Date: Sat, 13 Jul 2002 12:46:05 +0100 (BST) From: AC Subject: Dilemmas - The Tutor Any resemblance to real people or actual situations is purely acidental DILEMMAS THE TUTOR I am a young maths teacher aged 25 who works in an all boys school. I have always taken a very professional attitude towards work and consequently my private life and school are kept strictly separate. I deliberately chose not to live anywhere near the school because I don't want to meet pupils in the evenings or at the weekends. At school I'm very careful not to get too familiar with the boys, so much so that many of them don't think I'm very approachable. In my spare time I give private lessons to both girls and boys but this work is quite separate from my schoolwork and is arranged through an agency. In order to avoid unnecessary difficulties I refuse to tutor any of the boys at the school where I teach. At the moment I am sitting in the front room of my small one bedroom flat trying to work out the answer to a problem but it is not a maths problem. It is the kind of dilemma I have tried so hard to avoid. For almost a week it has been continually on my mind and I've not been able to concentrate on a thing. A couple of hours ago I decided that the only thing to do was to try and clear my mind by writing everything down. That is what I'm doing now. I had not been giving private lessons long when I started tutoring a fourteen-year-old boy called Shawn. His mother had contacted me through an agency and my first visit to his home was just after Christmas in the year before he took GCSE. His mother opened the door to me and in our preliminary discussions she did all the talking. Shawn just sat there. He was a small boy with a babyish looking face with two blue eyes, a small nose and fair hair. His voice hadn't broken yet and it was difficult to believe he was already fourteen. Intellectually, though, he was very bright and I didn't really think he needed extra lessons but when I suggested that to his mother she said that Shawn wanted to get an A in his exams and as there was no father she was prepared to do all she could to help him. For six months or more lessons were much as I would have anticipated. I visited Shawn once a week, except during the holidays, and he made such good progress that, from time to time, we would do more advanced work. At the end of the school year his mother told me that she wished to continue with lessons over the summer break but as I was going to the US for an extended holiday I said that would be impossible. Consequently I didn't see Shawn for over six weeks. When I returned in September I was immediately struck by how much he'd changed. Not only had his voice broken but also he was also taller and beginning to fill out. One thing remained the same, though, and that was his attitude to work. He paid attention throughout the lessons and always did the homework I set. For the next three months things were much the same as they had been the previous year. Just before Christmas, Shawn asked me if we could change the time of his lessons as he'd got a job at the local supermarket stacking the shelves. This came as no surprise to me as he'd mentioned a number of times that he wanted to get a part time job because he needed the money. Lessons had always been on a Thursday evening but now he wanted to see me at ten Saturday mornings. As he was such a good student I agreed, even though it was a little inconvenient, The first of the Saturday lessons was in the second week of January, just after the Christmas break. I arrived at Shawn's house promptly at ten. Shawn himself opened the door and not his mother, which always used to be the case, and I couldn't help noticing a difference straight away. As it was Saturday he was wearing a t-shirt and track bottoms rather than school uniform but it was not just that. Somehow there was air of confidence about him, which I had not seen before. I put it down to growing up and as soon as we started the lesson I forgot all about it. However I got the same feeling the following week and I began to sense that he wanted a slightly different kind of relationship with me. I couldn't explain it at the time but whenever he spoke to me it was as if he wanted me as a friends and not just a tutor. It must have been during the first lesson in February that Shawn's mother brought in a cup of coffee for me, as she usually did, but then announced that she was going shopping. As soon as the front door closed Shawn immediately moved his chair back a bit from the table, so his crotch was clearly visible, and from time to time he would swing back and start to scratch his upper leg. It was impossible not to notice what he was doing. The following week Shawn's behaviour followed a similar pattern except that instead of scratching his upper leg he started giving himself a squeeze. I began to wonder what was going on. His mother didn't go out for the next few weeks and things appeared to go back to normal. Shawn didn't move his chair, didn't swing back and didn't scratch himself but he did confirm my suspicions about wanting me to be more like a friend. At the end of one of the lessons he asked me if he could call me Mike. I hesitated a bit but agreed as I didn't really think it would do any harm. I'd been teaching him for quite a time and anyway he didn't know any of the boys at my school so there wouldn't be any difficulties there. On the Saturday before half term I arrived about ten minutes late. Shawn opened the door and half seriously demanded to know why I was late. He also mentioned that he was worried that I wouldn't be coming, as the following week was half term. I laughed and said ' Sorry sir' and we both went into the dinning room, where as usual his books were laid out ready for the lesson. We'd hardly sat down at the table though when he turned to me and said ' By the way my mum's not here so you'll have to make do with my coffee at half time.' ' I think I'll cope with that' I said As the lesson preceded it was clear that Shawn wasn't concentrating on the work. He was making silly mistakes, which was quite unlike him, and was continually leaning back on his chair and giving him a squeeze. He also started glancing down at my crotch when he thought I wasn't looking. After about half an hour of this he got up to make the coffee and as he did so he quickly turned round so he had his back to me. Even so I couldn't help noticing a bulge in his track bottoms. At first I thought it was a large handkerchief or a wallet but when I followed him into the kitchen and watched him as he made the coffee the bulge had disappeared. We took our coffee back in to the dinning room and resumed work. The second half of the lesson was just like the first except that Shawn kept scratching himself so obviously that he must have wanted me to notice. When I announced the lesson was at an end he said ' Pity' but again got up quickly. This time he didn't make such an effort to hide his errection. I usually go away at Easter but this year I didn't. I must have mentioned this to Shawn because he asked me if I could give him an extra lesson on the Thursday before the start of the Summer Term. I told him I didn't think that would be a problem and arrived at what I thought was the agreed time - ten o'clock. There was no reply when I rang the bell so I tried a second time but again there was silence. I was just about to go when the front door suddenly opened and there was Shawn looking a bit dishevelled. ' Sorry Mike.' He muttered ' I was busy doing things and forgot about the time' ' Don't worry ' I said ' It happens to us all sometimes.' As he was closing the door Shawn said ' I want you to help me with some IT today Mike, if that's alright and do you mind if we have a coffee first? I haven't had breakfast yet and anyway my mum would kill me if I took drink anywhere near the computer.' We went into the kitchen and Shawn started making the coffee. I couldn't help noticing that he wasn't wearing anything under his track bottoms and there was a small damp patch clearly visible. At one point I had to look away quickly as I thought Shawn had caught me looking at him. I didn't want him to get any ideas. We drank our coffee at the kitchen table and were talking about school when Shawn suddenly announced that it had been his birthday two days before and that he was now sixteen. I muttered something like ' Congratulations' and then, as a joke and without thinking said ' What are you allowed to do now that you couldn't do legally when I was here last? Shawn grinned all over his face and said ' Have sex' I gave a kind of uneasy laugh but didn't say anything. Shawn however just carried on without a hint of embarrassment ' The age of consent for both heterosexual and homosexuals is now sixteen so I can have sex with whom I want as long as they agree' ' Its not quite as simple as that' I said ' Come on let's get down to work. Where's your computer?' ' It's in my bedroom. It's a new one. Mum got it for my birthday so I don't keep on having to use hers.' We sat side by side at Shawn's desk and he began to explain his problem . All the time though he kept giving himself a squeeze and try as I might I couldn't stop myself glancing down at what he was doing. Then quite suddenly he turned to me and, slightly hesitantly, said ' I hope you don't mind me asking, Mike, but how old were you when you first had sex?' This was the last thing I'd expected. For a moment I was lost for words and laughed nervously. Then, hoping to put an end to the matter said jokingly ' I cant remember now. It much too long ago.' 'It can't be that long ago you're only about twenty five aren't you?' 'Yes' I said ' Come on. Let's get on with our work.' We both turned to face the screen again but after about another five minutes Shawn interrupted work again 'I need a piss.' He said 'Won't be long' He stood up, turned his back to me and made for the door but even though he moved quite quickly it was obvious he had an enormous tent in his track bottoms. As soon as I heard the toilet door close I had a good look round the room. It was quite tidy except for the bed that hadn't been made and a pair of boxers screwed up on the floor. I had never had any fantasies about Shawn and he had never featured in any of my dreams but now I could feel a change coming over me. I kept telling myself I shouldn't but I couldn't stop myself. I got up, went over to the boxers and picked them up. The front of them was covered in dry cum and there was a small damp patch. I then realised what Shawn meant when he said he was busy doing things and it occurred to me that when I said 'it happens to us all sometimes' he took my words as an invitation to talk about sex. I threw the boxers back on the floor and as I sat down a picture of him laying on the bed masturbating flashed across my mind. I was now tempted to go outside and listen at the toilet door to see if I could discover whether he was finishing off what I had interrupted earlier but I managed to control myself. When he eventually came back into the room the tent in his track bottoms had disappeared and we got back to work without any more problems. For the remaining half dozen or so lessons I had with Shawn his mother was at home for the whole of the time and things were completely normal. He stopped swinging back on the chair and as far as I could see didn't feel himself. He made no more attempts to cross-question me about my private life The last lesson was at the end of May and after we'd finished I told him I would ring him up to see how he got on but as I was going to be away for the whole of the six weeks holiday I asked him to e-mail me his results. He took down my e-mail address and I said good-bye, wishing him the best of luck in his exams. During the holidays I forgot all about Shawn but when I got back home and checked my e-mail there was a message from him saying that he had got the A he wanted and asking me to give his mother a ring. I did so straight away. She asked me if I could go round there the following Saturday morning as Shawn wanted to see me and anyway they had a little something for me. I'm always embarrassed when this sort of thing happens but I agreed and promptly at ten was standing at the front door of Shawn's house. Shawn opened the door to me and we went straight into the sitting room where his mother was waiting. She gave a little speech and presented me with a large bottle of expensive champagne before going into the kitchen to make some coffee. I was left alone with Shawn and almost at once he started to enquire about my holidays. I didn't say too much and tried to change the subject by asking him about school. As soon as his mother returned with the coffee the questioning stopped and the three of us chatted for about another fifteen minutes before I stood up saying I had to go, as I had to give a lesson just before lunch. Both Shawn and his mother came to the door to say goodbye and both shook me by the hand before I finally left. I thought that would be the last I'd see of Shawn. The start of the new term was a particularly busy time for me. I had a couple of new students to tutor and a lot of preparation to do at school. Shawn didn't cross my mind once. Then about three weeks into the term I got back home from shopping at about six o'clock one Saturday. I parked right outside my basement flat and had only just started unloading the car when I suddenly heard a familiar voice behind me. I turned round quickly. It was Shawn. My guard was down and I just stared at him. Shawn spoke first. 'Want some help?' 'What are you doing here?' I said in amazement 'Oh.... I've just been visiting a mate who lives down the road. I just saw you drive up and thought you might like a hand' 'Well.........since you're here... yes...thanks' We took the shopping down the steps which led to my flat and left it outside the front door until we had finished unloading the car. Neither of us said much while this was going on but all the time I was trying to make up my mind whether to ask Shawn in. Part of me said I shouldn't, part of me said it would be rude not to. I paused for a moment before putting my key in the lock, then turned to Shawn and said' Fancy a coffee?' He looked at me, smiled and nodded. I led the way to the kitchen where I suggested he make the coffee while I put the shopping away. Shawn agreed and we both got on with our jobs in virtual silence. When we eventually got into the sitting room with our drinks Shawn started to talk. First of all he wanted to know what school was like and whether I was tutoring any good students. He then started to quiz me about my holidays again, just as he had done the last time I had seen him but this time he started to ask me if I'd met any interesting people and where I'd met them. As you've probably already guessed my holidays are not spent visiting the sights but cruising for sex. During term time I am almost celibate but during the holidays my visits to the US and Europe are nothing but sex, sex and more sex. Naturally I couldn't tell Shawn all this and so I came out with some general comments which were quite meaningless. Shawn realised that I was trying to avoid giving straight answers because he suddenly grinned at me and said ' By the way Mike you didn't tell me how old you were when you first had sex. Come on you can tell me now I'm not your student any more.' Now I couldn't tell him the truth about that either. The first time I had sex was when I'd given a blowjob to a prefect at the boarding school I went to. I was only fourteen at the time. The same boy had fucked me twice at the end of the school year just before he left when I was fifteen. I had to think quickly. ' For all you know I've never had sex....' Before I could finish my sentence the telephone rang. It was my brother who needed some help setting up his new computer and could I go over there straight away. 'Sorry Shawn' I said as I put the phone down 'I've got to go but if you need any help with your Maths you can always give me a ring. I don't mind helping out if I can' As the words came out of my mouth I was saying to myself that this was madness and that I should not be encouraging him to come round. Shawn looked pleased and asked me for my mobile number because he said he would probably be able to get hold of me more easily on that. We both left the flat together and I knew that it wouldn't be long before I heard from him again. Within a week Shawn was on the phone asking me whether I could help him with a Maths problem he'd been set at school. I told him that I didn't want to spoil his social life but the only time I could manage would be seven on Saturday evening. All he said was ' Cool. See you then' When he arrived I took one look at him and a shiver went down my spine - he looked hot. In order to try and keep myself under some kind of control I suggested we do the work first and have a drink after. We sat down at the table and within a couple of minutes I knew that Shawn wasn't having any difficulties with his maths. He was only using that as an excuse so he could come round to my place. I didn't say anything though and we continued work on the problem he'd been set. While we sat together at the table I was trying to persuade myself that the best thing to do after we'd finished work, was to tell Shawn that I had to go over to my brother again so there would only be time for a quick drink. But I said nothing of the sort and after about ten minutes I sat back in my chair and said ' Well what would you like to drink?' ' Anything alcoholic' came the reply In the kitchen I showed him my array of beers and lagers' 'Take what you want' I said Whether it was deliberate I don't know but he grabbed hold of a bottle of lager I'd brought back from Belgium. Its alcohol content was 8.5o/o. Up to that point in the evening Shawn hadn't even hinted at anything to do with sex but I felt sure it wouldn't be long before he did - especially when he'd got a bit of that lager down him. I was right. We'd been talking for no more than about two minutes when he said 'What are you doing tonight then Mike? You got some bird lined up?' 'No' I said ' I'm staying in. What about you? ' ' Well yes and no' came the reply. I should have left it at that and immediately changed the subject but I didn't ' It must be yes or no Shawn. Don't you want me to know?.......... Don't tell me I know who the person is' ' Well it'd be a bit embarrassing if I told you and then didn't score wouldn't it?' 'So I do know who it is?' Shawn didn't reply but I was pretty certain the only person known both to Shawn and to me was his mother.' So I do know then?' I persisted 'Put it this way Mike if it works out you'll be the first to know. Now can I have another drink?' 'I don't want you going home fucking pissed out of your mind Shawn' I laughed. That was the first time I'd ever spoken to Shawn in that kind of way. It was an admission on my part that we were now friends and that the tutor-pupil relationship was a thing of the past. My remarks changed the whole atmosphere. Shawn grinned all over his face and replied ' Don't fucking worry about that Mike. I told my mum I was staying round a mates for the night so she wont be waiting up for me. Anyway she's found this new bloke and she's probably being fucked by him right now.' While Shawn was talking I was looking closely at him. He had stretched his legs out and had both his hands in his pockets. I knew that if I'd met somebody like him during one of my trips abroad I would already have made a move on him. My cock started to get restless and a shiver went down my spine. Shawn interrupted my thoughts by repeating his question 'Well can I have another drink you tight bastard?' I laughed' You can go and get what you want. You know where everything is.' I knew Shawn would have to take his hands out of his pockets when he stood up and I wanted to see whether he had a hard on. Sure enough he had, and as he walked round my chair into the kitchen I took a good look at it and almost put my hand out and gave his cock a squeeze. A few moments later Shawn called out to me ' Come here Mike. Can I have some of this? I've never tried it before.' 'What is it'? ' Come here and I'll show you.' I could see that Shawn was trying to get his own back. He knew I'd seen him tenting and now he wanted to see whether I was. I got up and strolled into the kitchen with my cock stretching down my right leg. Shawn winked at me and then pointed to a bottle of Port. I got two glasses out of the cupboard and told him to help himself and pour one for me. After a couple of glasses of port the alcohol was really loosening both of us up and Shawn returned to the topic of sex. ' Can I ask you a question Mike?' 'You've never had any difficulty in asking me things before so what's the fucking difference this time?' I joked Shawn, looked at me straight in the eye and, without a hint of embarrassment, said. 'Have you ever had a blow job?' I now wanted to know how far Shawn was prepared to go and I no longer cared about what I said. My answer was a straight ' Yes' 'What's it like? 'Is that what you are hoping for tonight then?' 'Yeah' As the word came out of his mouth he gave his cock a big squeeze ' And what will you do if you don't get one?' ' Have a wank I suppose....... Do you wank Mike?' 'What do you think?' ' Yes... probably three or four times a day' Shawn was grinning all over his face 'Well that depends on how busy I am but I reckon about twice a day' 'Same as me' I was now convinced Shawn wanted to go all the way so I decided to take the initiative. 'Of course if you can't get anybody to give you a blow job you can always try giving yourself a suck' A look of amazement came over Shawn's face. It was obvious this was new territory for him. 'The fucking pervs...have you ever done it?' ' No. I reckon you've got to have a flexible body and a long cock' 'Fuck Mike I want to try it' 'What's stopping you then?' 'Can't try it now can I?' Shawn gave me a hopeful look. 'Why not?' 'Do you mean that Mike ? Can I go into your bedroom right now and see whether I can do it?' 'Go ahead but get a towel from the bathroom and put it on the bed. I don't want a mess' Shawn shot off to get the towel. While he was in the bathroom I moved my chair so that if he didn't close the bedroom door I would get a good view of what he was doing. Shawn did what I expected and left the bedroom door wide open. As he took his shoes off, then his top and finally his track bottoms and boxers I watched him intently. He had a beautiful slim body and his uncut cock stretched straight out in front of him. Just before he got on the bed he looked through the door at me, grinned and said ' Here goes'. I couldn't believe what I was seeing and I nearly came in my trousers with the excitement. I don't think he was really trying very hard and he wasn't a success. He soon gave up and lay on the bed with his knees up in the air. Then he yelled out 'Come on Mike give us a hand will you?' I laughed, got up and made for the bedroom. ' Where do you want my hand then?' 'You know where, you bastard. On my cock.' I sat down on the side of the bed, stretched my left hand across and lightly gripped the tip of his meat before moving the foreskin up and down ' Thanks Mike' Shawn whispered and closed his eyes. I took my time, as I didn't want him to cum too soon. Every now and again I would stop and watch his cock throbbing and look at the contentment on his face. After a bit he opened his eyes and said 'Can I have a feel of yours?' I just smiled, stood up and quickly took every bit of clothing off before going and standing by the edge of the bed. Shawn rolled over onto his side and gripped hold of my cock and began to wank me slowly. It wasn't long before we were both on the bed lying side-by-side wanking each other. Then suddenly and almost without thinking I rolled over gripped hold of his head and began to give him a passionate kiss. Shawn responded and soon our tongues were playing with each other. I pulled him on top of me and began to stroke his back. As I did so I could feel his cock against my stomach. I knew he would cum soon so with our mouths still locked together I pushed his body away very slightly and gripped his cock. Soon the whole of his body tightened up and his cock began to stretch that extra fraction of an inch as white cum spurted all over my hand and body. Shawn fell back on the bed. I immediately got astride him and started to rub my own cock as hard as I could until his face was covered with my cum. We looked at each other for a while before he whispered for the second time that evening 'Thanks Mike' We remained together on the bed for about ten minutes, after which I got up, put my boxers on, and went into the kitchen. I got a pizza out of the freezer and put it in the oven. The meal was almost ready when Shawn suddenly appeared in the doorway. He had nothing on and his beautiful cock was dangling down in front of him. A towel was wrapped round his neck. ' Can I stay the night Mike?' was all he said. I nodded and he came and sat down at the table. After the meal we sent into the sitting room and I put a video on. It was one of those science fiction films that I usually like but it was obvious that neither of us was really interested and before long I glanced in his direction and said 'You haven't got what you came for have you, yet?' He grinned and said ' Can I have it now?' Shawn flung himself on the bed and I flung myself on top of him. We were soon in another passionate kiss but as much as I loved having his tongue in my mouth what I wanted now was his cock. I disentangled myself from his embrace and gradually let my tongue slither down his body, stopping every so often to allow my lips to do some of the work. Shawn began to moan softly and his cock started to bob up and down waiting for my mouth to arrive. When it did he let out a loud ' Ooooooooooooh' The prefect at school had taught me how to play with a guy's cock so as to give the maximum pleasure and I was a good student. Now I made good use of all the skills I'd learnt. Shawn had spread his legs out to give me easy access so I gripped hold of his balls and enveloped his cock with my mouth. This really got him going and I could hear a low moaning sound, which was almost continuous. Whenever I glanced sideways to look at his face I saw a young boy in ecstasy, enjoying the first blowjob of his life. In some ways it is difficult to believe this was the first time Shawn had had sex with anyone. He knew how to respond almost instinctively. He thrust his hips up and then relaxed in such a way as to give both of us the maximum pleasure. The point at which he reached a climax I shall never forget. He slightly raised his hips and yelled out almost uncontrollably 'Aaaah...aaaaah.............aaaaaaaaaaaaaaaaaah' as his cum pumped into my mouth. He then subsided onto the bed looked at me and for the third time that evening murmured 'Thanks Mike' We drifted into sleep and I was woken in the early hours of the morning with Shawn's hand on my cock. As our eyes met he said quietly ' I haven't done much for you yet Mike' ' Would you like to try something different then? ' I whispered as an almost overpowering desire to fuck him came over me. Shawn knew what I had in mind because he replied ' Not just yet Mike but can I give your a suck?' He didn't wait for a reply but leant over and took my cock in his mouth. I didn't last long but that didn't matter. The feeling I got when Shawn's tongue licked the head of my cock just sent me wild. The following morning we woke at eight and Shawn said that he had better get home but could he come back again that afternoon at about five. I agreed. I had two lessons Sunday afternoon and I just about managed to put Shawn out of my mind while I was teaching. On the way home though I couldn't stop thinking about what I wanted to do with him. I am a very careful person and always practise safe sex. Not only that when I get back from holiday I go round to see a doctor friend of mine who arranges for me to have a test just in case something has gone wrong. The results of my most recent test had come back during the week. I knew that I was in the clear. I knew that it would safe for me to fuck Shawn bareback. I arrived back at my flat just before five. Shawn was already there carrying some books. I looked at them with a quizzical look. He laughed. ' I told my mum that I was coming round to see you to get some help. ' Then he started to laugh. 'She doesn't know what kind of help though. ' I didn't want to force Shawn into doing anything he didn't want to so I'd decided not to mention anything about fucking him but as soon as we got inside the flat Shawn put his books on the table and turned to me with a smile all over his face ' You know what you said last night about something new?' I just looked at him ' Well I know you really want to fuck me so that'll be cool' I didn't know what to say. My body began to shake with uncontrollable excitement . I grabbed hold of Shawn and almost dragged him into the bedroom and in a wild frenzy we began to undress each other. By the time we were both naked we'd calmed down a little and Shawn lay back on the bed, lifted is knees and waited for me as I got on top of him. I took things very slowly and very gently - I didn't want to hurt him. When my cock finally got completely inside I couldn't believe it. I was fucking Shawn, the hottest boy I'd seen for years, bareback. I lent forward and gave him a gentle kiss as I slowly very slowly began to move my cock in and out of his hole. Gradually I began to quicken the pace and Shawn began to moan. He then gripped hold of me and pulled me close to him and I could feel the tip of his cock against my body That was the best sex I think I've ever had. When the explosion came it was almost simultaneous and we both lost control completely. I fell back onto the bed and we lay in each other arms for about ten minutes. The silence wasn't broken until Shawn said, in almost a whisper, that he thought he ought to be going. He then added 'Can I have a shower first I don't want my mum to smell stale cum' We both roared with laughter. Shawn had collected up the books he had brought with him and was ready to go. We agreed that he would come round the following Friday at about eight and if he wanted to he could stay the night. Then just as I was about to let him out he turned to me, looked me straight in the eye and said ' I want to ask you a question Mike but I don't want an answer now. I don't want you to even hint at what you might say. Tell me next Friday' He then paused ' Can I come and live with you?' With that he turned round opened the front door, ran up the steps and was gone. That is my problem. In a moment the front door bell will ring and Shawn will be standing in front of me hoping for an answer. My heart tells me one thing, my head another and I don't know what to do.