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Boys Halfway House – Incident #192 – When It Hurts – Dig Deeper – Will

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?