Cast of characters - it was always about the bets

By Mike Simmons

Published on Nov 19, 2019

Bisexual

Well I woke up in a super awesome mood and called Jim. Neither of us had an idea what we wanted to do and as we were chatting an idea hit me. I asked if he and Riley were free all day and he said yes, they had nothing going on. I said, I'll call you right back and I called Carrie and said babe real quick are you free all day and she said yes. I said I'll get back to you. I called Jim and said I have two thoughts 7 springs for hiking and fucking around or Cheat Lake for hiking and fucking around? He said 7 Springs they have rooms for the fucking around and I laughed. Dude, that's not what I meant. Ok, round up a date and get here for 10:30. I called Carrie and said I'll pick you up at 10:45 dress warm and we are going hiking at 7 Springs and she said awesome, we getting a room? I laughed and said no. I showered ate breakfast and struggled to find warm clothes as nothing fucking fit.

We piled in my car and it was fun 90 minute drive, great fall foliage a little past prime, and lots of joking and laughing. Then it got quiet and looked back and saw Jim and Riley making out. I said dude get a room. Mike you said no to that and I can't afford one so deal with it and we all laughed. I said asshole on the way home you are upfront with me. He did not laugh at that. We had a great time all day, rode the chairlift up and walked down, had a terrific lunch. Just a fun very low keyed day. The girls shopped and Jim and I sat outside I tried to get us a beer but damn this wasn't the club so we settled for warm cider. The girls found us and saw the cider and got some as well. I was getting hungry again so we had hotdogs and headed towards the car. Another 90 minutes home and we went into the game room and both couples were making out when dad came in and said excuse me and I'm sorry to interrupt but I really need Mike for a minute.

We went into the office and dad said, I'm leaving for California your brother was beat up in jail last night. Apparently he is a mess but will survive. I just need to get there and see if we can move things along. The attorneys feel I might be able to get him released and expedite things. Sorry but the Steeler game is off. I hugged him and said dad do want you need to do.

I went back into the room and said ok Carrie where were we? I grabbed her and started feeling her up and making out like mad. She finally said Mike slow down, whatever you dad said really got you intense and I said, Carrie for Christ sake just kiss me and I got slapped across the face. Michael don't be a jerk and ruin this almost perfect day. I said Carrie what would remove the almost? She said me and you naked in your room. I said babe can you wait 30 minutes? Jim chimed in and said dude what about us and I said your call guest room in 30 minutes if it is ok with Riley. Both girls just looked at me and Jim was shaking his head. We straightened up and were chatting when dad came in and said, Mike behave and I'll call tonight. With that he got in the car and left for the airport.

With that I leaned towards Carrie and said babe you want to go upstairs? She said Michael what the fuck do you think? I said I think you have a foul mouth and I need a yes or no. She said Mike will an absolutely do? I picked her up and said guys if you want you know the way Carrie and I will be back shortly. I laughed as Riley ran up the steps ahead of us. This time the sex was different. It was intense but slow and lots of fore play as we explored each others bodies and discovered a pleasure points that were previously unknown and finally she grabbed my nips and said Mike please slowly, make love to me and I entered her very slowly and very gently started to move in and out until she said Mike harder just do me. With that it didn't take long and I exploded collapsing on top of her. She pushed me off saying Mike you are so big I can't breath and I rolled over and we kissed until I said babe how about a shower? She said together and I said yes and she was up like a shot. The shower was fun and intense as we cleaned every inch of each other. We dried off and got dressed and went down stairs. No Riley and Jim yet and I asked Carrie what she was drinking and she asked for white wine and I said sure and went downstairs and brought a chilled bottle up, wondering how or why it was chilled. I poured her a glass and got a scotch for myself. Then Jim and Riley appeared, I said drinks are whatever help your self. After one drink, I said Jim it's time to get the girls home, Jim you staying here tonight? I have tickets to the game tomorrow. He said I'll check and most likely be back.

I got home and found Ryan cleaning up and he said I saw your dad leave and then the girls leave and knew the place was a mess so I figured I would get a start on tomorrow. I said dude Jim should be back any minute sit the fuck down and grab a drink and not iced tea. He came back with a beer and said Mike where is you dad off to? I said California my brother got beat up in jail. Apparently he is a mess but will survive. Just then Jim came in and Ryan said Mike I better leave? I snapped why? Damn, Mike you drive me nuts and now you have Jim here and he is super hot as well. Ok Ryan, I get it but everything isn't about sex and I'm off limits, the rest is up to Jim and you. Jim looked at Ryan and said dude, I'm betting sometime soon but not tonight. So chill the fuck out. Ryan relaxed enough to have another beer and then simply said good night. Jim looked at me and said we should tag team him and I laughed and said Jim there are rules. So we going to the game tomorrow or watching it on TV? He said TV please and I said I was hoping you would say that. We chatted for a while and finally he stood up and said Mike heads or tails and I said Jim I'm in a very kinky mood you sure? He said yes and I said let it hit the floor Heads. It landed and I said Jim you might be sorry my room and get nude and just stand there while I lock up. When I got to the room Jim was naked standing in the middle of the room and I said dude this will be unpleasant, last chance to opt out. He shook his head yes and I said lock you hands behind your neck and don't move.

Jim this is not about controlling you this is scratching a kinky itch I have, please kneel down and get on all fours. I left the room returning with an enema bag full of warm water. I gently pushed the tip in his ass with no lube and he asked what you doing and I said shut up and do not turn around. I unclamped the hose and he said holy shit Mike and I raised the bag to increase the pressure. He said please stop and I stood up. Jim there better not be an accident. The bag emptied and I jerked the tube out of his ass and said Jim please stand up. He did and I said hands behind your head and do not move. You will feel cramps, when that happens breath deep and thing pleasant thoughts and relax, you have 5 minutes before there is any relief. And I knelt down and started playing with his very erect cock and then I grasped his balls and squeezes and he screamed, dude that fucking hurts, I stood up and spit in his face and said shut the fuck up, that just bought you another minute. It 6 minutes I said hands and knees and crawl to the toilet and get on but don't let any out. He sat there and I know it was very hard to do but he held it. I leaned over and said now if you eat my ass you can let it all out. I turned around and he grabbed my hips and went at my ass ant squirted the enema into the toilet. When he said he was down I said let's take a shower and I cleaned him off and kissed him and said bud you ok and he said yes, that was something really different but you need to remember something I am not Ray. With that I turned him around and said you better bend over and I shoved my cock balls deep and he screamed. I pounded him till I was close pulled out and shot all over his ass. I turned him around and kissed him hard and made out and explored each other's mouth and I said dude, I'm not Ray either so keep up. You want another drink and we dried off went downstairs naked and had two mor drinks and a couple of cigarettes. Then I asked you ready for bed and he said yes. I grabbed him and said Jim, I know you are not Ray and I expect a very nasty original task next time I lose, let's sleep in my room. The sheets in the guest room are already messy enough. BTW, we need to strip both beds so Ryan doesn't have to deal with it. We climbed into bed together nude, piled on the covers and fell soundly asleep.

I woke up, pulled the covers off slapped Jim on the ass and said I'm going for a run, you coming? He said Mike you are totally nuts, no fucking way in hell am I running in the cold. However, I'll get up and start the laundry and breakfast. I smiled and said you will make someone a good wife. He pulled me down turned me over and shoved his cock balls deep in my ass and pounded me and at the last second pulled out and shot all over my ass. He scooped up his load turned me around and shoved his cum covered fingers in my mouth and said, I told you I was not Ray. So fuck you and fuck the bets, just deal with it. I reached up grabbed his ears and said James you are fucking awesome, I deserved that. Yes you did and it was not because of what you did to me last night it was that sick thing you do to get the last word. Now strip your bed and I'll get the guest room. Jim, stop for a minute, please. I looked him straight in the eye and said, bud your not in charge either, so you strip my bed and I'll do the guest room and we both laughed.

We finished the laundry, put new sheets on the beds and I started coffee and Jim started bacon and eggs. We sat eating and I said Jim. How was last night? Well with Riley it was different and more sensual and romantic than the other times and I guess less needed. Then the enema, I have had a few as a kid, but the way you adjusted the pressure to punish me was different and holding it for 6 minutes was hard. I almost lost it when you squeezed my balls. Jim, I don't care about all that how is your head? Mike, good I like experimenting but I was serious about not being Ray. Jim I really hope that is true on many levels, not just when you punish me. Jim, this morning when you took control, that blew my mind, that never happens to me. We need to remember that neither of us can be in total control or it will end up with one of us being Ray. He said Mike, earn it cause I am not second team. BTW, we both have offers from Penn State. I said that's fucking awesome but I bet neither of us go there. He said no bet, I'm not sold on the We are Penn State thing, I just laughed.

Just then Ryan came in and said Mike can I use the beer in the refrigerator that was left in the apartment? I said Ryan sure, you have a date and he said, Mike you are not available so I figured what the fuck. Yes, I am having a guy over to watch the game. I said have fun but don't ask silly questions, if it's up there use it. I said Ryan, Jim and I bet the Steelers lose and Jim screamed, no we don't and Jim and I laughed and Ryan shook his head and laughed. Just then the phone rand and it was dad. So dad how was the flight? He said good and I asked about Bill and he said he is a mess with a broken rib and two black eyes and a number of bruises, a real mess, but I actually think he got the message, he is not tough enough for a life of crime. Meeting with the attorneys and the prosecutor tomorrow. So Mike, did you wait till I was out of the driveway to take Carrie upstairs? Dad you know me better than that I gave it 10 minutes, have a good day and I hung up before he could say anything.

So Mike, were you serious about betting with Ryan and his date and I said nope, well not in the way you took it, I was just fucking with you. So Mike another bet before the game? Jim we just changed the sheets, well I am planning on winning and was thinking the basement. Dude,I need a break in case I win. He stood up and said heads or tails and I called heads and it wasn't. He said basement, strip and hug the pole. I got up and went down stairs and did as requested. He came down and rummaged around for a while and found some clothesline and secured me tightly to the pole. Then I was blind folded, and I remembered how much I hated that when Jeff was involves, I heard a swish and a crack on my ass and I screamed and Jim said scream again and I'll gag you. Another wack followed by two more quick ones and a third very hard one. Jim came over and said I don't know how you are not screaming but you will. He stepped pack and hit me hard across the legs just under my ass and there was a whimper, Jim said so that a good spot. He stopped and was gone for a while and I heard something swishing and the damn there was a wicket blow to my ass and I screamed. Fuck dude what was that? He said a rod, I found, you have a choice now 4 more with the rod or drink my piss, all of it the coffee makes me piss, I did not answer and he said so you choose both and there was another wack and another scream and two more sacks and two more screams. Mike, either you drink my piss or I breed you ass, please be man enough to answer. Jim, that's not a choice the bet rules say condoms or pull out. So find another choice, please and there was another wack and yet another scream. My bet, asshole my rules. I said then it has to be piss, that rule is important.

He untied me had me get on my knees and positioned the tip of his cock on my lips and said Mike, open please. I did and he let the piss flow and I swallowed and swallowed and swallowed. He finally stopped, helped me to my feet and said you ok? I spit in his face and he slapped mine and I laughed and said fuck dude that was fun but my ass will be hurting for days. Mike, you were a trooper and we both have very dark sides and will be very interesting to explore. I said Jim, you better fucking believe it. Let's go watch the game and no more bets. But fuck my ass hurt.

We barely paid attention to the game as we just chatted. Jim asked me so when I was beating you hard with my belt how did you not scream, I said Jim I can just manage and to be honest I think I won't scream with the rod the next time, I was the fucking blindfold that throws me off. So Mike were you an active participant or were you watching it happen to you. Jim both I was participating when you made me drink your piss. What about you? Mike I was participating and enjoying the shit out of it. Jim, to be totally honest if I would have know you had this dark side the enema would have been much more intense. Understand Jim this is what happened with my bets with Ray, they got very intense until he couldn't keep up and he was defeated. That scares me about this road we went down today? Jim, how bad is my ass? Well stand up and let me see, well the redness from the belt is almost gone but there are 3 pretty good welts on your ass and 1 on you upper leg just below your ass, I know that one really hurt. Ok, how do you know, were you ever beat like that? Yes Mike, I was and we are not talking about it, well not yet. I said Ok, what you thinking about dinner and Jim said home with the rents or I'll be grounded. See you in school tomorrow.

With me being home alone and nothing to do I went on that run that was derailed earlier, I did about 6 miles and took a shower. Retrieved the sheets from the laundry and put them in the closet and as I was walking by my room I looked in and thought this room isn't me anymore, it needs updated. Then I saw the extra math work took it down stairs, grabbed a beer and started working. I don't know what happened but I was so into it that I didn't eat and barely heard the phone and it was Carrie. I answered and she said amazing boyfriend, how was the game? I said Jim and I watched it on TV here. So who won the bet? Carrie there wasn't a bet, besides you wore me out yesterday. Mike thanks but I know better than that, but you were awesome yesterday and I said so were you. Especially when you screamed just do me harder. Michael, don't be a jerk. I said Michael is always a jerk so please talk to Mike. We chatted for a while and I asked what time it was and she said 10:30 and said shit, I've been doing math for 4 hours. Well see you in English tomorrow, I love you. Hanging up I looked closely at the math and 6 of the 9 were completed and fuck I have not eaten and was not hungry and there was no calculator. I just stood there rubbing my sore ass and stripped and climbed into bed, forgetting to set the alarm.

Comments are encouraged as this is my first story.

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Next: Chapter 54


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