Date: Sun, 1 Jun 2008 16:46:08 -0700 From: A Scribe Subject: Chess Coach The usual disclaimer applies. Please choose to read something else if it is illegal to read this story where you happen to be living or if you are offended by the thought of an older man having sex with a young teenager. All characters and events are a figment of my imagination and never took place in the third dimensional reality of this existence. Comments and politely worded constructive criticism is most welcome. A favorable response might result in more about the coach's adventures being revealed. Write to wordspenned@gmail.com. Chess Coach There was no longer any need to deny my attraction to the hard slender forms of the teenage boys that surrounded me during my work day. I thought if I placed myself in a situation of temptation and resisted I would find freedom. The experiment fell through when I fell into temptation. Let me explain how it came to pass that I ended up on my knees staring at three slender, naked, fully aroused bodies of the school chess team while the team captain fucked my ass. Before accepting my new post I worked as a science teacher in a middle-class, nondescript public school in Colorado Springs. Seeking a quiet little position where I could work through these new feelings arising within me. Unfortunately the gods seemed determined to tease me mercilessly from day one. They brought into my class a fourteen year old who immediately became the center of my jack off fantasies. Fortunately I managed to keep my feelings too myself long enough to one day observe him fucking a cheerleader in the shower. She was bent over. Bracing herself in the corner as he pounded her from behind. There I stood watching his tight ass clench and unclench as he fucked her. I never bothered to clean up the mess I made on the floor before I walked away. In that moment I realized it was not so much about fucking him or them as it was about being fucked by them. At least until I grew to realize that sometimes it was useful to use the one to get the other. I went through the motions of life for a week or two until I came across an online ad for a chess coach at an exclusive boarding school for boys. A move away from Colorado Springs might help me get a little spark back into my life. The position was for a chess coach. That was all I would be doing. More money, board and lodging plus the energy of teenage boys it was a no-brainer. My credentials as a chess coach were even better than my teaching qualifications. I had won numerous school titles plus been a state champion before my sexuality caused me a little too much emotional upheaval to continue with chess. A month later I was face-to-face with the school's top four chess players. They had lost the first two matches and were in need of a confidence boost. Their first workout with me was in the weight room. A pretty young personal coach put us all through our paces. Since I worked out daily this was not a great challenge for me. When we were done she left with the promise of having our workout routines completed in two days. Looking at the exhausted chess team I thought it might be two weeks before they recovered. The next day I played each of them twice. Despite being fatigued by their workout the previous day they showed some solid fundamental skills. They started to complain about meeting Sunday afternoon with the personal trainer until I reached into a drawer and pulled out a thirteen inch leather paddle. There is always one idealistic youth who foolishly believes he is protected by school regulations against corporal punishment. I merely handed the paddle to the team captain without saying a word and stepped outside. A few minutes later I heard the first of fifteen blows fall. When the last blow landed I walked off to my room and jerked off to the image of me applying the paddle to my chess team one day. The workout were tough but in my opinion fair. There were regular checks to monitor progress. I told them there would be no signs of a lack of progress at any time. Along with the weights there were yoga routines. We all went through our routines once to get a feel of the different poses. Susan would guide each of the guys through their routine in the weight room on Monday. How wonderful it was to be in a school with money to spare. Parents of the chess team had told me they would finance any extra expenses I felt were needed. They had suggested Susan who was a personal trainer for two of the families. Our first official chess practice session took place on Tuesday. A day that would result in me enjoying receiving the entire team's cum in my ass later in the year. Like most things sexual it began with an innocent incentive program. "Before we get to the examples I have for you to work through," I began "I want to say that I am aware you guys will work harder this year than most of the others in your classes. This is why I am going to allow you guys to choose a reward that you will receive if you win your league. Jason, as captain, you will let me know the team's decision in two days. The team must be unanimous in their choice. I want it in writing and signed by all team members." "Sir, we don't really need two days. We can sign the paper now if you want." Jason answered. "Really, how did you know I was going to make this offer?" "We didn't but we have all pretty much expressed the same wish since you started here last week. I think it safe to say I can guess what they others would like as their reward." The grins on their face ought to have warned me to set a few stipulations. I didn't and they took full advantage. "What is it you guys would like as a reward?" "Your ass!" Jason said without hesitation. "What?" "You said if we all agreed it would be our reward. We all want to fuck you and will do so in the order that we play our games. Me, then Tim, then John and Simon." "Do you guys mess around with each other?" "No, we only jack off." "What do I get if you guys don't win?" I asked while trying to figure a way out of this mess. "You get to fuck us in the same order." "You are all certain you want to go ahead with this as your reward?" Everybody nodded and smiled. "I will agree on one condition. Since I have never had anybody fuck my ass you guys must promise not to let anybody fuck your ass until after league play has ended. I am assuming you have never been fucked before." This was duly noted in the terms of our reward contract, which Jason would keep locked in his safety deposit box. The guys then surprised me by saying they wanted a weekly incentive package. "I'm pretty certain you guys have thought this through and have another offer to make." I sighed. "Whoever wins his game will be rewarded by you sucking his cock. Whoever loses will have to suck your cock. In the event that everybody on the team wins you will suck us all twice." Since they had my agreement to let them fuck me in writing I could see no reason, nor did I really want to decline their offer. What I didn't want was to appear a pushover. "I agree if you guys agree to two things. Winners can decide if they want to be sucked by me or if they want to suck me. I can decide to be sucked by the loser of a game or to suck him. The other matter is off-the-board discipline. Failing to keep your grades up; being sent to detention or any other bad behavior will earn you a paddling in addition to your other punishment. I get to decide every detail of your paddling." There were quite a few grumblings about the paddling until I pointed out that none of them had been in trouble at all for the past three years. I also pointed out that like the other reward system we had introduced if they played their part they would have nothing to worry about. Jason was the first to realize I was not going to budge. "As long as there is nothing sexual as part of the paddling I'm ok." He agreed. "Nothing non-consensual and you have the freedom to ask for or decline any suggestions. There can be no fucking until the end of the league anyway." This seemed to satisfy them and everything was duly noted. After an hour we finally got started on the chess. The guys worked hard that afternoon. We had two weeks to prepare for the next match and as the days passed I grew more and more nervous. I had never messed around with any other guys and was as nervous as a virgin bride on her wedding night. Winning the match meant I would have to suck at least three cocks. Then I reminded myself that the guys had never been sucked before so even if I did a below par performance it will still be incredible for them. Since they had initiated the sexual aspect into our relationship I felt a little more secure that they were not going to spill the beans. I visited a few websites and discovered they all pretty much suggested a similar cock sucking technique. They also agreed that anything I did was going to make my partner feel great. Keep the teeth out of the way and all would be fine. Jason won his game pretty quickly thanks to an error by his opponent that caused him to resign a dozen moves into the game. Tim and Simon had to fight hard for their victories. I think the added incentive our team had to win proved decisive in these two games. John managed a draw, which according to the decision of the guys meant we both got to decide what we wanted from each other. I was pretty certain that he would not want to be the only guy who did not get his sweet cock sucked. Heck, neither did I want to be that guy so it seemed the ideal result. On the drive home I set out the schedule for Saturday. Fortunately Jason was an early riser so he would be getting his blowjob before breakfast was served. By spacing our encounters a couple of hours apart, with the winners going first, everybody would be taken care of on Saturday. How quickly things change, I thought. In one day five guys would have their cocks sucked by another guy for the very first time. Two of those guys would be giving their first blowjobs as well. Now that the time for action had arrived I found myself eager to get started. Resigned to my fate I began to feel a strange sense of calmness. Jason let himself into my room promptly at seven the next morning. I watched him as he stood at the foot of my bed and stripped. We never said a word the entire time. He was so beautiful and so aroused. I simply lay beneath the covers as he crawled up over me. His hard four inch cock traveled straight up to my mouth. He never paused for a moment as he got to my open mouth. Jason kept approaching me until he was buried to the hilt inside my mouth and my hands were grasping his smooth ass. He gasped in disappointment when I released his cock to lick my fingers. "Trust me," I whispered as I slid a finger down to the entrance of his ass. "Press down for me." He hesitated and I slapped his but sharply with my other hand. The unexpected assault caused him to impale himself on my finger. Never mind Jason, I was in heaven. Sucking cock and probing a virgin ass with my finger. I nearly came right then. "Oh fuck! Oh yes, here it comes!" Jason cried out and began fucking my face faster. Taking advantage of his impending orgasm I buried another finger in his ass. A quick stroke over his prostate brought him over the edge. He fed me my first load of sweet boy cream. I savored every drop. We cuddled for a bit under the covers before we had to shower and dress for breakfast. He left ahead of me and told me he was certain I would be his favorite coach ever. I wondered how much of that was as a chess coach and how much was going to be as a sexual coach. Only time would tell and I was happy to simply savor this wonderful, new experience. Tim seemed a little nervous so I suggested we share a drink or two before getting down to his reward. I believed him when he said he had never had any hard liquor before so I poured him a gentle rum and coke. After the second he offered no resistance as I reached over to unbutton his shorts. Soon I was gazing at his slender, naked body as he sprawled on the couch with a close up of his cock right in front of me. My breath was causing it to twitch as I complimented him on how good he looked. I really wanted to try eating his ass but since Jason had not received this treatment I did not think it would be fair to offer it to any of the other guys. I contented myself with the knowledge that I was the first to taste his cock and probe his ass. Although we started with Tim sitting on the couch it was not long before I found myself with the back of my head resting against the couch while Tim fucked my face like there was no tomorrow. He was at the perfect height where he could stand in front of me and fuck me. I did not know how much of his moaning was sex related or drink related. I soon dropped this question as it became pretty evident he was going to feed me his load. "Drink it, bitch!" he commanded and emptied himself in a series of powerful blasts. "Don't waste a drop!" I had not intention of wasting a drop. Being bossed by a fourteen year old was a huge turn on for me but it was best he didn't know it. When I had finished cleaning him I told him if he ever called me his bitch without my permission I would whip his ass like it had never been whipped before. To ensure he got the message I gave his ass three hard slaps. He quickly apologized and after a few lingering kisses we parted on friendly terms. Simon had been outside kicking a soccer ball around with his schoolmates and had come straight to my room. Knowing that I could use a second shower I did not object too much. He told me he would not arrive for his reward all sweaty again unless asked. There was no hiding my state of arousal after my sucking of his two teammates. I simply stripped and stepped into the shower. Then I watched him finish undressing and kissed him the moment he joined me in the shower. After a few minutes of deep kissing I began to kiss my way down to my prize. I wasted no time toying with his nipples but left a trail of kisses directly down the center of his body. One of the memories that remain at the forefront of my mind is the immense enjoyment I derived from fondling two solid handfuls of ass with a mouthful of cock. How ironic that I went from never having tasted cock to sampling the delights of four sweet teens in one day. Jason was special because he was my first and so very cute but sex in a shower remains one of my all-time favorite past times. The warmth of the water on my back and running down over my naked body as I worked so diligently on Simon's cock felt so good. He gasped with delight. His slender hips bucked as new jolts of pleasure spread throughout his body. I held him firmly in place as his orgasm approach. I sucked harder. I probed the inside of his ass for that sweet spot. The moment my finger touched it he exploded. We soaped each other. We dried each other. We kissed each other good bye just inside the door to my room. Jason left saying he thought John was a lucky guy as he was going to be the first to suck my cock. Seems there is nothing like having your cock sucked to help you overcome shyness. That evening, after dinner, John and I met to enjoy each other as dessert. He surprised me by asking me if I was going to ask him to suck me or was I planning on asking him to let me suck him a second time. I told him that, like himself, I did not want to be the only guy who never got his cock sucked this lovely day. Besides, I joked, my mouth was starting to feel a little worn out. John then told me he would like to blow me before I sucked him. I immediately started stripping before he changed his mind. My cock had never been in such a lengthy state of arousal before. The prospect of dumping what promised to be quite a load of cum down his virgin throat almost set me off before he touched me. I picked him up in my arms and carried him through to my secluded reading area. I kissed his sweet lips several times before setting him down in from of the bay windows. The curtains filtered the sunlight and bathed everything in a soft golden light. I sat down on the bench seat with my legs spread apart. John did not hesitate to take his place. He did not hesitate to take me into his mouth. Oh god! There really is no way to describe the pleasure of that first moment when his lips made contact with my burning flesh. The electric jolt that ran through me must have been felt by the gods themselves. Sitting there being pleasured by a fourteen year old who was sucking his first cock was as good a definition of heaven as I have ever been able to come up with in my entire life. I clenched my teeth hard or else my cries would have been heard throughout the entire school. The orgasm felt as if it would tear me apart from the inside out. I did crack my head a couple of times on the window as my hips thrust upwards. When I had finished emptying myself inside of him I slumped motionless for a minute or two. John had managed to swallow most of my cum. A little bit trickled from the corner of his mouth. I watched as he scooped it up with a finger. He offered it to me but I told him I wanted to taste him. The mischievous smile should have warned me. Before I realized his intention his cum coated finger was buried up my ass. We both burst out laughing. I was still laughing when I told him I would have to spank him for being so naughty. "Didn't you enjoy it?" he asked. "Yes, as much as I will enjoy spanking you." I replied. I had planned on spanking him the next day but he got up from the floor and laid himself across my knees. I gave him a half dozen playful swats before the urge to swallow my fourth load of cum took over. His ass would be there on other days. Instinctively I knew John had a true submissive streak within him. Perhaps it is because it is so similar to mine that I was able to recognize it. Lifting him from my lap I had him stand on the seat. I ran my tongue all the way from his heavy balls up the underside of his erection. Pulling it away from his body I let my tongue work its way down the top to the crisp hair. Then I retraced my path back down to his balls. On the third pass a squirming John was begging me to take him in my mouth. I thought of extracting a favor but he had earned his cock sucking with the draw so I let the head of his cock enter me this time around. Fortunately John was able to hold onto a cross beam that ran above the bench seat as he squirmed in my grasp. I was really squeezing his ass cheeks firmly. I loved the way they clenched and unclenched as I worked him over. Lost in the play of his ass in my hands his orgasm took me by surprise. I was not too surprised to waste any of his cum. Every delicious drop was savored. I gently lowered him to the seat where he sprawled while trying to get his breath back. When he felt he had enough strength to stand I sent him off to the shower. "Aren't you going to shower?" John asked. "Yes, after you." "After me?" "Yes, after or this," I said pointing to my throbbing cock, "will be buried up your ass. We promised to keep our virginities until after the chess league ended. Remember?" "So you want me or is it any cute ass?" "Don't you think that if it was any cute ass I wanted I would have simply paid some kid on the street? There has to be more for me. We may have only worked together for a few weeks but the four of you are becoming quite special. That is why we will keep our end of the bargain." "You're right. I'm sorry for doubting." John said and grinned at me. "That is worthy of a spanking." "You don't have to be rude to get a spanking." I told him. "Just ask nicely." "Maybe I will." John headed off to the shower and I jerked off. He noticed the change and asked if I thought of him when I came. I told him he was naked, soaped up and bent over in the shower with my cock exploding in his ass when it exploded in my hand. He smiled, kissed me quickly and walked away. By now you will have put two and two together and realized we won the league. Between the first sucking and my first fucking there were numerous occasions when those same four cocks unloaded in my mouth. There were spankings for misbehavior but not as many as I had hoped. John made up for it by asking for some on the side. Although I never got sucked by the guys after their spanking they did allow me to fuck their ass cracks. I also got to taste my own cum as I licked them clean. Jason was giving me everything he had and then some as he claimed my virginity. All four of them were unanimous in their decision to fuck me one after the other. I was destined to go to sleep with four loads of cum in my ass. How tough my life had become since agreeing to be a chess coach for Addington Boys Preparatory School. Oh if only the parents could see how their four little angels were behaving now. Instead they had asked me to chaperone the chess team on an all expenses paid week at a luxury lakeside cabin. The boys had put forward the suggestion to their folks after informing me they simply wanted to extend their reward by a week. After all, they said, it would be cruel to give them only a single taste of the pleasure to be found in fucking their coach. They told me if I behaved myself I might find myself rewarded with a surprise gift. Since it would be odd to turn down an extra week of paid vacation time I really had no choice. You couldn't possibly think I accepted because I found the idea of a week long fucking by four horny teens attractive, could you?