Date: Sun, 17 Mar 2019 11:19:45 +0000 From: Andrew Passey Subject: School Days Part 9(young friends) I said this story would jump around a bit as sometimes and this one of those times. This one is spread over a year and started early in my fourth year. My life was good, no bullying. A fair bit of sex, still at it like rabbits with Rob. I'd got to do a bit of oral with my girlfriend but she wanted to wait till we were 16 for proper sex which was a while away. Dan had a new girlfriend who was a couple of years older and was getting lots of sex although we still caught up for it every now and again, and Chris and I still sneaked off on scout camps and residential for a bit of fun. Still there was always time for more sex! So I was out for a run in my football kit and bumped into Oliver in the street near his house soon after starting. He was wearing a t shirt and shorts that were too small for him and he frankly looked ridiculous. He invited me back to his house as he had a new computer game. His dad had just sold one of his businesses and they were swimming in cash. We'd got quite friendly and he was a nice guy. We got talking about girls and sex while we played and he started saying he thought he'd never get a girlfriend, and that even if he did he wouldn't know what to do etc. He said he "thought" was still a virgin (so I guess he had a memory of his 16th birthday but wasn't totally sure if it was true) and bemoaned being 17 and no chance of it in the near future. He said I seemed successful with girls and everyone loved me, and he was jealous. I told him it was simple and there were basic things you could do, and more complicated things but it was all a learning process. He thought about that and asked if I'd teach him, "I'll pay you, since Dad sold the business I've got shitloads of cash". I thought about it, Oliver was nice if naive and in desperate need of a makeover and getting laid. I also saw an opportunity to get out of doing my paper round and make enough money I'd almost be all set to go backpacking when I finished school. I said ok and that if he really wanted to get with girls there were a few different topics I'd need to teach him. "Ok Olly, I'm going to brutally honest. You're overweight. You need to lose weight. I'll help you do that, you can go running with me a couple of times a week and I'll help you with other exercises. It won't be easy but you'll slim up in time. We could do with losing the glasses, try contact lenses. Secondly, you need to learn a lot about sex. Not the mechanics of it which I'm sure you know but everything else. It's not just about your pleasure, it's about the other person as well. The more you do it with someone the more you get that and the better you get at giving and taking pleasure. Thirdly, you need to work on your self confidence, girls love a self confident boy. As you get better at the first two the third one should come. I like you Olly but this is a big project, it's going to take a term or two, maybe all school year. I'm going to need a fair bit of cash to turn you around as I'll have to drop my paper round." I then plucked a ridiculous figure of £1200 out of my head which totally shocked me when he instantly agreed. "Ok, that's fine, here's £100, I can get you the rest of the money this weekend. One thing though, the sex. You say the more I do it the better I'll get. But the whole point is no one will sleep with me so how do we cover off that." Here goes nothing I thought. "You need to learn in a non threatening environment about sex with a good friend you trust. You need to learn how to do it properly so both of you enjoy it. You need to learn how to sometimes do things you don't want to so that the the other person does so they get pleasure. You need to know how to last long enough to satisfy someone, how to use your dick properly, how to use your mouth and fingers properly. How to enjoy it when you aren't getting much pleasure or aren't necessarily up for it. How to take instruction.. You have a lot to learn and it's a fuck load of work for me. In an ideal world you would learn this with a girl, but unfortunately I'm not a girl, I'm a boy. I can teach you all this but it has to be between us with no one else knowing, I'm risking a lot here to help you out" Olly looked at me in amazement, "So you'll play the role of the girl? You'd do that for me?!" . "Of course, you're a good friend" I said and also thought "you're paying me a shitload of money.!". I wrote a list of things he needed to buy and gave it to him. "So er...can we start the first lesson now? Maybe lesson one is to suck this so I know how it feels?" said Olly and pulled his shorts down to show he was hard. I'd forgotten he had such a large dick although it didn't look too much bigger harder than soft albeit he'd probably slightly grown since I last saw him naked. "I guess so. Ok lesson one, cleanliness. Come with me". We walked to bathroom and I told him to always make sure his cock was clean." You never know when someone might want to suck it and most people are put off by the stink of piss. " I showed him how to wash himself properly and I did the same to me. "You washing yourself as well?" He said. "Well remember what I said about learning. After I've sucked you you are going to suck me". "Er, I'm not sure, sounds pretty gay and I'm not gay." He said. Realising I was probably going to have to be a bit hard on him over the coming weeks I had a bit of a go at him. "Fucking hell Olly, neither am I. I'm going to suck you and teach you all sorts over the coming months. But for you to learn I'll be doing it back to you as well even if you aren't too happy about it. Sometimes you might have to lick some girl or fuck her when you don't want to really. It's part of sex. If you don't want to learn then fine, keep the money. But if I'm teaching you, I'm in charge. Ok?" I said slightly annoyed. "Er yes , sorry" he said. "yes what?, "Er, yes Andy? Yes sir". " Better"I said and stroked his cock slightly. "Ok let's go into your bedroom and I'll see if I can handle this big boy in my mouth". He blushed at that and we went into his room. He sat in the edge of the bed and I got between his legs. "Ok as I do it, tell me if you enjoy it, give praise, stroke my hair, tell me what you like, and what you don't like, people love that and it will make it better for both of you". I took him in my hand and started licking his piss hole and around the head causing him to moan before taking him all the way in. I enjoyed having his big dick in my mouth and he stroked my hair and made appreciative comments. I kept sucking and he blew in my mouth with a "fuck!" and then a "thanks I really fucking needed that". I was hard and told him to get on his knees and suck me. He was reluctant but did as he was told, he asked me to tell him when I was going to cum and put my dick in his mouth. I gave him instructions and he did a pretty good job, I neglected to tell him I was about to cum and flooded his mouth which he choked on slightly, I held his head to my cock until he'd swallowed it all. 'fucking hell, you were suppose to tell me when you were going to cum". I said he'd be doing it a lot over the coming months so to get used to it and also that it was one of those things you have to get used to. If a girl squirts in your mouth you can't just spit it out, swallow and just take it as part of the bigger picture. We cleaned off and I said I wanted to finish my run and he should go with me. He faffed around but found some suitable attire and trainers and off we went. I kept a slow pace for him and we ran for half an hour or so with a couple of stops for him to catch his breath. I sped up slightly and as we ran through the woods, Olly was huffing and puffing and out of breath. I said follow me and ran off the path to a big tree. I pulled my pants down and had a piss, shaking it clean. He also had a piss on the the tree next to me. I then told him to come over to me. "This lesson is to show why you should keep your dick clean always, but also sometimes you may end up in a situation where the cleanliness of the person you are with is not quite as good as you'd like, but it's either that or nothing so you have to go along with it. So come and suck me off". He looked like he was going to say no but I gave him a stern look and did as he was told and I shot in his mouth and made him clean me up. i could see he was hard and said "you like like you enjoyed that" and he blushed and nodded slightly. I then said he deserved a reward and wanked him off, he shot over my hand and over the tree. We cleaned up and ran back to his house, I told him to get the stuff we needed when he got the money on Saturday and I arranged to meet him on Sunday at his house. He thought his parents would be in but i said we could go for a run to get some time together. He started to harden at the thought of that and I headed off to run home... Sunday came around after a sex fuelled night with Rob on the Friday, I went round to Olly's house and he was in a state of excitement. His parents were getting him contact lenses if his eyes could handle them. He showed me the lube he'd bought. "Probably the most embarrassing moment of my life, am sure the guy in Boots winked at me" he said. His parents were popping out to the shops and we said we were going to play a game and then go for a run. They were shocked and Olly said that I was going to get him fit and help him lose some weight. He went up to his room and his dad called me over and slipped £40 in my hand and said thanks. This was proving a very lucrative exercise! I ran upstairs and Olly was already naked on the bed with a massive hard on and the lube in his hand. "So, is it time for me to lose my virginity and learn the lesson on how to fuck you?" he said with a grin. "Not quite" I said and his face fell slightly. Foreplay is important as in anticipation. You'll enjoy it more if you have to wait. I am going to be fucking you first, then you can fuck me, and then maybe again if there's time." 'Erm...really?!" He said obviously reluctant. "Yes, that's the way it's going to work. I'll take your cherry then you'll fuck me. If you stay hard as I fuck you then hopefully that means you'll get used to it in future, but don't worry" I said pulling my pants down, "your monster cock will hurt me more than this will hurt you." I'd grown a fair bit in the preceding months but nothing like Olly size. He said ok and I got him on all fours on the bed and lubed him up. "Normally i'd wank you at the same time and I expect you to do that to me but I want you to be extra hard for what follows" I slipped inside him and he gasped a bit with pain "ouch that hurts". I told him it would pass but also reminded him it's going to hurt me more when he goes in me. "good point Andy, Ok I'm ready" he said and I started to fuck him using all my skills! He started to moan with pleasure, "Do you like that Olly" I asked, "mmmph...yes.i fucking do" he said back. "Do you want me... to stop? I said between thrusts, .."Fuck no".. "Do you want me to keep doing it to you". he grunted "fuck yeah". I could feel my orgasm approaching and put my hands on his balls and pulled them down slightly as i did causing him to moan in greater pleasure and I came in him with a big cry. 'Enjoy that, looks like you did" I said grinning at his hard and dripping cock. He grinned back and said "Fucking did, not a bad lesson although I might need a few more tries it before I learn" He then leaned over and said he was ready. He suddenly look nervous and I told him not to be. I lubed him up gently and also my hole. I got on all fours and told his to get behind me and line up his cock head with my hole. "Now very gently push forward, once you slip the head in wait a moment so I can get used to it." I said. He did as he was told, I winced in pain briefly as it went in but told him it was ok and to keep going till he was all the way in. He started to fuck me like a Duracell bunny and I told him to stop and gave him some tips. I also told him to wank me as he did. He did and got a lot better at it. After he came he burst into tears and thanked me and said he was grateful I was helping him so much. Over the course of the year I taught him everything I knew, he lost loads of weight and started to not look quite so unattractive. His Dad took a shine to me and kept slipping me money every now and again, and also offered me summer work when I was old enough at his company which sounded great. At the end of the year Olly was much slimmer, much better at sex and much more attractive, still no looker though. He did finally get a girlfriend the next year, not a good looking one but probably within his league! We stayed friends and while we didn't actually fuck again I did hang out there a fair bit and did work for his dad a few years later in my University holidays...