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Two Chums, Two Bums
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Two residents failed their tests, and I decided to get the job done all in one sitting. But - man! - I can't tell you how different these two are from one another. One is a blue eyed blond, who seems as innocent as apple pie (although he is anything but). The other looks like a hardened felon just out on parole. Dark hair and all inked up. They both respond to punishment differently, too. The goodie two shoes type, well he knows how to get out of potentially painful situations, and thus tends to do what you tell him, and do it well. The other, well, he just laughs and thinks everything is a joke.

I'll tell you what, though: that smile sure did get wiped off his face when I shoved my dick in his mouth. He sucked it, too, but not very eagerly. His chum, on the other hand, his mouth was like a vaccuum cleaner on my pole. Much better technique. I guess since the blondie did such a good job on the dome, I gave him a break and didn't blow out his ass too much. The other one, the idiot, I let him have it. Pretty sure it was his first time, too. That hole was so fucking tight it almost cut off the oxygen supply to my cock! I loved every second of it, though.

After I had fucked both of their holes, I didn't have trouble deciding where to drop my load. I picked the guy with the attitude, and I made sure that I let loose a massive load of cum right down his gullet. This prick better start taking his recovery seriously, or he won't be able to walk around easily anymore. So sad, both these dudes are only teens but they've already become pieces of ass. At least it's good ass.
No Walk In The Park
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Every blue moon, we receive a newly minted adult into our House from a facility for the younger delinquents. It's a mixed bag with these guys: sometimes they are already hardened to the ways of institutionalization, and sometimes they are like a young buck in a fresh green meadow. Usually they are covered in jailhouse tats, and have adopted the prison-chic clothing so loved by those school-to-prison pipeline types. This resident, however, was unlike the others. He had such an innocent look about him, you'd never guess half the shit on his rap sheet. Lucky for him, that rap sheet isn't going to become public, and thus, he has a real chance to start again from scratch.

When I called him into the bedroom and asked him to set down, you'd think he was in the principal's office. He looked worried, and like he might start crying any moment. While that was sort of endearing, I nevertheless was brusque with him while he was reading and signing the rules of the House. Although he looked innocent, I knew that he was just a used up dirty bitch like all the others, and decided to get my cock wet with him before he started causing any trouble.

I must admit, his little 18 year old lips felt nice wrapped around my dick, and he didn't seem to have much of a gag reflex. But the hottest part of the blowjob was just him staring up at me with those pretty blue eyes of his. He was desperately seeking approval, and you could tell it. I hadn't even stuck my cock in his fuck hole and I could already tell he was going to be my new favorite piece of fuck meat.

When I had him lube up my dick and stick it in himself, he slowly but gently let the head of my cock pop into his sphincter, and from that point on it was a go. He didn't need much loosening up, which made me wonder how many times he had been in this situation. His ass was so smooth and silky that it told me, "A lot of times," but the expression on his face told another story. Never in my life had I been fucking a resident who had such a dumbfounded look on his face. Who knows, maybe he thought that it all gets better once you turn 18. I hated to break it to him, but for his type it only gets worse.

To finish off, since his ass felt so damn good I had him ride me, at first facing me, and then facing away. Given the baby fat and not very muscular body, I was surprised that his legs didn't give out sooner. Sure enough, he rode that dick until I popped deep inside of him. What a people pleaser this young resident is! I bet his legs were sore the next day, though, not to mention his ass. When I smacked him good on his way out the door, his astonishment was palpable. It's nice to have a teen like this around, for sure. Even though it's no walk in the park, this job definitely has its perks!
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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.
Bareback Group Discipline
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One of the guys at the house had been getting a little too comfortable - as a matter of fact he was sort of a ring leader in getting some other residents to break some minor rules. We decided to put an end to it, and while his buddies were getting treatment a little less severe, he was getting roughly fucked completely bareback. While my buddy is fucking that guy, I am taking care of the two str8 19 year old's, but I am paying particular attention to one, primarily because he runs his mouth way too much. The best solution to that is to have it stuffed with a thick cock. He is from Georgia, and I love Georgia peaches! In pretty much every way, I make sure he sucks, slurps, and deepthroats to the point of halting a little. Yea, I let his friend have some dick too, but that one can have his own private lesson. Meanwhile, the ringleader fucked doggie, then he gets flipped over and fucked some more. The other manager's cock is by this point sliding in and out with ease, but he needs a little head again, so our prime bottom for the day gets a real ass to mouth treat, along with one of his friends. After some cock sucking, he is getting pounded again until he gets a load of cum in his ass. As for Georgia, after some great head, my buddy holds his mouth open wide and I shoot a big load onto his face and tongue. Very good stuff.
Barebacking A 19 Year Old Petty Offender
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Our 19 year old blond friend thinks he is really too cool, considering his stay with us as only a temporary vacation. Although by nature he is quiet enough and not much of a bother, he also thinks that because he seems like such a goody-two-shoes that he can break the rules when he feels like it. We here at the Halfway House, however, try to enforce a strict environment. A no-tolerance policy is just what these shitheads need if they are ever going to be useful members of society.

Having given him the speech, I decided to take it up a notch so that he wouldn't mindlessly forget where he is, or who he has to answer to for his actions. After having him strip down to his wifebeater and undies, I whip my cock out and have him start stroking it. Even with that, as he is looking up at me, I can tell he is being impertinent. I was just going to have him blow me, but he really just starts to piss me off. With that, I grab him by the hair and shove him down on his knees. He takes my cock in his mouth like without saying a word. That doesn't stop those tears from flowing down his cheek, though! As a matter of fact, it feels really good. I make sure, as I begin to face fuck him, that my dick is banging against the back of his throat as much as possible. When I move him to the bed to fuck his face some more, I notice that he has a raging boner! I guess he doesn't get touched by another human that much. I wonder what his supposed girlfriend would think about him popping wood while he has a cock in his mouth?

Once I'm done with his mouth, I go for his ass. His hole is pretty and pink, and it seems fairly loose already - which surprises me a little. I'm not sure that means he was getting fucked a lot on the outside or that is just the way his asshole is (maybe both?). Well, when I see that he is nice and loose for my dick, I take it, lube it up and shove it in raw. The first sensation was that he really is tight, and he was fighting it. I put more lube on and ease him in slowly the way I would bareback any ass virgin. I fuck him missionary, and doggie. By the time I've been going at it a few minutes, I can manage to shove it in deep, and I press the base of my dick against his insides as he lets out several deep moans of agony. Flipping him over once more, I fuck him fast until I am getting close, then I move up to his mouth and instruct him to get himself off while he is sucking me off. He cums, and then I cum right into his mouth. He gags at the displeasure of tasting cum for the first time, but he swears that he will never break the rules again. Time will tell.
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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