Cast of characters - it was always about the bets

By Mike Simmons

Published on Apr 28, 2020

Bisexual

Mike's rules, just a refresher

Rule 1. Quiet

Rule 2. What happens here stays here

Rule 3. We always have each other's back

Rule 4. Listen

Rule 5. stay in your lane

Rule 6. It's none of your business

Thursday's run was so good and relaxing that I did an additional mile and if it wasn't for school

I would have done more. At home, I said hello to dad showered, shaved and did my fucking hair, which needed cut again, grabbed a travel mug full of coffee and went to school. The morning classes went well and I was enjoying Spanish, which I assumed just reflected my fantastic mood. At lunch Jim pulled me aside and said he had all kinds of toys to try on Sam. I asked about that and he said an enema bulb, nip clamps, a ball gag and anal beads. Then he said I made another stop and got sounds. Now I was really excited. As lunch was over I found Sam and asked, if he was ready for Jim and I this afternoon. He replied, Mike is there a choice? I said that there is always a choice and he could opt out, but with every decision there is a consequence. He said Mike, I'm good. I said meet me at the car immediately after school and the task will be kinky, intense and last two hours. He took a deep breath and said fine.

As I was walking to the car after school I ran into Jim. He asked if the camera and pictures were a good idea? I laughed and said the camera is a perfect idea but no pictures, just so he thinks there are and Jim broke up laughing. Sam was nervously pacing by my car and I said, dude if you are man enough get in. There was another deep breath and he opened the door and climbed in. At home I offered him a beer and he jumped at the chance. Then I told him I would wait for Jim but he should go to my room and take his clothes off, put them neatly on a chair and stand in the middle of the room with his hands locked behind his head. There was another deep breath and I turned him around grabbed his ears and said, look this is the last chance. He said that he was good and went upstairs.

While I was waiting for Jim, I filled a pot with warm water and dropped in a bar of Ivory soap and waited for Jim. He looked at the pot and laughed, saying damn you are serious. I said upstairs just play along. I put the pot on the floor and asked Jim to drop his pants and told Sam, suck is cock. As Sam knelt down and took Jim's cock in his mouth I pretended to take a picture. Once that was done, I said that's enough, Sam get on all fours and head down and ass up. Then I filled the enema bulb full of the soapy solution, making sure there was as little air in the bulb as possible gently slid the tip in Sam"s ass and slowly squeezed until it was empty. I asked, Sam have you ever had an enema? He said no. I said well relax and I'm just getting started. After three more he was clearly uncomfortable and I said deep breath and that will help. Then I filled the bulb 3/4 full and squeezed the liquid and some air into Sam's ass. Then I said just relax and I got a butt plug, showed it to Sam and said there is no easy way to take one of these scream if you need to and I positioned the plug by his hole and shoved it it, till it held and Sam did not make a sound.

Jim and I helped him stand and and I looked at him and his hard on and said, are you enjoying this. He said it's not that bad. I went over and gave him a giant kiss. I looked at Jim and asked, how long should we make him hold this? Jim said 10 minutes. I got a pack of cigarettes and lit one and gave it to Sam, saying a reward. There can be rewards or punishments. He took the cigarette and took a big drag and blew it out his nose. I took the cigarette opened the window and threw it outside. I looked at his hard cock and he was leaking pre-cum. I went over slapped his cock and grabbed his balls and squeezed until he screamed. Damn he was still hard. Finally Jim said time and I led Sam to the bathroom. I said sit down and pull the plug out and if you make a mess you will lick it up. He pulled the plug out and there was a lot of soapy water expelled. He tried to hand me the plug and I said, dude that goes in your mouth. Empty out and come back in my room.

About 10 minutes later he came back in and I said what took so long? He said he was making sure he was empty. I smiled and said now for the real fun on all fours again. He was slow reacting so I went behind him and slapped his ass. He moved into position and I added some lube to his ass and started to insert the beads and Jim pretended to take another picture. The beads started small and got larger and I slowly inserted all six. Then I stood him up tied his hands behind his back. I asked Jim to gag him and Jim did using the ball gag. Then I got his underpants and put them over his head, so he would have difficulty seeing. I handed Jim the nip clamps and he attached them with screams being muffled by the gag. Then I went behind him and roughly pulled the first bead out and there was another scream. Jim and I took tuns with less noise as the beads got smaller. Then I went over and tugged on the clamps and saw tears in his eyes. I leaned close and asked, do you want to stop? He shook his head no and I noticed that his cock was still very much at attention. So I said Sam is this fun for you? He shook his head yes. I asked you want more? Again a shake of the head indicating yes. I took the gag off and asked, so you a sub fag? He just looked at me and I tugged on the clamps and he screamed and I said, that requires an answer. He said, I don't know. I said, ok let's find out, gust stand there we will be back.

Downstairs Jim and I grabbed a beer and sat in the kitchen. Jim said, so Mike what now. I said a hard ass beating, what do you think of a mouth soaping? Mike, that's a bit extreme. I said, yeah your are right. I said what about we both fill his mouth with piss, beat his ass and let it end at that? Jim said fine but ass beating first. I said you put the gag back on and I'll grab a couple of belts. While Jim was putting the gag on, I found 3 leather belts. I went up to Sam, pulled on the clamps and said would you like these off and he shook his head yes. I grab each clamp and at the same time I remover resulting in a scream. I said bend over the desk and I folded the belts and went hard at his ass. After 5 very hard swats I gave the bets to Jim and administered 5 more. I pulled Sam to a standing position removed the gag and asked, so how was that? He said, it fucking hurt. I said look at your cock, it's been hard for an hour so part of you are enjoying this. I said because you have been such a good slut we have one more thing, then your done. We led him to the bathroom, had him kneel in the shower, I unzipped positioned the tip of my cock at his lips and said, you need to open and drink and if any gets spilled I'm using the ivory soap to clean your mouth. He opened and I let loose and he kept swallowing till I was done. Then Jim took a turn with the same results. Then I decided to simply fuck him, I got a condom leaned him against shower wall and pounded his ass till I filled the condom. Then I said on your knees and take the condom off, no hands. He bit my cock and I slapped him and when it came off I said just spit it in the toilet. I helped Sam to his feet and said, take a long hot shower and join us in the kitchen.

Down stairs Jim and I were amazed at what he took and how turned on he was. Sam wasn't long and I tossed him the cigarettes and handed him a beer. Then he looked at us and said, that was fun but only Mike shot a load. I said so, he said I was so close but I thought for sure you would fill me with cum. He said, guys please jack off into a glass and I'll add mine and drink it all from the glass. I said fine but I want a picture of you doing that. He said, don't you have enough pictures? I assume that's to protect you from me breaking rule 2. They are not necessary and yes, Mike. I said yes, what? He replied I like being a sub fag, when we doing this again? Sam, we are not having that discussion today and to be honest with you that was not a serious question upstairs. However, at some point we are having that discussion as for me jacking off in a glass so you can drink it, NOT HAPPENING. Jim can do what he wants. Jim laughed and said, Sam you will have to win a bet to get that done. Ok, Sam I need to get you home and you are right about the pictures and rule 2. I'll keep the film and only develop it if you don't keep your word. Remember it is all those rules all the time. He got up and said, I don't give a shit, I'll never turn on you guys, didn't the game prove that? I said, ok get your ass in the car. Jim you going home or hanging around or going home? He said home, I need to be nice to the rents.

I don't think we were halfway to his house and I pulled over and said ok dude explain? Mike, I can't but fuck that was fun and I was turned on big time. Sam does Kathy turn you on or is it just sex? He said Mike, please stop asking me questions that I have no answers for. Fuck, I like sex, but this was awesome. I said, ok Sam give it some time and we will talk again. Again go slow. I just like sex of different flavors and today was fun but sex with your sister is very good and even awesome, besides I want kids. Ok, Mike please just be a friend and not my parents, I have enough of those. At his place, I went in and found Carrie was at work. Then I thought of something and asked Sam to walk me to the car. I said Sam, don't plan on loosing every bet because we will just change thing up and in winning you can't always be the sub. He laughed and said, I had to walk out here to be told something I already knew. Have a great night and he went inside shaking his head.

Back at home I cleaned up and was getting ready to eat when dad came in. He went right into the office and came out with two drinks and handed me one. I said ok, what's up? He laughed and said, absolutely nothing just waiting for you disrupt my day. I said Dad, I got nothing. Well nothing that involves you, I just need to move the Kyle thing along. Dad looked at me and said seriously, nothing going on? Nothing at all, just a quiet fun day. So what is Mason working on? I said, I have no idea and I'm not asking. We ate leftovers and chatted. I asked about Megan and he said the real work in DC started Monday so expect you new brother sometime Sunday. I said dad, you better set some rules as he will have friends over. Dad laughed and said, Megan and I have already had that talk and I'll let Cole fill you in and we can compare notes. Dad, I am his brother not his rent, so good luck with that. He laughed and said, I guess I asked for that. I said yup and went to my room.

I realized that while I was reasonably caught up, it was not caught up to my standard, except in math. I started with Spanish and while it was good and I caught up, I thought a better conversational approach might be helpful. I thought for a while and called Rob. We chatted about the game and what they expected from the final? He seemed confident. Then my radar exploded as he mentioned they were playing Central. I thought shit, do they have a kid named Allen on the team? He said no and I was relieved. Then, I asked about more help with Spanish and he said I should ask JJ as he is very good and with the state tournament he would have more time. He said 20 some games is killing his school work. I laughed and said your sex life? He said that too. He said, by the way thanks for dealing with the Freshmen. I said thanks and have a good night.

I reread the current English assignment and scanned the next one, then moved to history we were into the US build-up to WWII. Again I was into the economics behind all that. As I was finishing up my phone rang and it was Carrie. I asked how was work and she said she is learning CAD and doing build outs. I told her I was glad she was busy. She said she might have to miss the game Saturday. Then she said they were so busy that they were hiring one or two more architects and possibly a designer. She said Jorden has no idea where the business jump is coming from. She said that she had school work to do so she had to go. I said me too and hung up.

The list of shit I had to follow up on was growing and I was thinking of a half day at the office tomorrow. I went downstairs found dad in his office. He said I knew if you went upstairs there would be shit. Yes you can work half day tomorrow at the office. Dad, how did you know? Mike, I saw your reaction to Mason being up to something, then there is the Kyle thing and I'm betting on something else. I said dad, all of a sudden J & J Architects are getting clients and adding staff. Dad thought for a minute and said the Mayor? I said that's my guess but more importantly WHY? I thought for a minute and said, I think he wants them too busy so we can't use them or that it delays our current project. Dad, I'll take it slow until we get to the bottom of all this. Mike, once you do please meet with me and the Major before there is a reaction. I said absolutely.

Upstairs I called JJ and he asked about Sam and I replied rules 2 & 6. He said what the fuck are those rules? I laughed and said get a notepad and a pencil, 2 is what happens here stays here and 6 is none of your business. He said so MJ what do you need? JJ your phone to call out on occasion. However, I want Spanish lessons. He launched into a couple of sentences of Spanish. I thought a second and said exactly? He said you understood that or was it a lucky guess. I said I knew roughly what you said but could not reply in Spanish. What you couldn't say exactly? I replied, exactamente I couldn't come up with it that fast. He said you serious? I said yes. He said, ok I got this but it takes time. I said fine. I told him Carrie might miss the game Saturday as she has to work. Damn, MJ give her the day off. JJ she doesn't work for me. We can talk at lunch tomorrow, good night and I hung up. It was late and I took a shower, dried off and jumped into bed.

Friday it was the usual morning and a quick shower, the hassle with my hair and off to school. I went looking for coach and found him at his stadium office. I asked for a moment and he said, sure have a seat. So what's up? Can we check on my attendance second semester? Yes, but why? Well, I have missed a lot of school and I know there are rules for that for next year. Mike it's more than 20 days. Coach please check. Ok, let's go to the school office. Nancy said hi Mike long time since you have honored us with your presence then she said that new look is fantastic. I laughed and was called into coach's office. Coach said Mike this semester you have missed 11 days but 3 of those was for a funeral so they would be excused so 8 days. Please keep it under control, I don't want to have to go to the league to have them excuse some days. That's one of the disadvantages off being Mike. Coach, can I get released after morning classes with work release? Mike, I'll take care of it this time but how you doing all this and you are still first in your class. I said, coach I thought my grades were slipping. He laughed and said not as of 3 minutes ago. I said thanks and went to class.

I talked with Carrie between classes and told her about my day. She said that the game was not possible and I kissed here and said, it fine. You free for dinner? She said, Mike I'll let you know, but I'll be working all weekend there is a deadline on Monday and I might be out of school. Damn, you are busy. Spanish was interesting as JJ was showing off a little but shit I could follow him. After class he said so MJ were you following? I said, yes I'll be free for dinner. MJ said I'm buying when you can say that in Spanish. I thought for a minute and said, si, estoy libre para cenar. JJ laughed and said I could have starved waiting for that answer. He said mas rapido (more quickly) I laughed and said, so, te llamare (ill call you). JJ laughed and said perfectomo (perfect). Then I drove to the office.

On the was I thought that was easy and routine but fun. I thought I would call JJ and continue the game. He answered and I said, como estas, amigo ( how are you dude)? He replied, tengo boias otra vez (I have blue balls). I laughed and said thanks, but I'm not helping this time and he laughed. I pulled into the parking lot laughing.

Inside, I went directly to the cafeteria and grabbed some coffee and headed to my office. I stopped and chatted with Ruth and asked about Mason. She said he was in the building somewhere. I said ok and went to my office to a neatly organized desk. The first and most complicated call went to Jorden and voice mail. I called Jodie and also voice mail. That left Tim and when he answered he said in a pile on your desk, I said thanks.

I found a draft contract in a pile and started to read. The non-compete was there as we had discussed. The one thing I didn't like was the terms if he added something to Enterprises as I felt it was too costly to him. I revised it in red pen to mirror the same terms as J & J but limited his participation. Then I called Kyle and left a message for him to stop in my office when he was free. I started on the piles on my desk and realized that except for Kyle's contract and a few construction items everything was taken care of and shipped to the right person to resolve.

I then asked Ruth if there was a way to track down Mason and all of a sudden I heard Mason please see Mike Simmons. Thinking I was in school, I shook my head and said thanks.

Just then my phone rang and Ruth said there is Jorden on line 4 for you. I said thanks and picked up the line and said, Jorden I hope you are free to talk. He said sure, what's up? Well Jorden where is all your new business coming from? He laughed and said well you Mike and your dad. I replied, that's strange as neither of us has talked with anyone about our project or your firm. Mike, the 2 new ones said you recommended is for their project. I said nope, not us. He said, shit someone is trying to occupy our time. I said exactly? Ok, Jorden the business is good but how can you handle this influx? He said, well I hired another young architect and that helps a lot, we need a designer but don't have the money for that and we are cash strapped. Ok, Jorden how much do you need, he was quiet for a minute and said 20k. I said, I'll call Tim and get that added to your loan, but no new projects and there will be no more money. All the other terms remain the same. Oh, DON'T LET MY PROJECT FALL BEHIND SCHEDULE. Mike, I promise and you are about a week ahead and all the structural steel has been delivered. It's a happy project and keep Mason involved there, it helps a lot. I asked about the other projects and I took notes and was planning to get to the bottom of this when Mason appeared. I waved him in and finished up with Jorden.

Well Mason, what's happening, I hear you are working on something? He said, Mike the construction project, keeping your piles sorted. I laughed and said what else? Oh, my real estate license, there is course work. I'm taking 2 classes and one at night at CCAC. Ok, what's the rush? I want to be in commercial real estate and build fucking buildings, or rather see them built. The whole thing is fascinating. Ok, what are you doing at the site? Well I attend the construction meetings, general PR with the union workers and meet daily with Allen before I come here. Ok, do you need anything? He said, all good. Then I asked what Dillon was up to and he said you need to ask him. Well Mason, I'm asking you. Ok, Mike don't be upset he is working with Kyle, he is up to his ears in computers and printers and he attends the technology part of the construction meetings for Kyle. Thanks Mason, when you successfully pass the RE course submit the information and we will pay for the classes. There will be a non-compete if you accept the financial assistance. There was a big smile, followed by damn thanks. Just then my office phone rang and it was Kyle asking if I was free. I said yes and he said I'm on my way.

Mason and I were still chatting when Kyle knocked on the door, I waved him in and thanked Mason. I asked Kyle about the wife and kid and were assured they were good and that the wife was glad, we worked thing out. I asked if he had seen the proposed contract and he said that he received it this morning. He said he was good with everything and I said well I'm not, my proposed changes are in red on page 3. He flipped to page 3 read for a minute, grabbed a pen off my desk and signed it, saying your turn. I signed and called Mason in and said, please sign here as a witness. Then I said, Mason please make three copies and bring them back in here. Oh, don't read the damn things they are none of your business, other than Kyle will be staying for a while.

I asked about Dillon and Kyle said, Mike he won't be doing the real estate stuff, I want him taking night computer classes. Ok Kyle, how does he feel about that? Mike he is all I and I have him applying at CMU. Well, actually I'm telling the dean he is accepting him. I laughed and said so should I be looking for two assistants? Mike, you have 6 months, let's let the dudes find their way. Right now it looks like there are two future departments heads or more in your future. I said, Kyle, I'm seeing that, but it will be what it becomes. Just then Dillon was at the door. I waved him in and said please sit, we were just talking about you. He just looked at me. I said relax it's all good. I hear you want to take computer classes with the big boys? He said, I hope so. Well Dillon I have a proposal for you, you pass and I pay if you sign a non-compete. He smiled and said deal. Mason arrived with the contracts and I handed one to Kyle, smiled and asked if they minded if got some work done?

I called Brian and he said, 4:00 on a Friday and naturally you call with shit for me to do. Brian I have a couple of companies I need you to look into, this is a heads up. I'll email the info later. Oh, have a great weekend and hung up. Then I called Tim and told him that I made changes to the contract and the drafts were signed. He said great, what else? I told him about the dynamic duo and contracts would need developed and that details would follow over the weekend. He said, thanks and enjoy the game. I finished up a few things and called JJ and said, amigo, rees libre para cenar? (Dude are you free for dinner) He laughed and said no, tengo una. ( no I have a date) I said, cool get those blue balls taken care of and he said, exactamente. I called Cole and said, dude I hear you are moving in this weekend, do you need any help? He said, it will only be two trips and I'm good unless you are free Saturday night? I said, I'll let you know, what about Sunday? He said school work and I need to spend a ton of time on math, I said ok and hung up.

At home dad said, so how was work. I said good and that Brian is working on the Architect thing. I'm in for the night and just might drink. So where is the wife and I said working. He laughed and said it's early why don't you take me to the club for dinner? I said ok, coat and tie. He looked and I called Oakmont and said that I was Mike Simmons and would like dinner reservations for dinner, me and a guest for 7:00. I was told fine. It was a shower and a change of clothes and me in a blazer, grey shirt and a tie and dad in a suit. Traffic was reasonable and we got to the club 20 minutes early and inside we headed to the bar and the manager stopped me and said, Mr. Simmons your table is ready, unless you want to wait. Sir, I apologize but what is your name, he said I'm Clark Dillon but Clark to most of the members. I said thanks Clark, if our table is ready that will be great. We were seated and I ordered an Arnold Palmer and dad ordered a scotch. We chatted and I told him about the police thing the other night and our drinks came as ordered. As I was looking over the menu someone approached, introduced himself and said Mike, welcome to the club, it's great to have young members. I said thanks. It kept up one after another and dad was laughing and I said let's order so we can eat and stop all this. Before we ordered, I had talked with 6 members and 4 business cards. I thought damn, I need to carry that shit. Dad had his typical steak and baked potato and I had a veal chop, pasta and a salad. We both passed on desert and dad had coffee and I had a cappuccino. The visits started again and finally I said dad, let's just go. He laughed and said, I told you.

The ride home was uneventful, until we got to the same place where I was stopped earlier. A police car was behind us with lights on and I pulled over and said dad go slow. Again two officers one on each side of the car and damn it was the same officer and he said, good evening, license and owners card. I said they are still in the visor from the other night. He took the information and went to the car. He came back and asked, Michael have you been drinking? I said yes sir and ..... he smiled and said out of the car. He asked me to do an agility drill and I said no, I require a blood test, I let you off the hook 2 nights ago, this time I insist on a blood test and by the way I had 2 Arnold Palmers and a cappuccino. I was turned around and cuffed and I said dad call Tim and meet me at the hospital. I was helped into the squad car and I said ok boys let's get this done. I was walked into the ER and a blood test was ordered and blood was drawn, I stopped the tech and said drug and alcohol so these assholes are totally dead. While we were waiting for the results, Tim came in followed by the chief of police. The officers were told to un-cuff me and that I could go. I said, Chief I need to wait for the results. Ok that's your choice. Then I said, what's with these two? That's two stops in a couple of days? Tim, said Chief answer the question, he deserves an answer and it is a reasonable request. He said, no comment as it's a personnel matter. I said ok Chief and I called the Post Gazette told them who I was and said, if you can get a reporter to Jefferson Hospital we have a great story for you. Tim, looked at the Chief and said, game on.

Just then a doctor appeared and went up to the Chief and said, here are the test results and tell your boys enough of this shit, it costs money and we have real tests to run. This kid, is clean and I wish I had his fucking numbers. The Chief said, Michael you can go. I laughed and sat down saying the PG is on the way and they are going to be asked to call Robert Morris campus police and my school principle. Tim will give permission for all the information to be released to the media. The Chief asked if there was a way to end this? I saw Tim shake his head no, then pointed to me. The Chief came over and said Mike, I'm sorry. I said, Chief I hate that word, what happens now? Then he said, Mike your reputation will take a hit if you go to the press, this can be very hard or very easy. I just started to laugh and everyone was looking at me and I said said, you just went from a nice chat and a compromise to a total war. You should stay around for comments. Unless you want to resign, you see people just don't threatened me and walk away. I got up and changed my seat. A few minutes later the PG reporter and a camera crew from WTAE came in. I thought damn this will be fun. The Chief threw fire on the entire issue by shouting GET THOSE CAMERAS OUT OF HERE. Tim looked at him and shook his head. I got up and went outside and the media followed. Tim talked with them and then they came over and talked to dad and me and I was asked to say as little as possible. I said sure, thinking possibly. The Chief came out and approached Tim. There was a animated conversation and Tim said too late asshole. Then we were told we couldn't hold this demonstration outside the hospital. I went over to the media which were filming all this and said, guys I'm going home and gave them my address. On the way home dad and I talked about this and we felt that since this was twice in three days and that they caved the first time and I passed the blood tests, we were on solid ground. At home there were 2 more local TV stations. I looked at dad and said we needed to get a handle on this.

Thanks for all the comments, they are appreciated and keep me writing.

If possible during these trying times please support NIFTY. Stay safe and healthy.

Next: Chapter 121


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