Date: Tue, 22 Jun 2021 00:16:21 +0000 From: Mark Subject: Parental supervision 5 The next morning David came around at nine o'clock -- he always turned up exactly at the appointed hour because he lived so close. I sort of expected him to still be a bit shell shocked from the previous evening, but in fact the opposite was the case. He had a new assurance, which I guessed had come from having his first sexual encounter and getting through it. Yes, he'd spent most of the time gagging and then choked on the load that followed, but he'd done it and now he knew he could handle it. So whereas I'd thought that maybe we take a break from sex on that visit, he ended up sucking me twice. The first time was much like the night before, but instead of just sliding my cock into his mouth until I hit his gag reflex, a couple of times I held the head of my cock against the back of his throat and gently pumped. That felt sublime -- like a ten second massage on the head of my cock -- and I even thought I felt his throat open up to me a little bit. Once again it didn't take me long to finish and although he was less overwhelmed, once again he didn't manage to swallow much of my load. He showed just how much he'd learned from his first time, though, when he remembered to milk my cock to get the last of the cum out when he was sucking me clean. I felt like that kind of attention to detail showed that he really was enjoying our encounters. He managed to swallow most of my load when he sucked me again an hour later. It was probably because as it was my second load of the morning it was smaller than anything he'd had to deal with before, but nevertheless he was proud of his effort. There was still cum on his chin where a bit had leaked out, but I didn't have to wipe him down before we went to the shower, so it was real progress. I saw him four more times during the week and he sucked me every time. We experimented with positions and different degrees of force. Pushing harder didn't seem to get me any deeper, but we found a position which got me into the very top of his throat. He'd lie on his side on the bed with his head on a pillow and tilted back to make his throat a straight line. Then I'd stand on the ground in front of him and lean forward to get my cock in his mouth and either apply steady pressure or slide in and out, hitting his throat each time. When I got into the top of his throat he couldn't handle it for very long, but it felt incredible and it was a starting point. We also watched deep throating videos every day. There was one with a boy who was younger than David who absolutely inhaled a cock that was about the same size as mine. I could see David really studying it to figure out how he could emulate the boy. "He's probably had heaps of practice," I said, "and you're just starting out." On the Friday night I added a video of anal to the mix. It wasn't that I felt any great rush to fuck David, but I was aware that getting as deep in him as I wanted would probably take quite a long time. It made sense to start now so that he was progressing in his anal capacity and his oral capacity at the same time. Plus, I wasn't going to progress him anally in the most efficient way possible, so more time would be better. "I want to fuck you tomorrow," I said as the boy getting fucked in the video grimaced and moaned -- of course I'd chosen a video which would prepare David for a fairly rough fuck. "Would you like to try that?" "Uh huh," he said, still playing with himself although looking me in the eye now. "So there's two types of anal sex, dry and with lube," I said, which was about as true as saying there are two types of driving, drunk and sober. "I'd like to try it dry with you, because it will make your little hole feel even tighter. The tighter you are, the better it feels for me, even though it will hurt for you. And you'll never feel tighter than you do now, because you're an anal virgin and you're only going to get older." "Ok." He had more idea of his capacity for discomfort now and he didn't seem scared, as he had when I'd outlined how I wanted to use his throat less than a week before. We played with each other's cocks for a bit and then I pulled his head down onto my cock while I watched the video. It wasn't a particularly rewarding position for either of us -- I didn't need porn to get off when I had perfection right in front of me and the angles made it uncomfortable for him without exposing any of the good bits of his throat. That wasn't such a bad thing, though, as it extended the length of the session. After blowing in barely more than a minute our first time, I was gradually building up a bit more endurance. My cock had spent five minutes in David's throat the night before and it had provided a much greater test of his limits. Nevertheless after a couple of minutes of chair oral, we moved to the bedroom where I could use him more efficiently and our first week of oral came to a predictably sticky end. "Are you excited about anal?" I asked as soon as David walked in the front door at three o'clock the next day. I hadn't even finished the question when his father also walked through the door. There was a moment of electric awkwardness. "Oh, sorry. Hi Jason. Sorry, we're trying something new today," I said to break the pause. "I just came to invite you on a hike tomorrow. We could do it early, before it gets hot. Then we could be back in time for you two to hang out here for an hour before David comes home for lunch." "That sounds great." "Ok, I'll leave you two to it." Then he looked at David, said, "Have fun, buddy!" and left. David walked toward me giggling and as soon as we could no longer hear Jason's feet on the front stair he said, "Maybe don't shout about how much you want to fuck me when I'm basically still on the front balcony. I thought I was supposed to be the indiscreet one." "But I really, really want to fuck you," I said. "Do you?" he asked, pretending to be shy. "Yeah. Let me show you," I said and kissed him, pushing him backwards until he was against the wall. Then I lifted him up and held him against the wall with my weight while I ground my cock against his thighs and kissed him forcefully. I stopped kissing him for a moment and pulled my head back so I could see his face. We looked deep into each others eyes for a couple of moments before I carried him to the bedroom and placed him on the bed. He stripped off instantly and I did the same. He moved forward to start sucking my cock, but I put a hand on his shoulder and turned my cock away. "I want to do you bone dry," I said, and wiped the precum from my cock as further evidence of that. "Lie down on your back with your legs wide and held up." Despite that weird instruction, he knew what I wanted and in a moment he was lying there with his asshole exposed below his perfect balls and straining little cock. I really wanted to stick my tongue inside his asshole, but I had a plan and getting his hole slick with spit was definitely not part of it. "Down the bed a bit," I said as I climbed onto the bed. "That's right." Then I wiped off the precum that had accumulated just in the time it took me to get onto the bed and placed the head of my cock against his hole. Then I looked into his eyes and started to apply pressure with my cock. David grimaced a bit, but I didn't get anywhere. I adjusted my position and held my cock in my hand so I could get extra pressure and tried again. "Relax and push out like you're doing a poo," I instructed as I increased the force I was using. I could see his hole relax and the head of my cock sink in a tiny bit, but no real progress was made other than a very sex moan from David. I didn't want to give up that little bit of progress, so I held my cock there and started pumping, hoping to get a little bit deeper on each rhythmic thrust. David moaned or gasped each time, but I was pushing against his asshole with each stab rather than spreading it. We tried a few different positions -- on his stomach with his hips on a cushion, on his side with one leg held up, on all fours with his back arched -- but none got me any further inside him. I had to concede that my dream of a bone dry first time for David wasn't going to happen. "I don't think I'm going to get it inside you without splitting you in two," I said. "And even then that would just mean your insides were outside of you, so I still wouldn't be inside you." "What?" he said, laughing. "Like if you split a papaya in two, all its insides would then be on the outside, so it would have no insides." "Did you put your penis in a papaya?" he asked, feigning confusion. I laughed and lay down next to him in the bed, then kissed him. I felt so much love for him, his generosity and commitment to me, that I felt desire surge into my cock. I grabbed him and rolled onto my back so that he was now lying on top of me. Then I slid him down me until his butt was in reach of my cock, wiped myself dry with the sheet and pushed inside him. Or at least I tried to. Once again all I got were some lovely moans and frustrated desire. I tried putting my hands on his hips and then when I felt his hole relax I used as much force as I dared to enter him. I felt like there was a tiny bit of progress but then the pain made him tighten up as he tried to pull his body away from my thrust. In this position I could stop him from moving, so I retained whatever progress I'd made, but as he groaned in discomfort from me just holding steady, I realised that I was never going to get inside him. So I gave up and rolled over again so that he was next to me in bed. "It looks like it's not going to happen, baby," I said. "Why don't you just shove it in?" "Because that's not what we're about, baby. That's not how you feel about oral, is it? You don't feel like I'm just shoving it into your throat?" "No, but it's what happens in some of those videos you show me." "That's true. But you can watch a video -- or even read or write a story -- involving things you'd never do in real life," I said, and winked for some reason. "Why did you just look over there and wink as if there was somebody there?" "Never mind. The point is we do rough stuff, but you still enjoy it. I don't want to cause you pain just for my own pleasure." We kissed for a minute or two. I played with his cock and balls, which I did pretty much any time we were in bed together, without really noticing I was doing it. "So I guess we have four options. We can try to warm you up a bit for a dry fuck -- I could finger you and rim you and then have another go. Or I could lube up and we could try again. Or I could warm you up with lube and then fuck you with lube, which would be the easiest for you. Or we can try again another time. Which do you prefer?" "I don't mind, Uncle Rob. Whatever you want." "Ok. a) I love the new nickname and b) I don't know what I want. My first choice didn't work out, so I want you to decide." David thought about it for a little bit. "I still like the idea of your cock being the first thing that ever gets stuck up my butt. You know I have never put anything up there because I wanted it to be special the first time." "Ok, so let's try again with lube. Do you want to do it now or try another time?" "Now, Uncle Rob." "Ok, then roll over so you're facing away from me." I reached over to the drawer next to the bed and took out a pump pack of lube. I pulled David close to me, with his butt in my crotch and his head just below mine. "Lift your knees up toward your chest." I lubed up his hole and the head of my cock and started pushing into him. I felt him relax onto me and I pushed harder, very slowly sliding in. Once I'd got the head of my cock in, I started pumping very slowly. David moaned as I thrust in, finishing with a kind of whimper as my cock pressed against the sphincter inside him. After a little bit I got so turned on by the whimper that I just pushed my cock against the sphincter, slightly increasing and decreasing the pressure as I tried to find a way in. "Just relax," I said, and then increased the amount of force. He was really moaning now and I knew I was right at the limit of what he could take. I could feel him tensing up with the discomfort, so I eased off a bit and it must have given him the extra bit of relaxation he required. The second sphincter opened up and I got most of the head of my cock in there. It hadn't released entirely, and he grunted when I tried to push deeper. Still, I had almost two inches of penetration. I slowly withdrew a bit and pushed in again, then I withdrew further and pushed in again. Soon, I was pulling my cock entirely out of his ass and then penetrating his hole and his sphincter again on each thrust. He groaned every time each one gave way, and this plus the wonderful feeling of tightness soon brought me to a climax. I shot my load inside him and then pulled his top shoulder toward me so I could kiss him. "You're not a virgin any more, sweetie," I said after our first round of kissing. He smiled. I realise now that this has mostly been a story about firsts -- our first kiss, our first time masturbating together, his first time sucking cock, his first time being fucked. Over time there were fewer firsts, and I don't think I should try to document every time we had sex. There were some other significant firsts, though. There was the first time my balls touched his chin when he was deep throating me. That was a special occasion which I marked by throat fucking him until I came in his mouth, taking a five minute break and doing the same again. There was the first time he came, which happened during a long, deep fuck and I fed it to him and kept going until I finished. There was the first time I pissed in his mouth, which was possibly the wildest sex we ever had. I sat him down in the bathtub and pissed all over him. He swallowed as much as he could and I was so turned on by his dripping wet face and body and the taste of piss in his mouth that I lifted him up so his back was against the tiled wall behind the bath and fucked him and kissed him like mad until we both came. There was the first time he suggested something new. It was choking and after that one time I was relieved to find that he found it as scary as I did and never wanted to do it again. There was the first time I fucked him and it was his arse cheeks that stopped me going any deeper, not how much he could handle. That really showed how any first also represented an ending. It meant that if he lay on his stomach and put his hips on a pillow, I could just pound away without worrying if I was getting too deep or being too rough. But it also meant an end to his capacity to please me by taking me as deep as he could handle, and an end to my capacity to show my love by not exceeding his limits -- because I could no longer exceed them. But while some things have changed, we're still very much in love. He's just turned 18 and soon I'll be turning my life upside down to follow him to college. If that sounds like a crazy idea, it's still less crazy than his plan to go to college locally so he can still be near me. It will probably do me good to get out of this rundown rental that I've been living in for far too long. Either David will never fall out of love with me or he will finally grow up and move on with his life and I'll be left behind as a proud Uncle Rob. It's a win-win really, as long as he ends up happy.