I had just started working in a new town and didn’t know anyone. I was bored, horny and curious. So I checked out one of those online personal ad websites. I found a guy who was looking for exactly what I wanted: a no-strings-attached purely sexual relationship with another guy. Most of these ads were guys wanting a lot of kissing and things I had no interest in. I told him upfront I wanted to find a guy to fuck me in the ass and maybe watch gay and straight porn while we jacked off or sucked each other. He was cool with all of that and we set up a time to meet at his place. He was tall with dark hair. I came to find out he worked in the same business I did. That was a little unnerving, but we were fortunately not working in the same circle of people. After chatting for a bit he put on some bisexual porn that was really hot. The guys had enormous cocks and took turns fucking one of their girlfriends and blowing each other. By this time I had stripped nude on his couch and he was wearing just a tee-shirt. I could see his raging cock pulsing next to me. I wanted to suck him, but at this moment he got up and knelt down between my legs and took my whole 7 inches in his willing mouth. I watched the guys suck each other 69 style on the screen while the girl with great tits played with their asses. I got more and more excited until my cock couldn’t take it anymore. I told him I was going to cum and he just bore down more on my cock and let me explode a load of cum deep down his throat. I screamed out and didn’t care. He didn’t stop until I was spent. I finally looked down and saw him swallow the last of my load. He held up his hand and showed me that he had cum in his own hand while I came. I sucked his cum out of his hand and swallowed it all. After we had both recovered a bit we went back to his bed. He told me to lie face down. I did. He massaged my back and legs. Then he started to feel my ass. Soon he was fingering my ass. I had never had that done and it started to feel incredible. After a while I was rock hard and he kept going. I soon had my first anal orgasm. It was incredible. I soaked his sheets, but he didn’t care. We showered and talked some more. It turned out he had a girlfriend who was into a lot of somewhat kinky things. He showed me her pictures on his computer. She sent him an email from work talking about the fact his cum kept dripping out of her onto her panties during business meetings. He showed me several great nude pictures of her and I got hard again. He knelt down between my legs and told me to look through the pictures of his naked girlfriend. So I did. I got more and more excited and he finally put my cock back in his mouth. He sucked me off while I looked at his girlfriend’s hot tits. I had a great time but had to go after that. He said we should get together with his girlfriend next time. I didn’t realize she would like that kind of things. We parted and made plans to hook up again in a couple of weeks. I couldn’t wait. After two weeks passed I raced to his apartment. Unfortunately she had to work that day. I was disappointed. but it was okay because we started to fool around with porn some more. After he gave me another fantastic blowjob I started to suck him off. He asked if I had ever had a cock in my ass. I told him no and said that It was a fantasy of mine. He said he’d love to and I got up and led him back to the bedroom. He got out a condom and put it on. I laid down on the bed and he pulled me to the end. He put my legs up, one on each shoulder. He started lubing my ass. Soon he was hard and I felt the very tip of his cock trying to go in. After some work I relaxed enough that I felt him fully enter my ass. He was slow and deliberate. It felt great. I could feel him getting more and more excited. He started to pull out as he moaned a lot. I told him ‘no, cum inside me.’ He was shocked. I felt him relax and enjoy his thrusts deep in my ass. The pain and pleasure were exquisite. He leaned back his head and let out a loud shriek of joy as I felt his hot cock pulsate inside me and get warmer and fuller as cum filled the condom. He finished and pulled out. It was incredible the condom hadn’t burst with as much cum as he had in it. We met a couple of other times for various sex like this until finally his girlfriend could join us. I was so excited to finally have a three-way with this guy and his hot girlfriend. When I walked into his apartment that day, she was topless on the couch wearing only her panties. He introduced us and she promptly unzipped my pants and took them off. Soon we were all naked and feeling around each other. He and I took turns sucking her tits while she grabbed our cocks and jacked them for a bit. Before we got to crazy we talked a bit about what we wanted to do. I told them I’d like to pleasure them both at the same time. We went back to the bedroom and I laid her down on the bed on he back. I spread her legs apart and started licking her wet pussy. Meanwhile, he spread my ass open and started lubing up my hole. This time there was more trust and knowledge. I didn’t ask him to use a condom. He didn’t. I felt that hot cock start to push inside me while I focused on this shaved pussy in my face. She was squirming pretty good and had me reach up and squeeze her nipples. After ten minutes or so she started to cum.. and cum again.. and again. By this time her boyfriend was riding my ass with ease. He enjoyed watching me make her cum. I was hard even though I had a cock deep in my ass. I could tell he was getting close. I keep making his girlfriend cum. She almost pushed me away, but at that moment she came again as I felt this huge pulse of hot cum explode in my ass. It seemed like forever as he keep squirting more and more hot cum inside me. Finally he pulled out and I could feel it dripping out of my ass and down my leg. I stood there for a moment and they thanked me for making them cum. I said I wasn’t through yet. I asked them both if they would mind if I fucked her pussy. She was ready to cum some more. He was great with it. It turned him on. I was so excited my cock was jumping up and down. I pulled her closer to my dick and saw just how hot and excited her pussy lips were. I pushed my cock inside and it felt so wet and warm. She groaned a bit and started rubbing her clit. He started to lick his cum out of my ass by rimming me. I started to stroke my cock in and out of her with ease. She grabbed the sheets and came again. Her boyfriend move up and started sucking her tits with me. She came again, probably the 8th time so far. I felt I was getting close. She said to just pump her full of cum. He was okay with that.too. I finally couldn’t hold it any longer and let loose with a massive orgasm deep inside her pussy. I could feel the cum filling her. She came yet again. By this time he had gotten hard again. When I was totally done, I pulled out. Very quickly he slid his cock back inside her cum-drenched pussy. Yes, he was having his own girlfriend as ‘sloppy seconds.’ It was incredibly hot seeing my cum coat his cock in her pussy. After a while I got hard again and she beckoned me to put my cock in her mouth. So I did. We were all three sharing her holes for pleasure. She somehow managed to work my cock so that I came just as he came and just as she came for about the 10th time. That was it for us for a while. We were spent. Sitting there I told her we now shared something in common: we both know what it feels like to have her boyfriend cum inside us. They loved that and have had me over most weekends ever since for more than a decade.