You're a slut for cock aren't you, and you've been getting canings for a long time now I suppose?" "Yes Sir, I am" "Who gave you those welts before today's caning?" "One of my tops Sir, I meet him regularly for caning and sex." "How often does he cane you?" "He canes me once every few weeks, but I meet other tops regularly for caning Sir. I get weekly or sometimes twice or thrice weekly canings when I'm more horny Sir" "Slut, how many was the most you had in a week?" "I received 9 canings in a week once Sir. They were mostly different guys." "Do you always get fucked after?" "Yes Sir, mostly. I enjoy anal sex after caning, or even just assfucking alone." "How many cocks have you had in your boycunt, slut?" I thought for a moment before replying, knowing how much I opened my legs and asscheeks for random cock. I didn't want to deter him from fucking my needy shithole. "About 25, Sir." I knew full well I had been fucked bareback by at least twice that number. "Hot, you're a teenage slut aren't you, for cock, and for the cane." "Yes Sir." He started using his thumb to rub the spit over my asshole, applying more pressure as I relaxed my sphincter for him, allowing his thumb to slip easily into my fuckchute. Renewing my grip on my asscheeks, I pulled myself further apart as his thumb worked its way fully in, up to his knuckle. He then pulled out and pushed one finger in fully, then added in a second. I stretched easily and both fingers went in deep. I was even harder then I was before my orgasm by now, I moaned out loudly and my cock was twitching, jerking and oozing precum, as he deeply fingered my asshole deeply. "Fuck, that feels good, fuck my asshole hard." I groaned as his fingers slipped in deep and thrusted firmly. He fingerfucked my shitchute as he caned me, roughly and firmly, only considering his own perverse sexual pleasures, and I loved it. I kept my ass spread wide, thrust out and started slowly fucking back against his fingers. He thrust hard and fast, going knuckle deep each time and my cock practically throbbed with arousal. I grunted and panted as his pace built up. I did not need much lube apart from his spit, being seasoned at taking deep assfucks, and he penetrated me easily. I felt him withdraw abruptly, and I felt the sudden void as his fingers left my hole. He resinerted them quickly, and then I felt him squeeze in a third. I relaxed, and his finger entered fairly easily, my crapper feeling instantly tighter. I was swooning with lust now as he roughly manhandled my boyhole. "Slut, you are enjoying this too much aren't you?" I gulped with lust and nodded, my head still turned the side. He was fisting his impressive cock with his free hand as he continued his relentless assault on my tight backdoor. He seemed to have grown even harder, his head swelling up even more as he occasionally used his finger to smear the precum around the tip of his cock. He let go of his cock, and I watched it spring up against his stomach, rigid, ready to fuck. He then reached down and wrapped his hand around my cock now, his other hand continually penetrating my hole, stimulating. He pumped my hardness a few times, and I literally nearly immediately exploded in another orgasm as my asshole spasmed. He seemed to notice this, and let go of my pulsating cock, continuing to finger me hard. Even though he wasn't jerking me off, I felt another orgasm beginning to build up and my sphincter start to spasm around his fingers. "Ohh.. fuckk... I'm going to cum again." I moaned out loudly. The headmaster immediately pulled his fingers out of my asshole, leaving my hole gaping for a bit as I felt my impending orgasm ebb away. My balls were literally aching to cum and my cock strained, throbbing as he left me high and dry. He watched as I squirmed, and I begged him, "Please, let me cum, finger my fuckhole so I can cum, Sir." I kept my thighs apart and stretched my asscheeks even wider, I winked open my tight anal orifice and tried to open it up to entice him. "Slut, you really want it don't you." "Yes Sir, please," I begged. I watched him as he fisted his slick, hard cock again, and he walked towards the sofa beside where I was bent over, and sat down, speading his legs apart. His cock throbbed, fully erect, his cockhead glistened with precum, as he slowly started to wank himself, looking at this horny, fit teenager bent over his sofa waiting to be sodomised. I knew what he wanted before him even asking. I got up from my bent over position and got on my knees, shuffling over till I was kneeling in betwen his legs. He let go of his cock, and it sprang backwards, throbbing, hard, bigger than any other I had had in my mouth till then. I knew how to suck cock, I'd had plenty by then. I wrapped my fingers around the base of his cock, giving it a few strokes, it was absolutely steel hard. He looked down at me as I looked up at him lustily, then I opened my mouth and started licking around his huge cockhead, lapping and flicking my tongue over his pee slit, which was oozing precum still. It made for a good mouthful even as I swallowed his precum and continued my tonguework over his cockhead. He moaned out loudly as I tongued his cock, I slid my mouth and tongue down his immense shaft, leaving a trail of spit on his already slick cock. His cockhead filled up most of my mouth even before I could get much of his shaft down. I could feel him thrusting his hips, trying to get it down my throat and I gagged a bit, trying to get as much in my mouth as possible. I slobbered as I sucked on his hard cock, the spit running out the corners of my mouth and down my chin as I gave him as wet and sloppy and messy a blowjob as I could. He moaned out in satisfaction as I started bobbing my head back and forth, moving my lips and tongue up and down his slick shaft, maintaining a steady suction. I still couldn't get much of him down my throat so most of his cock was still outside my mouth, so I alternated giving him a good sucking and allowing him to skullfuck me, and pulling out his cock to jerk him off while I serviced his balls with my tongue and ran my tongue up and down the rest of his cock that I couldn't suck. He grabbed me roughly by the back of my head and hair, thrusting his hips out. I was determined to deepthroat him, take him balls deep in my mouth. I was pretty experienced at doing that as well, and could take a pretty big cock down my throat, but right now I was still working on suppressing my gag reflex to allow more of him into my mouth. I bent forwards and let the shaft slide down till it was pressing against the back of my throat, then relaxed the muscles at the back of my throat and forced my head down further, pushing his cockhead down into my throat as I stopped myself from gagging. He slipped in and I felt my neck bulge, spit running out my mouth and down his shaft. He moaned out loudly as he felt his cock slip into my throat. After the initial part, it was easier keeping my gag suppressed and letting his entire shaft slide in, though I literally felt the breath being forced from my lungs. "Ah fuckk, that feels good, you're a little cocksucking slut aren't you?" the headmaster groaned out loudly as I expertly deepthroated him. I didn't reply, instead concentrating on allowing him to fuck mythroat with deep thrusting strokes. I slobbered over his shaft as he skullfucked me, and sucked hard, my cheeks hollowing in. I ran my tongue along the underside of his shaft and licked at his balls when he bottomed out on my throat. He moaned out in approval as I did so. Once I had established a steady rhythmn and my throat had adjusted well to his large girth and length down my throat, I started giving him the blowjob of his life. I slid my hands down his inner thighs and pushed them apart, getting up into a squat with my thighs wide apart, and adjusted my position and roughly fucked my own throat down on his cock. My asshole pulsated in anticipation of having his huge fuckpole up my shitter. I kept up the pace, bobbing my head up and down energetically, the room filled with the disgusting squelching and slurping sounds of my blowjob. He lay back and enjoyed it, but showed no signs of being close to cumming. I guess he was used to getting hot sleazy blowjobs from sluts like me. I would come up for air every once in a while and fist his sloppy, spit slicked shaft and lick at his balls as I took a break from deepthroating him. I kept up at it for a good 20minutes, not rushing at all, making sure he had full satisfaction. Moving downwards with my mouth, I licked at his huge hanging balls, as I stroked his hard shaft, then moved down further. I was well used to giving random guys deep rimjobs and was about to show the Headmaster I kneww how to be a proper slut and eat ass. I placed both my hands at the backs of his knees and pushed them upwards and back, spreading them apart as I slid my tongue downwards to the area between his balls and asshole, tongueing the sensitive area. He reached down to hold his legs apart and I used my hands to spread apart his asscheeks before tongueing his shithole directly, flicking my tongue over it and sliding it around the rim. He moaned out loud again and relaxed his hole. My tongue sensed the give as he relaxed his sphincter and I pushed it firmly inwards, stiffening my tongue and pushing it deep inside, giving him a good, deep rimjob. He certainly appreciated the rimming, and I could feel his cock twitch in pleasure as I tongued him deeply. I knew how to eat ass properly and alternated flicking my tongue around the edge of his shithole, and applying pressure and tonguing around and on his asshole firmly, then pushing my tongue up his hole, flicking it around as i did. I kept rimming him, watching him moan and writhe in pleasure, my own cock throbbing at this lewd shameless act. Tasting his ass on my tongue gave me a heady, drugged sensation. I reached down, pumped my already hard shaft, using a finger to gather up some of my precum dripping off my cockhead, then reached down between my own widespread legs and lubed up my tight, pouting shithole. The rimjob I was giving him was wet and sloppy as hell, and I stopped awhile, spitting in my own hand rubbing my spit over my asshole, then thrust 2 fingers in easily and started fucking it hard, feeling my cock throb even more as I penetrated myself. "You fucking your own shithole boy?" he asked, looking down at me between his legs as I continued eating his asshole. "MMphh," I replied, nodding my head, not even stopping as I continued rimming him. After a rough fingerfucking off my own ass, I pulled my fingers out and pushed his legs further back and got my face deeper in his ass, giving him long wet strokes with my tongue along the length of his asscrack and kept working my tongue, lapping at his shitter and tasting him. I sensed him getting even harder and more aroused. I reached up and as I rimmed him deeply, started fisting and pumping his slick, hard shaft. I was literally trembling in anticipation as I felt how thick and long he was, wondering how it would feel taking his entire impressive length deep up my fuckhole. His cock was still wet and slick from my earlier sloppy blowjob, as I pumped him with my hand, getting him even harder, if that was even physically possible. I could tell he was close judging by the way he was breathing, and I desperately wanted to get him off properly. I took my tongue off his asshole and quickly wrapped my lips around his cock again. He put his legs down now and kept them apart as I resumed my blowjob again, thrusting his hips upwards to fuck his cock back into my mouth and throat. His shaft still felt immense in my mouth and down my throat even though it had just been stretching it open. I held his thighs down with my hands so that I could control the pace but quickly built up a good rhythmn, relaxing my throat and getting his shaft down all the way, slobbering all over his cock and balls. I bobbed my head up and down quickly, hearing his breathing get faster and more shallow, and allowed him to skullfuck me now, and he brought one hand down to grab a my hair and pull down at it roughly . I enjoyed it when my top gets rough and allowed him to treat me however he wished. He brought his feet up on the sofa, his legs still spread apart, and used them as leverage to thrust upwards, fucking my mouth. I saw him reach a finger beneath him and between his asscheeks, and push it up into his own asshole. This was extremely hot, I thought. As dominant and undoubtedly top he was, he wasn't averse to a bit of ass play himself. He thrust his finger in deep and fucked it in and out of his own hole. I stopped my blowjob for awhile and looked up at him. "Let me do that for you, Sir." I begged. He smiled knowingly and pulled out his finger. "Have a taste boy." he said. I immediately opened my mouth and allowed him to slip his finger in, swirling my tongue around his soiled finger, tasting his bowels. I replaced his finger with my own, as I felt him relax his asshole for me. I knew instinctively what to do as I hooked my finger upwards towards his prostate and started rubbing at it, stimulating him even more. I alternated rubbing his prostate with long, deep and slow strokes with my finger up his ass, all the while keeping up the messy blowjob I was giving his cock. I was frankly quite impressed with his staying power, as most other guys would have blown a huge load long ago. "This guy is probably going to be quite the stud when it comes to fucking later." I thought. Before long, I felt his balls tense up and his cock start to twitch in my mouth as he muttered, "Fuckkkk boy, I'm cumming," Immediately, I relaxed my throat and took him balls deep all the way down, and added a second finger as soon as I felt his asshole start to clench and then relax. Instead, he reached down with his hand and applied pressure against the base of his cock to stop his orgasm and got up quickly onto both feet, standing up on the sofa and pulling his cock out of my mouth. "I'm going to cum in your mouth and all over that fucking face boy!" he growled. He then spread his legs wide apart and got down into a squat, so his cock was back at my face level as I kneeled before him. Then he yanked me forward by the hair and thrust his cock back into my mouth. Reaching down and behind him, he pulled one asscheek to the side. "Put your fingers back in there cunt" he said. Hot, really hot, I though. I reached back and slid 2 fingers back into his asshole as he squat down lower. He undoubtedly enjoyed anal play himself, and I pushed in deep, rubbing forwards against his prostate. I gave his cock a few strokes with my mouth and he immediately exploded in an immense orgasm. "Arggghh fuck, bitch!" he shouted out. He shuddered and I could immediately feel his spincter muscles spasm and convulse so hard around my fingers I thought he would break them. His cumload was huge as I felt him nearly fill up my mouth within the first 2 spurts. His cock twitched as it spunked hard into my mouth and I could soon feel some cum dribble and leak out the side and down my chin. He immediately pulled out when he saw my mouth was filling up and he masturbated himself over my face as he spewed even more ropes of cum straight over my face, hair and eyes. It was the most impressive load I had ever dealt with and my face was soon criss-crossed with his load and I could tell he was hardly even done, as he continued stroking his cock, pumping more cum out as he squat down lower over my penetrating fingers. I rubbed at his prostate harder trying to milk more of his cum out as he now aimed back into my mouth and shot some more into me. "Fuck..... you're such a fucking cum slut." he moaned, shuddering as he rode out his orgasm. I could see his muscular thighs straining to keep his balance as he milked up the remaning drops of cum into my mouth. I was breathing hard myself, my own cock still hard, realising that in the heat and intensity of the moment I'd had pushed 3 fingers from my free hand deep up my asshole as he'd erupted in his orgasm. I must have looked quite the slut, kneeling before this stud, his cum all over my face and in my mouth, my cock hard and my own fingers up my butthole. Looking straight into his eyes, as he looked down at me lustily, I kept my mouth open, so he could see exactly how much of his cum I had in my mouth, then slowly and deliberately, I swallowed once, feeling the huge load quickly move down my throat. As he fisted his slowly softening, but still immense, cock, he slapped my face with it, then used it to push the ropes of cum he'd shot over my face, into my mouth, then slid his cock back into my mouth and slowly started pumping again. "Mmmmmm, very very good, boy," he groaned. "And I still haven't even fucked your asshole yet." I allowed him to continue fucking my mouth, feeling his cum and my tongue swirl around his now softer shaft. "You want to feel that cock up your ass boy?" he asked. I pulled my mouth off his cock and eagerly nodded. Opening my mouth again, I looked at hime as I swallowed again, making sure he saw that when I opened my mouth again, that it was completely empty. "Very good then, now you have to make me hard again." he said, rather matter of factly. I was so in heat now I would have done anything to get him hard so we could have anal sex, and I got up quickly, knowing what we could do next. I walked over to the cabinet where I knew he kept his canes. He had a wide assortment for sure, there were at least 12 to 15 different canes of different lengths and thickness, but one immediately caught my attention. I didn't notice it before, it was definitely a lexan cane (acrylic / plastic) and from personal experience I knew these hurt a hell lot more than rattan and were yet whippy and flexible. It was black in colour, and medium thickness like the one that was being used on me earlier. And in addition, the shaft was not totally smooth, it was kind of ribbed or segmented like a length of bamboo. It sure as hell looked more sinister and wicked than any other cane I had laid my eyes on. I immediately picked it up and walked back over to the Headmaster, who was now laid back, naked, against the leather back of his sofa, looking at me as I chose my implement of pain and his pleasure, and stroked his cock slowly back to hardness. " I see you have found my favorite cane, boy. This one is not for amateurs, but I'm sure you will manage, being the cane slut you are," he remarked. I handed him the cane, my cock sticking out shamelessly. "I know this definitely will get you hard again, and you are far from finished with my caning Sir. I can't remember where we stopped Sir, so I think zero is a good place to start again." I sluttishly told him. "You will regret this boy." he said as he took hold of the cane and stood up. "Bend over, show me that ass." Bending over again on the sofa, I felt my cock so hard it was flush against my stomach. Again, I spread my legs wide apart and sluttishly presented my buttocks to him, which were criss-crossed with the welts he so deliciously laid on just earlier. I pushed my ass buttocks back out towards him, and bent my knees, going up on my toes. I could sense him approaching me from behind. "Spread yourself open boy," he said. I reached back with both hands and once again pulled my welted asscheeks apart for him. Relaxing my spincter I pouted my fuckhole for him, flexing it open, knowing how slick my asshole was with my spit and how inviting it must look. He bent down and spit over my asshole, then I felt his thumb press against it, slipping in easily. A few strokes with his thumb to stretch me open a bit, then he pulled it out, one finger went in deep, then two. I moaned in absolute pleasure as he anally penetrated me. He started fucking my asshole harder with his fingers, spreading them apart inside me to stretch my hole wider, then I felt his other hand reach around and his fingers wrap around my throbbing, erect cock. He started pumping with his fist, and it felt incredible. His fingers deep in my shithole fucking me, and him masturbating me, got me right on the brink of an orgasm pretty quickly. I kept my legs and assceeks spread, my eyes rolled backwards in pleasure, a lump forming in my throat from my impending orgasm, and my thighs tense and straining. Just then, he pressed in a third finger, and started rubbing forwards against my prostate. My asshole had gotten tighter since I was close to cumming now, and coupled with him jerking me off, pushed me over the edge quickly, for the second time of the night. "Fuckkk, I'm cumming again!" I yelled. My body started shuddering hard as my cock erupted in another mind-blowing orgasm. I spread my legs wider still to keep balance, and kept my buttcheeks open as I violently spewed my cumload all over the Headmaster's sofa again. Even though I'd already cum once, this load was so pent up it seemed as large as the first, as my cock spasmed hard and spurted rope after rope of boiling cum. I was struggling to keep myself from falling down, my shitter spasming hard and squeezing the fingers still lodged deep within my fuck chute. "Ohh shittt.... just keep fucking my hole!" I cried out. I squirmed about, my head on the sofa, as I came so hard I nearly passed out, my chest heaving. The Headmaster continued wanking me hard, my cock now ultra-sensitive, and he pressed and rubbed against my prostate firmly, milking me out as I had done for him earlier. I even caught my own face with a few ropes of cum. I bent and straightened my knees, working my ass up and down his fingers in unison with his fuck strokes, as I finally started cooling down from the intense orgasm. "Shit, fuck, that felt really good, Sir. Thank you Sir" I moaned, barely intelligibly. "Get up boy, keep my fingers in your asshole and squat up on the sofa." he ordered His let go of my cock as I straightened up partially, enough to get my aching legs up on the sofa, my asshole now more slack and relaxed after the huge cum. I could feel my own cum under my feet and toes as I squatted on the sofa, the whole room smelling of sex and ass play, wondering what he had in store next. My cock was softening but still throbbing, aroused. "Tighten up your asshole," he ordered tersely. I did as he said, tightening my sphincter around his fingers, and he pulled one out, the remaining 2 fingers still deep inside me. I pushed my feet wider apart and spread my thighs open all the way, till they were splayed open as wide as they could go. Shameless position, I thought, and thrust my hips slightly forward and leaned back slightly, supporting my weight with one hand. He then pressed his fingers in deeper still, getting as deep as he could up my asshole, then again started applying pressure against my prostate. He knew exactly how to push my buttons, as my cock responded eagerly, regaining its hardness barely a minute after my most recent cum. It was aching slightly from being so hard, for such a prolonged period of time, but I was still itching for more action, having not been fucked yet. He reached around once again and wrapped his fingers round my cock and started stroking me to full hardness. The sensations were divine. "Tighten up as much as you can boy, it feels better," he said in my ear. "And this big orgasm is just going to make your caning that much more painful." I moaned and did as he said, keeping my asshole as tight as I could as he continued rubbing at my prostate from inside, and alternating this with long slow strokes in and out. Indeed the anal penetration felt more intense and pleasurable the tighter I kept my hole. My cock was caught in between pleasure and a deep ache, but I stayed painfully hard in spite of myself. "I want to see your cock hard for your caning boy," he hissed in my ear. After another few minutes of delightful torture and stimulation, he pulled out his fingers, leaving me thirsty and lustier then ever before. He yanked my head back by the hair and thrust his fingers in front of me. "Clean up the mess you made, cunt," I was slightly taken aback not by him offering me his fingers, but the state they were in. The huge orgasms and incessant anal stimulation must have pushed my shit down really low and 3 of his fingers were deeply streaked and smeared in a rich brown. The smell of my shit was strong and heady, but I was so aroused and horny I didn't hesitate opening my mouth and letting him push his fingers right in. I wanted him to know as I was nasty enough that nothing was out of bounds. The taste of my shit was acrid, not strong tasting, but the smell permeated my nostrils. I gagged only very slighty at first but started sliding my tongue around his fingers, cleaning them, as the Headmaster looked at his latest bitch performing this shameless act. I used my tongue to clean them as best as I could, getting in between his fingers and feeling the muck against my tongue. It was not unpleasant definitely and after I'd gotten used to the smell, I found the act erotic and submissive as hell. I pulled my mouth away, and, opening up, showed him what must have been a nasty, filthy, shit coated tongue, before I swallowed once, and showed him that everything went down. Swallowing was not a problem, given that it was only a small amount, and he definitely got turned on watching me. "Nasty, you're absolutely shameless aren't you. Bend over again, slut." he ordered again. Again, thoroughly horned up now, my asshole aching and begging for action, I bent over his sofa. I turned my head towards him, watching him as he walked over to his desk and opened a drawer and reached in. He then pulled out a string of anal beads and a large buttplug. The beads were huge, the biggest I'd seen up till now, each one roughly the size of a ping pong ball, numbering 5 in total and the buttplug was definitely generously sized, very wide at the thickest portion and fairly long as well. I immediately knew he wanted to stretch me out properly. Eagerly, I did what I knew best, opening up my thighs as wide as I did before, I reached back to once again stretch my asscheeks open as far apart as I could and pushed my bum out, immediately I flexed open my shithole, just as he came up behind me. "Good, very good, you better get used to this position," he said. "Tell me how much you want it." "Please Sir, stretch my asshole open with your toys, open me up for your cock." I pleaded, at the same time flexing and pouting my rosebud open. He spit on my asshole, making it even more slick, and I felt him press the first anal bead against my opening, I relaxed and allowed it to slip in, grunting a bit at the size of it, my asshole closing up after the bead. He advanced the string quickly and inserted 2 fingers in, pushing the bead in deep and then started with the second bead. I kept my asscheeks wide apart, helping him get better access at my asshole and relaxed each time he pushed a bed in. After he inserted one bead, he'd pull back and apply tension to the string, halfway pulling out at the freshly inserted bead, so that I felt my asshole stretch mightily around it. After a while, he'd pushed all 5 beads deep up my ass, and left me with my cock absolutely throbbing and me begging for more. Next came the buttplug. My asshole was warmed up now and I easily allowed the tip of the buttplug in once I felt him applying pressure against my shitter. He reached down once again and I felt his fingers again wrapped around my cock. Aching, throbbing, but hopelessly aroused, he stroked me till I was so hard I couldnt believe it, at the same time advancing the buttplug slowly but incesantly deep up my ass. I could feel the anal beads being pushed in even deeper, and the widest part of the plug now stretching my shithole wide open. All the while he was masturbating me, I was moaning like a bitch in heat. He eased the widest part in and my ass quickly swallowed the rest of the huge plug. I don't think I'd ever been this full before. He kept up the stroking and now started fucking my ass with the plug. It was delightful torture again as my cock and balls ached, and his plug slowing raping my asshole. He pulled out till it was nearly fully out, then reinserted it deep in, my sphincter contracting and relaxing as he slowly fucked me with his large toy. Finally, as I lay bent over, panting and hopelessly aroused, he stopped, inserting the plug fully once again, and he released my cock. Without saying in word, he walked back to his table and brought back something. He came back up behing me and I soon felt a firm strap being pulled around the base of my cock and balls. Looking down between my legs, I realised he'd fastened a leather cock ring and started tightening it firmly. My cock throbbed, steel hard, sticking straight out, and my balls ached as the leather strap pulled tightly around them. "This is going to keep you hard for me through your caning, and I want you to stay that way until I allow you to cum," the Headmaster said. This would be crazy, this would be torture, I thought to myself. My cock hard, bound firmly in a leather cock ring, a string of huge anal beads and a large butt plug in my ass, my legs wide open, ass sticking out and getting ready for a caning by a naked, muscular white hunk and a good round of ass fucking after, this almost seemed like a scene out of a hardcore porn flick and was to me a dream come true. I remained in my position, swallowing hard, the taste of my shit still in my mouth, waiting, waiting for him. He picked up the wicked looking lexan cane from the floor and once again lined himself up behind me, though this time naked, his cock, like mine, totally hard again. He started with a bit of a tease, using the tip of the cane, running it up along my asscrack, nudging at the flange of the buttplug wedged deep in my ass. He then bent over the suddenly started pulling on the buttplug hard. I gasped as he pulled it completely out, gaping me and leaving me feeling suddenly empty. Then once again, he ran the cane tip along my asscrack, this time pausing with the tip against my butthole. I relaxed and pouted, and I felt him push in the tip, sliding the cane into my asshole. "MMmmm..." I moaned out loud. Then he pulled it out, extending his arm, pushing the tip of the cane towards my mouth, as he once again inserted the buttplug fully. I grunted as the plug forced its way in, stretching me open, at the same time opening my mouth and licked and sucked at the tip of the cane pulled freshly from my ass. Then he pulled the cane away from my mouth and I braced myself for what was to come. He lined himself up again, legs slightly apart for balance and leverage, then, as he did the first time, tapped firmly a few times against my welted buttcheeks. "Buttocks out boy," he commanded. I obeyed, bending my knees and arching my back further to push out my buttcheeks. There was a loud swish and a resounding crack as the cane landed full force against my welted flesh. "Yeowwchh!" I cried out loudly, my legs and buttocks immediately started squirming at the sting and intense pain the lexan cane brought forth. I'm sure the pain would have been excruciating even on fresh skin but my buttocks were already reddened and severely welted by his earlier punishment and even though I enjoyed the pain from canings so much, the pain I felt this time was nearly completely unbearable. I felt a trickle of blood quickly form on my bruised flesh. The Headmaster must have enjoyed the view trememdously as he lined up his second stroke, the cane once again resting against my flesh. "I'm starting from zero again given that you have forgotten to count, boy," I heard him say Obediently, I once again pushed out my buttocks for him, getting ready for the next stroke and balled up my hands into fists, bracing for the pain to come. "Crackkkk!" this stroke stung even harder than the first. I yelled out again, gritting my teeth. he was definitely not holding back. This stroke was aimed perfectly, landing across the flange of the buttplug, pushing it deeper in my asshole. The combination of pain and the stimulation I felt as the plug was thrust deeper and rubbed against my prostate was strange yet pleasurable. My cock twitched noticeably. "One, Sir. Thank you Sir," I could barely manage saying. I could literally feel my heart throbbing across each new welt he lay across my buttocks. The pain was incredible, but in spite of myself and because of the tight leather strap around my cock, I remained absolutely erect, showing off my arousal shamelessly. The caning was slow, steady and relentless. Each stroke was carefully weighted, delivered at full strength, timed perfectly such that the next stroke followed the previous just as the pain reached it's crescendo. It was extremely clear how experienced the Headmaster was at maximising the pain of each stroke. I remained as still as I could, presenting my buttocks to him in a lewd a fashion as I could, legs spread, ass pushed out. The room was filled with the smell of sex, cum, sweat, and the sounds of me moaning and yelling in between the pain and pleasure, and the spine chilling crack of each cane stroke delivered mercilessly over my thoroughly thrashed buttocks. Each time I moved too much, didn't count promptly, or straightened up from my position, the stroke would not count, and another stroke was added onto the punishment. Numerous times, his good aim would land a stroke over the butt plug and I would have that pleasurable sensation of being fucked and caned at the same time. "Thwackk!" "Crackkk!" The sound of the lexan cane on my buttocks rang out crisp and loud through the empty corridor outside his office. I heaved and panted loudly, crying out with each stroke. I counted at least 14 or 15 strokes now, the searing pain in my buttocks now nearly unbearable. "Five Sir," I counted. The numerous strokes that did not count kept the number low even though my flesh was already burning in pain. With twenty more strokes to go, I was sure I couldn't take so many. I was bleeding again, yet I was immensely hard still. He put down his cane, reaching down to pump his hard cock with his fist. "Straighten up boy, come over here, put your mouth to good use," he said with authority. Grateful for the break from the excruciating pain, I straightened up and squatted in front of him again. His impressive length and girth was in front of my face again, and he was as hard as he was even before he came. Lifting one leg up onto his sofa, he thrust his hips forward and I immediately opened my mouth and took his cock in, allowing it to slide all the way to the back of my throat. It took me awhile before my spit started runnig freely again and I started sucking him eagerly. He reached one hand behind him to once again slide one finger up his asshole, his other hand grabbing the back of my head to skullfuck me deep. I felt his cock twitch in my mouth as he got even harder from the anal penetration and my sloppy blowjob. I came up for air gasping after a stretch of very forceful skull fucking, my face was a complete mess from my own spit, tears and his precum. He then forced my head under his ballsac and I went to work again, sucking at his huge, heavy balls and then as he pulled out his finger, I reached up to pull his asscheeks apart and went to work immediately with my tongue on his shithole. I rimmed him deep, as best as I could from this position, then decided to move behind him for better access. He bent forward obligingly and I stretched open his asscheeks and dove in deep, tongueing his asscrack, his shithole and inserting my tongue in deep, past his sphincter, to really taste him. He moaned out his approval before pulling me by the hair and bringing me to the front to work on his cock some more. I continued my sloppy blowjob for another good 10 minutes before he had enough and pulled me to my feet. "Bend over, cunt, there are still 20 strokes to go," I got up, my legs positively wobbling, my ass on fire and my rectum completely stuffed and full, and I was absolutely cock drunk and horny for more now. Quickly bending over again, I splaed my thighs open and awaited my punishment. "You can have me in your office to cane and fuck any time you wish Sir," I lustily said. He smirked, and replied, "I knew that the moment you took your shorts off and showed me your bare ass and hard cock, boy." He didn't waste any more time, lifting the cane up high and delivering an extra vicious, stinging stroke, immediately setting my ass on fire, as if to highlight his statement. I clenched my buttocks in pain as I felt the heat and an immediate new welt form. "Six Sir, thank you Sir," I uttered. "Swish, crackkk..." the cane again broke skin, my buttocks trembling. "Swish, crackkkkkk!' this stroke was even more painful, and my cock twitched and strained against the leather strap around it. I started sobbing now, tears finally flowing because of the pain. But I dared not move or straighten up. Each stroke was more painful than the last. It felt as if the Headmaster was increasingly turned on as the caning progresed, and as he got even hornier, he caned even harder. "Crackkkk!" the sound of my beating resounded through the room. "Arggghhhh, fuckkk!" I cried out loudly, and promptly earned an extra stroke. After he crossed 24 strokes delivered, the count was still at 10, and I was writhing in pain on his couch, still pushing my buttocks out high and keeping my legs open, my hole stuffed full with anal beads and his huge buttplug. He decided he'd had enough and reached down, picking up my underwear again and gagging me with it. "I'm giving you another 20 strokes, and that will be it boy. Now spread yourself properly and push your buttocks out some more, up high." he ordered again. I trembled as I obeyed him, my bum out high and my legs spread wide. At least the gag would prevent me from screaming out too loudly, and he could finish his caning as he pleased. But I knew another 20 strokes would be a killer. He took his time delivering the rest of his punishment, enjoying and savouring lining my buttcheeks with fresh. livid welts. My thighs bruned with pain from the strain of holding position, spread open, and my buttocks were seared red hot with every vicious stroke he lashed out with the cane. "Swish.... crackkkkk!" Another welt formed over my arse cheeks. "Gnnnnmmphhh," I yelled into the gag. "Smackkkkkk!" This one was particularly stinging and had me up on my toes, squirming in absolute agony. "Crackkkkkk!" Again and again the cane cut against my sore flesh, my asscheeks by now absolutely covered and marked with welts, by far the most painful, brutal caning I've had. I stayed hard, my cock throbbing against the firm restraint of the leather ring around it, and also because of the butt plug pushed deep into my ass each time a well placed stroke struck against it. I counted out 10 strokes, with another 10 more to go, when he suddenly stopped the caning. He came up behind me again and I felt both his hands on my arsecheeks, and they felt like fire burning into my skin. I was undoubtedly sore and bleeding as I felt him pry me apart wide with his hands. My asshole clenched involuntarily around the plug, sending a much appreciated wave of pleasure down my spine as he held my asscheeks open. Then I felt him release his grip on me and tug at the butt plug lodged in my rectum. "Turn over boy, lie back now," Grateful for the temporary respite from the caning, I quickly obeyed and turned over, lying down on the couch, awaiting his next move. I was covered in sweat still, heaving and breathing hard. "Pull your legs back, spread them wide," he said. I got my legs back to my chest and held them wide apart with my hands, giving him full access to my stuffed hole and hard cock. He squatted in front of me and spit once over my cock, and started pumping it slowly with his hand, and with his other, pulled firmly on the plug in my ass. "Mmmmphh, gnhhhh" I moaned, keeping myself wide open for him. He expertly stroked my cock, and it felt absolutely great, even though it was still aching. My shitter dilated then quickly allowed the plug to pop out my ass after the widest part had passed, clenching quickly as he pulled out completely. He gave me a few more firm strokes with his hand before I felt the firm pressure of the tip of the plug against my ass again, I relaxed and allowed him to penetrate my hole again. The pleasure was immense, him stroking my cock and now inserting the plug deep in. Then he pulled out again, and got into a steadier rhythmn, pulling out the plug and fucking it in deep, my asshole repeatedly dilating and clenching as he fucked me slowly with it. I looked down as he fucked me with the plug, the smell of my shit permeated the room, and I could see the plug was definitely deeply and thickly smeared in a layer of brown. He increased the pace as my moans got louder and he stroked me faster, my cock now aching for yet another release. My thighs were shaking as I was quickly approaching an orgasm. He looked up at me and smirked, sensing my impending cum, "You wanna cum, boy?" he asked I nodded my head eagerly, the gag still in my mouth. The tightness of the leather band around my cock effectively prevented me from blowing my load as he pushed me to my limit of endurance and continued his relentless dual stimulation, penetrating my ass deep and jerking me off. My cock was now spasming and straining against the ring and I was sure I would have blown a huge load by now if not for it. I was struggling at trying to keep my thighs apart with my hands and I was now shaking all over, needing desperately to cum. Abruptly, he stopped and pulled away, pushing the plug back in fully with authority, then stood up again. My body was screaming for another cum, and I remained as I was, spread eagled, hoping he would fuck me, jerk me off, anything, so I could blow my load. "Get up, boy, you have another 10 strokes to go," he said cruelly. I groaned into the gag, absolutely frustratingly horny. My cock throbbed obscenely in front of him, but I knew there would be no way out of this apart from finishing up my caning and waiting for him to thrust his cock up my shithole. Slowly I got up and once again bent over his sofa. Pressing my chest down low, I once again stuck my arse out for him, he way I knew he liked it, and waited. He picked up the cane once again and a split second later I heard the crack of the lexan cane once again breaking skin, and my buttocks burned with white hot pain. I screamed out loud, but it was muffled by the gag, and I flexed and straightened my knees repeatedly, trying to get rid of the pain. But this was quickly followed by a second stroke, equally stinging as the one before it. I squirmed again, taking a while before regaining my composure and spreading my legs apart, both for more balance and for his viewing pleasure. "Crackkkkkk!" "Thwackkkkk!" "Crackkkkk!" I counted each terrible stroke in my head, my arse throbbing as hard as my cock now, my flesh no doubt broken and bruised. The only consolation would be the strokes that hit squarely against the butt plug and each time remind me of what was to come soon, punctuated with the plug forced deeper in my asshole, and sending a strange wave of pleasure into my spine. As he always did, he timed each stroke perfectly, and now started paying a lot of attention to the area right between my lower buttcheek and upper thigh. "Crackkkk!" I felt like I was about to pass out now. The pain was incredible and I couldn't hold back the tears. I was groaning, moaning and screaming out into the gag. Another 3 strokes added to the excruciating pain, as I felt a few more drops of blood trickle down my welted asscheeks. "Crackkkk!" "Thwackkkk!' The last stroke landed emphatically once again over the butt plug, leaving me a trembling, shaking mess at the end of my punishment. Not daring to move yet, I remained spread wide and bent over on his couch, I kept my arse up high and waited for his next move. I felt his hand yanking me up by the hair again, straightening me up before turning me towards him. His cock was as hard as mine and throbbing as well, and I automatically knew what he wanted. I squatted in front of him, my legs apart and pulled out the gag, opened my mouth again, and took his cock in deep. Immediately I tried to relax my throat and deep throat him, feeling his thickness stretching my throat, gagging me as my spit started to flow freely. Once again he raised one leg up on his sofa and started to fuck my throat hard and fast. He held my head down hard, his cock buried all the way and balls deep, till my face and eyes were deep red and I was struggling for air, before he released me, then continued facefucking me. It was rough and hard, hardly giving me time to breathe, but I wanted this man to be pleasured as much as he could be. I sensed he got quite close to cumming, as he slowed down his pace, fucking my mouth in long, slow strokes now. I knew what he liked, and slid my tongue over his shaft as my cheeks hollowed out and I sucked hard, and then took him balls deep into my throat. I suppressed the gag as my spit ran down the length of his cock and my chin, and I reached up between his legs, rubbing my fingers along his asscrack then against the rim of his asshole. "Yes that's right, slide it in, boy," he moaned in approval as I deepthroated him expertly. I slid one finger in, then quickly added a second easily. I felt him squat lower and wider to get my finger in deep, as he continued thrusting his hips forward and fucking my mouth. I rubbed at his prostate as I finger fucked his asshole and once again felt him getting close. I felt his shaft start to twitch in my mouth, then he abruptly pulled out, gasping slightly. "Fuck, you nearly made me cum, slut." he said as I wiped some of the spit from my chin, still squatting sluttishly, wide open legged in front of him, my own cock sticking out, showing off how turned on I was. "Get up on my desk boy, then squat down, back facing me," he ordered me. I was not sure what he wanted to do next, but I didn't hesitate obeying him. I got up quickly onto his desk after clearing away some of his papers, then squat down in the centre. "Legs open boy, push your ass out towards me," he said. I did as I was told, opening my thighs, feeling the strain as he stood behind me, watching. I felt him tug at the plug in my ass now. "Shit it out, push it our for me," he said, from behind. The plug was fairly large and wide, I got up on my tiptoes and started straining, bearing down. It must have been quite a sight, my asshole dilating and flexing, trying to expel the large plug in my ass. I grunted a little as I felt my hole stretch wide, then the plug slowly start to inch its way out. In a way it felt like I was taking a massive shit, but more pleasurable. I reached down and stretched my asscheeks apart, trying to shit the plug out, my hands feeling like a red hot iron on my bruised flesh. Just as the widest part was about to push past my sphincter, I felt his hand on the plug, firmly pushing the plug deep in, all the way up inside me again. The sensation was strange yet extremely intense. "Ugghhhh," I grunted, and my cock immediately twitched noticeably. If not for the cock ring, I was sure I would have blown my load. "Now shit it out again boy," the Headmaster said. I repeated the action, straining and pushing the plug out, this time more easily. The widest part was right at my sphincter again and it was starting to feel really good getting stretched out like that. He then reached down and held the plug right where it was, not pushing in, but not letting it pop out either. He held it there, the wide part of the plug keeping me stretched open and at the same time, I was straining to push it out. It sent waves of pleasure through my groin and cock, and right at that moment, he reached around and started stroking me again. I wasn't sure how much more of this I could take before my cock would burst right through the ring. Finally, he let go of the plug and I pushed it right out, suddenly leaving me feeling quite empty. I looked down. The plug lay on the table, filthier than before and coated thickly in shit. I had no doubt what he would want me to do next. He picked it up and shoved it towards my mouth. "Suck this, and clean it up properly, then shit those beads out your ass." I opened my mouth, now pretty much used to the strong smell of my own shit. I suppressed the gag sensation quickly and allowed him to push the whole plug in my mouth. Its length quickly made me gag and I tried to slide my tongue around it to clean the muck off its surface. I quickly felt the dirt come off and fill my mouth and it felt nasty as hell. Hot as hell too, doing this for the man who just caned me. He pulled out the plug, which was now only semi-cleaned and waited while I caught my breath. I knew what he wanted, and looked at him as I closed my mouth and swallowed, retching only slightly as I felt the bitter shit make its way down my throat. He held the plug in front of me and I started licking at it, cleaning it as he watched me and fisted his own cock. I had no doubt he would want to go much further with regards to scat play as time passed. He then pushed the plug back in my mouth and I ran my tongue around it. Leaving it there, he looked beneath me again, I was still holding my asscheeks apart and straining hard, trying to expel the large beads from my asshole, distracted by the task he was having me perform with my mouth. Grunting, I felt the first bead start to really stretch me and with a slight tug from him, it popped out and my shitter quickly closed around the string. He continued pulling lightly but firmly against the string and soon the second bead was at the entrance of my shitter and I had to keep straining hard, feeling the stretch. I pushed my buttocks upwards and backwards slightly to give him better access to the string, and also a better view. The room started smelling even more strongly of shit and I knew the beads would be much more heavily soiled than the plug, given they were lodged much deeper up my rectum. The second bead popped out, and then followed by the third, each one sending a ripple of pleasure through my anal passage and it stretched me open deliciously before my sphincter clenched again. I was achingly close to orgasm as the last 2 beads stretched me open and the string of beads dropped onto the Headmaster's desk, my mouth still filled with the heady taste and aroma of my own filth. I released one hand from beneath me and brought it up to the plug, fucking my own mouth, cleaning it at the same time with my tongue. My ass now awkwardly empty and asshole still slightly gaping, I remained squatting on his desk with the plug still in my mouth. He came up to me again and I pulled the plug out, now completely clean. Once again, I closed my mouth and swallowed obediently as he watched me. "Good," he said. "Now get back down and back here." I clambered off his table just as he reached out and pulled me by the hair back to the couch. Roughly manhandling me, he pushed me forward. "Show me your hole, and open wide," he said as he shoved me onto his couch, stroking his hard, slick shaft. Finally, after all that torment, he would be fucking me with that cock. I hurriedly bent over, not holding back, and shamelessly spread myself wide for him. As I had bent over for his cane, I know adopted the same position for his cock. Naked, bent over, my chest pressed against the cool leather of his couch, legs apart, wide apart, knees bent, welted arse thrust out backwards, my hands reaching back, pulling myself open till it hurt. I could almost feel his eyes fixated on my shithole, and as a final silent act of submission, I relaxed and opened up my rosebud for him, flexing it open, shamelessly. I was up on my toes now, presenting my hole to him. "I don't use condoms boy, you take my cock bareback in your ass," he said matter-of-factly as he stroked his cock. I nodded in reply, "Yes Sir, please fuck my asshole however you want it, you don't have to use a rubber." I was sure my asshole was a mess and shit smeared and slick with spit, and equally sure I could take him without additional lube. He thought the same, as I soon felt the tip of his cockhead pressing against my shitter. "Open up for me boy" I heard him say. I didn't know if it was possible, but I tried to open my hole up some more, and he eased his cock past my sphincter and in a long steady stroke, pushing firmly. I moaned out loudly in pure pleasure now as I felt his cock go in deeper than any other before him, and fill me up deliciously. He pushed steadily and buried himself balls deep, and I could feel his thighs against my burning asscheeks. The stimulation was more intense than anything I'd felt before and I felt my cock stiffen and the cum literally forcing it's way out. "Ugghhhh, fuckkk, Sir, I'm cumming!" I shouted out. I felt my asshole and cock spasm rhythmically but my cum was kept firmly in place by the tight cock ring. I'd never felt anything like this before, and it was positively driving me crazy. Physically I was experiencing orgasm as all the muscles in my body tightened, but I couldn't spurt my load. "Fuckkk.... please, Sir," I croaked in the throes of my climax. "Please take the ring off, let me cum." I couldn't see him, but heard him behind me, "No slut, I get my pleasure first, you cum only when I allow it." With that, he started pumping his cock in and out of my asshole as my cock throbbed and spasmed. My sphincter rhythmically tightened around his cock as I came, no doubt intensifying his pleasure as he fucked me, as I tried to ride out my frustrating dry orgasm. It stung and hurt as his thighs slapped against my welted asscheeks, but he didn't care, fucking me deeper and harder. I tried my best to maintain my position, keeping myself spread wide open, as he sodomised me roughly. I couldn't make out when the orgasm subsided since I couldn't blow my load, giving me an aching sensation in my balls as his shaft kept me stretched open and well fucked. But his steady thrusting and his cock fucking me deep in my ass kept me on edge. I started moaning out loud, and started thrusting my hips backwards towards him, timing it with his strokes. "MMmmmm, fuck, fuck, fuck me harder," I pleaded. Instead of the sharp crack of the cane against my buttocks, the room was now filled with the sounds of steady slapping of flesh against flesh as he pounded my ass deep and hard. I wanted to show him I knew how to get my man off, and I knew how to pleasure someone with my asshole. I tightened up my hole around his cock, milking him firmly with my sphincter muscles. I would relax more as he thrusted in deep, then milk him hard as he pulled out. Before long, he was moaning out loud as well. "Fuck, slut, I'm going to cum soon," he said, trying to slow down the pace. I felt him shudder slightly and his muscles tightened and then he pulled out his cock, throbbing and twitching, as he breathed hard. He then walked back towards his desk, opening his drawer again and pulled out a tube of what seemed like some kind of cream or lube. I was still bent over and turned to look at him, my eyes glazed over with lust. "You don't need any lube, Sir. I'm wide open for you." I said. "This isn't lube, boy." he retorted. He uncapped the tube, then picked up the soiled anal beads from his desk and walked back towards me. His cock was visibly shit stained as well, I could make out as soon as he was back in front of me. "Straighten up and suck me clean boy." I got up from my bent over position and took his cock back in my mouth, it wasn't as thickly coated as the butt plug he'd had me clean, and definitely wasn't as filthy as the string of anal beads he was now carrying. I made quick work of it, wanting to get back to the real action quickly, and polished off his shaft and cockhead with a good, few practised, deep strokes with my mouth, getting him down my throat once again. He pulled out, satisfied I'd done a good enough job as he cooled off, and again yanked my head backwards by the hair. I had a good look at the string of beads now, and I could hardly even recongise them. I'd not prepared for anal sex prior to this caning and I'd been relatively full back door, and I hadn't taken any enemas or used any suppositories to clear out my ass. It was definitely messy. The beds deepest in my ass were completely covered in my shit, not just smeared, but it looked as if I took a shit and pushed out a big turd and the beds were buried in it. Even the fourth and fifth beads were heavily caked in filth. I gulped, not knowing if I could manage this. "Open your mouth boy," the Headmaster snarled. He remained as hard as ever, and he didn't flinch at the smell of the beads, as he lifted them up over my open mouth. I gagged a little as the heavy smell hit my nostrils hard, and he placed the first bead, or at least what was visible of it, and the large piece of shit right in my mouth. I closed my lips around it and immediately my mouth was completely filled with my own turd and the large bead. The smell was heavy and slightly overpowering and I retched two or three times, nearly throwing up. Having such a large piece in my mouth was vastly different from doing dirty ass to mouth or cleaning a soiled butt plug from my asshole. He let go off the string of beads and let the other four dangle outside of my mouth. He then squeezed the content of the uncapped tube in his palm. It was a white cream like substance, and he squeezed a good liberal amount out, then lathered his cock with it, spreading it and stroking it along his massive shaft. "This isn't lube, slut. This is a desensitising cream. Numbs my dick a bit when hot sluts like you are making me cum too soon, so I can fuck your asshole for longer." he said to me, fisting his cock and covering it with the cream. It soon turned colourless after a good few strokes, and he added some more, pumping his cock again after. "Mmmmphhh," I mumbled like a fool with the anal beads still in my mouth. He squatted a little with his legs apart and squeezed some more cream in his palm, then reached down and slathered it into his asscrack and pushed some in his asshole with his finger. I watched his cock twitch as he did this. The stench and heavy aroma around my face and mouth was quite intense, and I reached up to pull the bead out of my mouth, then took a breath of fresh air, and lowered it back in. I slowly bit off a large part of the turd and pulled the bead out again. I was seriously gagging now, and looked pleadingly at the Headmaster who was still masturbating himself whole watching me. "I don't expect you to clean the whole string and swallow everything boy, but you will do as you say. If you want to be my boycunt and cane slut long term, I'm going to expect you to be on the receiving end of some heavy scat play with me. Now start chewing, and I want you to swallow it," he ordered. He must have known that by now, I would do anything for him. I dared not disobey, knowing full well he could pick up the cane anytime and go to work again on my tortured buttocks. I started chewing on the big piece of shit in my mouth and immediately the taste and smell intensified heavily. I retched hard and felt my stomach heave, nearly throwing up, but I kept it suppressed. The whole experience felt both surreal but incredibly arousing. I'd been very submissive as soon as I started fucking, but this crossed a new level of submissiveness for me. In my mind, I'd thought there was nothing as submissive as chewing and eating my own shit fresh from my ass, cleaning my own shit off the cock of the man who would be fucking and cumming inside my asshole. I wanted to his bitch and scat slut, and I wanted to start now. I was squatting down now, as I was previously, and as much as the stench stung at my nostrils and in my mouth, I was extremely turned on. I spread my thighs and reached down to pump my cock. It was hard, slick, still wrapped tightly by the cock ring, and I shamelessly masturbated, my mouth full of my own shit. I retched again, as I chewed, and the acrid shit started to sting a bit on the insides of my mouth. But I was horny, definitely very very horny. I picked up the string of beads again and lifted it to my mouth. There was plenty more shit thickly caked over and covering the beads. I opened my mouth and but off another large piece, adding it to the big load already in my mouth. "Very, very good, boy, you are learning fast. Definitely the biggest slut I've had from this school so far," he said, as he continued leisurely masturbating himself. My stomach heaved as the taste intensified with this second load. I felt that I was getting more used to the heavy earthy taste now, and started salivating quite heavily, involuntarily. I chewed more and realised my mouth was really really full and my cheeks were slightly bulging. I closed my eyes and swirled my tongue around in my mouth, chewing some more. I looked deep into the Headmaster's eyes and slowly swallowed once. At least half went straight down my throat. I could literally feel my bile immediately rise up, and had a wave of an uncontrollable urge to vomit. Despite my arousal, my stomach heaved violently and I let out a loud sickening retch, fully expecting a torrent of shit to pour out my mouth, but somehow, I managed to keep it down. My eyes were bloodshot now and tears ran down my cheeks. There was still a big load in my mouth but the Headmaster showed me his approval as his cock seemed to get even more erect, his fist continuing to pump it. I knew what he wanted me to do, and I continued chewing at the foul tasting shit in my mouth. I kept masturbating, wanting to keep myself on edge and aroused. I slipped a finger down, in between my cheeks and stated rubbing at my anal ring, then penetrated myself again and started pressing at my own prostate to keep me hard. Bracing myself, I looked at the Headmaster again and clamped my lips shut, suppressed my gag reflex as best as I could and swallowed hard. The second time, it went down much easier than the first, and though I retched still, I wasn't anywhere near as I was just now to vomitting. The entire remaining load went straight down and I kept it down, my stomach heaving only slightly. I then opened my mouth and showed him that it was completely empty, though I'm sure it was still deeply brown stained. "Very good, cunt. I'm impressed enough. Do you want to eat straight from my asshole after I train you to, boy?" he asked I didn't hesitate and nodded my head, "Yes, Sir, I want you to feed me your shit and I want to eat it all." I couldn't imagine how far this caning had gone, and that I'd just swallowed a big load of my own shit in front of another man. He pulled me up by the hair and pushed me back onto the couch. "Lie down boy, on your back. I'm going to reward you." he said. I settled back down, and laid down on the sofa, as I saw him reach down for the now clean buttplug that had most recently been deep inside my ass, and then straddle me, his groin and cock close to my face. I opened my mouth, as he spread his legs wider for balance, and he squatted down low so I could suck him easily. He slid his cock right in and I started sucking him. He thrusted only slowly, sliding his cock with long, leisurely strokes all the way in, then pulled out till only my lips were wrapped around his cockhead. He rocked his hips gently back and forth, and it almost felt like a lover gently fucking my mouth and throat, not a rough, dominating, raunchy scat top. He placed the butt plug in my hand, the flange against my palm as he stroked his cock in and out of my mouth. I felt him shift a little and realised he was spreading his thighs wider apart. "Push the plug into my asshole, all the way in, and stretch me out," he said lustily. He continued pumping his cock slowly in and out of my mouth, and he reached back to spread his cheeks apart for me. I was still trying to orally pleasure him so I fumbled a bit with the plug. I stopped for awhile, realising the plug was quite dry now, so I put it in my mouth, fucking it, getting it wet, then spit more on the tip. He leaned forward a bit to give me better access, and at the same time, slipped his cock back into my wet, hungry mouth. I slid the plug along his asscrack, and felt him shudder slightly as the tip brushed against his shitter. I adjusted my hand and tilted the plug till it was at the proper angle and started applying pressure. "Uggghhh," he grunted. He relaxed his sphincter and I felt the give as his asshole allowed the plug entry. I pressed firmly and he relaxed enough as the plug inched its way up his ass. I figured that having a plug up his asshole would intensify the pleasure he felt when he fucked my mouth, and later, my ass. Slowly, the widest part passed his tight ring, and he grunted as it popped past, the rest of the plug sliding home, lodged fully inside him. Feeling the plug all the way in now, he relased his hold on his asscheeks and reached down to hold the back of my head with both hands, then started thrusting harder into my mouth, fucking my skull as he did earlier. I struggled a bit now as his rhythmn quickened, and tried to relax my throat as I knew he wanted. He started panting a bit as the sensations intensified, then stopped, and pulled his cock out, which was followed by a long string of spit, and me gasping desperately for air. He reached out for the tube of desensiting cream as he got off me, and squeezed out more on his palm, and slathered it over his cock. He lay back on the floor now, and stroked his hard cock. "Get down here, ride my cock, slut," he commanded. I clambered off the couch, gathering up the slobber and spit with my hand, and as I spread my legs to squat ove his hard cock, reached between my legs and lubricated my hole some more. His cock looked absolutely menacing, standing straight up, swollen cockhead, throbbing, veiny and immensely thick. I faced towards his feet, spreading my legs apart on either side of his thighs, and slowly squatted down, my own cock still tock hard and bound firmly. I reached down and guided his cock towards my asshole as I lowered myself down to him. Though relatively loosened now after all the penetration, his cockhead still felt huge pressing against my shitter. I relaxed my hole and opened it up, slowly allowing this cock to penetrate me. I spread my thighs wider open as I moaned in pleasure. "Ohhhh, fuck, that feels good," I sighed. Slowly I sank my hips lower as I engulfed his entire length with my practised, well fucked asshole, till he was balls deep in my ass. Feeling absolutely full, with his cock packing my shit in deep, I started to slowly fuck myself on his cock. Once again, I wanted to show him that I knew how to pleasure man-cock with my asshole, and built a slow, steady rhythmn. I would tighten my asshole hard and squeeze and milk his shaft on each upstroke as I raised my hips up, till just his cockhead was inside me, then relax my hole before plunging it all the way in again. After a few strokes, I felt very close to orgasm again, once again prevented by the cock ring wrapped tightly around my shaft and balls. I slowed down a little, and got up on my toes so I could work my hips down lower. He moaned and so did I, and he started thrusting his hips upwards in unison with me pushing downwards. I bent slightly forward and rested my hands on his thighs, feeling my body shudder with pleasure as I sluttishly worked his cock with m anal muscles. Undoubtedly, I knew he would be having an excellent view. He could have a good look at his handiwork with the cane, my buttocks undoubtedly welted and still very much stinging with pain each time he reached out to grab and asscheek. And I'm sure he could see how wide my thighs were spread apart and my asshole wrapped around his cock. I reached back and spread my asscheeks for him as I fucked myself on his cock, so he could get an even better view of his cock sodomising my horny, dirty shithole. "Tighten your hole more, slut," he said. "And when you push down on my cock I want you to bear down like your taking a shit. I want you to push that shit out, shit on my cock." "Fuck, that's hot Sir." I replied. I leaned forward again, my hands still spreading my asscheeks open, and tightened my assring harder as I pulled upwards, milking his cock for all I was worth. Then as I was pushing down, paused awhile and started bearing down with my shitting muscles, relaxing as if I was taking a shit. I could feel the shit move down lower in my rectum, and coating his cock in a thick layer of filth. At the same time, I fucked down low and engulfed his cock fully. I repeated this again and again, squeezing hard as I pulled out, then shitting down oon his cock and I pushed down. After awhile, I could feel the shit leaking from the rim of my ass, freely flowing down his cock now. The smell filled the room quickly as I continued impaling myself on his cock. I decided to give him a treat. I pulled up, his cockhead just inside my anal ring, and I kept it there for a bit, then grunted as I strained hard, up on my toes, taking a shit right there on his cock. My asshole relaxed, my fingers still pulling my cheeks open, and the shit slowly flowed out, first coating his cockhead, then squeezing out from between my anal ring and his shaft, and slowly inched it's way down, further coating his already heavily soiled cock. It felt immensely nasty, and dirty, and ultimately I knew I would be swallowing all of it. "Very nice, boy," the Headmaster said. I pushed and squeezed my shitting muscles some more, as more of my filth flowed out, till the smell got too overpowering. Then I lifted my hips and squeezed my shithole closed, releasing my cheeks and turning around. The results of my efforts were far messier than what I'd expected in my mind. There were a few clumps of my shit over his groin the entire shaft of his cock was completely caked in a thick layer of my filth. HIs cockhead was thickly smeared and covered in shit and the smell hit my nostrils immediately even from a distance. He lifted both his legs up and backwards and held them apart, his knees bent and hands pulling them back. I had a good look at how filthy it had gotten, my shit even completely covering his balls and hard flowed downwards even over the flange of the plug sticking out his asshole. "Clean up, boy. Start with the plug, then lick my cock and balls clean." he ordered. I got down on all fours in front of him and bent forward, between his wide apread thighs, my ass sticking up high. The smell was even stronger here, but after eating and swallowing and the intense scat play earlier, I found this much more tolerable. Besides, I was feeling hornier than ever. I used one hand to pull one asscheek to the side then started licking at the filth on his balls, and flicking the shit on the buttplug with my tongue, into my mouth. I could hear him moan in pleasure as he held his legs open and I performed a good cleanup. I swallowed quickly, in small amounts, sliding my tongue over his balls, and taking them each into my mouth, sucking and cleaning them till the thick layer of shit was gone. I tried to hold some of the shit in my mouth, and swallowed the rest as I worked at cleaning up. Looking up from between his thighs, I looked at him in and swallowed hard. This time it was much easier and I could swallow these small amounts without any difficulty or any retching. Then I moved upwards, his balls now clean, and started working on his cockhead. The smell here was much stronger as I had pushed a fairly large amount of my shit onto his cockhead. I looked him the eye and asked him, "May I suck your cock clean, Sir." "Go ahead, slut, put it in your mouth." he replied. There was nothing more submissive than asking permission to suck your own shit off the cock that had just been fucking your asshole, I thought. I opened my mouth and tried to put his filthy cockhead in my mouth but immediately gagged from the smell. The layer of shit was very thick and my mouth immediately was with with the earthy and bitter taste of my own shit. I struggled slightly to get it in and wrapped my lips around it, then used my tongue to flick at and scrape the shit off his cockhead, coating my tongue in a layer of foul smelling, bitter filth. I retched again, but forced myself to kep going at the task. Once I felt my mouth was pretty full, I stopped and looked at him and started chewing a bit, then held back to urge to vomit and swallowed as he watched. It was intense and I felt my eyes water, and the skin around my lips start to sting a bit. I kept the shit down in my stomach and went back to work immediately. There was considerably less shit coating his cockhead now though it was still thickly covered, and again I placed my mouth over it and continued my shitty blowjob. I ran my tongue around the whole surface of it and allowed a good amount of spit to flow freely around his cock. The smell in the room now was incredibly heavy as I remained bent over, sucking on his shit covered cock, as the Headmaster held his legs apart. "Reach down and start pushing the plug in and out while you suck boy," he said from above. "Don't pull it all the way out, just halfway, fuck me with it." I reached down and did as he said, pulling against the flange and stretching his hole slightly as I pulled it halfway out, then pushed it in again. I continued sucking on him at the same time, my mouth and cheeks slowly filling with more of my filth, before I felt that his cockhead was more or less clean now. I came up for air, and pulled his cock out my mouth. His cockhead was more or less clean now, just smaller bits and streaks here and there, but my mouth was absolutely full of my filth, a considerably larger amount than the first one, and the smell and taste very strong. I was slowly pulling out and fucking inwards with the buttplug, and I braced myself as I looked at him and swallowed. The wave of nausea immediately wracked my stomach with a huge heave and my throat clenched and squeezed, I turned to the side and nearly barfed out everything but once again, managed to keep everything in my stomach as the bitter, acrid load travelled the length of my gullet. He spread his thighs apart wider, moaning with lust both at the stimulation from the butt plug moving in and out of his asshole, as well as the vulgar, shameless display of shit- swallowing his new slut was putting up. I bent forward now and, with much less obstruction now, engulfed his cockhead with my lips and mouth and started another sloppy blowjob. There was still a fairly considerable amount of shit covering his shaft but lesser than what I had already swallowed, so I built up my rhythmn quickly, using my tongue to clean him and my throat to fuck his cock. I bobbed my head energetically back and forth and kept the plug fucking his asshole firmly. I swallowed as I went along, the mixture of my spit and shit running down my throat, with help from his cock that was fucking my throat. I'm sure the desensitising cream had been doing it's job, and she showed no sign of being any closer to an orgasm after I had been working on his cock and shithole vigorously for 15 minutes. The sounds of my disgusting, squelching blowjob echoed through the room. I then stopped pushing the plug and briefly came up for air. I looked at his cock, marvelling at how different it looked compared with it when it just came out my ass. It was shining in my spit, completely wet and slick, still impossibly hard, and there was no sign of shit on it's shaft, I'd swallowed the remainder as I was sucking him off. The only sign left of our filthy scat play were the clumps of shit left on his groin, which were now slightly smeared around. "Fuck, you're a very good cocksucker boy," he growled. "Grab that towel, towel my cock off and get that tube of cream, I want to fuck that shithole of yours." I did as I was told, and grabbed the towel, drying off the spit from his cock, and picked up the tube of desensitising cream. "Go on," he said. "There is still quite a bit left in there, and I have plenty more tubes. Squeeze out the remainder and cover my cock with it." I swallowed, thinking about how long more he would last with this much cream numbing his cock, but didn't dare disobey. I squeezed out a liberal amount in my right palm and wrapped my fingers round his cock, wanking him and giving it a good rub, working down to his balls as well. Then I squeezed out the remainder and continued the handjob, covering his cock well with the cream. I tossed the tube aside, now waiting for his next move. "Ride me boy, this time face me. Squat that asshole over my cock." he ordered again. I got up and straddled him once again, and opened up my legs. My cock was still throbbing with arousal and anticipation, still bound tighly by the leather ring, and I slowly lowered myself again on his cock. My asshole had tightened considerably by now and with his cock dryer than before, I had to strain a bit a get up on my tiptoes, grunting and really traying to flex my butthole open as he pushed his cockhead into my bowels again. My sphincter finally relented and he entered me with a pop. I leaned back with my legs apart and braced my palms against the floor and slowly started bearing down and allowing him all the way up my bowels. All the way as he worked his way in, my cock twitched lewdly in front of him as he fucked me. "Fuck, you asian boys are all sluts, and you're the biggest one," he said. "And that's saying a lot." "I've fucked a lot of you horny schoolboys after 5 years at this school," he continued. "You know how many?" he asked. I shook my head, my mouth and tongue numb with lust and from all the shit swallowing, and my body covered in sweat as I slowly started fucking my tightened asshole up and down his massive prick. "Twenty-seven, boy," he said. "And only eight of them have since graduated. So you imagine I get to fuck a lot of ass here every week." I was sure that he would have fucked other boys from the school, given that I knew that there were definitely a few others I knew who immensely enjoyed canings, but twenty-seven seemed like a pretty large number to me. "I've never used a single condom and in fact I dished out an extra 15 strokes on the boy who asked me to use one. He's taken me bareback each and every time since. I make sure I cum in each one of their tight assholes too. And the same goes for you." he said. I was dizzy with lust hearing him talk trash like that, wondering if I knew any of these other boys he was caning and having sex with. I slowly built up the pace, my asshole stretching comfortably now with the girth of his cock up inside me. I leaned back and rocked my hips up and down, gripping his hard cock with my practised anal muscles, my own erect prick bouncing obsecenely in front of him. We were both rapt with pure sexual pleasure now, and I moaned out loudly. He then leaned forward and wrapped his fingers around my cock and started pumping his fist, jerking me off as I fucked myself on his shaft. His cock deep up my ass, rubbing my prostate, and his hand wrapped around my cock, stroking me off, sent waves of pleasure through my body and up my spine. I kept up the pace, my body and hips bouncing up and down, slapping against his thighs as I started fucking myself harder, with my thighs still spread wide open. "Uhh, Ughhhhh, fuck, I'm going to cum soon. Please let me cum, Sir," I begged. I could literally feel a new load of boiling cum start to swell up my shaft and balls, trying to push past the tight ring wrapped around my cock to keep it from spurting. My anal muscles started spasming and clenching around his cock, my orgasm impending. I knew this would be an equally giant load. He sensed my huge orgasm about to tip me over, as my eyes started rolling back and my back and thighs started trembling, and my sphincter rhythmically pulsating and gripping at his shaft. He then let go of my cock and reached out to steady my hips, stopping me from fucking myself further. Then he started sitting up, all while still keeping his cock lodged deep in my shitter, then reached forward with both hands and held he by the hips. He was well built and undoubtedly strong, and he started standing up, lifting me with him. I reached forward and held onto his shoulders as he lifted me off the ground, then he let me lean back and lay me back down on the sofa. He roughly manhandled me now, using both his hands to hook them behind my knees and push them all the way back till I was folded in half. I was quite flexible and allowed him to push my legs back all the way. He splayed them apart and pressed them down hard, till my thighs were nearly pressed against the sofa. "You want to cum, boy?" he growled. "Fuck, yes! Please let me cum for you Sir!" I cried out loudly. I reached down and pulled my asscheeks apart, though I probably didn't need to do so since I was already so spread eagled. He leaned forward and leaned his weight into me, grinding his hips down, keeping me spread open with his hands, then started really hammering me hard. His strokes were hard, authoritative and forceful, he rammed hard into me, going balls deep with each stroke, and pulled out nearly completely before plunging again all the way. Each drive nearly knocking the wind out of me. "Uggh, fuck, fuck, Ugggh." I grunted repeatedly as he fucked me hard. My body was jolted and my cock flailed around with each stroke. His thick, massive shaft rubbed against my prostate, stimulating me, driving me closer and closer to my orgasm. "Fuck, boy, tighten up your hole, I want to feel that shithole grabbing my cock," he grunted. I tried not to relax my hole so much as he fucked me, instead tightening it as much as I could. I leaned my head back and closed my eyes as my orgasm approached. I started shuddering again, my back now arched up high, and my sphincter muscles once again started spasming hard, gripping his cock even tighter like a vice. I tried to keep still, my breathing shallow and rapid, and my body flushed and covered in a sheen of sweat, building up to my biggest cum yet. My cock twitched and spasmed in readiness to spew its load. The Headmaster could see this, and he reached down and started releasing the tight leather cock ring. Even before it was released fully, a steady, heavy stream of thick cum started flowing out freely, a result of my earlier pent up orgasm that was kept in check by the leather cock ring. He thrusted even harder, and it instantly pushed me over the edge right as the cock ring was fully released. "Oooohhhhhh, fuuuuccccckkkkkkk! I'm cummminnnggg!" I yelled out. My toes curled and I straightened out my legs while still folded in half, spread eagled. I wasn't even touching my cock, and I released my grip on my asscheeks, instead trying to grip at the sofa as the biggest orgasm I'd ever felt rushed through my body, making me flop and spasm uncontrollably. My cock absolutely erupted with a fountain of cum spewing hard and spraying me with ropes of cum right over my face and my open mouth. My asshole spasmed hard around his cock as he continued thrusting and fucking me, watching as my body jerked as I came hard and violently. "Fuckkk, shitt...." I mumbled, hardly managing to even form the words. I couldn't understand where all that cum was coming from, after already having 3 hard orgasms, but it continued spewing. My cock spasmed and shot thick ropes of cum over my own chest and face. The Headmaster continued holding my legs apart and vigorously continued thrusting his cock deep and repeatedly in my shitter as I came hard. He showed no sign of letting up, no doubt the cream helping a lot with his staying power. He reached down with one hand and stroked my pulsating cock as it continued to cum hard, and I moaned as my balls ached deeply. I rasped with short, shallow breaths, my whole body responding to the orgasm, and I slowly regained some composure after a minute or two. All the while, he remained inside my asshole, pounding me hard and mercilessly. I swallowed hard, my mouth still a numb pit of fetid bad breath, and kept my legs open. Finally, I started coming down from my orgasm, my face, chest and stomach a mess, ropes of cum splattered all over. My asshole relaxed a bit more, and I started to feel very aware of the Headmaster still pounding away. His thrusts were deep and hard, bottoming out each time, and he straightened up a bit, Still keeping my legs apart, he pulled out his dick completely, and I suddenly felt very empty, my asshole no doubt gaping widely open. "Fuck, you should look at yourself boy, your hole is wide open," he groaned, and reached down to spread my asscheeks with his hands. He then aimed his cock at my hole again and pushed it back in just as my shitter started clenching up more. The fucking continued at a furious pace, my body being thrown backwards with the force of each thrust from his hips. I started tightening my hole again, squeezing his cock as hard as I could, as I looked up at him. He was covered in sweat as well, his body deep in exertion, breathing hard. Judging by the pace he was going, I knew he was far from close, but I'd started feeling a deep pleasurable sensation centred deep in my asshole and spreading through my groin and cock. I'd softened considerably after cumming hard, but I reached down and started stroking myself to hardness again. My eyes were rolled back in pleasure, and I felt myself slowly getting hard again. He kept up the fucking like that for a good 15 minutes, till I was noticeably erect again, then he reached down and pulled me upwards by the hair, and pulled his cock out of my gaping asshole. "Bend over, I'm going to fuck you doggy," he ordered. Eager as ever, I got up and got into my favorite position again. Bending over, splaying my thighs and feet apart, and pushing my arse out, opening my asscheeks wide with my hands, showing him my well fucked boyhole. He grabbed onto my waist and pushed home quickly again. I grunted out loudly as I felt him penetrate me roughly. He thrusted just as hard, fucking me in my violated asshole as he would any street side hooker. I was slowly being driven over the edge again by the constant stimulation. I was hard again and breathing hard, panting. Each time he drove inwards with his cock, my face was pushed hard into the sofa. My cock throbbed as the minutes passed. Another 10 minutes, 15 minutes, his fucking was relentless, his stamina in top form. The room was filled with the sounds of his flesh slapping against mine, and both our grunts and loud moans. He then pulled out again, and quickly sat back on the sofa, fisting his cock as he sat looking at me, still bent over, breathing hard. I quickly got up and straddled his cock, facing him, thighs apart and cock erect, and impaled my shithole once again on his massive shaft. I knew I could control the pace better like this and placed my hands on his chest as I rode him more slowly, taking more time with each stroke. Once again, I gripped his cock tightly with my anal muscles each time I pushed up, milking him hard, then realxed my hole more as I sat back down. We looked at each other, both of us breathing hard, and I realised how good his thick cock was making me feel. He was extremely hard and his cock sprang back flush against his stomach each time I pulled out. And each time I put it back in to ride him, his cock rubbed against my prostate as I fucked myself on it, sending waves of pleasure through me. I decided to give him some oral, ass to mouth action, as my asshole started to feel a little sore from all the fucking. I would ride him for a good 5 minutes, milking his cock, then get off, and squat in between his legs, and take him fully in my mouth and throat, giving him a sloppy, wet deep throat. Suck him for another 5 minutes, then get up and ride him deep in my shitter again. I was started to get tired but I stayed horny as ever. He would moan his approval as I alternated between sucking and riding him. I must have fucked him like that for another good 20 minutes, and was now riding him, my thighs splayed open, my hard cock bouncing around, my hands on his chest and I found myself again breathing hard, my orgasm close. "Oh fuckk.... Sir, I'm cumming again," he cried out, as I felt my cock start to twitch and spasm. "Cum for me boy, cum hard." he said, holding me by my hips. I slowed down a bit, and wanted to really enjoy the penetration as I came. I tightened as hard as I could as I slowly pulled up, then squatted low as I could go as I pushed down. I felt my breathing turn ragged, and without touching my cock, a few deep thrusts deep in my ass brought me to my fifth orgasm of the night. I gulped and shuddered, and spasmed as he held me firmly by the waist, pulling me all the way down till he was balls deep up my shithole, and watched as I came. My eyes rolled back again and my asshole again milked his cock as I came hard. My cock spasmed but not much cum was coming out, after the previous four huge orgasms. The sensations though were not any less pleasurable as I felt warm and flushed all over as I tried to ride out my orgasm with him buried deep in my ass. The small amount of clear cum shit from my peehole, and slowly ran down my cock, which was still absolutely erect and pointing staright up. I tried to compose myself, and felt him starting to thrust again, and he moved me with his hands on my waist, slowly starting to fuck me again. I didn't know how much more fucking I could take. My asshole was very well fucked by now, slightly aching and wide open. My cock and balls were really aching now, after all the action, and I was in wonder how he could keep staying hard and fucking me all this while. But I knew I wanted to pleasure my new stud and get him to get his rocks off and shoot his load. He made me continue riding him, and I obeyed. The fucking continued as I rode him cowgirl, then doggy again, then missonary with my legs foled back again, then back to cowgirl again. I was so far gone now, totally spent, sweaty, horny, cock drunk and needing his cum load and quickly. I was panting again, I was hard again, and I was riding him hard. I could tell he was definitely getting very close now. His cock was deep in me, and I was milking him with my tightening ass muscles as hard as I could. My thighs spread and my cock sluttishly on display again, I reached down to wank myself as I rode him. I knew his load would be huge as he'd held back for so long, and before long I felt him tighten his grip on my waist and sit up a bit more. I slowed a bit, and renewed my grip on his cock with my anal ring, I spread my thighs even wider and fisted my cock slowly. My ass muscles now as tight as I cold get them, I slowly pulled upwards now, raising my hips up, then slowly as I had started, I kept my ring tight and squatted back down fully on his cock. I repeated this once, twice, thrice, and I finally felt his cock twitch hard inside my ass. I quickly buried him all the way in. He shouted out loud as he reached both hands down to squeeze and pull my asscheeks open wide, sending a wave of pain through me as they were still very much welted. "Fuckkk..... I'm going to cum!" he cried out. "Cum inside me, cum inside my ass," I barely managed to say. His cock spasming and jerking and my own hand around my cock pushed me over the edge right at that second too. We both reached a huge climax, his being much bigger than mine, at the same time. My cock again spasmed, but my orgasm was totally dry now, I was completely spent. Six delicious orgasms, I couldn't believe it, I thought to myself as I shuddered. I could feel his cock literally erupt a huge load of scalding hot cum deep into my bowels, my sphincter contracting rhythmically around his cock, no doubt intensifying his pleasure as he came and emptied his balls into my shit tunnel. I felt his cock pump again and again, sending his seed into my ass, deep inside it. "Fuck, that feels great. Knock me up Sir, make me pregnant with your cum," I said lustily, trash talking him as he rode out his orgasm. He continually came and shot cum deep up my asshole for well over a minute, breathing hard as I tried to keep all his cum deep inside me. I kept my anal muscles tight and warpped around him pulsing shaft, my legs were still spread wide and my hands on his chest. He was still pulling at my cheeks hard with his hands, and I stayed still, letting him cum as much as he wanted, bareback, inside my asshole. My orgasm was long over by now, but all I wanted was for my stud to get as much pleasure as he could. Finally, I felt his breathing start to normalise and slow down, and his cock stop throbbing. His eyes were closed and he was no doubt as satisfied as he could ever be. All the while, I remained still, keeping my anus tightly wrapped aorund his cock and my thighs spread apart. I was finally soft, the first time a few hours, and I knew what I wanted to do for him to round up our session. "I hope you enjoyed that as much as I did Sir," I said as he opened his eyes. "Fuck, that was amazing, slut. I've never cum so hard in my life," he replied, smiling a bit. "I want to show you something, Sir, you just sit back now." I said, teasingly as I pushed my hand off his muscular sweaty pecs. Slowly, keeping my anal muscles tight like a vice, I lifted my hips off his thighs, his rapidly softening cock sliding out of me very slowly. Just as I felt his cockhead about to pop out, I clenched my asshole as tight as I could and pulled his cock out, my ring shutting down tight as he cock left my bowels. I felt absolutely full of cum, and I could feel it almost swirling about inside my shit tunnel as I got up off him and cleared a small area on a non carpeted area in front of him. I turned around so my back was facing him, and slowly, I spread my legs apart, wide apart. I reached behind myself and once again spread my welted cheeks apart for him, putting on a nice show, and realised I was not hard. I wanted to show him I was turned on, and I wanted to show him my cock was hard as I performed for him, so I used one hand to slowly jerk myself off, trying to stroke myself quickly to hardness. I closed my eyes and revisited the lewd, pornographic images of the intense session we just had and my erection was quick to come. I felt my shaft quickly stiffen and point straight up. and I released it, bringing my hand back to once again spread my cheeks open. "I'm hard for you Sir, I want you to enjoy watching this." I said. I stretched my asscheeks as wide as I could, and showed off my hole, which he had just spent more than an hour violating and penetrating. I was sure it would have been pretty swollen and still pouting even though I'd clenched it tight, keeping his cum inside me. Slowly I squatted down, getting down low in a wide open legged squat, showing off my hole, my cock once again throbbing. I felt his cum start to leak out my asshole, and I slowly relaxed my shitter. I couldn't imagine how much he had shot off inside me, but the flow was incredible. An immediate torrent of warm thick cum started flowing straight out my asshole onto the floor. I looked down between my legs and was shocked how much there was. I quickly got up on my toes as the cum flowed freely out. It was shot so far up inside me, it was stained a deep brown as it flowed from my asshole. It was followed by disgusting wet farts as the flow slowly started to slow down and I continued pushing it out. I reached under me to slip 2 fingers deep up my asshole to try to dig more of his cum out of me. It was a nasty and disgusting display of whorishness that immensely turned me on. I looked behind me and saw that he was stroking his cock again, as he watched me. There was now a pretty big pool of cum below me, and I flexed and pushed my asshole out, getting the last bit of it out of me and onto the floor. The fucking had push my shit down pretty low as well, and as I shitted out his cum, a few pieces of my own shit squeezed out of my hole onto the floor as well. The smell, was once again, overpowering. I pumped my cock for a few more strokes with my hand to keep myself hard, then straightened up and turned around. I looked down at the floor beneath me. It was an absolute mess. A large puddle of cum lay there, most of it a deep brown, but areas of white were still seen, and a few small to moderately sized clumps of shit as well. I slowly got down on all fours, and bent my head forwards. I'd never done anything as nasty as what I was about to do, but I was dizzy with lust. I stuck out my tongue and slowly started lapping at the big pool of cum, it tasted heavily of both cum and shit. I looked at him as I did so, flicking his shitty cum into my mouth as I did so. Once I felt I'd got a decent load inside my mouth, I opened my mouth to show him what was inside it, and swallowed it all, feeling it go down my throat to my stomach. "Fuck.... you're nasty, boy. Eat it all, don't waste it" he growled as he pumped his dick, watching me. I was spurred on knowing that he was enjoying the show, and continued lapping at the cum over the floor, stopping and swallowing as I went along. It took me 7 or 8 times, but finally I'd gotten the last bit of cum in my mouth. The taste was absolutely nasty, but compared to what I had eaten earlier, it didn't cause any problems when I swallowed. I kept all of down. I looked at him, totally spent, sweaty, naked, totally used, humiliated, and well-fucked, his newest cane slut, and wondered what was next for us. "Very good, boy. It's getting late now. You can clean up here and get dressed." he said. "You can give a call home if you want, tell your folks you won't be coming home tonight. You can spend the night at my place." he winked as he stood up, walking away.