Date: Fri, 30 Dec 2016 23:15:09 +1100 From: Story Teller Subject: Jon's Family and Their Friends - Chapter 5 Jon's Family and Their Friends – Chapter 5 After that four way first session, things settled down a bit. Mark continued to fuck me and Ben, but Ben's ass got more of the attention as Ben made it pretty clear his ass wants, needs, LOTS of attention. When I got fucked, Ben always wanted to be there supervising and then grabbing Mark's dick for himself as soon as I'd come. We didn't see that much of Sam after this as he'd worked out that for all its voyeuristic potential our house had enough bottoms, but was a bit light on for tops, my best topping efforts notwithstanding. I went back to organising and going on occasional "dates", but Mark didn't bring home anyone for a while as his cock was clearly getting as much attention as it needed. When Mark did finally mention that he had arranged to hook up with a girl at her place in a couple of days Mark got all whinny and depressed. I realised then that it was time for the next stage in Ben's education as a bottom. It told Ben that if he stayed at home on Mark's date night I would make sure he had a good time. __________________________ In telling the boys that my "dates" usually involved being fucked I had not told them the full story. Yes, I was into being fucked, particularly by big cocks, but I was also into serious assplay. When Mark's date night rolled around, Ben and I had a light dinner and when we finished I asked him if he was ready. "Ready for what, exactly?" "You'll find out in good time, but I'm sure you'll enjoy it. Take your clothes off and go into the bathroom." Since I had given him the introductory course in douching, Ben had been douching before each play session and said he was getting better at cleaning himself out quickly. Now was the time for the advanced course. For this purpose I produced a flexible black douche attachment which was quite narrow, but about 18 inches in length. My bottom slut boy's eyes widened with excitement when he saw it. After he had cleaned out his rectum using the regular douche, I screwed on the long black attachment, applied a generous amount of lube and got Ben to bend over the toilet. With all the fucking and all the dildos Ben had been using, the first 8 inches went in easily, but then I had to feel around for the entrance to Ben's colon. When I found it the first few inches of the douche attachment slipped in easily and Ben gave a "hmmm" of contentment as the continuous flow of warm water was now being injected directly into his bowls. I rubbed Ben's belly gently and told him to relax his stomach muscles. After about a minute, with me continually checking how he was going, in noticed that Ben's belly had started to swell. Finally Ben grunted he couldn't take any more, so I pulled out the douche and let him release the water into the toilet. I then got him to walk around up and down the hall for a minute and then called him back into the bathroom where I gently rubbed his stomach again until Ben had to sit down on the toilet again because he had some more water to release. By my rough estimate, Ben had taken a couple of litres of water on this first try. As with anything to do with his ass, that was impressive, in fact, amazing, given he was a beginner. We repeated the process several times with me slipping the douche attachment further and further up into his colon until it was all in. Ben also seemed to be taking more water each time as his belly would swell up far beyond his usual slimness. As I gently rubbed his swollen belly, I kept getting hard thinking about how fucked up and perverted this all was. Ben seemed to be enjoying the process as his cock remained rock hard except at the point where he was getting very, very full and swollen and needed to concentrate on relaxing his stomach muscles while keeping is anus clamped shut. For the next stage of the evening's entertainment, I took Ben into my bedroom where I had set out a range of toys, all of which were either fatter or longer, or fatter AND longer, than the toys Ben had been playing with to date. Again I enjoyed Ben's eyes widen in excitement and sparkle with anticipation. "Wow Dad, where have you been keeping these?" "Well, you still don't know everything about this house and the things in it," I replied cryptically. I had previously given Ben a 12 inch black dildo which he'd been using for depth training. From among the toys I'd set out in my bedroom I selected a smooth blue Crackstuffers toy which was about 18 inches long and a bit thicker than Ben's black dildo. "Why don't we try this one first." I got Ben on his knees on the bed and rimmed Ben's pretty pink asshole lips for a few minutes and then started inserting a couple of lubed fingers. Ben shivered and squirmed in a very satisfying manner. Then I lubed up the toy and also squirted some of the cold lube up his ass. Ben was shaking with anticipation when I eventually took mercy on him and started working the toy into his ass. The first 7 or 8 inches slid in easily and then it was a case of feeling around for the entrance to Ben's colon. Ben had been working his ass with the black toy solidly for weeks now (and let's not forget Ben being fucked daily by Mark's huge cock) and so was used things going past the "second sphincter". I think Ben's bowels had straightened out and opened up a lot in that short time. It wasn't that difficult to find the entrance to the colon and soon I had worked a couple of extra inches in. "I'm really feeling that," Ben said. The blue toy was only slightly thicker than Ben's trusty black one, but was definitely a step up. Pretty soon I had 12 inches worked up inside Ben's ass, and then we were into virgin territory with Ben groaning up a storm. I didn't want to overdo it and so I just gently worked the toy back and forth, gradually going a little deeper. I think we got to a depth of about 14 inches in all. After losing his erection when I started going deeper, Ben's beautiful cock was now back at full mast and Ben was working hard it with his fist. When I saw he was getting close to cumming, I pulled his hand off his dick, slowly pulled the blue toy from his ass and told him to calm down a bit. I held up the toy to show Ben the lube high tide mark. "Oh my god! That was amazing. I want all that toy up my ass. Why did you stop?" said Ben. "Because you were about to blow and I have something else for you," I said, holding up a fat silver Square Peg silicone toy. This one, I thought would be good for width training and was significantly thicker than the bronze Square Peg toy I had given Ben after the first time I fucked him. "Uh, wow, shove it in me now. I want all of it," Ben groaned. Such a pig! (I wonder where he gets that from?) Needless to say I didn't shove it in him immediately, but covered it in plenty of J-Lube before pushing it up against his pretty pink asslips. Even with the taper at the top of the toy and the give in the soft silicone, it was a struggle to get the toy into Ben's young but expanding ass. In the end I had to get him to squat over the corner of the bed facing away from me while I held the toy in place from behind him. Ben quickly got the idea and was soon sitting down on the toy so that his whole weight was pushing the toy into his hole. Even then the toy did not go in immediately. I told Ben to take it slowly, breathe deeply and just let his ass open up and relax. Nothing much happened for a minute or two as Ben steadied his breathing and gently worked his ass back and forward over the top of the toy, and then Ben groaned as the toy slowly started to slip inside his overstretched hole. I got Ben to pause, ease off the toy a bit and continue the deep breathing. Once he had calmed down again I told him to start easing down on the toy. Once again Ben moaned as the toy started to slip inside and then suddenly, his ass was over the widest part and the remainder of the toy suddenly slipped up Ben's ass. "Fuck me dead," said Ben. "It feels so good. I've never felt so full." I was thrilled by Ben's reaction, but I could tell he was struggling a bit, so got him to lean forward so that I could slowly and gently pull on the toy. Nothing happened immediately, but I told Ben to push with his ass muscles and then it was out with a pop and a huge sigh from Ben. "That was the best, but now I feel so empty. Shove it back in Dad!" And so I did. Once again I got Ben to squat over the silver toy. It was still a bit of a struggle to get the toy in, but it definitely went in more easily this time and Ben seemed more comfortable with it filling his hole. After he'd squirmed around on the toy for a minute or two I again got him to lean forward so that I could pull the toy out. After repeating this process half a dozen times over about 20 minutes, I decided it was time for the next stage of the evening's entertainment. After pulling out the silver toy I grabbed a black solid plastic butt plug which was somewhat thinner than the silver toy. (In fact, it was my old, much loved trainer plug from many years ago.) After the silver silicone toy, the plug slipped up Ben's ass without too much difficulty. Ben was humming with contentment, so I told him to lie back on the bed and relax. I slipped into the en-suite briefly to relieve my swollen bladder. When I came back into the bedroom I brought a tray with another set of even bigger toys. Ben's eyes goggled and his cock jumped while he squirmed around on the embedded plug. "Fucking hell Dad, they're huge! I'm not sure I can take any of those," Ben said. "That's OK, as they're all for me." "What?! Shit!! Double fuck me! You're into huge toys?" Finally the penny dropped with Ben that he wasn't the only bucket bottomed slut in the house. Ben's eyes bulged when I selected a blue dragon toy, lubed it up and started working it into my ass. "Just for a warm up." I joked. "Wow, Dad. That toy is huge. You can take all of it?" "You'll find out soon enough." I quickly slid down the toy to until my asslips reached the huge bulge above the base. Then more slowly I started forcing my ass down over the bulge. I let out a solid grunt when I passed the widest point and my ass slid down over the remainder of the bulge and the base pushed up against my hole. "It's been a while since I was on this toy, but I guess it's like riding a bicycle." Another pathetic joke. Ben had climbed down from the bed and was sitting on the floor about a metre away from me with his eyes riveted on the blue toy and my ass. Now he started pulling on his cock again and looked around at the toy selection I had laid out for him earlier. He got up, pulled out the black butt plug and then grabbed its slightly fatter big brother. "Don't rush things," I told him. I should have saved my breath, as Ben pushed the bigger plug up his ass with his usually reckless enthusiasm. For the next hour we worked our way through the two sets of toys, the smaller ones for him and bigger for me. We concentrating on our asses so much that neither of us paid that much attention to our dicks. Finally, when my ass had had enough of the huge toys (though Ben still looked keen) I called a halt. I got Ben to reinsert the second smallest of the black plugs. I climbed onto the bed with Ben and got us into a 69 position and started working on his swelling cock with my mouth and throat. Ben in turn was eager to demonstrate his improving oral skills on my big cock. (He still has a way to go, but compared to his first efforts week ago he is definitely able to take my cock further down his throat with less scrapes from his teeth.) I lubed a couple of his fingers and guided them to my lose asslips, so Ben was soon exploring the folds of my ass while trying his best to get my cock down his throat. At the other end of the bed, I was working Ben's cock in and out of my throat with practised ease (if I say so myself) and gently playing with the plug up his ass. After the intensity of the full on assplay, it took us both a while to relax, recover our erections and start to build up towards orgasms. 17 year old Ben was, inevitably, the first to blow his load, which nearly drowned me; after catching me by surprise, Ben's cum spurted out of my mouth, was all over my face and the sheets and still he kept on shooting. This was too much for me – a hugely messy facial from my younger son after a long session of assplay sent me right over the top. Ben had kept his lips locked around my cock as he came and tried to swallow as much of my cum as possible, but it was the biggest load I'd blown in ages so a fair amount of cum ended up spread across his smiling exhausted face and in his fine blond hair. It was the most beautiful thing I've ever seen.