I show up at the corner where we agreed to meet at about 12:30. I'm pretty nervous, but also incredibly aroused, I can feel my crotch tingling with excitement. Since he'd sent me a picture of himself, I knew what he looked like, and could see as I walked up that he was already there. He was in his mid 50s, about 5'10", in good shape. I walked up and caught his eye. "Bill?" I asked? "You must be Brett?" he said smiling. I nodded and smiled back. "Well, I'm really glad to meet you" he said as he looked me up and down. I'm in my early 30s, 5'8", 170. "Are you up for this still?" he asked. "Yes, absolutely" I answered. We'd been communicating online for about a month now, trying to find time to get together for an encounter, but had never had any luck. Finally, we decided to go to a cheap hotel in NYC and have our fun there. Bill led the way, it was only down the block. We ducked in the front door, quickly paid for the room, and got on the elevator. As soon as the elevator door closed, Bill leaned over and pulled me in to him for a big hug, and whispered in my ear how hot I was, and how excited he was. He pushed his crotch into mine, and I could feel our growing erections pressing together. It felt great!
Once we got to the 3rd floor, we quickly got into the room we rented. Bill again took the lead, which was all part of the fantasy for me, so I was thrilled. We started making out, our tongues exploring one another, while his hands ran up and down my body. I put my hands on his ass and starting caressing him, while his hands began to explore my rock hard cock. He very quickly pulled my shirt and pants off, and I did the same for him. In almost no time at all we were naked and making out again, this time with our naked bodies pressed up against one another. I couldn't believe that this was finally happening, I was naked and making out with this hot older man, feeling his cock pressed against mine. I was so aroused, I didn't know how long I'd be able to hold myself off from cumming!
After a few minutes of making out and grinding our cocks and fondling one another, Bill pulled us down onto the bed, and asked me if I'd suck his cock. It'd been awhile, but I was happy to try. He sat on the edge of the bed, so I dropped to my knees and took his cock into my mouth. Trying to remember what I liked, I sucked and slurped, went up and down, used my tongue, and tried to get as much of him as I could into my mouth. I was really getting into it, it was such a turn on. I mean, I had this 55 year old man's dick in my mouth. It was so hot. Bill was really into it as well, calling me a "good little cocksucker," telling me to "suck it, lick it" and grabbing my head to guide my motion. Eventually he eased me up, telling me that he was going to explode if I didn't stop, and he wasn't ready for that yet. As I stood up he pulled me in to him, and took my cock into his mouth in one big gulp. He'd obviously done this before, he was amazing. He took me all the way in, and fondled my balls and ass at the same time. He stopped for a minute, continuing to stroke my cock with his hand, and leaned down and opened up a jar of KY Jelly that he pulled out of his bag.
"Will you let me fuck you?" he asked.
"Yes" I said. I was so turned on, that I'd have said yes to anything.
"Oh good, I want to plow that sweet ass of yours so badly. Come here." He pulled me in again and began sucking my cock again, while his hands began to lube up my tight ass. He pushed a finger in and began to explore my hole, up and down, up and down, while continuing to blow me. I told him I couldn't take it anymore, that I was going to cum. He nodded and kept sucking, which I took as a sign that it was ok. A few seconds later I exploded, it was one of the most intense orgasms I'd ever had in my life. Bill took all of my cum, and then licked my balls and cock clean.
Then he stood up and told me to get on the bed on my stomach, and to put my ass up in the air. He massaged his cock, and slowly but surely pushed himself into my tight ass. It hurt, but at the same time it felt so good. I'd wanted this for so long. He was very gentle, teasing his way in, pushing slowly, withdrawing a bit, pushing in a little bit more. At the same time his hand reached around and started playing with my cock, which, surprising to me, was coming back to life again. Eventually he got himself in, and began pumping his cock into my ass, pounding me. He would speed up, slow down, speed up, slow down. After a few minutes I felt him give one final thrust, then felt hot cum fill my hole. I'm not sure how it happened, but something about it got me aroused again, and with Bill stroking me, I had a small second orgasm a minute or so after he was done! We collapsed together onto the bed, where we lay and rested for a few minutes. Then, we showered, and I headed back to work, and Bill back home. We'd do this again, that was for sure!