Date: Wed, 31 Aug 2016 20:13:48 +0000 From: Andy Brown <andybrown2000@outlook.com> Subject: Tutoring Dylan - chapter 3 Tutoring Dylan - chapter 3 Disclaimer: The following is a work of fiction which features sexual activity between a teenage boy and a grown man. If you do not want to read such a story, or it is illegal for you to do so because of your age or where you live, then I recommend you go read something else instead. The characters in this story do in fact exist. However, none of the things in this story have ever happened. Also, clearly to protect the characters, I have changed their names and some facts about their lives. This story is property of the author; please do not post it elsewhere without the author's permission. Please support Nifty with a financial donation - whatever you can afford - so that this archive of stories can remain free and available. Just go to http://donate.nifty.org/ Thanks to all who've sent feedback so far, it really is a huge encouragement! *** From the end of chapter 2: "No harm done," Sandra said, giving her son's hair a tousle. "We're going to go out for a bit now to give you two a bit of time to talk about things. We'll take Imogen and Tommy with us so they don't interrupt you." And with that, the rest of the family headed down to the local pub, leaving me alone with Dylan. *** It felt strange sitting there with Dylan. I hadn't seen the boy for nearly two years and now here I was agreeing to teach him all there was to know about gay sex by showing him how it is all done. And the weirdest thing of all was just how much his parents had told me about him coming out, and the discussions they'd had about finding him someone to tutor him. I didn't quite know where to start. but thankfully he did. "Andy, can I just say thank you again for agreeing to this. It really means a lot." As he spoke I noticed for the first time in the evening that his voice had begun to change. It wasn't deep yet but the pitch of it was certainly a little lower than when he was in my class. "Yeah I gathered that by the bear hug you gave me," I replied. "Oh sorry about that," he said. "I hope I didn't hurt you." "No not at all," I said. "But I do have some questions for you about this whole tutoring thing." "Okay. Shoot." "Well first," I began, "your dad mentioned something about how there's an embarrassing story to do with how they found out you were gay. Care to tell me?" "Do I have to?" he asked, beginning to blush. "Yup," I replied, enjoying seeing him a bit flustered. "Otherwise I might change my mind about the tutoring." I had no intention of doing that, but I was dying to hear this story. "Fine," he sighed. "It was a Saturday morning a couple of weeks after the Easter holidays. Mum and dad had gone out shopping for a few hours, so they said, and Imogen had decided to take Tommy to play in the park. So I had the house all to myself. Well, what's a gay teenage boy to do? I was laid on my bed watching porn on my iPad with my earphones in. I was naked, obviously, and well..." he paused and blushed a little more, "having a wank. I hadn't heard my parents come back from their shopping trip. My mum opened the door and walked into my room to see me shooting my load all over my stomach whilst two guys were fucking on my iPad." "What did she do then?" I asked, doing my best to suppress a giggle. "You're enjoying this aren't you?" I nodded. "Well she let out a loud gasp, which caused me to turn around and see she was there. I nearly shit myself and grabbed a t-shirt off the floor to try and cover myself up with. Then she apologised for disturbing me, promised to knock in future and put a new can of deodorant she'd bought me on my desk before she walked out of the room, closing the door behind her." "Good grief, that's hilarious." "No it wasn't. A couple of minutes later dad knocked on my door and told me they wanted to have a chat with me downstairs. By that time I'd already cleaned myself up and pulled on some clothes so I trudged behind after him, scared to death of what they were going to say. But they were both pretty cool to be honest. They asked me if I was gay or bi or just experimenting, and I told them I was only attracted to guys. Then they promised to always knock in future and reminded me to make sure my door was closed whenever I wanted to watch porn or masturbate. Jeez, I nearly died of embarrassment at that one! They then asked me all sorts of questions about whether I'd done anything with another boy yet. I told them I hadn't but that I really wanted to." "Thanks Dylan," I said. "I'm glad your parents were so accepting. But the one thing I still can't get my head around is how come you want me to do this with you. Surely there must be some other guys at your school who are gay?" "Well, yeah, there probably are. But guys my age are complicated. After I'd come out to my parents I decided to find someone my age to mess around with. There's a boy in my history class, Luke, and he's cute and I thought he was gay too. We got on fairly well and I invited him for a sleepover. I thought that would be the best way of doing stuff with him. Things seemed to be going well. Mum let us eat our pizza in my room, we'd played some Playstation games, watched some youtube videos, the usual stuff, and we were getting on really well. It was getting late so I suggested we get into bed - we were sharing my double bed and he didn't seem to mind that. We both stripped down to our boxers and I got to check him out. I put some porn on my iPad and we watched it together - I'd gone with two guys and a girl to be on the safe side. It was obvious we were both hard and Luke sort of surprised me when he suggested we wank off together. I jumped at the chance and really enjoyed watching him as he stroked his dick. And then I must have misjudged things because I reached out and put my fingers round his dick. He just about jumped out of his skin and started shouting at me calling me queer and faggot and stuff. He pulled his clothes on and ran out of the room, bumping into my dad in the corridor and telling him he wanted to be taken home. I was mortified, particularly when he spread it all over Facebook. I dreaded going back to school on the Monday now that nearly everyone in my year knew I was gay. I even asked mum if I could stay home, but she said I had to go in cos I'd have to face it sometime. I was shaking like a leaf when I walked into school that morning. But it was okay in the end. Most people were fine about it. And the good thing was mum and dad saw how desperate I was. They started making suggestions about who I could try things with: a gay boy in my year called Joe who I find really annoying; Max in my sister's year who's gay but really camp; and Charlie from her class who's really fit and said he'd fuck me but didn't want to snog or anything like that so he was out too." "So that's where I come in then?" "Too right. And besides, I have a bit of a thing for older men. The porn I was watching when mum caught me was a guy in his 30s with a younger guy. That's generally what I watch, and I imagine myself as the younger one, and you as the older one." I looked at him blankly. "So you mean, you actually fancy me?" I asked. "Course I do, you're hot. I've had a crush on you since I was in year 5. And year 6 was nearly torture for me, seeing you in class each day but not being able to do anything about it. What if you weren't gay? Or what if you told me you weren't interested in a young boy like me? I guessed during the year that you must be gay too with you staring at me and the other boys all the time. And when you touched me when you measured me for my Tarzan costume, I don't think my dicks ever been so hard! But when you asked me to pull my boxers down I really wanted to do it but I just couldn't. I was sort of scared that you'd see how small my dick was and laugh at me." "Of course I wouldn't!" I responded. "But I didn't have a clue you were gay. I was convinced you were straight when you asked me after the puberty lesson about blow jobs and why a woman would put a man's penis in her mouth." I laughed at the memory of it. "That was such a cool morning, listening to you talk about penises and testicles and erections gave me butterflies in my stomach. I swear I was hard all morning. Especially when Oscar asked what masturbation was and you gave him the briefest answer possible with no explanation whatsoever of how you actually do it." It was my turn to blush now. "But don't worry, I told him how to do it afterwards." I rolled my eyes at him. "To be honest I'm not really sure why I asked you about the blow jobs. I'd heard Imogen and one of her friends talk about them so I wanted to check with you that they were what I thought they were. And I hoped you'd mention that guys could do it to each other too, but you didn't, and I guess I was too nervous to ask about that in case you got mad at me." For a few minutes there was a peaceful silence as I took in all that Dylan had told me. Then I had an idea. "Well Dylan it seems to me we need to make a plan for what we're going to do at these tutoring sessions of ours. Have you got some paper and a pen handy?" "Sure, just a minute," Dylan said as he raced out of the room. He came back a minute or so later. "Here you go." "You'll be needing those not me," I told him. He looked puzzled. "What I want you to do is write a list of 20 things you want us to do together. It can be anything. Whatever it is that you want to try out sexually." Dylan gulped. "Anything?" he asked. "Yes, whatever you like. I've been around the block a few times Dylan. There's not a lot that will shock me," I said. Within a couple of minutes Dylan had filled half the page with ideas, obviously things he'd been wanting to do for quite some time. He then began to slow down. After a while he stopped, lost in thought as he chewed the end of his pen. He wrote something else down on his list and then stopped again. I noticed that his pauses were getting longer - he was obviously running out of ideas. I knew 20 might be a bit of a stretch but I wanted him to really think about what he wanted to do with me. Eventually he stopped writing and slid the piece of paper over to me. "Finished!" he announced, proudly. I looked over the list. The dozen or so things were pretty much as expected. As I got further down the list there were some things that surprised me, and one or two that shocked me a bit. Where on earth had he found out about some of these things. A couple of them I hadn't heard of until I was well into my 20s. "Very interesting Dylan. And I must say, there are a few things on this list that surprised me. Like this one here," I said, pointing at one of the things near the bottom. So where exactly did you find out about that." "The internet, duh!" Of course, I thought to myself. Where else can teenagers go to get their minds so easily corrupted? Not that I was complaining in this case. "What I'm going to do now Dylan," I told him, "is to take this list home with me and then I'm going to add ten more things to it. Because there's some nice and easy things that you've missed off. And I'm also going to add in a few things that you've probably not heard of that will challenge you and stretch you but, judging by what else is on this list, I think you'll enjoy doing them. Once I've done that, I'll then work out a plan for our get togethers. Sometimes we might do one thing off the list, other times we might do several. You'll just have to wait and see." "Sounds cool, I can't wait! So when do we get started," he asked excitedly. "Ah, you're going to have to be patient with that one." His face fell. "Your dad wants me to have an STI test," I continued, "to check that I'm not carrying any infections or diseases. But once that's done and the results come back then we can get started." Dylan then escorted me back through the hallway to the front door. Just as I was about to leave, Dylan spoke. "Andy. I want to say thanks again. This really does mean so much to me." He put his arms round my chest and hugged me again. Then he stretched on to his tiptoes and kissed me on the cheek. It was only a quick kiss but it felt like a bolt of electricity running through my cheek. "Bye Dylan. And it's my pleasure. I'm really looking forward to doing this with you," I added as I walked down the driveway and climbed into my car. *** Over the next couple of weeks I added my ten things to Dylan's list and then worked out a schedule. I figured that we could cover all 30 things in just 20 sessions if everything went as planned. I also booked myself an appointment at the sexual health clinic to have the STI check that Dylan's dad had insisted on. Whilst waiting for the results I ordered a number of items we would need including lube, condoms and a few toys of various kinds. Finally I was given the all clear by the clinic and so I phoned Sandra to let her know and arrange a date for my first session with Dylan. *** It was a Saturday morning and I was once again parked outside Dylan's house for our first session together. I still couldn't believe this was happening. It felt almost like a dream and for a number of days after our first meeting I kept alternating between a light-headed giddiness with the thought of what I was going to be able to do with Dylan, and a sense of dread that this was all some kind of elaborate joke or that I was being set up and any moment the police would ram my front door down and arrest me. But I had to trust that this wasn't a set up, that this was really happening and that Dylan's parents were okay with it. It had taken quite some time to put the schedule for our sessions in place. I knew from his reaction that Dylan was keen for some sexual action, heck he was a 13 year old boy for goodness sake. I remember how I was at that age, trying to catch glimpses of other boys as we changed after PE (and especially after swim practice), finding whatever porn I could on the internet (and often waiting ages for it to load back in the good old days of dial-up), and wanking my dick every chance I could. But I also grappled with the fact that he was still just 13, with no sexual experience. By the sounds of it the nearest he'd got had been the sleepover with Luke and then he'd only had the briefest of touches before Luke had run off. And sure he's obviously read a lot and seen a lot on the internet about this stuff - his list was proof enough of that - but did he realise what he was letting himself in for? Was he ready? So I'd made the decision that we were going to take things slowly, work our way up. I'd decided that both blow jobs and anal would have to wait for a while. We needed to start simpler. He might think he's ready to go all the way, but I knew he'd find it far more enjoyable in the long term if we kept those things under wraps for a while. And more than anything I knew we'd need to talk. Explain what we were going to do, so he would know how things worked and what to expect. Discuss how he felt after doing things. Learn about him, his life, how he's feeling. I realised that these sessions were not about me. Of course, I knew I was going to enjoy them and enjoy what I would do to Dylan and what he would do to me. But they were more about him. About him learning who he is. What he likes. What he doesn't like. It was about him learning to be a sexual being, becoming intimate with someone else for the first time. I wanted this to be special. I cared about him too much for it not to be so. I began walking up the driveway of Dylan's house. His mum had arranged for the rest of the family to be out of the way for a few hours. I was admittedly a little nervous as I walked up the path. Hoping everything would go okay, and most of all that Dylan would enjoy what I had planned for us. Before I'd even had chance to ring the doorbell the front door burst open and out popped Dylan with a smile on his face. He looked perfect, today wearing a blue and white striped polo shirt, a pair of skinny black jeans, and black and green striped socks. His hair was just as it was at the meal, short round the back, thick on top and swept slightly to the right with a bit of a curl to it. "Hi," I said, startled by his sudden appearance. "Ready for our first session." "You bet!" Dylan replied eagerly. "So what're we doing today?" "Now that would be telling. Today's session won't take too long, I don't think, but I hope you'll enjoy it." "Okay," Dylan said, sounding a little less enthusiastic. I knew that he was probably hoping we'd be re-enacting some of the stuff he'd seen in his porn videos, but I had my plan. "So, are we going up to my bedroom then?" "No not today," I replied. "Today I thought we'd go in the lounge if that's okay." "Fine, yeah." And with that we headed into the lounge. Dylan launched himself onto the sofa and I took an armchair to his left. I could see Dylan looked disappointed. "Oh," he said. "I thought you'd be sitting with me so we can do things together." "Now Dylan, before we begin, there's something I need to say. You might not like it, but you've got to trust me. I care about you, deeply. And I want you to really enjoy our sessions together. Which is why we're going to do things slowly. I know you've probably been fantasising about this first session for weeks now, and you've probably been thinking that I'll launch myself at you, we'll kiss passionately, then I'll suck you, you'll suck me, then I'll flip you over and fuck you silly. Am I right?" Dylan looked a little embarrassed and nodded. "Yeah, I suppose." "And that would be all well and good if you were 18 and had done any of this stuff before, but you're not. You're 13. And I know that sounds patronising, but it's not meant to be. Because I care about you Dylan, I really do. And I don't want to hurt you. You're not ready for some of that yet." He looked downhearted. "But you will be. In time. It'll take a few more sessions, and eventually you will be ready. We will do everything that you put on your list. But some of it needs to wait. Because if we did some of that now, it would hurt." "I don't mind!" he protested. "I can deal with pain." I loved how tough he was trying to be. "I know. And I'm sure you can. But it will hurt emotionally too. Your first time being penetrated should be special. For too many guys I know, theirs wasn't. And many years later they still regret it. I don't want you regretting anything. I don't want you to regret me. Do you understand?" "I think so," Dylan responded. He still looked a little sad. "But we will get there in the end. I do plan to fuck you, you know." He grinned at that. "But we have to take things slowly. You'll enjoy it more that way." "Okay. I suppose you know best," he sighed. "So what are we doing first?" I stood up and moved over to the window where I twisted the blinds closed. "Oh I'm not going to do anything today," I replied as I sat back down. "This morning it's all about you." He looked puzzled. "First I want you to stand up and face me." He did. "Now take your top off." He reached his right hand round his back and grabbed hold of his collar. Slowly he began to pull his top off. At first I could only glimpse his lower back being exposed but eventually his torso began to be revealed bit by bit. First his cute innie belly button and then his flat abdominal area with some slight grooves which I had no doubt would be turning into a proper six-pack before too long. As the shirt worked its way further up it revealed his burgeoning pecs, each topped with a small brown nipple. Dylan lifted his arms above his head as he pulled his shirt the rest of the way off throwing it onto the sofa. He then swept his hand through his hair to ensure it was still styled correctly, and as he did so he inadvertently gave me a glimpse of the light dusting of brown hair in his armpit. "Beautiful," I said, as I admired the view in front of me. His skin had a wonderful olive complexion and was still as smooth as when I'd last been able to admire it two years ago. "Next take off your socks." Dylan reached down with his left hand and pulled the sock on his right leg down to his ankle. Lifting his foot off the ground slightly, he then did an impressive job of pulling it right off whilst maintaining his balance. His gymnastics training was coming in handy for something, I thought to myself. He then repeated this tricky procedure with his left sock, before balling them together and throwing them over to join his shirt on the sofa. Like the rest of his body, his feet shared his olive complexion. They were a nice size and I was pleased to see he kept his toenails short and clean. The tops of his feet were as smooth as his torso and I couldn't wait to suck on his cute toes. "Trousers next," I told him. Dylan unbuckled his belt and pulled the two ends apart. He then undid the button on his jeans and unzipped his fly, allowing me to catch a glimpse of the silver waistband of his underwear with a light blue 'n K' clearly visible. Dylan grabbed the top of his jeans and slowly pushed them down his legs, struggling a bit with their tightness and they came past his knees. Once down to his ankles, he crouched down to pull them off completely and then threw them over to join the rest of his clothing. He stood back up and he was breathtaking. His legs were long and lean, olive toned like the rest of him and I could see he had just a smattering of fine dark hairs on his calves. A pair of light blue boxer briefs were doing their best to contain his straining erection which I estimated to be about four inches long, and they were emblazoned with Calvin Klein on the waistband. My dick throbbed in my own boxers; I'd been hard ever since Dylan had begun taking his shirt off. "Okay hot stuff." He blushed at this comment. "Time to go all the way. Boxers off this time." Dylan visibly gulped and cast his eyes downwards, clearly nervous about what he was about to do. Unsure about fully exposing himself to me for the first time. He then surprised me by turning around and lowering the back of his pants. Little by little his pert bottom came into view, the same olive colour as the rest of his body, it was tight, sculpted and perfectly smooth. He slid his pants down to his ankles and kicked them across the room. He then moved his hands up and around to his front, and then he turned around. There he was. Dylan. My Dylan now, I suppose. The most beautiful thing I think I had ever seen, stood before me, his clothes cast aside, with only his hands covering his most private of areas. "You won't laugh will you?" he asked, a nervous expression on his face. "Of course I won't," I replied. "You're beautiful. I could never laugh at something as beautiful as you are." His expression changed, his nervousness replaced by a steely look in his eyes. Ever so slowly he moved his hands away and placed them on his hips. "Well?" he asked. "Wow!" was all I could say. He was perfect. Absolutely perfect. His smooth erection was a little over four inches long, and standing out proudly from his body with a slight upwards curve to it. It was about the same width as my thumb with a modest amount of dark pubic hair around its base. There was a glisten of pre-cum showing at the tip of its reddish head, which was unencumbered by the foreskin that had been removed several years earlier leaving behind a rather cute though not particularly noticeable scar. His erection was a shade or two darker than the rest of his skin and it throbbed in time with his obviously quickening heartbeat. Underneath his straining dick lay his scrotum, still totally smooth but tight, containing his two grape-size balls. "Dylan, you are just incredible!" He blushed but kept his hands on his hips. "Now I want you to lay on the sofa and jerk off." Dylan looked shocked. "You what? I can't do that in front of you!" he said. "Of course you can. After all, you've done it in front of your mum!" He frowned at me. "Look, if I'm going to eventually be sucking it and let you stick it up my arse, then this shouldn't be a problem." He blushed profusely as I said this. Without replying, he walked over to the sofa and pushed his clothes off. Laying down he grabbed his throbbing erection in his soft hand. "Have you got any lube or should I grab mine from upstairs?" he asked. I pulled a tube of KY out of my pocket and threw it to him. After unscrewing the lid he squirted a few drops over the head of his dick and started the motion that seems to come so naturally to all teenage boys. Dylan had clearly spent a great deal of time on his favourite pastime. As he continued to wank, he varied his pace and his grip, and after a few minutes he picked up the courage to look up at me with those big brown eyes of his. I walked over to the sofa so I could get a better view and pulled out my phone to get a video clip of this hot action. "I'm going to shoot soon," he gasped, "shall I carry on?" "Oh yeah!" I replied. "I want to see you cum!" A large smile broke out across his face as he sped up his wanking. His breathing began to quicken and he let out several small gasps and moans. His motion turned into a blur and with a final louder gasp his hand paused and then a small arc of watery cum shot out of his dick and landed on his smooth chest. This spurt was followed by 2 more smaller spurts on his abs, before the rest of his cum oozed down his dick and onto his fingers. Dylan's head sank back into the sofa cushion behind him and his eyes closed as he regained his breath. I stopped the video on my phone. "Wow, that was so hot," Dylan sighed. "It felt so different doing it in front of someone, in front of you. It was a bit weird at first. I've only done it in front of Luke before - oh, and my mum - but as I got into it, it was like I was putting on a bit of a show for you. Trying to make you excited. Did it work?" In response I just pointed to my dick which was clearly rock hard in my jeans. "That was amazing by the way. I'll certainly be thinking about that in bed tonight." Dylan blushed again. "Are you going to wank off now too?" he asked, sounding eager. "No, not until I get home," I told him. Dylan looked downhearted again. "We'll save that fun for another day." He smiled again, obviously looking forward to when that would happen. "And I hope you don't mind that I filmed you on my phone," I added. "No. I think it's kind of hot," he replied. He paused. "Do you think I could watch it sometime?" he shyly asked. I chuckled to myself, imagining Dylan lying on his bed wanking whilst watching a video of himself wanking. "Sure thing. But let me watch it first, okay?" I said. He nodded his head in approval. "And now we best get you cleaned up. Have you got a towel or something we can use?" Dylan paused, clearly thinking. "You can go get the towel I usually use. It's in the top drawer of my desk. My bedroom's the first door on the left as you go upstairs." I walked back into the landing and up the stairs. I followed Dylan's instructions and went into his room. It was a typical teenage boy's room. Desk, wardrobe, chest of draws, some shelving on the walls with books and DVDs on them. Around the room were a number of electronic gadgets including his iPad, laptop and PlayStation. There was less on his walls than I somehow expected, just a couple of posters of his favourite bands, and some pictures of famous gymnasts and divers. His floor was remarkably tidy, though his bed was messy and his blue duvet lay in a crumpled heap. I walked over to his desk and slid his top drawer open. Inside I spotted a light green towel with a tube of KY sitting on top of it. I pulled the towel out, letting the lube fall back into the drawer. I tried unfolding the towel but discovered that part of it was stuck together. This was obviously the towel he usually used to clean up after his wanking sessions, and by the looks of it it hadn't been washed for some time. There were small stains all over it. I lifted it to my nose and sniffed. The smell was unmistakable. I breathed in again. The randy little bugger, I thought to myself, he obviously wanted me to find this and see what it is. Walking back downstairs and into the lounge I reflected on what we'd just done together. Or rather, what Dylan had just done. I felt like the luckiest person alive. Being able to watch this 13 year old beauty strip had been unbelievable. But to see him wank and then cum all over himself. I couldn't believe it. I walked back into the lounge and threw the towel at Dylan. "You dirty little sod," I said to him, laughing as I did so. Dylan caught the towel and began to mop the remnants of his jerk-off session off himself. "I thought you'd like it," he said. "Did you have a good sniff off it?" Now it was my turn to blush and Dylan giggled. He finished cleaning himself up and began to pull on his clothes. "Thanks for today Andy, it was really great. I can't wait to see what we'll be doing next time," he said to me. "My pleasure. No really, my pleasure. And I'm sure going to enjoy watching your video when I get home," I told him as we made our way into the hallway. "Now who's the dirty little sod!" he joked, throwing my words back at me. I pulled him to me and hugged him close feeling the warmth of his body. I could still smell the remnants of his cum and my dick throbbed. I was pretty sure Dylan felt it, but I'm sure he didn't mind. I let go of him, and as I did so I lowered my head and pressed my lips to his. They were soft and warm. It was like an electric shock passing between us and both of our eyes went wide from the sensation. We stood there for what seemed like an eternity with our lips just touching, savouring the moment of our first proper contact. "See you next time," I said as I pulled away from him and opened the front door. *** End of chapter 3. A little longer than I anticipated when I started writing the chapter but we finally got Dylan naked. I wonder what Andy will choose for the pair to do next time? This is my first time writing on Nifty and so any feedback would be greatly appreciated - andybrown2000@outlook.com