Cast of characters - it was always about the bets

By Mike Simmons

Published on Dec 15, 2024

Bisexual

When I got to the gym JJ was there and was in the process of changing clothes. It was an awesome sight as he was stark naked and I immediately sprung a woodie. I just sat on a bench and started to remove my shoes and hiding my boner. JJ came up behind me and started to rub my back and massage my neck. MJ, I know that your hard so just get dress and we need a reasonable workout as it's been 10 days since we worked out. Then it's the Tavern for food and a long talk as we have woman troubles. I laughed and said well Winnie called me and I put that off till tomorrow as I wanted to talk with you. My bet is that she want to go to the Prom and is offering a no strings event. JJ laughed then said well her friend Alice called me and asked if I would take her to the Prom and we would double with you and Winnie. I just shook my head and we went to the weights and started our workouts. The workout lasted 90 minutes at a slow pace but we both got everything done and it ended with 15 minutes on a bike.

It was a quick shower and separate vehicles to the Tavern. The owner came over saying, damn it's been a while since you two were here. JJ told the guy that he had school and was giving flying lessons and didn't get home till dark. Then I almost laughed as JJ added he was between girls. Well JJ something will turn up but that's typical at this time of the year as you start to get ready for college. So what you eating? We both ordered Ruben sandwiches and added a basket of fries and iced teas. When the order came the food was intact but the drinks were changed to beer. JJ smiled and said MJ, why haven't we been here. Ok JJ how did you set this up with Winnie and Alice and what makes you think I want to be with Winnie. Besides Erin keeps calling me and her and a friend from VT want to come up for a few days. JJ laughed and said well I'll get us a couple of boxes of condoms and a couple morning after piss from Jim. Look JJ I'm not fucking the President of the University daughter. Besides she has an agenda and a ton of strings and compilations. That's a power couple I don't want to be part of. MJ, unless you shape up and do something on the field there won't be a power couple. Hell you will be a Rally Guy. Finish eating JJ and you coming to my place and we will see who is the Rally Guy. The owner came over and asked if we needed anything else. I said, just the bill. The owner sat down and said, do you guys remember back when you came here after games. We both shook our heads and I said well it was a good time. Mike I'm sure you know that each time multiple people paid that bill. You are still eating off that so it's no charge. He got up and said enjoy your evening. I still left $20 and JJ and I headed to my place.

At my place JJ went right to the refrigerator and asked, who is drinking all the beer. JJ, I'm must have been Cole, Megan was pissed about his drinking yesterday. JJ handed me a beer and we sat on the loveseat and started to make out. I was more than intense and he reached over and grabbed my dress shirt by my nips and pulled and buttons flew all over the room. Then he pulled my tee shirt off and started licking my nips, then sucking one then the other and I was so hard my dick was hurting. I pushed him away and asked why did you bother with the beers? There was no answer, he just got up, grabbed the beer and went to my room. He was sitting on the bed taking his shoes off. I simply pushed him on his back, grabbed one foot and pulled off the shoe and threw the shoe in the corner. The other shoe followed. I then undid his belt, un buckled his jeans and grabbed the bottom of the jeans, pulled hard and all that was left on was is underpants. They were off in a flash and JJ was laying on the bed with his feet on the floor and he was so hard his cock was jerking with his heart beat. I opened the night stand grabbed some lube. I smeared some on his cock and some on my hole. I spread his knees apart using my knees. When there was enough room I turned around and slowly moved around until his cock was by the hole and I sat down. I gasped as I went down so hard it hurt. I lifted up and went back down. Then I decided I wanted more so I stood up and had JJ get all the way on the bed. This time I knelt straddling his chest and leaned back until his cock found the hole. I then leaned forward and said fuck me and I kissed him. JJ started to move his hips as we kissed hard and intensely. Then I heard JJ shout I'm gone to fill your ass. Fill it he did as I felt 6 pulses of cum enter me gut. Before I knew what was happening JJ had my cock buried deep in his throat and it took no time at all and I filled his mouth with cum. JJ wasted no time and with his mouth full of my cum we kissed, sharing my load. When we finished we just laid there. JJ smiled and asked MJ, why do we need the chicks? I pulled him close and we kissed again and I didn't answer as we both knew the answer. Kids, image and the bigotry of the early 90's. JJ got dressed and said I'll see you in the morning and he went home.

I just laid in bed and was about to pull the covers up and get some sleep when my phone buzzed. I looked at it then connected the call saying, hi Erin what's up? Mike, why are you so hard to get a hold of and you don't return calls. Erin, I was in Florida on vacation then someone died and I was in New York for that, then home for Easter and then back in New York. Back here I worked out and then JJ grabbed a bite to eat. There was just no time. Well Mike, I want to come up for a visit and the first week of June works best for me. Erin, I told you that is my graduation week, so it's not the best for me. Before you go on Memorial Day weekend is complicated as that the Prom. Like I said before, I'd be glad for you to come but your time frame isn't the best for me. Well Mike, I was hoping you would make time for me. Erin, I'll see you on campus this summer. She said, fine and hung up. I just shook my head and set the phone on the night stand. I got out of bed, went to the bathroom. With that done I turned off the light and pulled up the covers and went to sleep.

I was up a few minutes before the alarm and quickly dressed in gym shorts and a short sleeved sweatshirt. I opened the door and took one step outside and went right back inside and pit on sweat pants and a hoodie. I was now running a tad late and JJ bitched about that saying it's cold out here and you are fucking around. I shrugged and just started off. JJ's mood improved but when we got to where we turned usually turned around I just kept going and JJ yelled, what the fuck dude. However he kept running. About half a block later I turned and headed back but picked up the pace. JJ simply adjusted but when we got to his place he said, ok asshole now you need to get you ass to,school and be super nice to Winnie. I want to go to the fucking PROM. Oh, and when you decide to change the run or the workout it would be great if you told me. I smiled and said well know you know, the run is longer and faster. As for the workouts TBT. with that I simply went to my place. Every aspect of the conditioning program was being increased, well, for me. JJ would have to adjust to a longer and faster run. My workouts were having increased reps and he could do what was best for him. Hell our programs were different in any case. I'll explain it to him and I'm sure things will be fine.

I put coffee on and took a shower and shaved. I dressed in clothes that met the bare minimum for work and a good bit over dressed for school. I filled my travel mug with coffee and jumped into the Wrangler and headed for school. I laughed out loud when I saw JJ was there sitting in his truck, obviously waiting for me. We got out of the vehicles at the same time and JJ came right up to me and asked, so what the fuck is going on with you? Look JJ, I'm in awful shape and I need a faster and longer run, I'm sorry I didn't talk with you about it. I'm just not in a good place. Ok MJ, what about the workouts? JJ, I'm increasing mine and you should do what you need to do, it shouldn't change things. JJ just shook his head and went into the building. I knew that didn't go well and I realized that I was super stressed out. We were a couple of days away from May 1st and a month from the end of school and for some reason that bothered me. I knew I needed an appointment with Dr. Adams, my head doctor. I was definitely setting that up this afternoon.

In both AP English and AP History it was a lengthy review for the pending AP tests and both teachers loaded me down with work that I missed. Physics was the same but much less interesting for me as I decided not to take that test. Too much work was piling up and I needed to finish shit for CMU. Wen class was over Winnie was quickly out the door and when I finished getting more work from the teacher she was waiting for me. She immediately asked Mick, when can we talk? I smiled and asked, so do you still have lunch next? She laughed and said, yes but do you really thinks that's a good idea. Us being together will cause a stir. Winnie, do you really thinks that's anyone still give a shit about what I do Winnie just shook her head and said Mick, I don't often get a chance to teach you a lesson so let's go to lunch. We chatted as we made our way to the South Cafeteria. When we walked in together there wasn't much of a reaction. We both grabbed a tray and I grabbed a burger and fries and an iced tea. Winnie grabbed a salad and also an iced tea. I paid for both meals and we found a table that was empty. As we walked to the table people started to notice. I heard, look who is here for lunch. Someone else said, more important look who he is with. I just took a deep breath and sat down. Now everyone was watching us. I took a drink of my tea and looked a Winnie and we both laughed out load. Then I looked at Winnie and said YES. Mick, what did you just agree to? I shrugged and said yes, we can go to the prom. Understand that doesn't mean more, at least not yet. There is a condition, well 2 conditions. We double with JJ and his date and you stop calling me Mick, I'm Mike. She smiled and said, well Mike I'm sorry about what happened, it was stupid but this isn't the time or place, are you free for dinner tonight. I thought for a minute and asked if she could meet me at work today? She agreed and I said any time after 5:30. I was going to take her to the new restaurant as it was open for employees until 11:00 and a big weekend event Saturday and a Grand Opening with a band, the Clarks, a local group named after the Clark Bar, a uniquely Pittsburgh candy bar manufactured on the North Side. With that done, I dumped the burger and fries and headed to the office to sign out. As I left the Cafeteria I looked back and Winnie was surrounded by group girls all chatting excitedly.

At the office there was the usual security check and very quick as I had nothing with me. I took the elevator and was quickly at my office. While my computer loaded, I called Dr. Adams and got an appointment at 9:00 AM Saturday. I was doing my routine end of the month review of the company and was as usual pleased with what I saw. There wasn't any division that wasn't making money and every trend was heading in the right direction. The Giant Eagle card thing was simply a cash cow and I smiled when I remember how hard a gave dad about the deal. The most improved segment was the grade book initiative and that was Dillon and his hard work. I needed to let him know how much I appreciate his effort. Just then the phone on my desk puzzled and it was the operator saying that there was a Jim McComas on the line for me. That name was familiar to me but why would the President of the university be calling and being so informal. I asked that he be told that I was in a meeting and to get his number and I would call him back when the meeting was over. I hung up and quickly realized that this was about Erin, his daughter. Before I could even think about it Heidikamp appeared at the door and asked for a few minutes. We sat in the casual area nd he put three folders on the table and said that the folders were for three condos. The locations were the strip District, Mt. Washington and Station Square. I immediately cut the place in Mt. Washington as it was no convenient to getting around but would have the best view. It was also the most expensive. I told him we could look at them on Thursday starting at 3:00. With that done I went back to my desk and picked up the phone and dialed the Blacksburg number I was given. On the second ring the call was answered by a woman who said Dr. McComas office. I said, hi this is Mike Simmons returning Jim's call. There was a moment, well actually a couple of moments of silence and then I heard, please hold.

The wait was longer than I expected and when Dr.McComas got on the line he said Good Afternoon Mike, sorry for the delay, I had an internal issue to deal with. I smiled and said, well I hope I didn't cause an issue by asking if Jim was available. He laughed and said, well Mike I deserved that as I didn't use my title and knowing you, your reply was expected. Well sir, we haven't met. Mike , I had to sign off on you academic arrangements here and with CMU. As a result I know a lot about you and yes I had conversations with your High School Principal and coach. Oh and of course the people at CMU. Those guys are very unhappy that they have to share you with us. Well Dr.McComas, what is it that I can do for you? Well I'm going to be in Pittsburgh for Big East meetings May 28, 29 & 30 and I would like to meet you and was hoping you could be fr for dinner on the 28th. Mike, if are free that day, I'll contact Jim Messer and see if he could join us. I understand you are both busy and the end of high school causes further complications. Well Doc I'm free, where will you be staying? Mike, I'm at the the Sheraton at Station Square. Well Doc there is a great restaurant there or we could go to my Country Club. Mike, we should stay close so the restaurant near the hotel would be great. Ok Doc, I'll tend to the reservations. Mike, I'm thinking 6:00 would be goos and it will be just the thee of us. I let out a sigh of relief as this didn't involve Erin. We chatted a for a few and then we ended the call. There was nothing to do but wonder what he fuck was up. I called JJ and left a message and told him about the conversation and to expect a call. I ended the message by asking him to be in charge of the morning run tomorrow and reminding him that we were working out on Wednesday.

With that all accomplished and nothing left to do but meet Winnie I went for a walk around the construction site. I hadn't done that in like forever and I really enjoyed talking with the workers. I know that I should do this more often both because the workers appreciated it and I enjoy it a lot. As I walked back to the building I wondered if construction would become my thing. I must have been out there longer than I thought as my phone went off and security told me there was a young lady there saying she was to meet with me. I decided to play a game and asked the security guard to ask the young lady her name. The security guy got back on with me and said Mike, she says her name is Mrs. Simmons. I laughed out loud and said I'll be right there. Well so much for that game and the new score was 1-1. Back at the building, I thanked the security guard and went to where Winnie was sitting and when she stood up I pulled her into a big hug and whispered in her ear, you being Mrs. Simmons is so far out there that NASA hasn't detected that yet. She shrugged and said well I guess we will find out. I laughed out loud and said let's go for a walk and then we can grab something to eat. My new sports bar is open this week to employees and the grand opening with a band all that is this weekend.

Outside we walked through the construction site and a few workers yelled, hey Mike and I waved and we kept going. When we got to the marina Winnie asked Mike, isn't this a bit much to house your boat? Laughing I said Winnie, I don't have a boat and there isn't going to be one. The rivers are finally clean enough, especially the Monongahela, that they will be used. Most of the mills are closed and this is one of the ways to move forward. We have more waterfront property than almost everyone else and we need to use that for fun as well as industry. I notice that she was getting cold so we headed to the restaurant. When she saw the stage she asked about the band that would be playing. Winnie it's the Clark's. Mike isn't that the group that started at IUP and are struggling a bit. Winnie that correct but they are very popular locally and have just signed a major record deal. As with everything else I stress local ties. Mike, at some point will that hold you and the company back. Winnie, the company is national with many government contracts and a nice mix of local and National companies. It being located at the site of an old mill is huge for the region. As for me, I'll always remember my ties to the region, lets eat.

At the restaurant we were quickly greeted and seated at a t booth with a view of the stage. The place was less than half full and I was ok with that. Jake appeared quickly say in it was good to see us. Mike, we were very busy for lunch but dinner is usually slow. I smiled and said Jake, don't stress out as it takes time. Jake got called away and I told Winnie that there was no alcohol available. When the water came over, he said good evening, I'm Ryan and will be your server. We ordered drinks and it was 2 iced teas I also ordered wings in honey barbecue sauce. I was looking around basically seeing if anything had changed and the only thing I noticed was thar there were 2 more tv's. Winnie was looking at the menu, then asked what's good? I shrugged and said, I have no idea as I haven't eaten here before. Ryan appeared with the drinks and I asked for a few more minutes to decide what we wanted. When the wings arrived Winnie ordered a chicken sandwich with lettuce, tomato, mayonnaise and fries. I decided to order a Ruben and fries and wanted to compare that to the Tavern sandwich. While we were eating the wings, I looked at Winnie and said so you hooked up with that skinny dude because you thought I wasn't paying enough attention to you. First of all, you never said you felt like that. I'm hoping that that little walk around the place today gives you an idea what I am ultimately responsible for and then you need to remember that about 500 people works for the company and while I have a lot of help I'm ultimately responsible for all that as well. So tell me was there more than a few sessions of swapping spit With that dude? Michael, we were broken up so what Paul and I did or didn't do together is none of your fucking business. Perhaps you want to talk about the girls you were with? Winnie, I never cheated on any of them and you can't say that. Mike, I already said I was sorry and that it was a stupid mistake. We are good together but understand if you play games like asking that guard to ask me my name, I'm playing a game right back at you. When you answer a question with a question I'm coming back with a question. I laughed and said, well Winnie you seem to think this is more than a Prom date and I'm committed to only that. If there is more all I can say right now is that it will be what it becomes. The food was very good and my Ruben was outstanding. Ryan came over and said that there was no charge and I shook my head, opened my wallet and handed him $50. He looked surprised and I said, do what needs done with that and keep the change. He smiled and said, thanks.

I walked Winnie to her car and she leaned against the car and I just stood there and she said what no kiss? I opened the car door and smiled nicely. To my surprise she took a step closer gave me a hug reach for my crouch and squeezed and said well Mike at some point this will want attention and I might have the same reaction. I shrugged and said well I guess we might find out, drive safely. Walking to my ride I noticed her feeling me up resulted in no reaction. Damn she has started to push back and that was something she didn't do before, I liked that. Back home, I started on the work from school and was at that until a little after midnight. I simply stripped, pulled up the covers and was instantly asleep.

I was awake because of the alarm and that always pissed me off me off but I was determined not to be upset today. I checked the weather and dressed in shorts and a sweatshirt and walked to meet JJ. He was waiting and said we were doing 10 - 40 yard sprints and I saw a cone up the street so he had actually measured the area. It was just a tad up the hill and we took off and JJ beat me by a lot. We walked back and did the sprint again and again. When we finished the last sprint, we were both exhausted. On the walk back JJ asked, so Mike what did you get us involved in, I was hoping never to meet the University President and now I'm having dinner with him? JJ, I have no idea, all I'd did was returned the call. Then JJ said I heard you had a less than romantic evening with Winnie. JJ I had no intention of being romantic and when I didn't kiss her she hugged me and at the same time felt me up. JJ, I had no reaction to that at all. JJ laughed and said well I'll have to check to see if you are still functioning after we workout this evening. Dude, that sounds good to me, I'll see you at school.

At school, I went straight to English and handed the teacher my work. He looked at it and said Mike, I'm going to spend more time looking at this than you did working on it. I shrugged and replied, well then you shouldn't have given it to me or given me something that required more time. I happen to think it's very good but it didn't require me to read as I had read that a while ago. Back when I had time to read. With that I sat in my seat and waited for class to start. I turned in the work in History and got no reaction. Physics was different as I wasn't quite finished with it. I couldn't do lunch at school as I had to change clothes and meet Heidikamp to look at 2 condominiums. Without seeing them I was leaning to the one in the strip district. At home I changed to black jeans and a light grey mock turtleneck shirt and a light jacket and very casual shoes. With that done I got into the Mustang and drove to work.

As I was doing the security shit I was told that Jordan wanted to meet with me as soon as I got here. That concerned means it was unusual for him to want a meeting, it was typically me asking him for a meeting. I asked the security guy to let Jordan know I was here. Going to my office I saw Dillon in dad's old office and I stuck my head in and asked him to stop in for a chat once Jordan was done with me. Mike, that would be great as I want to chat with you as well.

In my office I went right outside as it was a nice day and things were turning green but the river was still dark and dirty. Jordan was quickly there and asked, Mike why are you looking at places to live. Why can't you stay where you are for two months. You will be moved to Blacksburg soon enough. Jordan, I'll need a place when I come home on breaks and I'm giving my place to Cole. Mike, the places you are looking at are expensive and renting is a waste of money. Jordan, I don't want anything permanent, just something for three years. Mike, stay away from the North Shore, it will be the place to be in 10 years or so but they will build a stadium or two there. The strip district will develop sooner and you should buy there. I laughed and asked Jordan why are you telling me this and not my real estate expert? Jordan said, Mike I'm the financial guy and I think the other guy is a jerk. Just find a place and let me deal with the details. That sounded like a win to me so I said, thanks Jordan I'll do that. We chatted for a few and I asked Jordan to let Dillon know I was free.

About 5 minutes later Dillon appeared joining me outside and asked, so Mike what's up? Well Dillon, we haven talked for a while and I wanted to tell you how much I appreciate you efforts with the Grade Book program. He smiled and said thanks but the Navy Cadets are driving us nuts. It's a damn good thing they have an honor code because they are very good at finding ways to skirt our security. The upside is that the system is very secure. Mike, to be honest I could use help with that. Dillon has Doc been around? Mike some but I can't till I can turn it over to him. Dillon, can you hang in for another month? Dillon smiled and said sure. Great, so how is the new office? Dillon shook his head and said, it's very big and I'm looking to spend some time there soon. Just then my office phone rang and I told Dillon, I have to look at apartments, stop in for a visit anytime. With that I took the elevator to the lobby and greeted Heidikamp saying I'm driving and we are only looking at the one in the Strip District. He shrugged and said fine.

Thanks for reading and the notes.

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