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“Well it seems you’re not so tough after all, eh Banks?” came the voice of my English teacher to my ears.



 



At the moment I was unable to answer because I was biting his handkerchief to prevent myself from crying out in pain. Just then the metal edged ruler connected with my bare and exposed ass again almost making me jump but I was unable to move much, restrained as I was. My young body was bent over his desk with my hands tied to the seat in front with Mr. Middlebrooks’ silk tie leaving me helpless for all practical purposes.



 



Only two hours earlier if someone had said that I’d find myself in this position I wouldn’t have believed it. But here I was sore, red assed and powerless. It was too late now but I wished I hadn’t messed with my teacher earlier like I had. It wasn’t like I had anything against him but the school year was almost over and class was now more like a holding cell with finals already taken last week. For the most part we were just being babysat instead of learning so most of the kids were talking or goofing off during the last class on a Friday afternoon.



 



I was engaged in a contest with Brian Costello to see which one of us could hit the other more often with thrown erasers and wadded up pieces of paper. He had just tossed an eraser my way and I had managed to deflect it away from my head. Unfortunately for me when I redirected the eraser it had gone in the direction of Mr. Middlebrooks’ desk. In fact it struck a corner of the desk before ricocheting beyond. That certainly got his attention. Before that he had been ignoring his unruly class while paying attention to his open laptop.



 



“Banks - front and center now” he called out in his clipped English accent. (How funny was that - the English teacher actually being English.)



 



Dragging myself to my feet I sauntered to the front of the classroom. Brian was looking the other way as if he had nothing to do with what just happened. I approached his desk and stood there with a cocky grin on my face.



 



“Mr. Banks I believe you threw the eraser that’s now on the floor in the corner.”



 



“Incorrect Mr. Middlebrooks, what I did was deflect it like a hockey goalie does with the puck or they do in soccer which no doubt you know about” I replied with a smug expression.



 



“I see. You know Banks the school year isn’t quite over yet in spite of my allowing you students to act like it is. In fact detention hall is still open for another seven days. Perhaps you would like to spend your afternoons after school there until then?”



 



“No I wouldn’t but I really can’t control that.”



 



“That’s true Banks but at this moment I’m undecided. However either way I want you to pick up the eraser and put it on my desk. And in future when you speak to me you are to address me as sir or Mr. Middlebrooks if that’s not too difficult.”



 



“Yes sir, Mr. Middlebrooks” I sarcastically replied.



 



He arched an eyebrow over his hazel eyes but said nothing. Walking around the desk I was about to crouch down and retrieve the eraser when an idea came to me on how I could mess with him. Even before I was in his class I’d heard rumors about Mr. Middlebrooks and how he and another teacher, a male gym teacher, shared a house. The consensus was he was gay but it had never been confirmed. Just to mess with him I bent at the waist as I reached down to pick up the eraser so my butt was facing him.



 



Not being vain but I knew that it looked good. I’d been working out lately to add a little muscle and I had a nice six pack not that he could see that but for some reason I also had a muscular ass for my size. I was naturally on the lean side with a low percentage of body fat and weighed around one hundred and thirty pounds but whether due to exercise or genetics I did have an ass. It might not be a true bubble butt but it certainly filled out my jeans.



 



I fumbled around a bit before I picked up the eraser and when I did I turned my head back so I could see behind me. Mr. Middlebrooks’ eyes were glued to my ass as I was bent over. Slowly I straightened up my body and as I did I thought that my experiment was a success. As far as I was concerned Mr. Middlebrooks might as well have yelled out he liked guys. For what other reason would a man stare at a guy’s butt? I turned to go back to my seat and as I passed him I heard Mr. Middlebrooks almost whisper to me his voice was so low.



 



“Oh you think you’re clever Banks, do you?”



 



With a serene expression on my face I ignored what he said and strolled back to my desk. For the remaining fifteen minutes of class I chilled and did nothing. The only thing that bothered me was that every time I looked up Mr. Middlebrooks seemed to be looking my way. It got to the point I was feeling uncomfortable about it all. Its not like I was trying to attract him or to piss him off. I was just having fun but he seemed to be all obsessing. The bell finally rang and I headed for the door as fast as I could. I was just about to slip out when I felt a hand grab my arm.



 



“Not so fast Banks” Mr. Middlebrooks said as he kept a hold of me.



 



As we stood there the rest of the class filed out of the room leaving us the only ones remaining. He then closed the door and led me toward his desk. Once I was besides it he released me and sat and for the next few minutes he ignored me while busying himself with his laptop. I remained quiet but as time dragged on I began to shift my feet around. My guess is he noticed as a moment later he raised his face and looked at me.



 



“You know Banks being its almost summer recess I was going to be lenient about the eraser but you had to push it further. So now you can cool your smart ass in detention the rest of the year. Have anything to say in your defense?”



 



“What for? You’ve made up your mind already. I don’t think I did anything worth getting detention over. I’m sorry that when I protected myself from an eraser it hit your desk. But other kids were goofing off as much as me…Sir!” I said leaving a long pause before saying sir.



 



“We both know its not the eraser but the fact that when you picked it up you shook your bum in my face” he retorted.



 



“My what?” I said acting all confused though I knew what he meant but I played it dumb.



 



“Oh that’s right, you Yanks don’t understand the proper King’s English. What I meant was your arse, understand that boy! No, then how about your butt. Better now Banks?”



 



He became all worked up during this outburst and his pale face reddened considerably.



 



“No need to get upset Mr. Middlebrooks - now I know what you mean by bum. Okay” I told him raising my hands up with the palms facing out.



 



He narrowed his eyes as he stared hard at me and I saw his lip curl into a sneer.



 



“I’m quite sure” he said as he brought his hand to his chin and stroked his neatly clipped beard. “But believe you me Banks, back in my homeland I would still be allowed to properly punish you. There would be no need for detention. In fact I’ll offer you a deal if you like. Thirty minutes of your time and in exchange no detention. Since each session is an hour that will add up to a lot of time cooped up in school when you could be out with your friends in the sun.”



 



“Sounds good, but there has to be a catch. What would I have to do?”



 



“Do? Very little Banks. In fact I’ll be doing most of the work” he replied as he stood.



 



Once he did he towered over me. Mr. Middlebrooks was a tall man, around six foot four I would guess while I was a few inches shy of six feet. On top of that he was a big man, neither fat nor muscular appearing but just a naturally large limbed person. As I watched his hand took hold of his tie, first loosening and then removing it.



 



“Banks stand here” he ordered indicating a space directly in front of his large, wooden desk.



 



Once I sidled there I looked at him as if to say what now when he caught me off guard. Moving faster than I expected from one of his size he jammed his leg against the back of my knees. To remain standing I was forced to throw my hands against the desktop and in spite of this I still almost lost my balance. Before I was able to say or do anything he pressed his much larger body against my back preventing me from moving while forcing my chest toward the desk. Quickly he wrapped his tie around my wrists a few times then knotted it leaving one end dangling.



 



“What do you think you’re doing?” I sputtered out indignantly.



 



He didn’t answer but instead he took the tie end and tied it to his chair which was an old fashioned high backed style made of solid wood with four legs rather than the kind with wheels. Once he was satisfied I was securely bound I felt his body rise off me at which point he walked to the front of his desk. The first thing he did was move his laptop to the far end of the desk away from me. Now he had a smirk on his face as he opened the drawer and removed a wooden ruler. It was eighteen inches long with a metal edge to it.



 



“Though I’m not a math teacher I still strongly believe in using rulers with troublesome students like yourself Banks.”



 



“You aren’t planning on doing what I think with that, are you?” I asked my eyes suddenly wide.



 



“Well if you’re thinking that I plan on spanking your bare bottom with this ruler then you would be correct Banks. A little corporal punishment goes a long way in keeping naughty schoolboys in line and more importantly obedient. Now lets pull down those trousers so that we may begin.”



 



“That’s not a good idea Mr. Middlebrooks” I said trying to sound more confident than I felt at the moment “at the least you could lose your job teaching and maybe even be arrested.”



 



My words seemed to have no effect on him as with me helplessly restrained he reached under me and unbuckled my belt, then unfastened my jeans. Grabbing my waistband he yanked downward, not only lowering my jeans but also pulling my briefs down as well. He followed that with a low whistle and to my shock his hand cupped then squeezed one of my ass cheeks.



 



“Mr. Middlebrooks you better stop now before you do something you’ll regret. I swear I’ll call for help if you don’t let me go right now” I demanded of him.



 



“Oh will you now Banks. Not very nice of you trying to get me in trouble. I believe I will have to up the ante so to speak” he said but he took his hand off my ass.



 



The next thing he did however was to grab my briefs which were around my knees. I heard a tearing sound and I felt some pressure against my leg and the next thing I knew he was holding up what was left of them.



 



“Fuck this, there’s no way I’m going….” was all I could get out before he forced his wadded up handkerchief in my mouth muffling me.



 



He then wrapped the remnant of my briefs around my face over my mouth and tied it at the back of my head holding his handkerchief in place. Now I was getting a little scared. I was bound and gagged with my jeans near my ankles and my teacher had already felt me up and was now planning on spanking me. I attempted to cry out but for the most part I was silenced and though I struggled I was unable to free myself. Suddenly I felt a sharp pain as Mr. Middlebrooks delivered his first blow to my bare unprotected ass.



 



I cried out but due to my being gagged all that was heard was a muffled squeak. My lower body moved as far away from him as possible under the circumstances but he easily connected with his next blow to my upturned ass. He paused after each blow he delivered, allowing me to feel the full impact before giving me the next. Though I writhed about from the pain with the added hope that I might lessen their impact Mr. Middlebrooks was having none of that.



 



“Enough with your squirming Banks, take your punishment like a man. All you are doing with your gyrating is extending the length of time this will take. In fact the more you move the longer I’ll spank you so its up to you really. I don’t mind dragging this out as watching your delightful bum tremble and shake is having a profound effect on me.”



 



After he said this I managed to turn my head and look his way and if I wasn’t gagged my jaw would have dropped. He stood to the side of me with the ruler suspended over me in his right hand while his left hand was fondling a large and growing bulge in his trousers. Seeing me looking he winked at me before delivering another swat to me, all the while continuing to lasciviously rub himself.



 



The skin on my butt felt red and raw from the repeated blows but at that moment I had a bigger problem so to speak. The fact was that as he continued to spank me I was getting an erection. As I felt myself hardening my face reddened as much as my ass and I prayed he didn’t notice. Maybe it was because those things just happened at my age. It was hardly the first time I had gotten a woody at an inopportune or embarrassing moment. Often me and my friends would joke about such things but this was much worse than getting one in church or in a public place where anyone could see. Mr. Middlebrooks had shown himself to be gay and that he found my ass attractive and he was now playing with himself as he spanked me. Terrified I shut my eyes tightly and a moment later the blows ceased.



 



“Well, well Banks and what do we have here?” I heard him ask in his cultured voice and the next thing I knew I felt the touch of the ruler against my half hard dick. “It seems that either young Mr. Banks enjoys being spanked - a lot! Or he is thinking about what’s in my trousers and what I’m going to do to him with it.”



 



As he pushed and prodded me I felt it stiffen further until it felt fully erect. Mr. Middlebrooks again walked to the front of his desk and reached into the open drawer. This time he removed then placed a bottle of skin lotion on the desk near me. He squirted a generous amount onto his left hand and moved next to me. I felt like a mouse that was helplessly awaiting a rattlesnake’s bite and unable to escape it. With a wicked grin he reached down and wrapped his large, warm hand around my shaft forcing a muffled moan from me.



 



His hand fully engulfed my erection, covering its whole length easily. He slowly stroked me, paying extra attention to just below my head and unconsciously I spread my thighs allowing him greater access. His hand coated me with the lotion as he resumed spanking me but I barely felt it due to all my attention being centered on the pleasure his hand was giving me.



 



It seemed obvious to me that he knew what he was doing, no doubt he had handled many before mine. I had jerked off a lot since I’d discovered the joy of masturbation but I couldn’t remember it ever feeling so good this quick before. He’d been stroking me for less than a minute and my breathing was already rapid and I could feel my heart beating fast. Mr. Middlebrooks seemed to know just the right amount of pressure to apply where it greatly stimulated me without being too tight. When he slid his hand over the head he managed to do it with an upward sweeping flourish that had me on the edge in no time. He clearly perceived what he was doing to me and was enjoying himself greatly.



 



“Its plainly evident that you like what I’m doing Banks, no point in denying it. You’re leaking pre-cum like mad and I don’t think you’re going to last much longer.”



 



There was no way I could refute him even if I wasn’t gagged and anything I might say would come out garbled. My body was clearly signaling its approval of what he was doing by its reaction. And he was certainly right about me being close. It took less than a minute from when he spoke for me to feel the familiar sensation of my balls drawing up towards my body and my dick swelling. I moaned into his handkerchief as my cum shot out of me like a torrent.



 



The first shot of my cum hit the floor with a splat as Mr. Middlebrooks had me pointed down as he stroked me. He continued milking me of all my cum, not slowing his movement until no more came and the floor below was marked by multiple white droplets. He gave me one last stroke and he made sure to squeeze my now overly sensitive head making me shudder from the feeling.



 



“Enjoyed that Banks? Good. That was some nice cum you had. Very impressive amount you produced. Quite frankly I’m surprised considering the size of your equipment. Back when I was young in England we used to talk about everything being bigger in America. Obviously that isn’t always the case” he said with a smirk.



 



My face turned red as a beet from what he’d said to me as I knew it was accurate. The fact was at four inches erect the best I could be considered was on the smaller end of average and I wasn’t very thick either with a circumference of just over four inches. My balls were also on the smaller size too if I could go by the average size I saw while in the showers after gym class. I had hope that I could still grow there but while my body continued to mature my private parts had a spurt where they got bigger and sprouted hair at twelve but in the time since then had stayed the same.



 



“Well don’t feel bad Banks. Not everyone can be hung and in your case nature gave you a cute bum as compensation. Believe me I don’t care how big you are, my interests are more focused on other parts of your anatomy. However if you would like to see what a man’s cock looks like…”



 



He moved to where I could clearly see him at which time he unfastened his trousers and pushed them down freeing his own cock. His hand grasped it and he stroked it for my benefit as I stared dumbfounded. It was the biggest I had ever seen in person but then I hadn’t seen any except for other teens in the locker room and none of them were hard. Of course I had seen porn on the internet but those guys tended to be freaks of nature and it was still hard to guess their real size from videos.



 



Mr. Middlebrooks might not have been as large as the real freaks but from what I could see he was plenty big. On top of that he was uncut which I had never seen before in person. His hand was stroking himself and as he did his foreskin slid up and down over his swollen head. The head was red and coated with his pre-cum and as I watched he stepped close to me so that he was standing right by the side of my head.



 



His free hand untied my briefs and dropped them before he plucked his handkerchief from my mouth and put it on the desk. I worked my jaw around after he freed it making sure everything was still in good working order. A dry mouth was all I seemed to be suffering from when I felt Mr. Middlebrooks’ hand touch my cheek. I turned to look at him and I was almost poked by his stiff cock it was so close.



 



His hand was still wrapped around it stroking and I could now see that it had a slight upward curve to it and I’d certainly been right about it being large. His was certainly two or three inches longer than mine but it was the girth that was truly impressive. When his hand was wrapped around my much thinner one his fingers had easily overlapped it but on his shaft his fingers barely met his thumb. Meanwhile his balls were at least twice as large as mine and where my pubic hair was light and sparse his was a thick jungle of wiry coarse hair. His voice snapped me out of my musings about his superior cock size.



 



“Well Banks I gave you a nice cum and now its time for you to return the favor. Be a good lad and open wide for me” he told me while pressing the mushroom head to my lips.



 



Just because he’d masturbated me to orgasm was no reason for me to give him a blowjob I decided. It wasn’t like I asked him to or even had a say in the matter. He had taken advantage of me while I was tied up and helpless. Plus I had never sucked a guy off before and had no desire to honestly. I was attracted to girls not that I’d had much success with them but that wasn’t the point.



 



Managing to twist my head away first I answered him. “I don’t know about that Mr. Middlebrooks. I’m not into guys and I don’t want to.”



 



“Oh that’s how it is then. I show you a good time and you don’t want to reciprocate, hmm? Two things Banks, I believe you are in denial about liking guys. You came far too fast and hard for someone who’s not into it. Two if you don’t want to suck me I won’t make you. I’m not going to spank you again or anything else to force you to do so. But I do plan on cumming and since you have closed one path it seems I have to use what’s left available to me.”



 



While continuing to stroke his cock Mr. Middlebrooks reached out with his other hand and felt my ass. He slid it down until his finger was between my butt cheeks where it pushed against my entrance.



 



“W-w-what are you doing?” I asked though it seemed plain what he was attempting.



 



“You’ve left me no choice Banks” he said as his fingertip managed to push a tiny bit into me “if you won’t cooperate then I’ll do what I must to get off. To be honest with you I believe I’ll enjoy buggering you more than a blowjob anyway. You probably don’t know what you’re doing so how good could it be. For this it doesn’t matter, I’ll just pound that tight bum of yours until I can’t take it anymore and cum in you.”



 



While he talked he continued to force his long finger deeper and as he did he began to wriggle it around. I realized he had me good. If I didn’t do what he wanted he would just do as he pleased with me, in fact that was what he’d been doing anyhow since restraining me. One way or another he planned on getting off using me and I was unable to do anything about it. But it seemed to me that giving him a blowjob was the lesser evil.



 



“Wait Mr. Middlebrooks, maybe we can, you know work something out” I said hopefully.



 



“And how would we do that Banks?” he replied as his finger continued to probe me when he touched a part of me that made me shudder and my still erect cock twitch. “Oh I see I found your prostrate Banks. You appear to like this” he continued as he kept massaging it and he was right about me liking it. It felt weird yet good at the same time and as he did it my erection moved of its own accord, dancing to an invisible song that he directed. “Wouldn’t you rather I fill your arse with my hard cock?”



 



In spite of his finger feeling good in me I didn’t think his much thicker cock would have the same effect. It was so large I was afraid it could severely damage my virgin ass.



 



“No, no Mr. Middlebrooks, I think you would hurt me if you did that. Maybe I can do for you what you did to me” I suggested.



 



“Not really a fair offer Banks. I doubt you could do as good a job wanking me as I could do myself. Besides at this point I need more than a hand job. I suppose I could let you suck my cock but you have to do a good job of it. Agreed?”



 



“I’ll do my best…” I began but that was as far as I got as his head slid between my lips as I replied to him.



 



My lips stretched wide to accommodate his girth as he pushed more into my mouth. The taste of musk and salty sweat almost overwhelmed me as I tasted a man’s cock for the first time ever but it somehow seemed appropriate. Mr. Middlebrooks groaned with pleasure as my mouth engulfed him. He kept his right hand wrapped around his thick base while his left hand finger continued fingering my ass.



 



“Okay Banks, start sucking my cock. Use your lips and tongue. Don’t think I’m going to do all the work for you. And mind your teeth, I don‘t want to feel them.”



 



I did my best to follow his instructions but it wasn’t easy. My mouth was stretched wide already just to accommodate his thick cock not giving my tongue much wriggle room to move. On top of that Mr. Middlebrooks had begun to work his hips back and forth. He wasn’t going fast or deep but still it made things that much more difficult. All I could do was suck a little as he slid his hot flesh between my lips.



 



Maybe he realized this so he started to thrust deeper with his large head hitting the entrance of my throat with each forward move almost making me gag. Suddenly he pulled his cock from my mouth while also removing his finger from my ass. His left hand now grabbed me by my hair as he slightly shifted his position.



 



“Suck on my balls Banks. Take one in your mouth” he ordered me in a no nonsense voice.



 



I opened my mouth and managed to take one of his large hairy balls inside. He groaned as my tongue rolled it around as I also sucked on it. I could see that he was now rapidly pumping his cock and he seemed to be concentrating on the big head and right below it. He started groaning more the longer this went on when without warning he pulled back freeing his ball from my mouth.



 



“Oh yes, I’m going to cum! Open wide Banks” he cried out loudly.



 



I opened my mouth as much as possible as Mr. Middlebrooks frantically stroked when with a grunt he erupted. His hand held me in place and as I watched his first blob of cum came directly at and into my eye catching me off guard. It burned a little and I blinked trying to get it out. Meanwhile the second spurt hit my nose and cheek before he was able to perfect his aim. The third and subsequent shots found their way into my waiting mouth.



 



It tasted bitter to me as I swished it around on my tongue. Mr. Middlebrooks produced a lot of cum befitting someone with such big balls and by the time he was done I had quite a mouthful. Looking up at his face with my good eye I saw that it was red and that he had an expression of pure ecstasy on it. Once no more cum came from him he pushed his cock into my mouth. I knew what he wanted so I sucked on the head while running my tongue across it provoking a moan of pleasure from him. His hand stroked my hair as I did so until with a gasp he pulled out of my mouth.



 



His fingers found the stray drops of cum on my face from when he missed and he brought them to my lips where he fed me with a laugh. He even removed what he could from my eye and gave me that as well and I swallowed it down with a sour expression.



 



“Well you passed your test on cum eating Banks. Unfortunately your grade for cocksucking is incomplete at best. You will need a lot of tutoring to pass I feel. While I did cum it was more because of my own hand then anything you did with your pretty mouth. And if I hadn’t been so excited due to everything else we did I wouldn’t have cum so easily. So it seems to me that you didn’t live up to your part of our bargain.”



 



“That’s not fair” I replied.



 



“Life isn’t fair. Deal with it. These days all people talk about is self esteem and fairness as if by throwing those words around everything can be made perfect. Well it can’t and fair or not you didn’t make me cum with your mouth so to my mind you still owe me a cum. However I consider myself a decent chap so I believe we can work this out to benefit us both.”



 



He walked behind me and delivered a sharp slap to my sore ass which caused me to jump a little before he leaned down and kissed me in the same spot. His hand snaked around my leg and again encircled my erection and gently stroked it making me gasp. Mr. Middlebrooks then slid a finger from his other hand back into my ass to its full length.



 



“You like that Banks, me stroking your young hard cock as I finger your tight little bum. Feels good no doubt. Maybe you’d enjoy another finger there, hmm?”



 



I didn’t answer so he worked another one in me forcing a groan from my lips. He proceeded to build up a matching rhythm where he timed stroking me as he finger fucked me until I thought I’d go crazy from the feeling. On top of that his hot mouth was kissing me all over my ass while he did this. Between my youthful horniness and his skillful handling within a few minutes I was moaning like crazy and on the verge of cumming again.



 



“Yes Mr. Middlebrook don’t stop! It feels so good, please don’t stop!” I begged him.



 



Whether it was because of what I said or he sensed how close I was to orgasm he suddenly stopped all his movements leaving me to cry out in frustration.



 



“No! Why did you stop? Please Mr. Middlebrooks!” I implored him.



 



“You want to cum again I see. Well so do I Banks so I’ll tell you what is going to happen. I plan on giving you the best orgasm of your life and in return you will give me a great one in return.”



 



As he said this he gave my young prick a gentle squeeze causing my body to shudder with delight. Then he released it and also slid his two long fingers out of my ass. Next his hand grabbed the bottle of lotion from the desk. Twisting my body at the waist I turned so that I could see what he was doing. Mr. Middlebrooks squirted a generous amount onto his hand and began to work it into the skin of his smooth hard cock, adding a little more as he did so. Then he held the bottle over me and let some go. I felt the smooth lotion drip onto my ass crack including some right on my hole. His fingers then smeared it around even slipping back in me to coat my anus so it was fully lubricated.



 



“Mr. Middlebrooks wait…” I began but he cut me off curtly.



 



“Hush Banks! This is going to happen. It will hurt some to begin with, possibly a lot as I am quite thick but I promise you it will get better and before we’re done you’ll be loving it. I’m not going to gag you now but if you make too much noise I’ll be forced to. Now the best thing you can do is relax as much as possible and breathe in a slow and deliberate manner.”



 



After saying this he again reached around and took my prick in his hand and held it while his other hand pushed my chest flat against his desk. He didn’t stroke me now as much as he gently squeezed it then loosened his grip. Following his instructions I tried to relax as best I could but I was very nervous about what was coming. Still I regulated my breathing, taking in slow deep breaths and then slowly exhaling.



 



“That’s a good boy” he said as he pressed his large head against my puckered hole “just keep doing what you’re doing.”



 



After he said that he again squeezed my erection as I continued to breathe. We must have been like that for a minute standing there still. He continued to gently squeeze me on and off while his cock patiently waited at my hole. Though I knew it was going to happen I was able to relax some and when I next took a deep breath Mr. Middlebrooks thrust his hips forward very hard.



 



With all the lubrication and the fact that his fingers had loosened me some already he was able to drive his head and a few inches of his shaft into my tight ass immediately. I cried out from the pain while at the same time Mr. Middlebrooks let out a gasp of pleasure. It felt like I was being split in two and as he attempted to push deeper I couldn’t take anymore.



 



“Please stop Mr. Middlebrooks! Its just too big! I can’t take it, it hurts too much!” I gasped out and I already felt my eyes tearing up.



 



“Calm down Banks. Stop being such a crybaby! I won’t try and go any deeper for now. Keep breathing and relax.”



 



“I’m trying but it really hurts Mr. Middlebrooks. Please take it out” I begged him.



 



“You’ve got to learn to handle things with a stiff upper lip like we do in Britian. Really I’m sure its not that bad Banks.”



 



He stroked my hair softly then without warning clamped his hand over my mouth as he forced the rest of his thick cock into me. It hurt even more than before and I attempted to scream but his large hand muffled me so it came out as a low moan. He pushed forward just a little more and I could feel his pubic hair brush the raw skin of my ass. He leaned down and whispered in my ear then.



 



“I’m all the way in you now. You’ve taken my whole cock boy. I’m going to stay like this a minute while you get used to it before I move. Keep trying to relax.”



 



True to his word he didn’t thrust or move his cock in any way. He did however begin kissing my shoulder and back and his hand started to stroke me again. I’d lost most of my erection due to the pain when he’d forced his way up my ass but he kept stroking me and in spite of the pain he managed to cause me to start growing again.



 



“Good boy! Get that little cock of yours nice and hard for me. Just think how good it feels while I play with it, concentrate on that.”



 



His hand soon had me fully erect at which time he moved the hand off my mouth and turned my head to the side. He leaned in and his lips found mine in a kiss. He was insistent and demanding and soon his tongue had slipped into my mouth and explored it. All the while his hand continued to play with me and I could now feel pre-cum oozing out my hole. Reluctantly he broke our kiss so he could speak.



 



“Very good. Here’s what I’m going to do now. We’re going to move our bodies together to start so you can get used to it. Nice and slow to begin with.”



 



The hand that had been on my head he moved to the top front of my thigh and after that he pulled me back while at the same time moving his own hips backward. For the next minute or so we continued with this, moving our hips in rhythm with each other so that though he moved slightly in me I was able to bear it. All the while he did this he continued to slowly stroke me until there was more pleasure than pain.



 



“How are you doing Banks? Are you ready for a little more?” he asked.



 



“It still hurts sir, but its getting better I think. Your hand feels really good though.”



 



“You like me stroking your little cock then, good. I tell you what I’m going to do. I’m going to start to fuck your tight ass now. Slowly to start with and as I do I’m going to speed up my hand. Would you like me to make you cum again?”



 



“Yes I want to cum Mr. Middebrooks. But please take it easy on my ass. This is the first time I’ve done this and you are sooo big.”



 



“Yes I am Banks. I’ll do my best to go slow but I’m using all my willpower as it is to not pound you like you deserve for waving your bum in my face. Now hold onto the chair and don’t move.”



 



My fingers grabbed hold of his wooden chair as he moved his hand from my hip and placed it on my lower back right above my ass and pressed me into the desk. Then he slowly pulled back until around half of him was in me before slamming the rest back in. I let out a loud moan but he didn’t seem to care. He kept sliding back and forth in me driving his full length into me with each thrust while pulling out halfway.



 



Mr. Middlebrooks was now stroking me rapidly while doing his best to keep from fucking me as hard as he wished though it was plain he was still enjoying himself. With each forward movement his large balls slapped my flesh and his hairy legs collided with mine.



 



“Your bum is so tight on my cock Banks. It feels delightful let me tell you. I haven’t felt one so tight since, well since my last virgin schoolboy. Now listen up! You have a minute to cum and after that I’m really going to let you have it whether you’ve cum or not so do your best.”



 



I did my utmost to think of how good it felt as his hand stroked me and I was beginning to enjoy the feeling of his big cock in me as well. His hips had increased the speed of his thrusts also but he was still partially in control of his body.



 



“Come on Banks you can do it. Hurry now, time’s running out!”



 



“Don’t stop please!” I cried out “I’m so close sir!”



 



“Well do it boy! Shoot your load!” he said with his hand now a blur on my hard prick.



 



“Yes! Yes! I can feel it!” I managed to gasp out before letting out a long drawn out moan. “Yes I’m cumminggg!”



 



“That’s it Banks! Cum for me” he ordered as he buried his impressive girth with each thrust.



 



I felt my balls tighten as the feeling overwhelmed me and as Mr. Middlebrooks continued fucking me I lost it. With each thrust of his a shot of cum erupted from me and hit the side of the desk as his hand milked me. My mouth was just making unintelligible noises by now as my whole body tightened up. With every spurt I came I felt my cock, balls and ass contract though his thick cock kept my ass wide open. My breathing was ragged while my legs now felt like rubber. Only my chest resting on the desk and his cock deep in my ass kept me on my feet.



 



He squeezed me a few more times to force the last bit of cum from me at which time he released me. Placing that hand on the desk beside me Mr. Middlebrooks was true to his word. Now that I’d cum he began to fuck me in earnest, greatly increasing his speed. For the next few minutes he pounded me like there was no tomorrow. If I thought he had been going hard before then I was set straight by him now. My legs went on me though I remained in place due to the other factors in play. While technically I was still on my feet it was more the sides than the soles and my legs just trembled and shook as he thrust in and out of my ass. By now the saliva was running freely from my mouth and pooling on his desk.



 



Seeing what condition I was in Mr. Middlebrooks stopped what he was doing and slowly pulled out of me. When he did we both let out a groan at the same time due to the feeling. His hand grabbed my leg and with an effort he lifted my lower body and muscled it onto the desk. He yanked my sneakers off and then removed my jeans as well.



 



“Let go of the chair and roll onto your back boy and be quick about it” he ordered once he’d put me on the desk and stripped the clothing from my lower half.



 



With a groan I managed to comply so that I was now flat on my back with my lower legs hanging over the side. Mr. Middlebrooks then reached out with his handkerchief and wiped the drool that covered my lower jaw and chin from me.



 



“Banks you are a mess” he said simply as he also looked at my slimy half hard cock.



 



“Yes sir, I am” I answered not that I cared how I looked then.



 



“Don’t get me wrong. You look very hot when you’re well fucked boy. Now answer me this and truthfully. Did you enjoy that last orgasm?”



 



“Yes very much sir! Thank you sir, I enjoyed it a lot.”



 



“I told you that you would. How did it feel cumming with my big, thick cock fucking your tight ass?”



 



I paused for a moment before answering as I wished to get it right. “You were right sir. I never felt like that when I came before. It was…incredible!”



 



His face broke into a broad smile but he didn’t let it slow him down any. First he lifted my right leg in the air and gripped his fat cock right below the purplish head. He pushed it to what was now my fuck hole and slid it in. Though I still felt discomfort and it still seemed to be tight for him it went in much easier now. Once his cock was partially in me Mr. Middlebrooks took hold of my other leg and raised it as well then drove balls deep.



 



“Uuuhnn” I groaned as he filled me fully with his wide cock.



 



Putting his weight on my legs he again pounded me hard and fast. This time it seemed to be getting to him more. The sweat was dripping from his face and his complexion was reddening as he drove in and out of me.



 



“Oh yes Banks! Your hot arse is squeezing me good. Its going to be my turn now. I’m getting close boy. I’ll fill your bum with my cream. Ohh yes!”



 



Mr. Middlebrooks didn’t stop but continued relentlessly thrusting until it finally proved too much. With a loud gasp I felt his large cock swell inside me then I felt him ejaculate in my ass. I clearly felt it throb with each shot as a virtual deluge of hot cum filled me. He came a lot but eventually it stopped shooting though he remained buried in me. After catching his breath he spread my legs wider and then leaned down and kissed me. I eagerly responded and when his tongue entered my mouth I sucked on it hard.



 



We kissed a bit but all good things must end. He pulled away and then withdrew his softening cock from my ass with a slight popping sound. When he did I felt some of his cum escape and roll down my leg. Dropping my legs he managed to retrieve my torn briefs which he used to wipe his cock clean with. Once satisfied with his efforts Mr. Middlebrooks moved to where his chair was at which time he untied my hands.



 



Though I was now free I was so spent that for a minute I didn’t move but just lay there. It wasn’t until he beckoned to me that I reluctantly sat up before sliding from the desk and standing on shaky legs.



 



“Come Banks. You’ve done well but there is another task for you remaining. First kneel down.”



 



I did as he said and once I had he stepped right before me. His hand held his half hard cock and he brought it close.



 



“Pay the proper respect to my cock! The cock that claimed and defiled your virgin ass. The cock that fucked the cum from you. The cock that taught you your place. Kiss it!”



 



I didn’t hesitate but instead eagerly bestowed his still mighty member with the respect it deserved. In fact I even opened my mouth and sucked on the head making him groan as it still was quite sensitive. Finally when he felt it was sufficient he pushed me away playfully.



 



“So how did you enjoy your first lesson in all male love Banks.”



 



“Words fail me sir. It was incredible and I’d say unbelievable except since it happened I have to believe.”



 



His hand absently pet my head as his other pulled his trousers up and in a minute he looked presentable though I preferred him with his glorious cock free.



 



“Get dressed lad” he told me as he sat heavily in his chair.



 



Looking at him now shyly I did as he told me while he wrote something on a piece of paper. When he finished he looked up and his eyes met mine.



 



“Well boy you know that in sucking cock your grade is incomplete. How do you think you did on taking a hard cock up your bum?”



 



“I know I greatly enjoyed it sir but I’m not qualified to grade myself. You are in as much better position to say sir.”



 



“I have to say Banks you certainly get an A for obedience. You have properly addressed me since I corrected you earlier. Good job.”



 



“Thank you sir” I said blushing from his praise.



 



“As far as your other grade now is not a good time to give it. Due to the situation I’m afraid that I might be unfairly biased in your favor right now. I do believe you will need much more tutoring on theses subjects this summer though. Any thoughts?”



 



“I agree sir. I still have a lot to learn if I can find the right tutor.” When I said this I looked straight at Mr. Middlebrooks.



 



“Quite correct Banks. For your first lesson report promptly to this address tomorrow at seven in the evening. If you are late even one minute you will be disciplined. No questions now. You are dismissed” he said brusquely handing me a slip with an address printed on it.



 



“Yes sir, thank you sir” I said taking it from him and leaving without another word.



 



That night after dinner I didn’t go out and when my parents asked why I was staying home on a Friday I told them I felt a little sick. I went to my room and thought about what had happened earlier and I became very excited. I had to masturbate twice in order to be able to fall asleep but I knew that tomorrow my education would continue. I smiled before rolling over and closing my eyes.



The End?



If you liked the story and want more let me know and give me comments and messages and stuff.



 



 



 



 



 



 



 



 



 



 



 



 



 



 



 



 



 



 



 
30 comments

ethanschoenheitReport

2014-08-28 05:18:31
I love this story I have it bookmarked and I have read it more than 10 times I hope you write one or two more sequels!

Anonymous readerReport

2014-08-28 04:08:07
Should a sexy story, please write more

Anonymous readerReport

2014-08-12 22:04:39
Dont judge us u inbreded peice of shit if we have dirty stories and we post them dont be coming on here and leaving comments like u all need to be in prison or call other ppl pedophiles them the writers got freedom of speech u dumb fuck

Anonymous readerReport

2014-07-25 05:28:46
Honestly one of the best stories I've read on here. Bravo

Anonymous readerReport

2014-06-17 18:18:37
What the fuck is wrong with you all
You are ether cops or pedophiles

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