Cast of characters - it was always about the bets

By Mike Simmons

Published on Oct 22, 2022

Bisexual

Winnie's POV

That was the first meeting I have ever had with a boy friend as he scheduled dinner to talk. But this knight in shiny armor is different than anyone I have ever dated and I like that. I just wish he would remove some of the armor. There is rarely a crack in that armor and that's why I was caught by surprise the other day when he said "I love you" as he ended the call the other night. I was was so shocked, I didn't react. Then nothing since and I know he is working through a lot. He worries me as there is that history of addiction that runs through the family. Mom and booze and Bill and drugs but nothing with his dad, well except money. Mick seems to need a lot of caffeine with the coffee and the iced tea. I also wonder about his need to work out all the time. He is obsessed with that. That might be his addiction but he is fucking ripped and I hope that doesn't go away anytime soon.

When I first saw Mick, in 8th grade, he was polite and very nice. I mistook that for him hitting on me and when I said I wasn't interested in a jock, he shrugged and moved on. He was still very nice to the new girl in school. I was just not interested in getting involved with the biggest man on campus while adjusting to a new school. He stayed that way until the end of 9th grade and he was still nice but there was this don't mess with me attitude. There were people he simply ignore and he had a very close knit group and the center of all that was Ray his cousin. With the start of 10th grade he was running the building. He was super intelligent and yet worked at it. When with a group he was the "star" and the bigger the group the more control he seemed to have. He wasn't the star of the football team but everyone knew that was a matter of time. He never acted like he knew it but you became special the second he paid any attention. Then Ray was gone, Jeff was gone and he rebounded right to Carrie. That was so cute and so public that I wanted to puke. She was one thing around Mick and a conniving bitch when not at his side. Then there was rebound after rebound until I got hooked up as his lab partner. He was still dating someone and when he started flirting, I knew I was next if I wanted that. I simply kept resisting and the more I did the more he flirted. Then the teacher threatened to split us up as lab partners. The first date was just that a first date and he was charming and polite and honest. I knew that because dad had worked for is company and was super impressed. I had watched him for years and knew a lot more about him than he did of me.

That overnight trip to his cabin was super fun and him checking with my parents was cute. When it was obvious that I wanted sex that night, In front of the giant fireplace, I knew he was thinking no way but settled on what the fuck, I'm horny. Thinking back that was the last time I was in charge. He plans everything even when we have sex and I won't force the issue but the damn condoms are a pain in the ass. I was surprised there was no reaction about my college choice and like the "I love you" comment, I'm just waiting for the other shoe to drop. Well as he always says, it will be what it becomes. Well unless I find a crack in that armor.

Once JJ left, I jumped right into the shower and took my time enjoying the hot water and for the first time in a while I was relaxed after what I thought was a good day. Laying in bed I thought about Winnie. It was funny that she asked if I was going to make her break up with me. It was funny as that is what occurred with everyone but Carrie. Well thanks to Jodie here she was again but this time I just laughed as some day soon she would be gone. All her belongings scattered in a place she hated, all that was left was finding that place. I simply fell asleep.

I woke in a great mood, well rested and no visit from Carrie. The run was good and JJ and I were normal again, so much so that Cole asked, was the make-up sex good. JJ laughed and said dude, that wasn't a fight and if we ever have one it will be a mess as one or both of us will be in the hospital. Then he laughed and said Cole, remember you are one day closer to the breakup with Jessica. Cole smiled and kept running and was very quiet. I reminded JJ about the gym and he laughed and said for sure. School was good, well until I signed out and Dr. Johnson saw me and asked Mike, will you be here tomorrow or are you feeling sick? I laughed and said well Doc, I have a meeting tomorrow at 11:30 at the Naval Academy so I won't be in. Mike are you changing your mind about VT? Doc, do you think they will let me graduate in 3 years with 2 degrees and wave the military obligation. He laughed and I said me either. It is however an important business meeting and when I get back, I have something that might interest you. What did you need? Mike, on letter of intent day we would like to show off the the 6 of you signing with D 1 programs as we were going to have a press event and each of you verifying your selection. We were thinking in the auditorium around noon with media and any student that wanted out of class. Doc, that's sounds great but I'm not changing anything at this point so there will be no surprises from me and that letter is going via fax at 12:01 AM. With that I headed to the office.

At my office I found Liam and Dillon drinking coffee and chatting. I laughed and asked, do either of you have an office of your own. Dillon said Mike, we were just saving you from having us summoned. I laughed and said well next time bring coffee for me and Liam held up a mug of coffee. I sat down and Liam said Mike, Dillon has a request and I'm here to stop you from killing him. I laughed and looked at Dillon and asked, what's up? Mike, I need you to wear a jacket and tie tomorrow for lunch with the Admiral. I shrugged and said fine, what else? Dillon laughed and said, nothing else. Hell, I didn't expect to get that much. We discussed the two meetings and I agreed to be respectful and professional with the Admiral but the cadets will need to be relaxed and less formal by a lot. We need to work and those guys could turn it into a shit show. Dillon looked at me and i said LOGIN INFORMATION. If they share that information it could get messy. He shook his head and said, well my concern is that we have it encrypted using the best encryption codes possible but there is someone on that campus can crack that code and change grades. Mike, I assure that if there is an attempt that fails alarms will go off and the system goes down, but it could happen. We then moved to a discussion of the agenda for Friday, the Hotel and dinner. Reservations were made for 6 at the Chart House, which had great views and seafood and steaks, it was one of the best restaurants in Annapolis. Then I confirmed wheels up at 7:30 and said we can discuss a return time later. With that Dillon went on his way and I asked lim to stay.

Once we were alone Liam said Mike, I thought about what we discussed yesterday and it scares me a bit. I know Allen is excellent but I'm going to fuck up. I smiled and said Liam, that's a given and it won't upset me unless you don't learn from the mistake or if you make the same mistake more than once. You have no idea how many times I fucked up on this building. Sometime for fun ask Allen about ceiling tiles. Liam, we have a deal about Cole and gold and I'm not looking to change that unless you two ask for a change. Right now you are making around 20K and starting the first of the month I'll have that increased by 5% then when I leave for school, starting in August, I'll have it increased another 10%. There is a catch, we will be providing a list for you and me to discuss for whom you will not be able to work for should you leave or are terminated. Liam the list will be 10 companies all doing business within 100 miles. Mike, for how long? Liam, one year from the date of separation. Liam just looked and I said dude, we are giving you a lot and I trust you but we as a company need some protection. Liam, Tim has a couple of new guys please feel free to discuss this with them and you will find this isn't unusual. I hope this doesn't upset you. Mike, I hate these types of discussions. I laughed and said Liam, there could easily be a time in the not too distant future when you will be sitting where I am. You could simply decide on a simple non compete and the list would be a hell of lot longer than 10. If you want a different attorney, I'll pay for that personally. Just push the start of the restaurant. Roger that, Mike.

Tim knocked and I waved him in asking what's up? Mike, some information on the hanger. I know you are taking the Jet to Annapolis tomorrow but Jim is taking me to Blacksburg in the twin tomorrow. What do you feel you need in a hanger? Tim, I'm not looking to do much more than house my jet but by building it a bit bigger we could accommodate some smaller rentals. I actually don't think many jets would be there at any rate. The basic size would be 100' wide by 80' deep but the door need to be at least 53'. That would easily get my jet in and that's the most important. Mike, how are we paying for this? Tim, I'll simply write a check. I think about $76,000 should be enough and hopefully less as we is in Virginia and not near DC. Tim was quiet for a moment and then he asked what else aren't you telling me? Tim, there is a lot that follows this. Once constructed, we need a management company to run the hanger and to service the jet and I would want it available with 45 minute notice, fueled and at the service line. I'll find that company. Tim, I just want it there and that management group will be expected to have it rented to me and others. Hell, they need a hanger really bad. Tim, the jet belongs to Enterprises and that company will pay the rent, well to me. Tim laughed and said thank God, I'm not involved with your taxes. Then he said Mike, I'll shoot for a 20 year lease and we can deal with that once you are out of there. Tim, I made an offer to Liam and he might ask one of your guys about it. He gets an honest assessment, ok? Mike, how about we take hike along tomorrow and see how he like negotiations? Tim, that would be awesome. Oh, he needs to know it was your idea to include him. Mike, that won't be hard as it was my idea, he left shaking his head.

Once I was alone, I got up and went to my desk and called Jordan, CFO, and asked for a meeting early next week. He laughed and said well did you bankrupt us? I laughed and said not yet but I'm working on it. He laughed and said well this is more than unusual so what do you need? Well, it's personal finances. Ok Mike, Monday say 1:00? Jordan, that's perfect, I'll have everything we need. Mike, I'll need investment statements and banking statements. Jordan I'll have all that and clear the afternoon. Mike, I'll see you Monday.

I spent the next hour looking at the financials for Enterprises and laughed as I saw lots of numbers and and a lot of commas and I really liked all the commas. Then I looked at some bank statements and knew Jordan would throw a fit about the cash. My investment statements were at home in a pile of mail that I look at weekly if that. Hell, I but everything on a card and that was paid by someone here. I did look at the statements and sort out personal and company use. I knew that was all coming to an end and there would be two cards one for company nd one for business. With all that done, I locked a bunch of shit in the file cabinet and put the key in my wallet. It was time to get to the gym and see what type of mood JJ was in.

At the gym I found JJ walking out of the locker room. He went right to the weights and was setting them for his workout and I quickly changed. When I got out of the locker room JJ was all business and we did his bench work and then changed the weights to the amount I use. JJ stopped and asked so is it the fucking added weight or more reps? JJ, neither as I'll do the regular workout. There was a big smile and and he spotted for me. The workout became casual at that point and I did add 10 more sit-ups and that went without comment. In the sauna I sat against the back wall and JJ was beside me but on the side wall. We each had towels over our junk and I figured he was hiding a boner like I was. So MJ, does your choice of rides have something to do with your mood? I laughed and said, I have no fucking idea, I just needed to clean off and started the Stang, so I figured I would use it today. What made you ask? MJ, you seem to be back to normal today. Well JJ, work is sorting itself out and Tim and Liam are going to Blacksburg tomorrow and start negotiations bout a hanger and I have found a place for Liam that doesn't make it look like he is my spy. So yes, I'm good. So JJ do you want to grab a bite to eat. JJ shook his head and said nope, dad is insisting I do an IFR flight plan. He get really nervous when we fly near the capital as there are so many flight restrictions. Approaching Annapolis from the south is the easiest but it is much longer so my plan will be a fine line between DC and Baltimore. He will check it over seven ways from Sunday but I have a 3 redo limit. After that he does the damn thing. MJ, I have Mia meeting me at the airport and I told her if she was a minute later that 7:15 she was staying home. Do you want a ride or are you getting Winnie. I shrugged and said, no idea I'll let you know. JJ said MJ, I'll see you there at 6:45 if you don't need a ride but I'm driving so park you toy cars. I'll be leaving my place at 6:20. With that we both took longish hot showers.

At my place with an easy evening I decided to stop in the house and check on the rents and Ashley. Colleen came right to me and said Lad I spent a couple of hours cleaning your place today nd that is quite a pile of fancy rags thrown in the corner that need to be dropped off at a dry cleaners. I smiled and said well I'll need another fancy rag tomorrow so I'll deal with that on Monday. She laughed and asked lad, so you have more that 4 suits? I smiled and said well 5 that fit. She shook her head and asked are you here for dinner as well? I replied, yes please. In the game room I found dad, Megan and Ashley. I grabbed Ashley and sat her on my knee and was bouncing her and she was laughing. That was fun for a while as she started to fuss so I sat her on the floor and she immediately leaned forward and crawled to dad and grabbed his pants and pulled herself up. I was amazed but as soon as dad picked her up there was a loud fart and I just laughed as she had filler her diaper. Megan laughed and said well that's on you, I think you know how to deal with that by now.

Once we were alone Megan asked Mike, what do you have going on this weekend? Well, I'm leaving early tomorrow for Annapolis. It is lunch with the Admiral and some of his staff and then a meeting with the 4 cadet leaders. Wh have installed a grade book program and it was tested and the Cadets are about to find out about it. Everyone will know exactly where they stand at any given moment. There is also many options that the professors can access and assignments can me sent via the program. If this works as a grade book program for school districts dad and I can retire. She laughed and said well that might work for your dad but that better not be an option for you. Megan, there will always be politics. She shook her head about that. So Mike, when you flying back? Megan JJ nd Dillon are long and so are the girls. The weather will be warmish, mid 60's. They can show while we work and then dinner and fly back mid morning Saturday. She laughed and said, thanks for leaving the after dinner plans out. Mike, why JJ? Oh, Megan he is the pilot as we are taking the jet. Speaking of leaving things out where is Cole? Mike, he left right after class for Latrobe as AP is in town for business and he was invited for dinner and a chat. Mike, I don't think he knows what's up but there wasn't much of a choice. Megan, I doubt that it is something bad as it isn't a special trip. He might just be showing Cole off to some members. Megan, how are thing with him and Jessica? Megan laughed and said no change that I'm aware of and I reminded him that if she got pregnant I would castrate him. I found that hysterical and said Megan, you might never know if that happens. Thankfully Colleen yelled, dinner is ready.

Dinner was a salad and lasagna and bread sticks, which were home made. We had a great time at dinner and I was amazed that dad was as aware of what was going on at work. One of the trusted team members must be keeping him up to speed. He did ask a lot of questions and I wondered why as he seemed to know the answers. Megan said she was starting a jury trial and said she liked them after the lawyers were done selecting the jury. The case involved a dispute over a trademark and that was all we were getting as she didn't want us to know what she thought. We could go to jail for inside trading. I laughed and said well, I'm only buying Apple stock, so I think I'm good. She smiled and said, yup. The whole time we ate Ashley sat in a high chair munching happily on a biscuit. Once we were finished dad and I cleaned up and Megan got Ashley ready for bed. Now I had things to do and said goodnight and went to my place.

First thing I did was to check the clothes and found my last suit which was charcoal and I added a blue shirt and red tie and appropriate accessories. Then it was Jeans and a hoodie for the flight home and casual slacks and a sweater for dinner. Next I called Winnie and I filled her in reminding her that we wouldn't get into the room till 3:00 and that she would need to dress for shopping and lunch. Dinner dress was casual and that there was time to shower and change before. Then I said she should dress for temperatures in the 60's for a high. She laughed and asked if I wanted to come over and pack for her as well. Well babe, I don't care what you wear but you do need to be civil with Mia. There was no reply to that so I asked if she wanted picked up at 6:15 or if she wanted to meet at the airport at 7:15. Mick, if I can sleep longer, I'll see you at the airport. With that, I simply said good night. I immediately called JJ. He answered laughing saying, I just god dad and when he asked for the flight plan, I handed him one that took us right over the Supreme Court, the Capital, the Whitehouse and finally that Lincoln thing and then to Annapolis. He laughed and said well if you can do that I'm sure there is a real one that keeps you out of trouble, I'm not even checking. Have a great trip. Well JJ, pick me up in the morning and if you are attending lunch with the Admiral it is a coat and tie nd we can't get into the rooms to change. MJ, as a future business major, I'm coming to the meetings. Besides I know the military shit better than you or Dillon. Oh, I told Mia she needed to be nice to Winnie. I'll see you in the morning. With that I was done for the night and spent some time on my finances and then took a long shower and jumped into bed.

I was up way before the alarm and put coffee on and quickly dressed and put my other shit in a large backpack. It was cold but I wasn't putting on a dress coat and when JJ beeped I grabbed my bag and suit coat and was outside in a flash. I laughed as he was in his truck in a dress shirt and tie. JJ was on a mission and we went right to the airport. The jet was there as was our twin engine and the jet was being filed and JJ went right over and I laughed when he asked if that was jet fuel. The guy found that anything but amusing and JJ went right inside. I started the walk around and outside check and JJ and I finished with him double checking a few things. I opened the cargo hatch and put our bags inside and Dillon and Lexi appeared with him carrying 6 coffees and Lexi having a bag of breakfast sandwiched. JJ was all smiles as he grabbed a sandwich. Their luggage was loaded nd Dillon had on a very conservative suit and a red tie. Lexi was in Jen's nd a leather jacket. I almost dropped over dead when Mia and Winnie arrived in Mia's car and seemed very friendly. We got everyone on board and JJ secured the hatch. I got on first and went to my seat on the left and JJ fired some instructions to the passengers.

JJ sat in the right seat and immediately strapped in and once he adjusted his head set he looked at me and asked if I had the check list. I shrugged and he went right to work and with no notes or list did it perfectly. Then he looked and asked ok mister perfect memory was that acceptable? I simply said yup and somehow you knew that. We were facing in the right direction and JJ asked, are we clear on the right? I checked and gave him a thumbs up. It was a perfect battery start and the same start on the left engine, no battery. His coms were spot on and as we were taxing he got on the intercom and said, good morning this is your pilot James Messer welcome to MJS Air. We will be in the air shortly. Flight time to the Naval Academy is approximately one hour and 20 minutes. The weather is clear with a high of 67 degrees, enjoy the flight. Once in the air JJ asked if I wanted to take over and I declined wanting to watch this guy fly. He wasn't relaxed but not nervous, simply comfortable and in charge.

Once we were on the ground and at the service area JJ looked at me and said, why didn't you take a turn? I smiled and said it was more fun watching you be so professional. Almost immediately a bunch of people appeared and were securing the plane and I heard someone say, where in the fuck is the adult who flew this thing? Someone else said better yet how did they get a NASA jet? JJ just watched what was going on and one of the ground crew came up to him and said, we have done this hundreds of times, it's good. JJ smiled and said well it's the first time you did this for a jet I flew in here so what you do and how you do it is important to me. Just then a van pulled up and out jumped a fully uniformed guy who was definitely a captain. I went right up to him and said, good morning Captain I'm Mike Simmons. Mike, I'm Wes Carlton and unless the Admiral is around Wes will work. I immediately like the guy and introduced the group. Wes then said, unless you have other plans we have breakfast waiting for you guys in the officer's mess.

Breakfast was anything you wanted and I was careful not to over eat as there would be lunch and later dinner. Wes said that he was an instructor and taught nuclear safety. Once we finished the girls were dropped off in town for shopping and we showed them where the hotel was and said we would meet them there around 3:30. They couldn't be happier and we were taken on a tour of the grounds. I laughed at the number of groups running in formation all in uniforms. The tour ended at 11:10 and 10 minutes later we were seated in the Admiral's private dining room. Right at 11:30 the Admiral and another guy entered the room and he was introduced as Commander Dobis. I shook hand with the Admiral and introduced Dillon (that was unnecessary) and JJ as Jim Messer. The Commander asked Jim, how is your dad? Well commander he is well and enjoying life. He is on a business trip with the company attorney. Oh, when I heard that there was a NASA jet here I assumed he flew you guys dow. I said Commander, actually the jet was partial payment for a project we did for NASA and JJ flew us down and I was the copilot. JJ needs the hours as PIC, we both can operate that jet.

That was enough small talk for the Admiral as he said, I have spent some time looking at the program and I have to say it exceeds our expectations. However, I have one concern. There is a lot of personal information contained there, how secure is it. Dillon immediately spoke up and said Admiral, our company does a good bit of government work and those clients include DOJ, DOD, FBI, NASA and State. We have the best encryption available and any unauthorized attempt to access the program will meet more than one stone wall and your administrator will be alerted immediately. With that being said with enough time and determination there is a very remote possibility that the system could be hacked. Your midshipmen need to have strong passwords and NEVER share them. The Admiral smiled and said, well that is exactly what the people at the Department of Defense told me. Thanks for being more concise than they were. In your meeting with the 4 midshipman you will need to be direct and not take any crap, they tend to stick together. The Captain will be there if you need assistance. I looked right at the Admiral and said Sir, I wanted this meeting off campus and understand that wasn't possible but we will meet with them alone and I will deal with any attitudes. The Admiral smiled and said, I'm sure you will and the Captain wait outside. Just then a Porter appeared and lunch was ordered. I ordered a Cobb salad and JJ had a club sandwich as did Dillon and we all had iced tea. I laughed at what the others ordered as it was a lot and none of it was good for someone to eat.

The Admiral and Commander left and we stayed in the dining room with the Captain. Wes's was much more laid back and we had a great time chatting with him and I learned a lot about the life these midshipman have. Eventually we were seated in a conference room. It was a large table and we spread out trying not to have it look formal. JJ laughed and said MJ, the minute you stepped on campus it became formal. Right on time there was a knock on the door and the Captain got, went outside and closed the door behind him. A couple of minutes later the door opened and 4 midshipmen entered and stood behind 4 chairs all together. At least they were not at attention but not at all indicating the relaxed state I wanted. Before I could say a word JJ said Good Afternoon gentlemen. I stifled a laugh as the responded in unison good afternoon, sir. JJ just laughed out loud then he said guys, I am James Messer and I know that doesn't mean shit to you guys but I am a Air Force brat. I spent time in Florida, and 5 years in Colorado Springs Nd just as I was entering junior high dad joined NASA as an astronaut and he flew 3 missions and two were as mission commander. I survived Texas football and partied and fit in with all that while being tops in my class. With no more missions possible dad moved me and the family to Pittsburgh where I Met Mike and continued to excel in football and academically. I'm along because I felt that NASA jet here. That's the long way of saying I know the games and how to play it so sit the fuck down and cooperate. They looked at each other and sat down.

JJ continued and said this dude isDillon and he is President of MJS Technologies and was in charge of the project here. He graduated with a 3.8 GPA from the Kay's School of Business at the University of Pittsburgh with a Minor in computers. He is currently taking graduate computer classes at CMU. He knows this system better than anyone so when he talks listen. That character sitting over there with his jacket on the back of his chair and his tie hanging like an ecclesiastical stole is Mike Simmons, it would take an hour for me to list all his accomplishments so here are the Cliff Notes. He is number 1 academically in his class, could have graduated last week, will enter VT next Fall as a Sophomore and graduate in 3 years or less. He is current enrolled at CMU in computer science. He is Chairman of his Company, MJS Enterprises and has a charitable foundation that provides scholarships to caddies and he his a member Oakmont Country Club and 2 others. Oh, he was my copilot as he is certified in that craft as well, it was just my turn. With that JJ looked at Dillon and said your up?

Dillon looked at me and I shrugged and he said guys, I'm not the type to just talk and present. What do you know about this application? They looked at each other and I guessed the Senior guy spoke and said, we were briefed after breakfast and have been in class all morning, so not much. Is this program running yet? Dillon said yup but you have to setup an account and login. They went outside in the hall and returned with laptops. They instantly logged in and Dillon was asked, now what. Dillon spent the next 10 minutes walking them through the process and most of that time was lecturing them about password security. Dillon explained that this was current and then showed them how to send a message to a professor. There were a lot of questions and Dillon was on top of every one of them. The entire thing lasted just under an hour and they were pleased as it was scheduled for 2hours and they had free time. On the way out one of the midshipmen looked at me and asked, so what do you do? I smiled and said, as little as possible. He smiled and said well you would make a good Admiral. With that we briefed the Captan and headed for the van and the girls.

Thanks for reading and for the comments.

As always if possible remember Nifty in more than your thoughts and prayers - a donation is always welcome

Next: Chapter 353


Rate this story

Liked this story?

Nifty is entirely volunteer-run and relies on people like you to keep the site running. Please support the Nifty Archive and keep this content available to all!

Donate to The Nifty Archive
Nifty

© 1992, 2024 Nifty Archive. All rights reserved

The Archive

About NiftyLinks❤️Donate