Cast of characters - it was always about the bets

By Mike Simmons

Published on Dec 25, 2020

Bisexual

I was wide awake and excited to get the day started and when I looked out the window and saw another great looking day, I threw on gym shorts and running shoes and woke JJ. He was barely awake and managed a groggy WHAT THE FUCK DUDE. I said skinny dipping and are you coming or sleeping. He jumped up went to the bathroom threw on a pair of gym shorts and a tee and we were off. It wasn't the leisurely walk like the last time, just directly to the spot, stripped and jumped in. It was the usual splashing, dunking and horsing around. We climbed out and were drying off nude on the rocks and I was laying there with my eyes closed when I heard "you boys enjoying this spot, two day in a row." I looked closer and saw Charlie. I was uncomfortable so I got up and started to put the shorts on and Charlie said don't do that on my account, I had two sons who used this spot as well. Charlie are they around now? He said well one was KIA, a marine in Viet Nam and the other is working and living in Washington DC. We see each other a couple of times a month and the grandchild is getting big. He said it's nice to have young people here, I hope your dad lets you come here often. I said Charlie, I'll visit the shop every time I come up here. Then he said well the business isn't as good as it once was and I don't make all that much wine, pretty much the grapes go to the jelly makers. That makes enough for my needs and I put a lot away. JJ and I finished dressing and I said Charlie, thanks for understanding about the skinny dipping. He laughed and said, I hope to see you around some.

JJ and I started back at a slower pace and I was feeling sorry for Charlie and was quietly walking. At some point JJ said Mike, land that spaceship your on and talk to me. I laughed and replied NOT A FUCKING WORD TO THE OTHERS. I want to make sure that's all true and see real numbers. If we do this, Charlie is a complication as I will want him taken care of. We would be buying a business and he would be selling his life's work, all he has ever known. JJ said, damn where is that calculating businessman we all saw last night? I said, adding in all the elements. As it's never just businesses as people own them. It is so fucking much easier when it is simply corporations.Like I said last night this is complicated and more so now. I need time to figure this out and detach myself from the emotions.

Back at the house breakfast was just rapping up and Jack asked so where were the two amigos? I said at a cool spot we found yesterday. Jack asked so skinny dipping? I smiled and said yup and the water's warm. I grabbed a mug filled it with coffee, found my book and went outside. On the way out I heard Jack ask, what's with him and JJ replied he is sad as it's the last day. Then Major Jim said well Jack and I talked it over and we are thinking wheels up at 9:00 PM. The read continue to be shitty and when I finished it I was glad as I remained in a good mood. I went inside filled my mug and sat with the others. The conversation was casual and I finished my coffee and went downstairs to wash the lake water off. I had just pulled my shirt off and Jack came in, he came up to me and pushed me against the wall and asked, WHAT'S GOING ON WITH YOU, WHY THE MOOD? I started to laugh and asked so you want to get physical with me, seriously. He backed off and I said smart move. Jack, there is nothing up with my mood, what has happened you guys all changed after that discussion last night.

Mike, what happened while you and JJ were skinny dipping? Jack I told you all if something substantive happened you will all know. Nothing happened that is important to this process. Jack, you are special to me and you know that there are, however, lines that you better not cross again. Now, can I shower and get back to the vacation? Jack came up to me and we hugged and he said make it a quick shower. I did just that and quickly joined the others. The women were quickly off on the shopping trip and indicated that they would eat lunch out. It was the 5 minute walk to the marina. I chatted with Jason while he got a couple of tubes ready. Once that was done and Jim was again driving, it was the slow ride till we cleared the no wake zone and it was full speed ahead. We were chatting and I was a little bored so I got up grabbed a tube, yelled JJ catch and I tossed him my sun glasses and tossed the tube in the water and jumped in after it. It was further away than I thought as we were going pretty fast. The swim was no problem and I jumped in the tube and just laid there. Now this was fun but suddenly a rope hit me and I attached it to the tube and fuck it was a ride. I bet Jim wanted to flip me for the jumping in the water with no jacket. He finally slowed and I was pulled close and Jim jelled, asshole get in the damn boat and give someone else a turn and Dillon was in the tube in a flash. JJ looked at me and asked, so what is you need to jump into the water with no notice or regard to your safety. I just laughed and said damn, I wish there was beer. After Dillon it was JJ's turn and then Jim actually got on skis. I asked Jack, isn't swimming good for your back? He said yes and I said I bet I beat you to that pier over there. He said bet and I dove in the water with him yelling THATS NOT FAIR. Fair or not I beat him to the pier by a few minutes. I helped him out of the water and laughed saying you are pathetic. I almost shit when JJ pulled up figuring there will be damage to both the boat and the pier but there were no issues. Then it was back to the marina and, I settled the tab with Jason and told him I would be back soon.

Back at the cabin, I went right to the room and jumped into the shower I was immediately joined by Jack who said MJ, I'm sorry about before. I said just said shut up and suck my cock, you fucking owe me. He got on his knees and worked my cock till I shot in his mouth. He looked up and said, damn I got off easy. So MJ are you still pissed? I said no I'm fucking hungry. I threw on a pair of shorts and flip flops, no shirt and fired up the grill. I threw on the remaining hot dogs and grabbed a beer. When food was ready, as if by magic the guys appeared one at a time and it was dogs and beer, all around. JJ came up and asked why so reckless and I said FOOTBALL, I'm getting ready. Just in case I need to get that down and dirty. Oh, I missed the last game last year as I was in the hospital, I needed to make a play and barely did it, well so I was told when I was given the metal in the hospital. Oh, Jim tells that story better than me and that's why the picture of Jim and me in my room is from the semi finals. JJ it's no fear when it needs to be. He said WOW and drained his beer and got another beer.

I got Jack aside and said dude I need a favor. Sure MJ what's up? We need to go to the winery and buy three boxes of wine. I can't and then they get flown back with us. He said JJ, just ship them. Jack, we live in Pennsylvania and you can't do that. I said three boxes one red, one white and one in between. He laughed and said damn you know your wines. Oh, please don't make a big deal of it, it's research. He said ok, let's go? I said please take Dillon and get some of each, I'll pay for it when we get back. A few minutes later I noticed Jack and Dillon were missing. I got another beer and went outside and was leaning against the railing and thinking about how this place and even this cabin was growing on me. JJ came up behind me and asked, what you thinking? I smiled and said something about how this place is growing on me. JJ stay here I need to ask your dad a question, I'll be right back. Inside I asked Jim if we could fly some wine back with us, about 3 or 4 cases? He said sure buy why? I said research and he laughed. Back outside I asked JJ if he thought pizza would work for dinner? He said well you should ask the women, I'm just interested in getting trashed and food get in the way. I laughed and said well then I'm betting it will be a messy time in bed tonight, just don't puke. JJ looked at me and asked, when was the last time you had sex when you were blitzed? JJ tonight will be the first time. He laughed and said fuck, I love messing with drunk rookies, I'm boned thinking about it. I leaned in and said I bet drunk you are one and done. He said, I'll take that bet.

Jim came out with a bourbon neat and I said now I see why it's wheels up at 9:00 PM your drinking tonight. He said, well I'm guessing that the plan all the way around. Just then Jack and Dillon came back and he said well there are 5 cases in the van, a box of each kind they currently make and damn they need to raise their prices. He looked around and said well, I guess I need a couple of beers as Dillon and I are behind. The ladies returned from the shopping trip and immediately started on the wine and mixed drinks. The night went on with snacks and drinks and stories and finally, beer or not I needed to eat and ordered a bunch of various pizzas. I was having blast. Around midnight I was looking for JJ and he was no where to be seen. I went in our room and found him passed out naked on the bed, laying on his back. I left him laying there and went upstairs and started to clean up and was told that it could wait. I said good night and went back downstairs. JJ had not moved and I decided to see how out of it he was and I stripped and laid in bed beside him and started to play with his balls, getting no reaction I started to jack him off and neither he or his cock stirred. Then I decided, what the fuck and started to lick the tip of his cock and he started to moan and I heard him call Dee. I decided that was enough so I covered myself in a sheet and was soon asleep.

At some point I felt a strange sensation and realized that JJ was playing with my balls and I just laid there and wanting to know how far he would go. When he swallowed my cock and I was hard I reached down grabbed his ears and pulled him into a kiss. Then I said well JJ I was ready a couple of hours ago but now that I'm awake, let's see how hungover teens have sex. Before I could react, I was flipped over and he was in my ass and his hands were around my neck. I move up on my knees and made it easier for him to work my ass and damn he pounded me, slowly at first and towards the end he was almost out of my ass and drove it home and his balls hit my ass over and over again and he finally shot and collapsed on top of me and I fell forward and rolled over so he got off. We made out some and then I whispered my turn and got him on his hands and knees and it was great doggy style fuck. It took me a while to get off and I returned the favor by slapping my balls against his ass. I finally filled his ass and we both laid there. We were both dozing and I asked, so one and done? He laughed and said well we have a bet to settle so mutual oral and if I win we can settle the bet at home. Then he said I bet yiu come before me, I laughed and said bet. I knew I had him on that but then I would lose, damn the fucker set me up so best I could get was one win each. I started sucking him and was playing with his ass and had a finger in his ass and as I was getting close I shoved 3 fingers up his ass and swallowed his cock to the base and sure enough there was a load in my mouth. I just held it in my mouth and I shot in his mouth. When I thought he swallowed, I went up to him and he was expecting a kiss and I spit his load all over his face. I smeared it all over and said goodnight and rolled over.

I woke and it was way later that normal and I got out of bed and was in the shower and enjoying the hot water and was starting to feel human again and JJ appeared and I laughed as his face was covered with dried cum. He said don't you know cum is good for you completion and he jumped in. Neither of us was feeling the best and the long shower helped. Upstairs almost everybody was up and the place was clean. I thought damn, this is great and I grabbed a mug of coffee. JJ joined me and asked, what we doing today? I said not a lot but possibly skinny dipping. JJ laughed and said, well I watch this time or is that code for your checking out grapes? I said well who the hell knows, it will be what it becomes.

My mind was already morphing into football mode and I knew there would be a price to pay for this fun vacation, but that was water under the bridge. After three cups of coffee, I was feeling pretty good and asked JJ if he wanted to go skinny dipping? MJ, there is no way I'm letting you jump into that fucking lake alone, so let's get this over with. We started off and Dillon yelled, hey wait for me. I thought well that ended the grapes. Once we got to the spot by the lake and I sat on the big rock, JJ told Dillon the story of the first time we visited this spot. Dillon just listened and was quiet for a bit and said, JJ I'm surprised that you didn't expect that. Then me looked at me and asked, how did you know because I'm positive you didn't take that chance. I laughed and said, well finding this spot was no accident as it was on the map dad gave me and I was told to be careful as the water is very deep here. So while it was a risk, it was reasonable. Then Dillon spotted the vineyard and started off saying so this is what grape vines look like Dillon kept walking and we were following and I could see in the distance a house. I didn't want to get any closer and gathered every one together and we started back, what I realized was that there was a lot of property and all filled with established vines.

On the walk back JJ asked, so no swim, why was that? Well because it was no fun as you knew it wasn't a big risk, but was about as big of a risk that I take, unless there is a game on the line. We took our time getting back and I was impressed that Dillon had it figured out. I learned a lot about him on this trip and was glad he was on the trip. Back at the house I was sitting on the deck with yet another cup of coffee and a cigarette when Jack sat down beside me and said, thanks for the weekend this was fun and both Riley and I were glad to see the teenage kid you keep so well hidden. Jack you haven't been around here for football, I am really a stud, jock teen and at times I even disgust myself. Jack laughed and said well, I can't wait to see all that. Well it all starts tomorrow and builds till Halloween and then thanksgiving and then Christmas. I said 16 games, nothing less. So MJ, running back or backer? I said, yes. I looked around and asked where is everybody? He said packing and I laughed and said well if you don't unpack you don't have to worry about that.

I found Major Jim and thanked him for all the flying and driving the boat. Mike, we appreciate the vacation and Kathy is finally relaxed about you and how close you and JJ are. I said Jim, he has become my main man and things are good. MJ, I know I shouldn't ask but what are your thoughts about the winery? I said Jim it is very complicated and I don't want to blow this group apart with a business fight. We are all strong willed people and there will come a time when collectively you will tell me to shove it up my ass. So Jim, where are you? He said interested and thinking this could be a lot of money as there is a lot of land. Jim, I'll put Hillgrove on it and then said well his young associate Alex, I liked him for the job, just not enough experience and that will happen soon enough. Besides, it will be a good loyalty test. Ok MJ how do you do it? I asked, do what? Slip into business mode so easily? Jim, business is who I am becoming and between you and me football isn't so easy for me this time. Mike, I believe that's rule 2 and I am good with that.

Inside I found Lexi, Riley and Kathy cleaning and I asked, so what's going on? Lexi said so Mike, are you unfamiliar with the concept of cleaning? Well Lexi, I actually am but are you familiar with the concept of hired help? You know the people who make a living cleaning resort houses. They get paid no matter how clean or how dirty the place is. By the way, they are welled paid. I went downstairs leaving them standing and looking at each other. Downstairs I changed into jeans and a golf shirt, threw everything in the suitcase and took it outside and put it in the van. Back on the deck, I checked my messages and I owed Cole a call back. I returned the call and it went to voicemail. The message was, you have reached the number of Cole Simmons, Sr. I left a message saying I would be home by 11:00 and be there as we are talking. I like the Cole Simmons thing but you can shove the Senior thing up your ass, I love you. There were no other messages so I sent an email to Tim, asking for a meeting first thing Monday and to have Hillgrove's associate with him. After I hit send I sent that schedule change to Ruth.

Everybody was just sitting around and Jim said damn this is silly, just load up and we can be in the air in an hour, I'll call ahead and have the thing fueled. There was a scurry of activity and the vans were loaded and we were off to the airport. The jet was fueled and The Majors split the pre-check, the bags and wine were loaded and we piled in. Then Jack was on saying, Welcome to MJS Airlines flight 102, the weather in Pittsburgh is clear and flight time will be under an hour. Strap in and enjoy the flight. Once we were airborne I asked every one for their personal email addresses, so I could keep them updated on the Winery. Then I filled them in on what I had discovered and stressed the acres and acres of mature grape vines and what that could all mean. Then I told them that meetings were scheduled and the process would start Monday morning. Kathy laughed and said, damn it's a good thing you were on vacation.

I was shocked to hear Jack announce we are ahead of schedule and will be landing in 15 minutes, please remain seated and thanks for flying MJS Air. As we were landing I yelled, so Majors no go around and I heard them both laugh. Once we were on the ground cars were loaded and soon enough I was on my way home. Once there, I discovered that I was there alone so I took my shit to the basement and started laundry. Once that was done it was a beer and a cigarette and out to my special place. I don't know how long I was there but there was a lot of noise in the house. I went inside and dad said, Mike your early and Cole said who the fuck cares, just so he is here. He is back to driving you two, I can't stand it. I just started to laugh and said damn, it's good to be home. Determined to stay out of it, I went to my room.

Almost immediately the door flew open and Cole jumped in my arms and said, please don't leave me alone for 4 days again. Cole, calm down and I'll be right back. I went downstairs grabbed two beers and went back to my room and handed Cole a beer. I opened a window, lit a cigarette and sat down and asked, so two backseat drivers are hard to take. Cole it gets better. He laughed and said well it can't get worse. Put the roof up, turn on the AC, why we in this lane, slow down, use turn signals, go faster. Cole, it's get better. So how was your dad? He said well that went well as he signed the papers and I don't think he gave a fuck. He is really pissed that mom got married. I asked how that was my fault and he said that I always took her side and ignored him. I told him it wasn't hard to ignore him as he was never around. Either it was work or his friends and the other women. He didn't think I knew about the affairs. He couldn't sign the papers fast enough. Hell I even changed the visits to be more convenient to me and only if I wanted them at all. Fuck, he didn't even read it just asked for the fucking pen and I haven't seen him since. I got up gave him a hug and said you are one tough fucker. What did he think about the car? MJ, he actually liked it and damn a lot of people think it's a great color.

Ok so how was golf? He laughed and said fuck, I thought you would have heard. Wednesday I played Oakmont with my pro and it was good, Thursday Michel and I spent the day together. Friday, I pulled strings and played Latrobe with Liam. Once they found out I was there, they all wanted me to hit a driver on #3. Shit, I was offered $500 if I did it again. I was tempted and Liam and some dude they called Doc put an end to it. After the round, we simply went right to the car but there was note asking that I stop at the pro shop. We went back and I was told AP asked that I stop at his office, I thought Liam was going to faint. Once again it was sandwiches and Liam got a tour and pictures and they will be signed and mailed to him. I was asked if I was going to try that shot again and Liam jumped right in saying I was simply going to snap his driver over my knee. AP said well next time I need a caddy I'm calling you. Liam blushed and said it would be an honor.

So how is the girlfriend? Mike, it was great and she spent the night and that is totally awesome. Then he said you might want to have Jim get you more raincoats, we used a lot of them. I laughed and asked if there were some left for tonight? He smiled and I said later as I have to talk with dad. I found dad in the office and sat down with a beer and lit a cigarette. He just laughed and said enjoying that shit for what the last time till Christmas? I ignored that and asked so how bad is Cole's driving? Mike, actually he is good and Megan and I chatted and we will back off. I ignored that and asked, a cabin? Dad laughed and said a mistake, I liked it when it was a cabin. Dad, so why? He said rule 6, I should just sell it. Dad, I don't disagree but not all the land there are spots up there that I really like and a real log cabin would be nice. Mike, so when you jumped into the water who did you scare? Well besides myself, JJ almost wet his pants and I got a big time lecture, then he joined me.

I put out the cigarette and took a drink of the beer and dad said, just fucking spill it. Dad what do you know about Charlie and C& J winery? Dad just laughed, he said until the wife died it was a very active regional winery, now he only does a little, there is a great manager who keeps it going. Mostly he sells the grapes to the jelly companies and that is way more enough for him. So you buying the place? Dad, everyone on the trip wants that to happen. It's complicated and you know me, I need to look at the numbers and potential. However, it's a big group, and a lot of upfront money and then there is Charlie and what he wants going forward. If we do this do you want in? He smiled and said well actually I'm working on something and might be asking you to house it in Enterprises. It's like you situation very early. Dad, just so you know that was my last cigarette and I'm cutting way back on the drinking but football is different this year, I need to win and yet have no interest in it totally taking over my life. Dad laughed and said, if I remember correctly you said that last year. Dad, last year was before you changed my life, fuck it's different now. Oh by the way, I started my Summer reading on the trip. He said well that's typical what did your read? Well it turns out it was about your relationship with my mom. He laughed and said so you read, WHO'S AFRAID OF VIRGINIA WOLF? I smiled and said have a good night, I have a busy day tomorrow and I have to deal with my step-brother some more.

In my room I found Cole laying in my be in just his boxers on. I asked so you spending the night and he looked at me and said, please. I said well in that case, you are over dressed and I turned off the lights and joined him.

PLEASE!! contribute to the continuing operations of the Nifty Erotic Stories Archive website using a credit card or other methods of donation, we encourage our supporters to make a donation to the Nifty Archive Alliance. Please consider doing this, it is important.

THANKS FOR READING AND THE COMMENTS

Next: Chapter 200


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