Cast of characters - it was always about the bets

By Mike Simmons

Published on Sep 1, 2019

Bisexual

I got home in plenty of time before dinner with dad so I opened the last folder - trust. I started to read and was immediately overwhelmed it was unlike the other 2 which were in normal language, this was all legalese. I needed help. I looked at the clock and said, SHIT I need a shower and it was getting late. I did the works, showered, shaved, fixed my hair, brushed my teeth, but on a pair of kaki pants, a blue long sleeve shirt, casual shoes and a blue blazer and went down stairs. Dad looked at me and said, damn I didn't think you owned clothes like that, I smiled and said I guess it is like the place in Florida, dad just said shit, let's go.

We got to the club, went to the dining room and I was looking for a quiet out of the way table, when dad said Mike over near and it was anything but private. I sat down just shaking my head. It started right away, a guy came over and started to snooze dad. The waiter came over and ask what we were drinking dad said my usual and I said iced tea, dad just smiled. Then a teammate came over, slapped me on the back and said, Mike, I hear you have been working out like a maniac, I just said, thanks, Jim. I'll see you next week. Our drinks came and mine was gin and tonic, dad just said, Mike I got your back, enjoy. I ordered a salad and steak, dad had a steak and a potato. It was also a continual stream of people chatting with dad. We finished dinner and dad ordered another round of drinks, his scotch came and this time I got an iced tea. I shot dad a look that said get me fuck out of here. Then one of his golfing buddies came up and actually sat down at the table, I was furious. I got up went to the men's room and then stood on the patio. Jim saw me and came out and we started to chat. So Mike, I see you enjoy these dinners at the club as much as I do. I replied, I would bet I hate it more than anyone else. So how do you think the season will go I asked , Jim replied, who knows a lot depends on Jeff and if we can keep him focused. I replied that's true for sure, but I'm working on that and he seems agreeable. Jim said, I didn't think you two were that close. Well Jim, Jeff and I are very different types, his image and mine are totally different as are our ultimate goals. Right now I'm about football and school, then it will be about school and something else. This is a big year for both, I feel my classes will be a bitch. He said, Mike I get that we should be in a lot of the same honors classes. Well, see you Monday, back to dad and the club noise. Try to enjoy you evening, I added.

I went back to the table and dad was there with a third or fourth drink. Where were you, he asked, on the patio I said, didn't think you would miss me. Are you ready to go? He said soon I sat drinking my iced tea, furious. Dad finished his drink and said ok, Mike we can go, I looked at him and said keys please, he reached into his jacket pocket and tossed me the keys. We drove home in silence, I pulled in the driveway got out of the car and went directly to my room and locked the door. Stripped, reached for my headphone and hit play and tried to relax and calm down. There was a knock on my door and I replied, good night, dad.

I just laid there for a while just chilling out. I took the headphones off found my phone and called Carrie. She said hi, what's up? Just wanted to say hi and thanks for for this afternoon, I hope I did not disappoint you? She said, while I wanted your sexy jock ass, I appreciate your wanting our first time to be special. I'm not like that often it is just that I find you so hot, I can't help myself. Look babe, it was very close for me to do what you wanted. I'm still horny thinking about it. Please understand, I am more than a sexy jock and you need to discover the other things I am and I need to help you do that as I need to discover who and what you are and you have to open up to me. If we do all that the sex will be mind-blowing. I'm not an expert, by any means, I just want our first time and every time to be great. Also, I will never have sex without a condom, no matter what. We chatted about school and our classes and found we will both be in honors English and history. She said, wow I am starting to see what you mean about being more than a sexy jock. I laughed and said, good night babe.

It was Saturday and just two days before football camp, I got up early dressed and went for a run. I was on my usual route and as I passed Ray's house there he was and said want some company. I said sure, but slow and easy, I'm in camp mode so not pushing it. We finished the run at his place and he said, juice or coffee. I said juice and we went inside, sat at the table and chatted for a while. I sensed there was something up but I let him get to it at his pace. I finished my drink and got up to leave and Ray said, you want more, I said nope, but I'll have a coffee. He said great and started to brew the coffee. As it was brewing he said, Mike can I ask you something? I said sure and he asked, where is your mom? I replied that she was in rehab and that when that was over she was not coming back, her and dad are getting a divorce. Ray got up gave me a big hug and said, how you holding up? I mean no wonder you are messed up in your head. Ray, that is only the tip of the iceberg. Bill quit school, got a girl pregnant, married her, has no job and is a drug addict. He left dad's condo and it is now for sale. The rest of it and there is more, I can't talk about. So you ready for football Monday, he replied, I think so. You want to double date, I was thinking Kennywood, if I can get Carrie to agree. Damn, Ray said when did you start dating that hot chick? Just a few dates and we are just settling in. He said I'm sure Amy will be up for it. Great I'll call Carrie and let you know.

I got home and dad was in his office, I stuck my head in and said good morning and went right to my room. Went to the shower turned it as hot as I could stand soaped up and started to stroke my cock and play with my balls. Eventually my finger found my ass and I rubbed the hole and inserted a finger and immediately shot a load. I cleaned the shower, dried off, grabbed my phone and called Carrie. Hi babe she said, what's up. Nothing that would be of special interest to you and I laughed and so did she. Seriously, you want to go to Kennywood with Ray and Amy? Well she said are you joining us or are you sticking me with those two. I laughed and said if you insist. She laughed. I ask if she would be ready at 1:00 she said sure, see you then. I called Ray and said, I would pick him up a little before 1:00, he said great Amy is good to go.

I stayed in my room and just chilled and cleaned up, changed the sheets and got things ready for the laundry. I went to the basement and threw a bunch of things in the washer, turned it on and went upstairs. I saw there was coffee and poured a cup and started for my room when dad say, Mike you have a minute? I went in sat in a chair and dad said, I'm sorry, I needed that. I replied fine, it was not what I expected, I mean to have dinner with someone and be ignored. What else is on your mind, he asked how is your reading going, I got up and said, I'll be right back. I went to my room and took two of the folders and went back to the office and said here dad, I have no input into these and basically I have no thoughts as they are what they are. The trust, that is another issue. The legal language I'd beyond me and I need help. Dad said I'll tell Adam you need help. I replied, if I want Mr. Finnegan I'll call him, but to be honest, I don't want him. Why is that Mike, because he told me there was nothing I needed to do, but I was able to decipher enough to see that i need to sign papers agreeing to the conditions you place on me. I want a different attorney, someone under 30 that I am comfortable with, so what I am asking for is a list of three attorneys I can meet with and see which one I am comfortable with. Also, I expect the money for this to come out of the trust. I understand he is your attorney and the legal guy for the company and the trust, I just want my own attorney. You alright with all that. Dad took a deep breath and said I'll get that done. Is there anything else. I said YES but not now I have a date. I won't be around for dinner see you tomorrow.

I picked everyone up and started to the amusement park, the place was packed as it was one of the last weekends for the year. We walked around and Carrie said, thunderbolt and off we went, we got in line catted and when out turn came we got on and strapped in. That's is a great one of the best wooden coasters in the country. We rode a number of rides and then to the old mill, a slow dark boat ride. Once we were inside Carrie leaned over and started to make out. We must have crossed the line or something because suddenly there was a light in our faces, we stopped and I just laughed. Then Ray decided he wanted to win Amy a prize, I figured I would try as well. Ray said, Mike I bet I win that bear before you do. Both Amy and Carrie money and said, here we go the damn bets. I looked Ray and said enough dude and he shook is head and agreed. The girls were all smiles. Ok, I asked who is hungry, everyone said yes, so it was to the potato patch for cheese cover fries and a drink. We had a great time and Ray won a bet and I won a bet. We got to the cars and I drove to Amy's house and they both got out with Ray saying, I'll call tonight. We got to Carrie's house I leaned in for a kiss and she asked if I wanted to come in, I took a big breath and she said, I'll keep all my clothes on, I promise. I laughed, turned off the car and we went in. Damn, she was right about the clothes as both her parents were home, I went over to her dad and said, hi Mr. Carter, I am Mike Simmons. He said nice to meet you Mike, I have been hearing a lot about you. I just looked at Carrie and her dad said, not just from her but from a lot of other people. Go downstairs and and have fun, well not too much fun and I smiled and said, thanks Mr. Carter, he replied I am Dave, and off we went. Carrie and I sat on the sofa holding hands and said, Mike, I had a lot of fun today, I smiled and kissed her. We just sat there quietly for a while then she asked, so what's with you and Ray and the bets. I said we have been doing this since we were10. We are both very competitive and it is just a silly game. So what happens to the loser, she asked, I replied he has to do whatever the winner says. So what will Ray make you do since you lost a bet today, hey, I said I won one too so in all likelihood they cancel things out. Mike, I can't help but notice you are way more intense than Ray in everything, you ok? I said, sorta, mom and dad are getting a divorce and my older brother Bill dropped out of school, got a girl pregnant and got married. No job and he moved out of my dad's condo where he was living. Your dad has a condo in California? Well it is for sale and in LA it should sell quickly, he hopes. Carrie, being around you, really helps, unless you are being a sex maniac. She leaned over and kissed me and said, Mike, I can't help myself around you you are smoking hot. I grasper, pulled her close and kissed her and started to nippled her neck and this time she pulled away and said woe tiger your turn to slow down. I said, yes it is and it is also time for me to get home and fight with dad.

I got home and found dad in his office drinking, he said, hey Mike you are home earlier than you said. Want to chat, I replied I said all I needed to say before I left this afternoon. Beside you are sitting there drinking for the third night in a row and I'm not saying another serious word. So either stop looking for answers like mom in the bottom of a bottle, we can talk then or if you prefer I make an appointment with you at work. Let me know and I got up and left.

I called Ray and it went to voice mail, shit. Just then dad was at my door and I said, now what he came over I got up and he tried to hug me and I looked him straight in the eye and said, please get out of my room, come back sober, I'm serious. You are better than this. My phone rang and thankfully it was Ray, I said good night and please close the door, which he did. Hi Ray, what's up, I had to get dad out of my room. He said I have been thinking, we both lost a bet tonight and that makes for interesting possibilities, you have any thoughts, I replied I hadn't thought about it at all. Ray said we should come up with something and both have the same task, I asked how far did he want to go? Ray said we should both think about it merge our thoughts into one task. Deal, I replied.

I tried to sleep in, but woke at the usual time, there would be no running, no working out, nothing as it was the last day before football practice. I just laid in bed and Ray and his damn proposal flew into my head. This was something really different, we need to find something we could do to each other at the same time. My first thought went to a flip fuck, but that lacked something. The I thought about a 3 way, that could work and I could involve Jeff. He would be all over that in a second. Then I thought about how this all started, four simple words "dude, suck my cock". That was it, we would simply strip and 69 till we both shot our loads and kiss with a mouth full of cum. Damn I was hard thinking about it.

I called Ray, I forgot how early it was and he was not happy to have been waken up. Dude, I figured out the perfect task and we can do it today. Dad will be going to the club for golf around 8:00. Come over around 8:30 we can have breakfast and then do the task. You going to tell me what you are so excited about, I replied, eggs or pancakes for breakfast. He replied, eggs and toast and this task better be hot.

I went down stairs and put some coffee on and was thinking I hope Ray is excited about the task as I was. Dad came in and asked, so Mike, you in a better mood, I replied it depends are you hungover? Cut the shit he said, I'm getting sick of your attitude. My attitude, I screamed, you're the one that is drunk all the time and I'm to just put up with all the shit you dumped on me this week. So where is the list of attorneys I asked for, you will have them before dinner tomorrow, anything else? Yes, it I wanted to take a date to the club for dinner, is that possible. He replied, Mike, I am the member and you hate that place, why would you do that. I hate the place because of all the attention you get, you are never left alone. Besides I want to do something very nice for Carrie. Ok, Mike I can set that up for you, but there will be no drinking, I replied, thanks I'll let you know. Oh, I almost forgot, give me your credit card. Dad can I ask why, he replied sure. Ok, dad why, he laughed and said you now have your own card and will be paying your own bills and there is a 15k limit on the card. You have to work out with Adam some financial shit, but there should be no problem. I assume you can work with him before you settle on an attorney. Sure, dad. With that he left for the club.

Ray came about 30 minutes later. He said what we doing and I said eating breakfast. I made scrambled eggs, a few strips of bacon, poured juice and we ate talking about football. When we were done and the counter was cleared I sad Ray let's go in the game room. He said sure. I said do you remember the task that started us down this path? Sure Mike, I said suck my cock. dude? Correct I said, there was no drama no foreplay, just me gettin on my knees and you shooting a load in my mouth and me spitting it out, he said yeah, something like that. So Ray, we are going to get naked and suck each other until we both shoot and then we are going to kiss with a mouthful of cum each, until the cum is gone. So let's get naked and get to it. You good, I asked and he smiled and took his shirt off. Before long we were both naked sitting on the couch, Ray leaned in to kiss and I said no foreplay, laid down on the sofa and told Ray to figure out a way we could both suck cock at the same time, he punched my arm and said you are an ass. Before I knew it his dick was in my face and he was sucking me. I started by playing with the head of is cock, licking the hole, and teasing him, then I went balls deep and gaged but kept on sucking, Ray was in a steady rhythm on my cock and started to play with my balls so I started on his as well. I could sense a change in Ray, his breathing was heavier and he was getting a little harder if, that was possible. Then I felt a pulse and my mouth was flooded with his seed, that brought me to the edge and no matter how hard I tried not to, I shot 6 squirts into his mouth. We separated and Ray turned around, staying on top he kissed me and we each opened our mouth and the cum mixed together. We kissed for a long time with cum dripping all over our faces, until I pulled away and said swallow whatever is left in your mouth and clean my face with your tongue. When he finished, I licked his face clean and swallowed what I had in my mouth. Damn, Ray said that was hot, can we do it again, I laughed and said well, we would both have to lose a bet, so I'm guessing not. Let's take a shower, I said and he said, together, why not, I replied, let's go. I turned the water on pretty hot got in and Ray followed. We soaped each other, I turned around and felt Ray's finger enter my ass, I swung around put my two hands on his neck and screamed, who the fuck said you could do that. I waited to see Ray's stunned reaction and burst out laughing, Ray said you scared the shirt out of me, you are such an ass. I turned back around pushed my ass into his already hard cock and said no fingers, just cock, fuck me dude. He did and because it was his second load it took a long time and he just pounded my ass. He pulled out and shot on the shower floor. Mike, that's not fair, your turn, I turned him around stroked my cock to get it harder and said bend over and drove it balls beep. I held it the till I felt him relax and I went as fast and as hard as I could. I was barely able to hold off till I pulled out and shot all over the floor as well. We dried off went back to the kitchen drank coffee and it was all as if nothing had happened. He said, I have to piss, I replied you know the way or do you need help? Ray laughed and said you are such a jerk. When he came back, he asked, why did you do the fucking, there was no task? Because, I wanted to, you alright with it? Yes, the whole morning was fun. Good, he said, I thought it was a lot of fun, I needed to cum and get it out of my system and I am going to be too tired to do shit like this with football. It is going to be a tough camp. He smiled and said I'll see you tomorrow morning, enjoy your day and he left for parts unknown.

I went upstairs to my room, looked for something to read, could not find anything so I put some tunes on and just sat thinking. The peace and quiet was ruined by the ring of my phone, it was Jeff. Hey Jeff what's up, you ready for tomorrow, he said? I guess, I replied. There is a lot of pressure this year. He asked how I was doing, I said, I agreed about the pressure but I was good. He asked if I wanted to hang out, I replied that this day was special for me and I was not doing a thing. He said, I'll never figure you out, see you in the morning. I replied, have a fun day, go fuck someone, he laughed and said exactly. Once agin I hit play, and put my headphones on and tried to relax.

I must have dozed off because I was awaken by a knock on my door, I looked over to see dad. He asked what I wanted for lunch, I replied what are my options, he said he didn't care but the would call for anything, I replied ribs and fries, he replied good choice. I got up, brushed my teeth, combed my hair and put a shirt on and went down to the kitchen. Dad, sat at the counter, drinking coffee. Your home early, what's happening. He said, you had a point and I wanted to talk with you and did not want to fuck it up by having a few beers. Dad, I'm actually not sorry I have given you such a tough time, I needed you and you were MIA. Ok, Mike, I get it, I'm back and focused. So dad, what's the story with the joint in Florida? Mike, it is a tax write off, a reality company rents it all year around and, I have only been there once. Ok dad, what's the story with you and Adam, I'm not at comfortable with him. Mike, I told you before when you are ready the three of us will meet and we can discuss absolutely anything you want, what's next. Why you so paranoid about me having sex? Mike to be honest, I understand but you have been having a lot of sex, or so it seems, there are health issues, that concerns me as does what appears to be the randomness of all of it, care to explain. You sure you want to know, I asked. Until recently we have been open about everything so why stop now. Well dad, you sprung a lot of shit on me these past few weeks, you are drinking and are very distant, but I'll tell you everything. Ray and I have been experimenting and before you ask, it is about the bets, damn it has always been about the bets with us, I assume, you knew that. I have had sex with one girl, Samatha and don't get pissed off it was a three way with her and Jeff. Oh, and before you ask, I used a condom, any questions? None, just a request, slow the fuck down.

I switched gears, how is mom? He replied I have no idea. What if I wanted to see her, I asked? She is in central Pennsylvania and with your schedule how the hell will that happen? Dad, don't get mad, eventually I will want to see her, we have never gotten along, well since I was about ten but she is my mother. I also want to make sure she has enough money. Mike, she has enough and if you give her more it will just disappear, I think you know that, but trust your instincts, besides it will be a while before you can do anything more. I said FINE, in a tone he did not appreciate. Now, I said what about your other son? He replied, I have not heard from him or his wife and I really did not expect to, well not yet. Oh, just so you know, there is an offer on the condo he said. It should close in about a month, Adam is dealing with all that. Thanks for the talk and thanks for not drinking, well for not drinking to the point where we can't talk, but this is my last day I want to be alone and relax, see you later, I got a big hug and went to my room and called Carrie. Fuck it went to voice mail. I left a message laid there thinking and could not get mom, out of my head. Then things turned to football in my head. Linebacker or running back, damn linebacker might be fun as I would be hitting people instead of getting hit. Then there is Jeff, the typical high school jock, sure he had a good second have of the season last year and he is a natural athlete, but damn the baggage with the drugs and the sex all the time, but I guess I don't have any room to talk. Just then my phone rang and it was Carrie, I answered hi babe. She replied, want to come over, I miss you. I miss you too, but can I please pass without you getting mad? I just had the first of a very long talk with dad and I need to be here, he is a mess, over my brother and my mom and he has been drinking a lot. I promise we can get together soon. She sighed and said ok. I added, besides I am making very special plans for us next weekend. I could sense the big smile on her face. Later babe, I'll call tomorrow after practice.

I went downstairs saw dad on the phone in his office and did not see a drink, so I was happy. I went in the kitchen made a sandwich, went back to my room. I ate, then stripped, went to the bathroom and look at my self in the mirror, damn I had gotten bigger over the summer and was truly ripped. I figured I grew a couple of inches I saw the scale, looked at the numbers, got off and back on again, dame same numbers it said 190. Damn, I gained 20 pounds and there was not an ounce of fat on me. No wonder dad had Adam ask if was natural or enhanced. I got in the shower and started to rub one off and I heard dad calling, I threw a towel around me and went in the the bedroom, he took one look at me and said, damn. Get dressed, anything will do, we need to talk. I slipped on some baggy shorts and a tee and found him in his office, with a drink. I just asked, what's up. He said I just heard from the Hershey Medical Center, you mom is in ICU there, she tried to kill her self and might have been successful. I have to get there ASAP. I'm coming with you. NO YOU ARE NOT, there is nothing you can do and I'm fine. You need to live your life, have a great start to football tomorrow. I went over gave him a big hug, took his drink saying you really don't need it but I do and I drained what was left in the glass, fuck dad what is that shit? Scotch he replied and don't ever do that again. I'll call in the morning. He got up threw a few things in an overnight bag and left. About an hour later I heard the garage door and in walked dad. The hospital called and she is gone, now I'm going to my office and get drunk, just deal with that. We can talk after practice, tomorrow. I'll make plans in the morning. Try to get some rest and please close the door. Dad I'm sorry, he replied, you have nothing to be sorry for, he said. Dad, please take it easy on the booze, I need you. I promise he said, have a good practice. I went up to my room closed and locked the door threw myself on my bed and cried until there were no more tears. Sometimes when it becomes what it will become it sucks, I screamed FUCK I CAN'T DEAL WITH MORE. Tried to sleep but tossed and turned till about 3:00 and then my alarm woke me up at 7:00 I grabbed my football shit and drove to school. So it starts and I'm not in the place mentally I prepared for all summer.

I went to my locker, started to put my equipment on and coach, yelled Mike Simmons, my office now. What the fuck, I thought as I got to his office and he said close the door. Well I thought this will be whatever the fuck it becomes, what's up coach? I asked.

Next: Chapter 16


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