The Chess Bet
Every Saturday evening, I go to my friend, Joe's, house to play chess. We play a few games, chat about strategy, and drink some beers. Every once in a while, we smoke a little pot, which leads him to make ridiculous bets, which he often loses because he doesn't do well under pressure. We've been playing chess together for about 6 years now and in that time, Joe's made about a dozen bets and has lost all but one. Once, as a result of a bet that he made, I didn't have to do any of my yard work for the entire summer. Another time, he completely re-did the front end suspension system on my car. He also has a stupidly hot wife. I can't tell you how many times I've jerked off thinking about her. When he's having an especially bad night of chess, he'll invite her down to the basement to watch because he knows that she throws me off of my game. One night, we're a wee bit high and his wife, Sandra, is downstairs knitting and watching us play and Joe decides that it's betting time. He says, "How about a bet? Something interesting. Something that I know you want. If you win, I'll let you fuck my wife however you want for as long as you want." I started to protest that I didn't want to fuck his wife and he said, "It's OK. Sandra and I have a moderately open relationship. She gets to fuck someone if I get to watch and then I get to fuck someone else while she watches some other time. Is it a bet?" Without trying to look to eager, I agreed. Joe then said, "If I win, what do I get?" I responded, "I'll suck your dick and swallow your cum." I don't know what came over me; I think I was just trying to throw him off of his game. His wife sat up straight and gave him this unmistakeable look that said, "I'm interested."
He said, "OK. Let's go." We played one of our most intense games. There were times I was certain I was going to win and times I was certain I was going to lose. His wife kept coming over to check in on the game. Towards the end, she came over solely to distract me: she looked me in the eyes and started lightly running her fingers over her tits and the insides of her thighs while licking her lips. It had the opposite effect because instead of becoming distracted, I became determined: I was going to fuck this woman. Two minutes later, it became obvious that I was going to checkmate Joe. Instead of conceding, he made me play all the way through, probably hoping that I'd make some stupid mistake. By the time I checkmated him, my cock was hard and throbbing in my pants. As soon as I knocked over his king, I stood up, whipped out my dick dripping with pre-cum and told Sandra, "Suck my cock." To her credit, she got right to business with no complaints.
She was as talented with her mouth as she was beautiful. She sucked me slowly and deeply, going balls deep with no resistance or gagging. After about 5 minutes of knee-weakening sucking, I grabbed her head and started thrusting hard and deep into her mouth. She didn't make a sound. She just took what I had to give her. We were only a few feet from one of the support beams in the basement, so I walked her over there without taking my dick out of her mouth. I pressed the back of her head against the beam and fucked her mouth like I was fucking a pussy. Out of the corner of my eye, I caught movement, so I looked over at Joe and he was stroking his huge dick with both hands. I was so surprised that I lost concentration and passed the point of no return, to my dissapointment. I started thrusting more deeply and urgently and blew my huge load down Sandra's throat. Still, she didn't falter. She swallowed it all down and then looked up at me. I pulled my cock out her mouth and I was still rock solid and I knew I was going to be for a while still.
I pulled her to her feet, stripped off her clothes and turned her around and bent her over. I looked down to shove my cock in her pussy and I could see that she was dripping wet. As I pressed my cock against her pussy, it slid in with ease. I fucked her with a****listic desperation. I ended up pressing her onto her hands and knees and mounting her from behind as I stood on my feet. I fucked her so hard I thought I was going to break something. I looked over and Joe was still stroking his dick, but now he was completely naked. I couldn't tear my eyes off of his fat cock and pendulous balls. He got up and came closer to us. He then stood with Sandra between his legs and his huge cock pointing right at my mouth. He said, "It's OK. You can suck it. I saw you staring." At that point, I wanted nothing more than to have his fat dick in my mouth.
I couldn't take him completely into my mouth, but I got a generous portion down my throat. As I sucked his cock, I continued to fuck his wife. After a few minutes, he removed himself from my mouth and walked around behind me. All of a sudden, I felt something hard, wet and warm pressing against my asshole. I looked back and it was Joe: he was rubbing his huge cock head on my asshole. He just shushed me and turned my head forward. He then grabbed my hips and started pushing slowly but inevitably. After just a few seconds, I felt him fill my ass with his thickness. I drew in a sharp, audible intake of air and his wife looked back in response. She saw Joe behind me with his hands on my hips and she smiled. She rocked forward and withdrew me from her pussy. She grabbed my dick, smeared some lube on it and deftly inserted me into her ass. She turned back around at me and said, "Fair's fair." She then started pushing back forcefully. I had her pushing back against me and Joe pushing into me from behind. I had never felt such pleasure before. I don't know how much time passed: minutes? An hour? I felt Joe grab my hips more tightly and he started thrusting completely into me. Then, he pushed all the way into me and let out a groan. Joe was cumming deep in my ass. At no point did Sandra let up. As Joe was cumming in me, she continued to push back and forth and, all at once, I felt my own orgasm start to wash over me. I reached behind me, grabbed Joe's back and pulled him along with me as I came in his wife. I felt 12 or so waves of orgasmic bliss as I pumped out rope after rope of hot cum into Sandra's rectum. We then collapsed into a pile on the floor and lay there unable to move. After a few minutes, I got up, got dressed, said, "Good game" and left. We had many more sexual adventures, but those are stories for another time.
He said, "OK. Let's go." We played one of our most intense games. There were times I was certain I was going to win and times I was certain I was going to lose. His wife kept coming over to check in on the game. Towards the end, she came over solely to distract me: she looked me in the eyes and started lightly running her fingers over her tits and the insides of her thighs while licking her lips. It had the opposite effect because instead of becoming distracted, I became determined: I was going to fuck this woman. Two minutes later, it became obvious that I was going to checkmate Joe. Instead of conceding, he made me play all the way through, probably hoping that I'd make some stupid mistake. By the time I checkmated him, my cock was hard and throbbing in my pants. As soon as I knocked over his king, I stood up, whipped out my dick dripping with pre-cum and told Sandra, "Suck my cock." To her credit, she got right to business with no complaints.
She was as talented with her mouth as she was beautiful. She sucked me slowly and deeply, going balls deep with no resistance or gagging. After about 5 minutes of knee-weakening sucking, I grabbed her head and started thrusting hard and deep into her mouth. She didn't make a sound. She just took what I had to give her. We were only a few feet from one of the support beams in the basement, so I walked her over there without taking my dick out of her mouth. I pressed the back of her head against the beam and fucked her mouth like I was fucking a pussy. Out of the corner of my eye, I caught movement, so I looked over at Joe and he was stroking his huge dick with both hands. I was so surprised that I lost concentration and passed the point of no return, to my dissapointment. I started thrusting more deeply and urgently and blew my huge load down Sandra's throat. Still, she didn't falter. She swallowed it all down and then looked up at me. I pulled my cock out her mouth and I was still rock solid and I knew I was going to be for a while still.
I pulled her to her feet, stripped off her clothes and turned her around and bent her over. I looked down to shove my cock in her pussy and I could see that she was dripping wet. As I pressed my cock against her pussy, it slid in with ease. I fucked her with a****listic desperation. I ended up pressing her onto her hands and knees and mounting her from behind as I stood on my feet. I fucked her so hard I thought I was going to break something. I looked over and Joe was still stroking his dick, but now he was completely naked. I couldn't tear my eyes off of his fat cock and pendulous balls. He got up and came closer to us. He then stood with Sandra between his legs and his huge cock pointing right at my mouth. He said, "It's OK. You can suck it. I saw you staring." At that point, I wanted nothing more than to have his fat dick in my mouth.
I couldn't take him completely into my mouth, but I got a generous portion down my throat. As I sucked his cock, I continued to fuck his wife. After a few minutes, he removed himself from my mouth and walked around behind me. All of a sudden, I felt something hard, wet and warm pressing against my asshole. I looked back and it was Joe: he was rubbing his huge cock head on my asshole. He just shushed me and turned my head forward. He then grabbed my hips and started pushing slowly but inevitably. After just a few seconds, I felt him fill my ass with his thickness. I drew in a sharp, audible intake of air and his wife looked back in response. She saw Joe behind me with his hands on my hips and she smiled. She rocked forward and withdrew me from her pussy. She grabbed my dick, smeared some lube on it and deftly inserted me into her ass. She turned back around at me and said, "Fair's fair." She then started pushing back forcefully. I had her pushing back against me and Joe pushing into me from behind. I had never felt such pleasure before. I don't know how much time passed: minutes? An hour? I felt Joe grab my hips more tightly and he started thrusting completely into me. Then, he pushed all the way into me and let out a groan. Joe was cumming deep in my ass. At no point did Sandra let up. As Joe was cumming in me, she continued to push back and forth and, all at once, I felt my own orgasm start to wash over me. I reached behind me, grabbed Joe's back and pulled him along with me as I came in his wife. I felt 12 or so waves of orgasmic bliss as I pumped out rope after rope of hot cum into Sandra's rectum. We then collapsed into a pile on the floor and lay there unable to move. After a few minutes, I got up, got dressed, said, "Good game" and left. We had many more sexual adventures, but those are stories for another time.
3 years ago