This is the first time, of many, that I met and had a sexual encounter with someone I met on Craig's List. If you don't know they have a personal's site to meet people. Just be careful in your exploits. Depending on what people think I will write more of my sexual encounters.
I was incredibly horny. The kind horny where you just squirm around in your pants because you have to cum, which is what I ended up doing at my own hand. It only satisfied me briefly; it worked for maybe an hour before I had the itch again. I needed cock and I had to have it tonight.
I had already known about Craig's List through my late night porn adventures searching for material to look at. I had even chatted with a few guys occasionally so I felt okay with posting my own personal add so I could meet someone. It was late though, nearly 1:00 AM, and I wasn't sure who or how many men I would attract.
"I am searching for a chubby/bear type top. I am strictly a bottom boy. I enjoy sucking, swallowing (mmmmmmmmm), receiving anal, doing blowjob/fuck videos, being tied up, and having sex with multiple men at the same time. I would be the center of a gang bang type sex romp, for example. I do prefer much older men (60 and up) but I am not limited to that age group. I do make exceptions for men who are younger, but generally only if you meet my body type requirements. If you are hairy it is a plus. I prefer bareback only. I am clean. Please be so also. I am up for doing kinky new things."
I posted it and let it sit for a half an hour or so. I checked my email and was surprised at the amount of responses I had received; it was somewhere around a dozen. I made my final choice of a man based on proximity. It's not always the best choice but I was not about to drive an hour or more to meet some of these guys, especially the ones who blatantly disregarded my stats that I preferred. A 20 year old muscle bound stud is far from what I requested.
I contacted the guy whom I chose through his email. I asked what he was looking for. He stated he wanted "...to get sucked off and cum down my throat. Plus, I want to bend you over and just fuck that ass for quite a while. You up for it?" he wrote. I was. So, he gave directions to me how to get there, it was about 30 minutes.
I was extremely nervous. But I was extremely horny too and that trumped everything at the moment. I remember the butterflies got so bad as I got to his street. It was an awkward location but it seemed safe enough. As safe as it could be, I guess. I was meeting a man I had never spoke to and only exchanged a couple of emails with. The knock on the door got no immediate response so as I was about to knock again, the door opened. "Max?" I said (that was his name), hi, I'm Mike."
"No." The guy at the door said. "I am his roommate Fred," he told me as Max walked up behind Fred. Fred left as Max approached and sat on the couch to continue watching TV. At this point I will say I was feeling awkward, especially since I hadn't realized Max was black. I had never been with a black man before. He met all my preferences. He was 56, balding, and very chubby. I certainly have nothing against being with a black man so I continued in as Max welcomed me.
The place was really weird. It was basically a studio type of apartment or a refurbished old business, or something, that was set up to be an apartment now. It was wide open with no separate rooms. There were just some room dividers, if you could call them that, giving some separation to the two beds I saw in the place. There might as well not have been anything dividing the room up because I knew the beds were on the other side of the dividers because I could pretty much see through them! At any rate, I walked in at sat down on the couch with Fred and Max.
I will spare the boring, awkward details because we chatted for like 5 minutes then Max got up and said, "Come on, you came to suck my dick and not Talk all night." I didn't know what to say so I got up hesitantly and followed Max to his section of the apartment. I literally stared through the room divider and could plainly see Fred watching TV. Max new that I was nervous and could tell I was thinking I wanted privacy. I asked him if there was somewhere else we could do this. He said, "You want sex. I want sex. You said in your add that you fuck multiple guys at a time. What the shit does it matter if he can see us?" I asked if I would be fucking Fred too tonight? Max said would it really matter? I replied that it wouldn't, I suppose, but I would have liked to know what was going on. He agreed and said, "I guarantee you won't give a shit what is going on when my dick is in your ass. The more cock in you the better."
From that point, he just took off his clothes and told me to do the same. We were naked quickly. He walked over to me as I sat on the bed and said, "Well?" I knew what he meant and I immediately began to suck his dick. It was smaller than I imagined. I had the idea in my head that it would be huge because he was black. It was normal I guess. Probably 6 inches, but very thick. I had never really had one that thick in my mouth. If felt weird to suck at first until I got used to it. I sucked, nibbled, and licked his balls for him for about 5 minutes as he stood there. Then he started to shove it in my mouth and hold it there until I choked. He put in all the way in and told me to get the balls in too. He would force the shaft and balls in my mouth and hold them there for several seconds at a time. He did that a lot. I think he like that I choked on his cock.
Shortly thereafter all of that, we were both on the bed and he immediately had me get on all fours. I saw him get out the lube and he got busy. He lubed up and then put a generous helping in and around my ass. He inserted a finger full of lube in my hole to get some inside me. Then, he was in me in an instant and did not waste any time thrusting back and forth. The thickness of his cock was amazing and the pressure it created was like nothing I had ever felt. After about a minute or so of him doing me I noticed his roommate, Fred, walking toward us. I was positioned on all fours (knees and elbows) and my head facing the TV area, so I could clearly see him walking toward us massaging his package.
I would let out small grunts and as Max fucked harder, I grunted louder. As Fred got to the bed where Max was violating my ass Max asked his roommate, "Are you going to get in on this?" I could see Fred nod yes and get undressed. At that point I was sweating a lot and starting to moan loudly because Max had picked up the pace and was pushing very hard and deep. I was getting to my usual tolerance of being ass fucked. Most guys don't last too long. I felt it might be different with Max. I was right. I ended up being fucked for what seemed like 10 minutes or more as I took in his cock. I didn't know how much longer I could take it. Somewhere during that stretch (it is kind of cloudy to me now), Fred had put his cock in my mouth and been fucking my face. He was big. He was not chubby by any means and actually very well toned. He was hairy however. I don't think it really mattered at that point what he looked like. I know that I was being fucked from both ends by two black me, hard. Every time I gagged and spit out Fred's cock he quickly shoved it back in, barely giving me a chance to catch my breath and Max would in turn seemingly fuck harder.
Finally, I felt Max jerk awkwardly and he started to grunt hard, and he just absolutely nearly fucked me off of the bed to the point where I was completely deep throating Fred's cock and gagging nonstop. "Awwwerrrrgghhhhh," he said several times as he came inside my ass. At least I think that is what I heard over my own gagging and choking. I just really remember he pulled out finally so I could pull my mouth back and catch a breath. I felt his load dripping out of my ass and I know he was watching it slowly pour out of my hole because I remember him working his finger in and out of my butt. I am pretty sure he just watched me suck Fred as he leaned back against the wall to relax. I know he didn't get out of bed.
Within a few minutes of Max cumming, Fred came down my throat. His was not nearly as dramatic. He just left his cock in my mouth. The only warning he gave that he was cumming was when he said "Make sure you swallow it all!" as he basically stopped thrusting and let me suck, swallow and gulp him down. He was very quiet through most everything. I don't even think he said a word to me as he left and went back on the couch to watch TV. I had just sucked and swallowed a guy that I had barely said two words to in my life, yet I was fine with it. I felt satisfied.
I turned around when it was done and asked Max where the bathroom was. He was just sitting there out of breath massaging his cock, still. He pointed the way and I immediately walked over and sat on the toilet (this may be gross but we all know it to be true if you have been ass fucked and didn't prepare properly, which I hadn't). I had to go so bad I am surprised I didn't crap while he was fucking me. It felt so good to go. I finished, cleaned myself up with toilet paper, getting as much of the lube off as possible.
I walked out of the bathroom to them watching TV on the couch together naked. I got dressed and walked over to them. It was pretty simple. They, well Max anyway, said thanks basically and let's do it again sometime. I said alright and that was it. I never did talk to them again. It wasn't fantastic but it certainly satisfied my craving for cock. I realized on the way home I was getting hard as I thought about the experience and then it clicked, I didn't get to cum! I got home and just fantasized about what had just occurred while I jerked off. I came in like a minute. I felt so stupid as I laid there on the bed with cum on my belly. I just got fucked from both ends and ended up back in bed jerking myself off. I was back to where I started.
This experience led to many, many other sex rendezvous with many different people. My experience only got better and I started to do much more kinky and dirty things. Through Craigslist I have been tied up all night, gang banged, taught how to drink from the tap (Drink pee directly from a guys dick. Yes, it was gross at first but when you get so horny you do anything, at least I do. I actually started to like it.), made several fuck and blowjob videos for lots of old men, etc. I will see how responses to this are and maybe I will tell of more sex encounters.