This erotic literature contains explicit sexual content and should only be read by adults. If reading descriptions of explicit sexual activity would in any way be offensive to you or illegal for you to do, you must stop reading this immediately. Continuing to read beyond this point is your agreement that you are aware of what lies ahead and legally allowed to read this material. Thank you. The author of this story (Mikes_Fantasies) reserves all rights to this story--reproducing this story without the author's permission is prohibited The Usual Wager (MMM, cons, anal) Author: Mikes_Fantasies July 2004 While we were young and in college in the early 70's, my roommate, Jimmy, and I had a standard wager. The bet could be on anything, from a which elevator would arrive first to a football game to an athletic contest. The winner had his choice of the loser's mouth or butt, on demand, for sexual satisfaction. We considered ourselves basically heterosexual, but enjoyed pleasing each other. Being very competitive, we used this wager often and for convenience we just called it "the usual." The "on demand" factor meant anywhere, anytime the winner wanted it and led to some interesting payments. In those days, before racquetball became popular, we played a game called handball. The concept and the court were the same but, instead of racquets, we wore leather gloves and hit the ball with our hands. The ball was slightly smaller and more solid to slow it down a bit. Jimmy and I were both pretty fair players and pretty evenly matched. We often bet the usual. Handball is usually played one-on-one but can also be played with two-person teams or three people can compete in a game called cutthroat. One day we played cutthroat with a mutual friend named Jack. The courts are completely enclosed. There is a door at the back of the court, flush with the wall, with a small window for viewing. It was a hot day and we quickly worked up a sweat. Our shirts came off after the first game. I enjoyed watching Jimmy and Jack's trim bodies as their muscles worked and sweat made their skin shine. Jack was also a pretty good player and after three games, it was one win each. As we were about to start the last game, Jimmy glanced over his shoulder at me and asked, "The usual?" "Of course," I said. Jack looked confused, but didn't say anything. The game was close all the way to the end, with the lead changing hands several times. After the final serve, Jimmy won with 21 points, Jack had 19 and I trailed with 18. We shook hands and I went to the back corner to pick up my shirt. In my wildest dreams, I never expected what happened next. Jimmy said to Jack, "Mike and I had a small wager on this last game and he lost. Since you came in second, that means he lost to you too. Would you like part of the payoff?" My eyes got wide as I looked over at the two of them. Jack said, "Sure, what did I win?" Jimmy explained that our standard bet included anal or oral sex, on demand. Jimmy said, "I intend to get mine now. You're welcome to join me if you want." From the way Jack was looking at me and smiling, I could tell that he definitely wanted. "Why don't you hit the ball around while Jack and I decide how we want to collect," Jimmy said to me. The sound of play would keep other players from entering the court. As I hit the ball against the wall, I listened to Jimmy and Jack discussing my payment. I knew what Jimmy wanted. He always wanted my ass. He and Jack debated the merits of taking me together, one in my mouth and one in my butt, or separately. In the end Jack said, "I want to fuck his butt, too. Let's play one volley to see who goes first." Jack served but Jimmy won the volley. Jimmy said, "I'll go second. He's all yours. There is KY in my bag. I'll keep the ball bouncing while you're collecting your debt." Jack and I went to one of the back corners of the court, out of sight of the window. As he pulled the lube from Jimmy's bag, he said, "I've been watching your butt all afternoon. I can't wait to sink my cock into it." He pulled his trunks and jock off, displaying his cock and low hanging balls. "Alright Mikey," he said, "Let's get those shorts off, but leave your jockstrap on." I saw Jimmy smiling as he continued to knock the ball against the front wall. I was getting pretty excited by this point and when I pulled my shorts off, it was obvious that I was coming to attention in the pouch of my jock. Jack gave me a slap on my right butt cheek and said, "I know I chose your butt, but you are going to use your mouth to get me hard. On your knees my boy." I lowered myself to my knees and took Jack's cock into my mouth. I just held it for a moment and felt him begin to stir. I rubbed my tongue back and forth and the stirring immediately turned into serious growth and I had a mouth full of hard cock in no time. Jack moaned quietly and pulled himself from between my lips. Without saying a word, he motioned, with the tube of KY for me to stand up, turn around and bend over. I placed my hands against the wall and bent at the waist, fully offering my ass to Jack. This was well before anyone had heard of AIDs and HIV, so there was no fooling around with condoms. Jimmy squeezed a healthy glob of KY onto his fingers and spread it between my cheeks. I sighed as I felt him insert one finger into my anus. He moved it in and out slowly then added a second finger. I was breathing heavily when Jack pulled his fingers out of me and grasped both of my cheeks, spreading them widely. I felt the head of his cock at my anus and, with a smooth but gentle stroke, Jack slid it into me. I tensed slightly but immediately relaxed as he held it still for a moment. When I fully relaxed, Jack started pumping, sliding his six inch cock in and out of my slippery asshole. I was into it, arching my back and moving back against him, taking it all the way into my butt. After a few minutes, I felt Jack begin to tense. I knew he was going to come soon and I used my sphincter to grip his cock even tighter as he worked it in and out. Jack moaned loudly and I felt his cock twitch and jump as he shot a load deep into my willing ass. He continued pumping until he was totally drained inside of me. As Jack pulled out of me, Jimmy yelled from across the court, "Don't move Mike, I've got something for you, too." Jack pulled his shorts on as Jimmy came over and dropped his. I looked behind me and Jimmy was already hard as a rock from watching Jack fuck me. Let me tell you a little about Jimmy's cock. Fully aroused, it is just slightly over seven inches long. It has a huge mushroom shaped head. This is why Jimmy almost always chose my butt as his payoff. He liked fucking me because of the way that big head popped past my anus on the way in and out. I liked that too and I also loved the way it felt as it moved back and forth against my prostate. Jimmy came up behind me and placed his hands on my shoulders and his cock against my back door. "I think that between the KY and Jack's load of cum, you should be pretty well lubed, don't you?" "Yes, Jimmy," I managed to gasp. "I'm ready for you to fuck me." I heard Jack stop hitting the ball in order to watch Jimmy slip me his big cock. "OK then," I heard Jimmy say as his cock head popped past my anus and into my willing butt. I gasped as he kept pushing, all the way in, until his balls slapped into mine. "Oh Jimmy!" I moaned as he pulled back and I felt his head massaging my prostate. My cock got harder and began twitching wildly. Jimmy slapped my ass a few times as he found his rhythm and pumped smoothly in and out of my ass. After several minutes I couldn't take any more and came in my jock pouch. I shot a big load as the spasms continued to come from deep inside of me. The contractions set Jimmy off and I felt him come and come deep inside my ass. It felt like the hot jets of cum were shooting way up where my stomach should be. Jimmy always shot a big load, but this one seemed even bigger and judging from his reaction and the sounds he was making, he enjoyed it as much as I did. "It was a pleasure doing business with you Mikey boy," Jimmy said. "As always," I replied after I caught my breath. I felt Jimmy's erection starting to fade and he pulled it out - the head making another satisfying pop as it slid out of my ass. Jimmy pulled his jock and shorts back on and I slid my shorts on as Jack gathered our gear. I had a wet spot on the front of my shorts from where I came in my jock, but it was hard to tell it wasn't just sweat. We left the court sweaty and tired and began the quarter mile walk back to our dorm. All of that humping had pushed some air into my ass and as we were walking I felt a little fart coming on and let it go. My mistake! Along with the air came some of the cum that had been following gravity lower and lower. I felt it run out of the legs of my shorts and down the inside back of my thighs. Once it started, there was no stopping it - my ass was a little stretched at that point and I couldn't squeeze tightly enough to stop it. Jimmy and Jack laughed at my predicament and told me to just keep walking as we approached our building. I began getting embarrassed as we walked past guys and girls we knew. Not very many noticed the creamy liquid running down my legs, but a few did and I can still hear the quiet laughter and see the surprised looks when they realized what it was. Just "the usual" I thought.