This scene was filmed last summer about 2 months after Landon Matthews turned 18. I had already filmed him in a solo, and he had also literally walked out on a shoot I scheduled because he got so nervous about gay sex. Of course, I wanted to get into his hole so bad, and it took a lot of effort. He has since that touchy start not been bashful about sucking dick or fucking dudes, but at this point in time he was nervous as hell. And I suppose he had good reason to be nervous - he is tighter than a lid on a jar of pickles. After I warmed him up and he had given my knob a nice polish, I turned my attention to his teenage hole. He liked my tongue in there, I could tell. His toes were curling up as I licked around his cunt, and when I dug in past his sphincter, he let out some audible moans. He also had a nice hard on going. But when it came time to do the deed, his asshole was a struggle. He even did some poppers, but they didn't seem to have much effect. I've left in pretty much the whole show, so if you are interested in seeing an 18 year old "straight" teenager get his virgin hole defiled, screams of anguish and all, this scene is for you. I kept at it until I could get a nice pace going, but it wasn't until after he had literally jumped off of my cock a few times that he finally just gritted his teeth and let me break him in for real. By that point he was clenching at anything he could get his hands on, and his moans were extremely loud. It wasn't until he started screaming, "Please!" that I nutted. It was a good nut, too. I imagine that so many emotions and thoughts were swirling around that redneck head of his as he lay with my jizz leaking out of his hole. But to his credit, he was thinking of the money more than the discomfort. I'm pretty sure that he hasn't let anyone else fuck him but me, and it's become sort of a regular thing. I guess baptism by breeding might just do the trick after all.