Jonathon and I
I met Jonathon on a gay hook up site about 20 years ago. At the time I was in my 40s and had been getting in shape. I was a runner and went to the gym several times a week. I was lean and tight about 150 lbs.
Jonathon was older, maybe 60ish and I think he may have had a heart attack a couple years earlier. He was slightly shorter than me and heavier, not really fat but solidly built.
Once we hooked up we met at a state park and hiked out on one of the trails to chat. By the time we stopped we had already talked about top/bottom interests. He said he was versatile, but what I really wanted to be was a bottom boy for a dominant man.
When we stopped, he suggested that the one with the biggest dick should be the top. Well, I am only 6" on a good day and I figured I might just get what I wanted. I pulled out my dick, which was already hard and he gave me a knowing smile. I hope you know how to suck cock, he said as he pulled out about 8.5" of fat meat. I didn't take his dick all the way down my throat that first day, but I did taste and swallow his cum. After, he got behind me and stroked my cock as he rubbed his dick in the crack of my ass. He complimented me on how far I shot my load and I said Thank you Sir. He liked that and said I should address him like that in the future. I would also come to call him Master, but that's later in the story.
The next time, he took me to his house. He was married, as was I, but his wife worked. He took me into the den and told me he had to take care of a couple things. Although I hadn't been told, I decided to strip. When he returned I was naked on my knees facing the door with my hands behind my back and my head bowed. Ah, someone has trained you well was all he said. He walked around me, checking me out, feeling my muscles. Once he was again in front of me he wrapped his hands around my head and brought his crotch to my face. I went to move and open his pants, but was told to stay still. First he unzipped and placed my nose in his fly. As I breathed in his scent, my cock throbbed and I nuzzled his cock with my nose. Finally, he opened his pants and I was told to lick his balls as he removed his shirt. His pants soon followed and I got another taste of his cock. This time though wouldn't be just a quick suck on my knees. He had fucked his wife before she left for work so this load I would have to work for. This was also my first training on getting a big cock down my throat. He was patient and coached me along. It wasn't long before I heard him say, that's it baby, you've got it all. I looked up at him through my tears and he wiped them away with his thumbs. He fucked my throat for awhile and then pulled out. He left me and opened a condom and started to lube his dick. I was still on my knees with my hands behind my back when he knelt behind me. He rubbed against me and slowly forced me to bend forward. My hands automatically came forward to support myself. He moved them and forced my chest to the floor. Ass up boy was all he said and I answered, Yes Sir. He slowly forced his way into my ass. I felt the head pop through and there was a tremendous stab of pain. He stopped for a few moments and watched. He then started forward and stopped again. This time he told me that he enjoyed watching me suffer for him. And suffer I did, through the entry and then the fucking. I was allowed no time to adjust. Of course I was also soon enjoying myself, with my hard cock bouncing around under me. As he rode me he would pinch my nipples and occasionally stroke my dick. When he asked how I was doing and I said, Sir I'm going to cum he stopped playing with me and told me to wait.
He then rode me till he was on the verge of release and asked me again. I responded, Master permission to cum. As he started to again stroke my dick he said, Cum for me boy. I immediately shot my load with my ass clenching his cock. He let out a roar, pulled out of my ass and pealing off the condom shot his load up my back. He pushed me flat on the floor and laid on me sliding his chest in the cum on my back. We lay that way for some time until we recovered enough to move.