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Trailer Trash 20 Year Old
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Some Guys Never Learn
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He left our care a year or so ago with some promise, but within a week he was in trouble and back on house arrest. After a year of having to remain inside with no one else around except his grandmother, he begged to be shifted once again to our care. We can't say we were too surprised, because some guys much prefer the occasional ass drilling to the loving nurture of their next of kin. What a world we live in.

When I found out that he had returned, I wanted to set the pace for his new stay. After all, he sucks a pretty good dick. His hole, though, still needs a lot of work. It is so damn tight! Getting through his sphincter takes a hard cock and a lot of patience. After a year away, and not in an institution, I was pretty sure that he had tightened back up to practically virgin territory, but in fact he actually felt tighter than he used to be! After slobbing on my cock for a few, and some careful fingering, I thought his ass might be ready. It took a while to ease it in, but damn if it wasn't a rough go. Finally he was getting fucked proper, but the way he was grasping onto the bed sheets was an indicator of how much he disliked it. It did feel quite good, though, and his ass was still nice and grab-able. Overall a very satisfying fuck. I liked the was he worked a cock with his mouth too much, though, so instead of dropping my load, I told him to finish me off with a blowjob. It didn't take him long to make my load explode into his pretty little mouth. Unlike fucking, giving good head is one thing you never forget. It's kind of like riding a bicycle. Only in his case, a bicycle he picked up in prison. Damn that felt good, too. Some guys never learn, but it's good that they also don't forget certain skills along the way.
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Dumbass's Pristine Hole Defiled
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The residents at the House think they are so smart, but in reality, they are just a bunch of dumbasses. There's a good reason for every rule, and if you let just one small infraction slide, the House Managers immediately begin losing control. Thus, something as simple as wrapping papers can be indicative of a huge problem, and the perp must be dealt with accordingly. No one rolls their own tobacco anymore, especially some high school drop out who can't keep a job for more than three days.

This guy in particular - I had been waiting for him to fuck up, because he has an awesome bubble butt. In spite of his complete laziness when it comes to meaningful work, he manages to hit the gym quite often, and it shows. But having a chin strap and looking like a Gladiator extra doesn't pay the bills, nor the Halfway House rent. Even worse, it pisses all the Managers off that this guy can work on his body but not the more troubling personal issues that cloud his judgement every day.

From having chatted with him, I was assuming his butt was virgin ground, and boy was I correct. What surprised me was how good of a blowjob he gives. Damn! Some guys must just be born with this skill innately. I let him linger with my cock in his mouth for some time, and alternated between him working it and me skull-fucking him. When we told him to roll over, exposing his fine ass, I was already extremely happy that this fuck up was in our House. When I spread his muscled ass cheeks to take a close inspection, I was in for a great surprise: unlike a lot of guys who lift, his hole looked perfect. Pink, soft, inviting. I lube up my finger and slowly slid it down his fuck canal to get a measure of how tight this guy was. I swear that his sphincter could have cut off the circulation to my fingertips.

I wanted to fuck him good, so we decided the best way to loosen him up would be some dildo play first. I worked in the toy, and after a few I had him work it while he simultaneously worked on my dick. After several minutes, once we decided he was ready (if anyone like him actually can be ready), I slathered my dick with lube and began working my way in. It was still tight. It's as if his asshole was as strong as his legs! I managed, however, and thankfully he didn't make much of a fuss. By the time I had him rolled over and was going hard on him, he seemed to be getting the hang of it. I dropped a massive load of jizz onto that freshly defiled hole, then used my cock to deposit it deep inside him. That pristine hole got defiled, and he probably won't be breaking the rules again for some time now.
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He Plays The Hand He's Dealt
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I only went into his room because one of the other House Managers told me that he gave good head. He'd been in trouble so many times, it's not as if I really needed an excuse anyway. He was reading a book, which frankly, surprised me. Good for him. All kinds of good habits can be acquired at the House, as well as certain useful skills.

At any rate, I started rubbing on him, he didn't bother flinching or acting like he was upset about being molested like that. When I pulled out my dick, he grabbed it diligently. And when I finally gave him a light push down on his knees, he took my cock in his hand, and then smoothly worked it over with his mouth. The guy's god nice lips and a great tongue, so my buddy wasn't lying when he described how silky his blowjobs are. I could have just busted a nut down his throat and gone about the rest of my day. However, being in the room alone with him, and with him already half undressed, I figured that I might as well fuck him.

I told him to remove his shorts, and it's at that point that he realized this wasn't ending with his mouth full of sperm. Now, in addition to describing his great cocksucking, the other Manager told me he wasn't that easy to fuck. Maybe it's because he is straight and was a virgin at the time? Maybe he's just extra tight? Who knows, but I like a challenge, so I stepped up and did it. With his legs in the air, I took care to put extra lube on my dick. It was tight as first, but it didn't stay tight for long. It only took a minute or two before I had his limber legs crossed and I was slam-fucking his little twenty year old butthole. Damn, it felt good! In fact, the longer I fucked him the more I sensed that he might be liking it. Or at least not hating it. I stopped for a second and gave his willy a tug. He popped a boner instantly! So of course I stuck my dick back in him. I jerked him off as I thrusted, and then when I got close, I told him to try and cum. With a minute his ass tensed up around my dick, and he shot an impressive load. Go figure. Knowing this guy and his predilections, I don't think he's anything but straight. However, he has definitely learned to play the hand he's dealt. And he's been dealt the role of a cock slurping cum dump. At least for now.
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Bareback Cum Infliction
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Recidivism is high among these guys, which is why it's important that they learn their lesson thoroughly before they can be given a clean bill and sent on their way. The House Managers try as hard as they can to instill an internal sense of moral order in these guys' brains. It's hard since the IQ has been slowly eaten away by bad habits. We know most of them are going to stay with us for however many months, get back into the real world, and fuck it all up within two weeks. Such is life, but nonetheless the House Managers tirelessly carry on as best they can with their instruction and admonition. This resident in particular has been a thorn in the side of everyone in the House, and he really is on his last straw. He's cute and all, and his ass feels amazing. That said, there's a new teenage delinquent every week, so his beautiful pink hole isn't that special. In a final attempt at saving him from incarceration, a few of the House Managers decided to take it up one more notch.

After barging into his room for (yet another) shakedown, it wasn't too difficult to find some contraband. This guy's a real idiot. Well, before he knew it he was naked and down on his knees. By now he's gotten really good at slobbering knobs. That will definitely be a skill he can use in jail. His innocent face, with those baby blue eyes, immediately makes him cell bitch material. It's doubtful, however, that he will be able to get by with his oral skills alone. Why? Because his hole feels so fucking fantastic.

Unlike most of these losers in the House, he can actually ride a cock. Really, really well. Every time he rides any of us House Managers it's all we can do to keep from busting prematurely. But our trusty manager kept his calm in order to keep going in this instance. Doggie was next, followed by several other positions. All the while, he was being spat upon and choked out like a little rag doll. This Manager finished him off in pile driver, though. As he was upside down on the floor, his little boy hole was getting pummeled as he was getting yelled at. There's nothing like a teen looking up at you saying "Yes, sir." while his colon is getting cleaned out. It's definitely one of those moments that keeps us all going.

When we were done with his ass, we made him take a huge load of jizz into his mouth, and then made him gargle the cum for a good while before he was told to swallow it all. This resident is definitely in the top ten total cum dumpsters we've ever had at the House. It'll be a shame to see him go if he fucks up one more time.
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