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Prepping His Ass For Prison
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Smirking Only Makes It Worse
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The worst type of residents are the ones who grew up with helicopter parents and then went astray. Their entire lives they have gotten into trouble only to be rescued. As such, there is zero sense of responsibility or accountability. When push comes to shove, they think that they can slide by with a pass. Unfortunately, at some point in their young lives there comes a reckoning. With this dipshit, the bill is due here at the Halfway House. While the other residents, who are working fervently to get themselves the hell out of here, go to work in order to pay rent and become normal citizens, this asshole wakes up feeling tired and just goes back to sleep. Then, he just sits in his room doing who know what.

We make the decision to put him in his place using our own unique methods, and it turned out to be quite the late morning fuck fest. Even as we were admonishing him to mend his ways, this jerk kept smirking, as if his situation were a joke. Well, the joke was on him. Before long, he was throat deep in cock. He sure can deep throat, too. So at least he is useful for something. The real prize, however, is that ass of his. He works out, so his bubble butt - well, you could bounce a quarter off of it. It looks even better getting pounded. The weekday House Manager lubed his fingers up, slapped his cunt a few times, and then went to town.

Our precious resident got fucked good, too. After getting dicked down on his back, he rode dick like a pro. Now, if he can do such a good job here in his room, why the hell can't he work at a real job? Maybe he is just meant to be a whore. If so, maybe he will have found a profession that can keep some money in his pocket. Judging from the way he takes cock, it is something he should think about. But in the meantime, he's just going to get fucked in vain until he seriously adjusts his attitude.
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Delinquent's First Creampie
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This teen got into a lot of trouble in order to be with us, and within a day of his residency, we all knew just why. He's a stellar example of a chaotic and disheveled life. It's a wonder he can dress himself, it seems. Unfortunately, this led to a lot of self-medication, and generally speaking this doesn't work well when cars and 19 year olds are involved. That said, he's one of the sexiest motherfuckers we've had the chance to rehabilitate, so each of his missteps will definitely bring about just rewards.

After humiliating him and showing this wanna be alpha male that he is just another member of the pack, he was introduced to my cock. I've never seen someone look so sad and scared at the same time. He knew what was coming his way. He took it, though, and he took it well. I was railing his asshole like it was the last party before Prohibition, and although he sure made some interesting grimaces and noises, he didn't beg me to stop. That cum dripping out of his ass at the end of the session was almost like a sacrament of his beginning on a new journey of recovery. Let's hope he makes the most of it.
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A Pretty Boy's Descent
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Contraband in the House is a huge no-no. But finding this shit in the personal effects of a conceited, bratty little snot like this new resident just makes our blood boil. Two of us confronted him right away and then proceeded to make sure he'd get with the program immediately.

Aside from some county jail time, this guy has never been institutionalized, and it shows. He's messy, he talks back, and he thinks his "pretty boy" looks will help him out of any situation. Problem is, when you're in a House full of dudes, being the pretty boy usually just means you're the one getting fucked in the ass. Just in case he didn't understand that concept, we demonstrated for him. It was important to me personally, and my buddy, that this low life was quickly disabused of the notion of skating through his time here. We mean business about helping people get better and become productive members of society.

We basically threw everything but the kitchen sink at the guy, and he kept up, which actually was quite impressive. He was going back and forth on our dicks with his mouth, and then with his ass. He didn't even slow down when he got drenched in his own stash. He might have had a cock tear or two dripping down his cheek. I even half believed him when he said that he wanted to get better. I wrote on his chest while I was thrusting my cock into him, and he didn't even look down to see what I wrote. This one is a cocky son of a bitch for sure. But at the end of the day, we House Managers were satisfied and this guy was lying on the floor in a pool of cum that had just dripped out of his ass, his face affixed to the floor with my foot. I wonder if it occurred to him that he might not be on top of the totem pole at this place? Well, even so, he is going to have a hard road ahead of him. But at least he won't be sneaking bottles around. And since he likes shots, I gave him a shot of my jizz. He almost didn't keep it down, but he managed. He's OK at blowjobs but his ass feels amazing, so we're going to be keeping a close watch on him from this point onward. If it's a descent he wants, then a descent he shall have.
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Teenage Bully Gets What's Due
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Difficult residents call for difficult measures. We were sure, just having known this guy for a few weeks, that he was a troublemaker. Not only that, but it seemed that he completely lacked a moral compass. Along with this deficiency comes the resulting issues of lack or respect for authority, and flouting of the rules. In addition to being a slob, we were certain that he was breaking some of the most important rules. When we confronted him, he laughed, playing the whole thing off. Well, a quick trip to the bathroom to get his specimen into the test cup was all we needed to proceed.

When he failed (which was really never in doubt), his smile turned around, but only because it suddenly dawned on him what was coming. This teenage bully was about to get what was coming to him - and good. Having just turned 18 a few months ago, he was used to getting a pass. Sure, he had been in and out of trouble for years, but the worst that was ever handed to him was a slap on the wrist. We changed that.

Not gonna lie, his dick sucking wasn't that great, but just knowing that my dick was probably the first one he ever had in his mouth made me throb even harder. He grimaced a lot, which frankly I was thinking was all part of his act. He seems to over-react to anything if it has to do with his own discomfort. We were yelling at him, though, and keeping him off guard. It was a good rehabilitation session. Hell, even when I told him to spread his cheeks, and he finally realized the extent of what was about to happen, it just seemed so right that he was getting what was due.

He was a difficult virgin to crack open, that's for sure. And he howled like a little wolf cub. But after fucking his sweet 18 year old hole in doggie, mish, and from behind, his moans turned into whimpers. Once I was to the point that I could feel his ass just swelling around my cock, I knew that he had about had enough. I dumped my load on his hole and shoved it deep inside him. Even then, he had a terrified expression on his face. But I just slapped him around a few times more for good measure. I think he is starting to get the message... finally.
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