This is a story about finally hooking up with a guy that I'd be in touch with over the Internet for a few months. I'm Brad, an early 30's MWM who happens to have a yearning to hook up with older, mature gay men periodically. I was going through one of these phases when I started communicating with Jim, a very mature gentleman in his 60s. We exchanged emails for a few months, one time tentatively setting up a date, but then I got cold feet and backed out. Finally, a few months later, I was ready to act. We'd had a particularly erotic set of email exchanges, where we talked about our other experiences, and Jim gave me a very hot description of what I could expect when we finally got together. It was so hot we both wound up jerking off. Anyway, we set up a date, and we were on.
I snuck out of work a little early, and took the train up to his apartment. I got out front, took a deep breath, and rang the bell. Jim buzzed me in, and I took the elevator up to his floor. He opened the door as I was walking up the hall. I was definitely nervous, but also very aroused and excited. Jim was, as I'd said, in his early 60s, about my height and weight. He looked exactly like the older, dignified gentleman that I'd fantasized about hooking up with for the past few months, it was perfect!
Anyway, he made me a drink, and we sat on the couch and chatted for a few minutes. After a few minutes of small talk, he asked me if I'd like to watch some porn, maybe that would help me relax. I actually had not really seen any gay porn, but was definitely willing. So Jim selected a tape, and put it on. When he came back to the couch, he sat down much closer to me then he'd been before. The porn was definitely getting me aroused, it was a group scene, in an outdoor pool setting, so there must have been 8 or 9 different groups of men together, fucking and sucking. It was pretty hot. After a few minutes Jim began to massage my leg, slowly working his way up towards my crotch. I had a pretty obvious bulge in my pants at this point, and I could see that he did too. Finally, Jim placed his hand directly on my hard-on, and began to caress me through my jeans. He also leaned in and kissed me. I felt his tongue probe deep into my mouth, and began to kiss him back. We did this for a few minutes, pushing our tongues deeper into each others mouths, as he caressed my crotch. Stopping for a minute, Jim whispered in my ear "play with my hard cock" and placed my hand on his pants. I imitated what he was doing to me, and caressed and rubbed his hardness. Within a few more minutes, still kissing each other, Jim had managed to undo the top of my jeans, and got his hand into my pants. I felt a jolt of excitement as his hand finally grabbed my engorged tool. It didn't take long for him to have my pants and shirt off, and soon I was sitting on his couch in my boxer briefs and an undershirt, with my cock rock hard and at attention!! Jim excused himself for a minute to go into the bathroom, and shortly came back out with only a tight pair of briefs on. He stood over me, and told me to kiss his dick and suck on it a bit through his briefs, he told me he was going to take charge now. I was so aroused, and I leaned forward and did what I was told. I sucked and licked him, and then he pulled his underpants off, and his hard cock sprung into my face. I took his tool into my mouth, and tried to get as much of it into my throat as I could stand. It tasted really good, and I was really getting into it. I could tell by Jim's moans that he was enjoying it as well. Jim pulled me away when he said he felt ready to cum, pulled me to my feet, and quickly took off the rest of my clothes. We then started making out again, Jim said he loved to taste a man's mouth after a man had been sucking his cock. We kissed passionately and ground our cocks together, and were rubbing each others asses with our hands. I was so turned on, I couldn't believe that this was finally happening. Our cocks felt so good rubbing into one another, I really thought I was going to explode. Luckily we stopped before that happened, and Jim said that he thought we were ready to go upstairs. He sent me up before him, so he could massage my hot ass on the way up, he said!
Once we got upstairs, we got onto Jim's bed, and Jim quickly dropped down and took my cock into his mouth. He really got into it, I couldn't believe how good it felt, he'd obviously done this before. I told him that I couldn't hold on much longer, and he looked up and smiled, stroked my cock, and told me that didn't want me to hold on, he wanted me to blow my load in his mouth, and he wanted to swallow my sweet cum. He went back to my cock, and within a minute I looked at myself having a mind blowing orgasm, brought on my this hot older man sucking my dick. It was so intense. He took all of my spunk, and then licked my dick clean.
After lying and relaxing for a few minutes, Jim told me that he was going to introduce me to rimming. He turned me over and started to lick my asshole, and then positioned himself so that I could return the favor, and telling me to stroke his still rock hard cock at the same time. I simply could not believe how good this felt, to have my asshole caressed in this way. After a few minutes I found that my erection was returning, as Jim had been massaging me back to life while he tended to my asshole. I must have been doing a pretty good job myself because I could hear Jim moaning in pleasure, and I could feel a little bit of pre-cum on the tip of his cock. Finally, Jim stopped and pulled me around and lay me on my back, then pushed my legs up in the air. I guess the rimming had loosened up my hole a bit, because within a few minutes Jim was able to push his cock into my asshole. Now I was rock hard again, watching this man drive his cock in and out of my ass. He plowed me pretty hard, and it did hurt a bit, but it was so arousing at the same time, that I soon got lost in the thrill of it all. I closed my eyes and let myself enjoy the moment. When I opened them I could see Jim's face clenching, and then I could feel him emptying his hot cum into me. The intensity of it was overwhelming, and I began playing with myself. Jim smiled and said that he would handle that. After pulling himself out of me, and cleaning up a bit, he took me into his mouth again, and, incredibly to me, brought me to orgasm again. This time he didn't swallow, but pulled me out of his mouth at the last minute. I blew my wad all over my stomach and chest. Jim cleaned me up, and we lay together in total contentment for 15 minutes or so. I left shortly thereafter. I've not been back to visit him yet, but we still communicate via email, and I think I may wind up back there sooner or later....