I'm always amazed when I meet a teen who is a parolee. I can only imagine the trouble this guy Karl must have gotten into in order to have been arrested, convicted, and served his time, all before his 20th birthday. At any rate, he either became accustomed to getting fucked in the pen, or the life experience taught him that there's no such thing as bad way of making money. I have to say that I'm afraid Karl might have fallen back into some of his old habits, so after he and I initially talked, it only took him a few weeks to come around. And then he showed up on my doorstep. Now, I always get excited about new guys, but I especially get a kick out of the reluctant ones. They are typically only reluctant that first time, but I really get off on their guilt, and it makes that moment where I dump a load up their asses even more special. We began, though, with some chit chat, and then moved on to getting undressed. I can't say that he was the best cock sucker ever, but he tried his best, and gave it a go for quite a while. By the end I was definitely enjoying his mouth. But, as per usual, I enjoyed his ass even more. He has a great butt, and I relished shoving my face inbetween his cheeks and tongueing his hole. He seemed to like it, too. So much so, that when I rolled him onto his back and kept rimming him, that daddy tongue was making his toes curl. I knew then and there that he was going to be a good fuck. I started doggie, and let me tell you, he was tighter than I thought he would be. However, I perservered, and before long I was pounding him good. As I was on top of him, I asked him to call me daddy and to make some noise for me, and he did a great job. It turned me on, just because it was him doing it. What a great whore. After the from-behind action, he rode my cock for a while and then rolled onto his side. I was about ready to give him my load, so I picked up the pace. Before long I had deposited a good amount of fresh sperm into his backside. I sent him on his way dripping, just the was I like to send out the teens. I was wondering if it reminded him of prison. I also checked to make sure all of my stuff was still in the house, I thought he might have sticky fingers.