Giving Him The Help He Needs

Giving Him The Help He Needs

This resident spent much of his late teenage years scraping together money for tats and other vices. It’s the other vices that landed him in prison, but based on his attitude about it, he must have had it relatively easy. Not everyone comes out of the pen with such a cheerful attitude about it. What he is not cheerful about, however, is his court-ordered stay with us. As a term of his early release, we are stuck with him for a short while, as he holds down a job and supposedly re-adjusts to life on the outside. His outside gig certainly shows – he’s got a deep tan that only outdoor work can give a guy. It looks really nice on his small, fit body, and especially accentuates his perky little bubble butt. Most guys who are trying to walk the straight and narrow gain a few pounds, but due to his persistence, he has kept in shape. So, overall, not a bad kid. His biggest problem, really, is that he is a magnet for being taken advantage of. His sister and girlfriend pretty much control his life via the phone calls he is allowed to receive, and it makes me kinda sad that he lets them needle him so much. Like a lot of other cons, he pretty much told me as much when we first met him. Guys like him usually blurt out their entire sob story within the first half hour of meeting them.

Needless to say, I was pretty bored with hearing about his personal life, but I definitely wanted to see what was beneath those gym shorts. Once he was finished filling out the paperwork on day one, I let him know exactly how his life at the House was going to be. He takes off his shirt to show me his numerous tats, and then I help myself to getting a nice glimpse of his ass. When I ask him if he got fucked in prison, he tells me “No one is ever gonna fuck me!” Well, I guess he hadn’t planned on it, but he sure was incorrect. After guiding his hand to my cock, he almost starts crying. This must be his modus operandi when confronted with unpleasant realities. No worries, though, because we are used to his type, and it doesn’t bother any of the Managers. He gave me a good cock slobbering, and I also face fucked him. But what I was after was that pert little hole of his. To add insult to injury, I have him lube up my cock and stick it in himself.

You know what they say, the smaller the build, the better they take dick. The rule definitely applies to this guy. It wasn’t a few minutes in before it was smooth sailing, and I made sure to fuck him good. On his back and in doggie, I was really enjoying myself. When I had him sit on my cock, though, he started riding it like a pro – surprising me a little bit. I almost came, but I didn’t want to because I wanted him to lick his ass juice off of my cock first. He hops off and takes my dick in his hand, just jerking it for a minute while he stares at it. Finally, he wraps his lips around it and starts sucking. I love degrading the former prisoners the most – these guys are the bottom of the barrel civilization-wise, and they deserve every second of the humiliation. I roll him over and drop a huge nut right into his mouth. After I do, I ask him if he thinks he’ll do well at the Halfway House. He says that he needs the help. That’s for damn sure!