Cast of characters - it was always about the bets

By Mike Simmons

Published on Dec 13, 2019

Bisexual

I arrived at Carries house and while waiting for her I was chatting with her brother who was 14 and no longer a pain in the ass. I asked about school and his girlfriend and he blushed and said Mike, she is hot and messes with my mind and I constantly have a boner. I said Sam, I'm glad she is hot, they will always mess with your mind, it's what they do and the boners are part of being 14. Just be careful with what you do with it. He said Mike can we talk sometime? Sam, absolutely and I gave him my number. Carrie came down and we hugged and I whispered in her ear damn it will be fun getting you out of all those clothes and I saw Sam snicker and go to the other room.

We got to Rob's and Riley was already there. I looked at Rob and shook my head and he laughed. The girls were talking in the kitchen and Rob said Riley said she was off limits except for me and I said Carrie feels the same way. We grabbed beers and Rob had wine for the girls. We chatted for a while and I asked Riley for a minute alone. We went into the kitchen and I said Riley understand something, you have fuck two of my best friends and since Jim has moved on I'm ok but mess with Rob's mind and you will never recover. What's going on? Do you have to be fucking the highest profile player of the season. She tried to slap my face and I grabbed her hand and said you are the highest profile jock in the school and I'm not fucking you. That's correct Riley and you never will. Just keep Rob happy and we will be fine. Back in the living room Carrie just glared at me and I leaned in kissed her and said babe that bitch is a slut and I'm the only jock she will never have a chance with. With that she kissed me and we started making out. I looked over and saw Riley looking at me and Rob grabbed he and was all over her.

Rob was going at it pretty hot when I asked if he wanted another beer and he said sure and both girls were less than happy. In the kitchen Rob said Mike, I know I'm the jock of the season with that bitch but I'm fucking horny and I guarantee you she will be walking funny. I might put one up her ass. We got the beers and the wine and went back to the living room. The girls were chatting and I handed Carrie her drink she said Mike you scared Riley and I said good, but Rob has this. I look Carrie in the eye and said babe I love you and I need you and this is not a simple fuck, please kiss me and let's get started. She unbuckle my belt and was feeling me up and we were kissing and she suddenly stopped and was looking across the room. Rob and Riley were naked and he was eating her ass. Carrie I said don't watch just let's pay attention to us. She pulled my dick out and went at it sucking and licking and I stopped her and started taking clothes off and soon all four of us were nude. Then I started on Carrie's ass and was licking that sensitive spot between her pussy and he ass when we heard a scream and Riley yelled Rob that fucking hurts we both looked over and saw Rob had is Dick in her ass and was pounding away. Then she screamed Rob stop. He pulled out looked at her and said we either continue that way or you get dressed and leave. I thought shit, now what. She threw herself in his arms and said so what you waiting for and he flipper her on her back lifted her legs and shoved is cock back in and she was screaming and crying. I looked at Carrie and said babe where were we. She kissed me and I reached behind her and started fingering hers asshole. She tensed and then relaxed and as we were kissing she pinched both my nipples and I swatted her hands away and she whispered, Mike every time you go there I'm going to your nips. I laid on the floor rock hard and said babe just hop on and she rode me till I shot my load. With me still inside her she kissed me and pinched my nips and I said babe you know what that means and I put a finger up her ass. This time she did not tense she just moved her ass. I wasn't going there just yet but since I was instantly hard enough pulled her back on my cock and said just ride it hard cowgirl. She really went at it and finally pinched both my nips hard and I shot another load and we both collapsed. Rob was laughing and said damn that was quite a show.

Once everyone was decent Rob said Riley I know you can't stay late do you need a ride home and she looked at him and said asshole I drove here so I'll drive home. He walked her to the car and came back laughing and said that's is one pissed of bitch. He went into the kitchen came back with a round of drinks and said that bitch just broke up with me on the way to the car, she said I was a nasty animal. Carrie, why did you treat her that way? Carrie, she is a cock hound and was scamming Jim and fucking at least two other guys while she was running a game on everyone. I simply decided to teach her a lesson. What the fuck, I had fun and she learned a painful lesson then he added anal sex does not have to hurt unless you want it to. We had a quiet rest of the evening. I finally got a call from Jim and he said Mike, we got our asses smacked and it was the mercy rule. That damn school had 5 D1 recruits and there was only me and he laughed. Call me in the morning. I leaned over and whispered in Carries ear, thank fucking god it's over are you still my wife to be or moving on to the next available jock and before I could react I got slapped across the face. Then she yelled MICHAEL JAMES SIMMONS you are a total asshole but your my asshole, I love your rude ass and Rob was on the floor laughing.

I announced that I was hungry and ordered pizza. While we were waiting for the pizza I said to Rob, you should have kept Riley around for a second round and he laughed and said that ass breeding she got was round two and Carrie and I both laughed. The Pizza came and we ate and talked and had a great rest of the evening. We were getting ready to leave when Rob said hold on and disappeared and returned with my Spanish work for the week completed and the calculus that I missed unfinished. He said, Mike here you go I know you love that shit, have fun. As we drove I asked Carrie if she knew all that about Riley and she said yes and she did not get involved as both were getting exactly what they wanted. I said damn, babe, I need to get a social life and she said no shit Mike. Why we going to your place and I said to fuck again as we still have time. She laughed and started playing with my chest and started to laugh. We pulled into the driveway and shit dads car was there but we went in anyway. He was no where around and I went upstairs and heard noises coming out of his room and I laughed and told Carrie and she laughed. I said babe a very quick and quiet one you good with that? She said why not and we went in my room and it was quiet, romantic and intense. We cleaned up opened the door and fuck there was dad and his date in the hall. We all just started laughing. Mike and Mike caught in the act, what could one say. I drove Carrie home and returned to an empty house so I just went to bed.

Saturday morning was sunny and cold and the run was fantastic. I made coffee and toasted a beagle and was reading the paper when dad came down grabbed a cup of coffee and said so I guess you skipped the game last night? I said yes and so you are thoroughly pissed off that time in my room was the third time last night. He said Mike I'm not mad and it was actually funny both of us sneaking around. Just then the phone rang and it was Bill. I said dude, how are things? Mike, I got a reward for being on good behavior want to visit tomorrow? I said absolutely what time. He said 2-4. Ok see you then and I put dad on. While dad talked with Bill I remembered about the 1:00 meeting and had no idea where it was. I called Tim and when he answered I said, so you and the bean counter and I have a meeting? Mind telling me where the meeting is? Mike, your place and Brian and your dad will be there as well. I said WTF, YOU NEED TO HAVE YOUR ASS HERE AT 12:30 I don't want to ever go into a meeting blind. He very quietly said Mike, that's not happening and he hung up. I was fucking furious.

At 1:00 I went down stairs and found dad, Brian, Tim and Rob I went straight to the scotch poured a drink and said guys this better be fucking good. Dad said ok everyone out but Mike. Once we were alone dad said Mike I have no idea what this about either, but that team you have put together deserve your patients and respect, so calm the fuck down. Remember you and I control things. He got up, opened the door and invited every one back in.

They all looked at me and I said ok guys, I don't like being totally out of the loop, that resulted in a reaction I'm not proud of. I trust you guys so what's going on. Brian said Mike and Mike, the plot of land next to the one you just bought is available. It seems like the previous plans were disrupted by your purchase. I was silent and dad asked Brian how much? Brian replied 1.875 and I laughed. Then I asked, how would we pay for that? Mike, we already have the new building potentially full and need you and your dad to review the potential tenants. Again I asked how do we pay for it? Brian said Mike the company can buy it. I just glared at him, so now I find out that the major tenant for my proposed building will buy land and I'm guessing build a building and I have no tenant, is that correct? There was silence and I glared at dad? It was my turn and I politely said everyone out except dad.

When the room was cleared, I looked at dad and said WTF? Mike, I had no idea. I looked at him and said but you offered to buy the property? Mike, I wasn't thinking, I just thought buying the property was a good idea. Dad it isn't. It simply is too much way too fast. I looked at him and said dad please don't let this come to a vote. Mike, where did that come from? Dad ask the team because I don't understand at all. I got up and opened the door and asked Tim and Rob to come in.

I looked at Tim and said where in the hell did all this come from and how involved are you in this? Mike, you flew off the handle and..... I stopped him and said Tim you stay put dad and Rob please give us a few minutes. Once alone is looked at Tim, took a deep breath and calmly said please explain. His reply was that he found out about the property and since the potential tenants was way above what we could handle I asked Brian's opinion. Then I invited Ryan to better understand the economics and here we are? I leaned back in my chair looked at the ceiling and took several deep breaths then said Tim you fucking work for me so why everyone but me? Mike, you are tough to deal with and I wanted all the facts to present and was hoping for a calm discussion and you blew the fuck up. I said thank you and please send Ryan in.

He got up and Ryan entered looking more than a little sick. He sat down and I said dude can this possibly work? He relaxed some and said Mike, it is one hell of a stretch. The land can't be worth 1.875 and you would be stretch to the limit. You could always buy the land and let it sit. I said thanks and ask dad to come in, please.

Dad sat down and said Mike what you thinking? I replied everyone out there should be fired. Mike, really? Well dad they were operating behind our back and this is just stupid. I asked, dad what do you think? Mike it will be taking on too much and too soon. I looked at dad and said well I want to make a ridiculous offer and see how people react. That plot is smaller that ours and they want almost twice as much. Dad asked, Mike what's a ridiculous offer and I replied 900 k and dad laughed. Then he said Mike, what if they accept it, dad they won't and if they do the Trust will swallow hard pay cash and put it on the market and get the money back. Dad, you good with that? Dad said, Mike I'm good but why run the game? I chuckled and said simply to teach the employees a lesson and yet keep them close. Dad shook his head and I said you deal with Brian and I'll deal with the dynamic duo, send those two in, please.

Tim and Ryan came in looking a little pale and very nervous. I started on Tim asking who started this and he said Brian came to me with the offer and the idea. Tim, did he mention the company buying the land and building a building? His face lost all color and he said Mike, I promise he did not. Tim he was trying to do an end run on me and you did not think of that? Mike, honest I did not and he could not do that without the Trust voting it's shares. Tim, he was working you so I would be out voted, do you get that yet? He thought for a minute and said Mike, that will never happen. I'm sorry and I'll avoid pissing you off going forward. Tim, don't do that; first, don't be sorry and simply own up to your mistakes; second if you are actually doing your job you will piss me off a lot.

I turned to Ryan and said, dude you get a pass. I put you in a tough spot and you we're doing well until the legal team tried to take advantage of your inexperience. We need to have a long talk and find your comfort level. You, tonight served me well. You are right this is not a great idea especially right now. Are you ok? Mike, thanks. However, I knew this was too fast and somewhat over my head and I told them this was a bad idea but no one listened. Mike, I like working with you as it is fun and never dull. To answer you question I'm very good.

Then I said, guys we are making a counter offer on the land it is $937,500 contingent on the property being rezoned commercial. Tim said damn that's a strange number and Ryan laughed saying, asshole that's exactly half of the current asking price. Tim, you are to tell Brian that dad and I are talking things over and will get back to him, in the meantime make that offer and not a word to Brian. Understand that dad already knows and the 2 of you are helping me and dad teach Brian a lesson. I looked at Tim and said dude, Brian will be leaving the firm right after the first of the year and dad and I will be talking with your managing partner, we have your back. Then there is the possibility that you have your own firm. Ryan just looked at me and said Mike one Trust does not justify an entire firm, I laughed and said dude broaden your horizons. Now both of you get out of here and get to work? Oh, Ryan you free for dinner? He put his head down and said, Mike I'm busy, I have a date. I said dude, have fun and it's about time. The two of them walked out somewhat stunned and subdued. I just sat there waiting and poured a drink.

A few minutes later dad came in sat behind his desk then got up poured a drink and lit a cigarette. I reached for one and dad said, Mike you quit remember and I lit the cigarette and leaned back in the chair. We sat silently and I finally asked, so dad how is Brian? Mike, very worried and he underestimated you. Did what was he thinking, he would have had to outvote us. Mike, they had him under a lot of pressure and two partners were beating him up about cooperating. He is a tough guy and I think he devised this approach to pissed us off, well you mostly. Dad I am pissed but I'm never stupid. Ok Mike, now what? Well first of all I asked Tim, without telling Brian, to make an offer for the land of $937,500 subject to a rezoning to commercial. Brian is being told you and I are thinking things over and will let him know Wednesday. Mike, Tim might be fired. Dad we both need to talk with the managing partner and Tim gets made a partner or our business goes elsewhere. Mike, we need to protect him but your approach will tie him to that firm for good, not sure we want to do that. Mike, I'll call Brian and tell him that unless he and the others let up on Tim, I'm pulling the business and that as of now the offer to join the company as full time legal council is on hold. Dad, do you want to lose Brian? Dads reply well this year I discovered attorneys are a dime a dozen and the relationship should always be purely business. I poured another drink and lit a cigarette dad got out of his chair, I thought to get a drink but he went behind me put his arms around me took the drink and cigarette off me and whispered in my ear, Mike get the fuck out of here and go be a teenager. Just go fuck off with your buddies and I don't mean that literally, now go.

I called Jim and asked if he was free to hangout and he said absolutely. I said so what we doing and he said the mall and the arcade. I laughed and said great, lots of opportunities for bets and he laughed. Then I said can I invite Rob? His reply shocked me, as he said wingman we are flying solo today. Fun, games and bets and my place is free all day. I said so let's just skip the mall and we can buy a new video game and play at your place. He screamed DEAL, I'll pick your ass up in 20. I took a quick shower and dressed in a sweat suit and as I went down stairs Jim pulled into the driveway. It was off to the video store and we couldn't agree on a game so we bought 2 and it was off to McDonalds for a Big Mac and fries and a shitty soft drink. We talked about football and how glad we were were that it had finally ended, what we had accomplished, what next year would be like and what we would do with all our free time. As we were getting into the car a Jim said, Mike, are you going to visit VT soon? I said MLK weekend and he smiled and said can I join you and your dad? I said WTF, when did that happen and he said while you were unscrambling you're head and we both laughed. As we drove to his place I asked about Ray and he replied dude he hangs with a new group of friends and it is interesting he seems to be the ring master. I thought for a minute and said so he is settling for being the top dude on the second string. I got a strange look from Jim but changed the subject to Jim how aware were you aware of Riley cheating on you? Mike, he replied, it was never like you and Carrie, I mean Riley for me was just someone to get my rocks off on and while the sex was fun, she was never worth a serious thought. I said damn, Jim I never thought that, I need to pay more attention and get a social life. Mike, relax you are good it is just that if you walked into a room of naked hot chicks and if Carrie was in that group you would not even see the others, you are so focused on her and her on you. Hell, half the seniors on the team have tried to hit on her and she usually says sure I'll ask Mike if he minds. It's a damn good thing I wasn't driving as I would have wrecked the car no doubt, I was laughing so hard.

We got to Jim's place and he handed me a beer and lit a cigarette. I just looked and he said Mike, relax dad has just given up, I drink, I smoke and I fuck multiple chicks and try as he might he can't stop it, just relax. Wow, Jim you have changed. He replied dude it is the wingman influence, I have to keep up. We just chatted for a while drinking and smoking and finally started playing the new games. We were heavy into it and after three beers I hit pause and said dude, I have to piss, Jim laughed and said dude, why tell me or do you need help and I said sure. To my surprise he got up and followed me into the power room and he unzipped my pants and pulled my cock out and said well what's taking so long or are you piss shy? I grabbed him and put his hand on my cock and said dude you got me hard and now I can't piss, please fix the problem. He said gladly but not here upstairs. We went into his room and I was looking around as this was the first time I was in his room. There was his gold metal and a team photo, there were pictures of his family and I was shocked to see a picture of him and me walking off the field after a game. He said Mike focus we are not here to look at my room. I pointed to the picture and said dude can you get me a copy. He went to his desk, pulled out a folder and said, asshole I have been saving this. I said what the fuck for? Jim pushed me on the bed and he said for this very moment when I realized you and me are for real and he hugged me and started to cry. I held him and whispered dude big girls don't cry and he laughed. Then he wiped is eyes and said wingman what can I do for you, right now and I said dude when you family get home and he said tomorrow? I smiled and said let's get shit faced drunk and fuck our brains out? Jim said Mike, no bet? I said asshole wingmen don't need a bet, just breed my ass. He pushed me flat on the bed and I was nude in less than a minute. I sat up pulled his pants and boxers down and was going to suck him and looked at his hard cock and just get to work, you obviously ready. He stepped out of his jeans leaned in and was kissing me and I whispered please use lube, I want you to last a long time. He reached to his night stand grabbed a tube of lube squeezed some on my hole and started to work his fingers in when he got to 4 I started to complain as it hurt and just kept fucking my ass with his fingers. Finally he stopped added more lube and leaned in and said, ok where were we and we were making out and he slowly with no effort slid into my ass. We kept kissing and he slowly was moving in and out. Then he stop the kissing and went at my ass for real. I was loving every second but shit I was getting close and I reached up grabbed his ass and held him deep inside me. I got another kiss and then the fucker teased my nips and I blew a load. He pulled away and cum was on both our stomachs and he went balls deep time and time again until I heard Fuck I'm going to breed my wingman and he shot a ton of cum in my ass. I pulled him close and we hugged and just laid there.

We laid there just snuggling and I eventually said dude, remember why we came up here? I had to piss and you wanted to help. I got up took his hand and led him to the bathroom, turned on the shower and we climbed in together and I started to piss as he held my cock, I reached down and collected some of my piss in the palm of my hand and put it towards my mouth and drank it. Jim just looked and as my stream was subsiding he did the same thing and he said dude your piss is awful, I said well I liked it and we both laughed. We soaped each other up and and as we were ringing off he started to piss and I grabbed his cock and squeezed stopping the flow. I got down on my knees and positioned his cock at my lips, opened my mouth and released the flow. It shot out in a big stream and I swallowed some and then let his piss fill my mouth and I stood up and started to kiss and when he opened his mouth I let his piss flow into his mouth and he really got into the kissing and piss. He pulled away and said Mike that was so fucking hot but let's get dried off and get to the getting drunk.

Downstairs I asked how mad his dad would be and he said not at all as long as you are spending the night. Would you fucking relax. We opened another beer and lit another cigarette and just talked about our lives. We started another video game and it was a disaster as we were into our 6th beer each and I threw the controller on the sofa and said dude I need to piss again. Then Jim just started to laugh and said Mike that's the worst excuse I have ever heard and he opened another beer and lit a cigarette then said asshole where is my beer? He got up came back holding a beer and was nude. I laughed and said there better not be a choice involved because I'm taking both. I grabbed the beer and started drinking and lit another cigarette. Then I pulled Jim to me and was not in a romantic mood at all. He grabbed my nips and said your turn breed me and I said I have something else in mind, pull my pant off and when he did I was already hard and I said sit on my cock. He went in the other room came back and sat right down and my cock slid right in and I just let him sit there and I was getting soft and when that happened I started to piss and I filled his ass with my piss. When I slipped out of his ass he ran to the powder room and was gone for something like 10 minutes I just lit another cigarette. He came back, looking upset and I asked if he was ok? He said no, I'm pissed I did't think of that and he got on his knees and started licking my balls. He eventually moved to my cock pulled off and said you need to try this sometime, butter, ass juice and piss, it's actually tasty. I said just suck it and shut the fuck up. I laid back and just enjoyed his working my cock. He stopped after a while and said dude, is there a load in there? I stood up grabbed his head and started to fuck his face and he pushed me back on the bed and started to work my cock and then he simply ended it by pinching my nips and I shot in his mouth. He kissed with a mouth full of cum and we shared another load.

Downstairs Jim complained, I'm fucking hungry. I asked what he wanted and said I'm buying and he said ribs and a lot of the from wherever you and your dad order that shit. I ordered the Ribs and called dad. Tried to act sober and told him I would be spending the night at Jim's and going straight to visit Bill. He said Mike, don't you dare drive. I said dad check the driveway my car is there we are playing video games, drinking and I ordered ribs, we are in for the night. He well silly mi I said be a typical teen, good night. Then I looked Jim and said butter? He replied fuck that took a while to register, that's what I used to lube my ass, I didn't want to go upstairs. We opened another beer and tried a calmer video game, but shit that was just fucking dumb. Neither of us could play. The food came and we ate drank and told stories and talked about shit. I asked how his dad's independent pharmacy was doing and he said great as it is almost all prescriptions now and not much of a store. Then he asked about Bill and my mom and dad and I opened another beer lit another cigarette and laid it all out with how I as the second child was junior and how that led to mom being a drunk and to Bill being a pampered ass. We ate drank and smoked till we both passed out on the sofa.

Jim woke me up saying he had to piss and he was not kidding he needed help getting to a toilet. He was slurping his words and I said fucktard how do you think I can help, I'm every bit as fucked up as your are. I handed him a beer can and said use that and passed out again. I don't know how long I was passed out but I woke with a strange feeling and found Jim licking my pits and was starting to my nips and I grasped him and said anywhere else, simply stay away from the magic buttons and we both laughed. Shit he was all over me and was nibbling at my neck and I jumped up and said if I have a bite mark I'll kick your fucking ass. He laughed and said as drunk as we are it would be a pillow fight, shit neither of us can stand. I laughed and said but I'm sober enough to fuck and I started kissing him and we were making out until I flipped him over and started eating his ass. Then when it was all clean and wet I drove balls deep and pounded him hard shooting yet another load in his ass. I flipped him back over and said dude next time I pissing in your ass clean up better butter, piss, cum doesn't mix well with you ass juice and we fell asleep in each other's arms. I woke first, feeling like shit, took a hot shower, put some coffee on, cleaned up some and emptied the beer cans and found one almost full and went to dump it in the sink and started to laugh it was full of piss. I went upstairs found Jim still sleeping and I sat on the bed and kissed him and he said oh, Riley, I do love you and I pulled back and he burst out laughing and I got a big hug. He showered, we had coffee and talked for a while and I finally said ok wingman let's get in your jet and fly me home, I have shit to do today.

Comments are encouraged as this is my first story.

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Next: Chapter 67


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