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Spoiling An Untouched Boyhole
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There aren't a lot of residents as disliked as this one. He is sullen, anti-social, and frankly, a little strange. He mostly spends his time alone, and has a fuck-all attitude about everything and everyone. As long as a guy like him sticks with the program, no one much cares. You meet a lot of unsavory people in a program like ours. But even residents with a fairly good track record of staying out of trouble will falter. All of us House Managers were looking forward to that day, too. Not in the least because this teen had a nice cute butt that we all were hoping to smash. We got our chance when the dude dipped out in the middle of the night and tried to sneak back in unnoticed.

Me and our new junior House Manager decided to give him the full treatment. We marched into his room and woke him out of bed. He had one of those fucking annoying smirks on his face, like we couldn't do anything to him. That really got us going, and before too long that smirk was wiped off of his face completely. When he began sucking one of our cocks, you could already see in his face that he was planning on how to get the hell out of there. His mouth was soft and warm, though, and eventually we both dipped our cocks in it. He was sucking one of us while jerking the other, looking up at us almost as if he were a little lost. Well, I'm sure he was, since he doubtful had been in a situation like this before. The gears in his little brain were definitely working overtime.

We instructed him to lay on his back and lift his legs. He had a nice boyhole, with a small tuft of hair surrounding it. It definitely looks just as untouched as it really was. But not for long. We lubed him up and began the task of taking his anal virginity. His hole was tight. It didn't really loosed up too much, either, but it pulsated as he got fucked, and it felt great. After a good spitroasting there was nothing left to do except keep pounding the fuck outta him. He deserved it, and he knew it.

Since he seemed to like cock sucking even less than he liked getting his cunt torn open, we ended his recovery session with two loads of jizz right in his mouth and all over his sullen face. One of us came a good minute or two before the other, and it was actually better this way, because we got to see him squirm as he just let the cum linger in his mouth and stream down his cheeks. Then he got the other load. Chalk up another straight virgin ass taken!
Opening Up 18 Year Old Virgin Ass
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This down on his luck 18 year old did not know what he was in for, but he is so desperate that he let us do whatever we wanted to him. He has nowhere to go but the halfway house or jail, so he just took it - in the mouth and up the butt. After he is groped, stripped, and his mouth is spat in for some dick-sucking lubrication, we finger and play with his asshole to prime it up. His hole is so tight it takes a while for my buddy to get his fat cock in there, and the whole time we are taunting him. I smeared lipstick on his mouth and made him suck my dick like a cock-sucking whore, and while my friend was fucking him he wrote -SLUT- across his chest. After sufficiently loosening his hole so that it was gaping, me and my buddy shoot huge loads on his pathetic face.
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Str8 19 Year Old Bareback Torment
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This guy was new to the Halfway House. He had gotten busted while about to cross the state line into Florida. Apparently on the way from Atlanta to Tampa with a shipment, he reached out of the window to try to grab a box of peaches from the truck next to them and the driver immediately got pulled over. Well, after a suspended sentence and probation he ended up with us. We decided to go into the room (he shares with a guy on probation) early in the morning and let him know how his stay was gonna be. He sucks the manager's cock, and I get his ass loosened up with a big thick dildo. After his ass is ready, my buddy fucks him hard, deep and raw while he sucks my dick. Overall, he was great for a first-timer. My friend nuts on his asshole, then the resident cums on himself, and I jizz right into his mouth. Then I tell him to go back to sleep. Ha!
When It Hurts, Dig Deeper
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The most annoying residents are the "nice" ones. I don't mean the guys who are actually polite, well-mannered, and thoughtful. I'm talking about the guys who have a veneer of nicety in order to slack off and break the rules with impunity. or example, this fuckwad always agrees and smiles at just about everything, but then he turns around and does either nothing (when you want him to) or the wrong thing. He was raised to somehow think that if your attitude doesn't correspond to your crime, you won't get caught or punished. Unfortunately for this pipsqueak, his time has come. He's not living with family anymore playing video games. This is the real world, with real consequences.

In this resident's case, the consequences are getting your little virgin butthole completely blown out. We didn't start with the de-flowering, however. After I confronted him with his contraband, I had him go right down onto his knees. It didn't take me ten seconds to realize that this boy knows his was around a cock. Hot damn, his mouth feels good! And he has some skills rarely seen at the House, orally speaking. I could have just kicked back and let him blow me until I nutted in his mouth, and I almost did nut, too. But given the seriousness of his offense, and also the fact he has a pert little teenage butt, I definitely wanted to make sure I gave his cunt a whirl.

Given that he is orally blessed, I was almost shocked at how tight this guy was. Definitely hasn't had anything in there bigger than a little finger. So, needless to say, it was a struggle at first to get his hole capable of accepting a thick dick. Patience is a virtue of all good House Managers, though, and eventually his fuckhole waved the white flag and let me in. From then on, I'm not going to say it was slam-fucking, but it was a decent feeling, and the looks of shock and awe on his youngish looking face got me off. When he spread his cheeks to reveal a proper gape, I knew that I had done my part, and so then I continued to fuck him until I was ready to release my load on his ass. He was wincing, so I'm sure it hurt a little bit, but every time it hurts, you gotta dig just a little bit deeper, right?
Str8 Dude and Two House Managers
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It was his first time in a halfway house, and he had a pretty despondent look on his face. After being read the rules, he was cavity searched. During the search, one of the house managers starts stroking his cock. He got hard, so we figured he must like it. Soon he was on his knees with a huge cock in his mouth and a fat cock up his ass. After he gets fucked by both house managers, they each get off, and then, as he is holding back tears, he nuts all over himself. His load was big, so despite the girlfriend story, he is definitely already enjoying his recovery.
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