Nineteen, Broke, And Tight (with Hugh Deep and Clay)

When I first met Hugh I paid him to jerk off for me. This documents the second encounter I had, which proved to be much more satisfying on my end. I drove about an hour to pick him up one morning, and he was waiting for me patiently. Since it was another hour back, we had a lot of time to get to know one another, and I came to like him quite a bit. I was quite wrong about him, though, in that I thought he would be a tough nut to crack, figuratively speaking. In fact, he was very amenable to getting butt-fucked. The tough part came in actually doing just that, because this is perhaps the tightest straight teen hole I've come across in a while. All holes do stretch in time, though, so it worked out OK in the end. After some photos, we traded hand jobs. All good so far, I thought, so I took a look at his hole. It is beautiful. Pink and smooth, just like it should be. Then I shoved my cock in his mouth. He took to it well enough, and although he used some teeth, he started getting the swing of it. While he was on his stomach in between my legs, I was also admiring that butt of his. Nice and pert, for sure. I ate him out, and even then I could tell he would take longer than most to loosen up. His sphincter was fairly resistant to my tongue, even! But I did the best I could, and I enjoyed the taste of his boy cunt for several minutes before lubing up my cock and his hole. I slid my dick into him slowly, and encouraged him to breathe. Sure it wasn't as easy as some, but those tight boys are usually worth the trouble. He was staying hard, too, which both surprised and excited me. I ended up fucking him pretty good, and he literally screamed, moaned, and winced the entire time, but he kept his dick hard. I pulled out and began making out with him while he finished himself off. He later confessed that he had never kissed another guy before, but at the time it seemed like he was pretty darn comfortable with it. And he nutted while we were making out, which was hot. Sure, he was doing it for the money, but I was glad to see that he learned something and got some pleasure out of it as well. It's all about expanding your horizons at the end of the day, isn't it?