Cast of characters - it was always about the bets

By Mike Simmons

Published on Dec 31, 2022

Bisexual

I was up at my usual time and Winnie was there in bed with me and soundly sleeping. It was easy enough to sneak out of bed as we weren't near easy other in the king bed. I grabbed some clothes and a jacket and went for a run. It was a bit nippy but the cold air was great and it wasn't a long run. Back in the hotel, I got two coffees and went to the room. Winnie was in the shower so I set the coffee on the table and stripped and went in the bathroom and stuck my head in the shower and asked, do you want some company? She smiled and said sure but you are behaving. I laughed and said no problem but grabbed her and gave her a kiss. That was the extent of extracurricular activities as there was still some lingering feelings from the previous evening. As she dressed Winnie asked so Mick, what we doing today or is it everyone for themselves? Babe, I told you I had a meeting at the airport so I was thinking breakfast and we could both go to the airport. Then come back here and checkout then we could stop at the bookstore and see if there is anything fun o buy. At some point we need to track down JJ and see when we should be heading back. Winnie, if there is something you want to do we can easily adjust anything but the 10:30 appointment at the airport. Mick, as long as we get to the bookstore I'm good. With that we but on a warm jacket and went looking for breakfast.

We were walking through the lobby when Winnie stopped and said Mick, looks we are eating here and she pointed to the breakfast area and there was JJ all lone drinking coffee and eating eggs and sausage. When we got to the table I asked, so do you have room for two more? He smiled and said, well if it you two absolutely. Winnie immediately went for coffee and left JJ and I alone. So JJ, where is Kathy? MJ, I think she is in the room packing but I really don't give a fuck. I told her that she should rent a car and drive home and I would give her the money for it. JJ that's a bit extreme but I offered to do that for Carrie but what happened. Well MJ, she told me that all she wanted was to fuck a D1 recruit at his school. She knew you wouldn't do it so she conned me into bringing here down here. Winnie dropped off the coffee and went back for food. I took a sip of coffee and asked JJ, did you give a fuck about her? He laughed and said fuck no but the sex was good and I figured it was a prom date. MJ, I have never been used before like that and then simply dumped, it hurts. I didn't say anything but wondered how many girls he dumped and then I thought about my rebound girls but that wasn't intentional. Winnie reappear d with fruit and an English muffin and I went for food. I took my time in case JJ wanted to talk with Winnie. The food turned out to be good, well a lot better than I thought it would be. I grabbed a muffin as well but took three links of sausage skipping the fruit. We told JJ of our plans and asked if he wanted to join us and he said sure but he needed a coat and would be right back.

As soon as JJ left Winnie said MJ that's a side of JJ I haven't seen before, vulnerable. I sustained shook my head and said Winnie, there are a lot of layers there that he hides really well. JJ was quickly back and said, I told Kathy that I would be back to pack and that we would be wheels up around 3:00 and we would take the shuttle to the airport and that if she wasn't around I would assume she found another way back or someone else to fuck. That I wasn't waiting around and I didn't care what she did today. She said fine and that she would be ready to go when I got back as she didn't want to drive. Oh, Winnie she said you needed a ride home from the airport as she wanted nothing to do with any of us. Winnie got up nd before she said anything I reminded her that I had a meeting. Besides she could deal with her on the plane. With that the three of us were off looking for the shuttle.

We arrived at the airport 10 minutes before my scheduled meeting. I asked Winnie and JJ if they wanted to go into the town or come in with me. There was no hesitation as they were coming with me. Inside I went up to the older woman sitting at the desk and said, Good morning , I'm Mike Simmons and I have a meeting with Mr. Scullen. I thought it was strange but she got up and went to the back, I was expecting her to simply pick up the phone and ,eat him know I was there. When she came back she said Mr. Scullen will be ready when your dad gets here. I laughed out loud as did Willie and JJ. I looked at her desk and saw a name plate and reached for my wallet and took out my driver's license and said Trudy, Pat has an appointment with Mike Simmons, Jr. would you please remind him of that and then hand this to him. She looked at the license and as she walked away I heard her say "Oh, shit". She quickly returned and behind her I say a guy with red hair and a scruffy beard and I would guess that he was around my dad's age.. He was about 6' tall and I would guess he weighed about 230 lbs and was wearing blue slacks and a white shirt and a tie. All of the clothes looked like they had been worn before. Well the general appearance was of a rumpled guy who didn't see many guests. I was handed back my license and he held out his hand to shake and I simply reached for my wallet and replaced my license. Then I looked at him and he again stuck out his hand and said, hi Mike, I'm Patrick Scullen. I said nice to meet you Pat. Mike, I prefer Patrick. Well Pat I prefer the person I am about to meet with know who I am. I have a couple of people with me, Winnie Tillison my girlfriend and JJ Messer he is my best friend and we fly in and out of here a lot and it will be a lot more starting this summer. Then Patrick asked, did you two actually fly the jet here? I shook my head and said yes and we will fly it out of here later today. Pat, I understand we have some papers to review and hopefully sign. He smiled and said well that's partially correct, we have papers to sign. I looked at Trudy and she smiled and said Mr. Simmons, help is on the way. I smiled and said thanks. So Patrick while we wait can I have the lease so I can review it, this is already taking more than it should have.

We were taken to a small office and Trudy was there with the lease. I made sure to be real nice and thanked her. Once she was gone I looked at JJ and said, always treat the secretaries extra nice. I started to read the lease and it was exactly as Tim had told me it would be. We sat ther chatting and it wasn't long at all when a very fit guy a few years younger than Patrick appeared and he had a VT shirt on. When he came in, I stood up and said I'm Mike Simmons. He laughed and said well I'm Jim Scullen and it's nice to meet you. He looked at JJ and asked, Mr. Messer how are you? JJ smiled and said, nice to meet you Jim. Then Jim looked at Winnie and said, I'm sorry but I don't know you. Jim, that's my girl Winnie. Then Jim said guys, my older brother is often a pain in the ass and I apologize that he wasted our time as you should be on your way and I shouldn't be here on my only day off. It's my fault as I should have simply been here. So Mike, is everything in order? I smiled, picked up a pen and signed the lease. Then Jim signed for the airport and we were set. Then I asked Jim, if he could make sure that there were no issues and that construction not be delayed. Mike, trust me as us Hokies stick together. I said thanks and we started for the bookstore.

That involved a shuttle ride to campus. In the summer it would have been a reasonable walk but it was cold out and we were getting short on time. We arrived at the bookstore and Winnie looked around and bought an apron for her mom and a golf shirt for her dad and one for herself. When she grabbed a tie I figured it was for Uncle Bill as I knew her dad would never wear that tie. It was burgundy and orange, the school colors, and had a VT at the bottom. Actually it was a fun gift. JJ was all bummed as they didn't have a cowboy hat but when he asked about that they showed him a picture and he ordered it on the spot. I really didn't want anything but grabbed a grey hoodie with the VT logo and we were all set.

Back at the hotel, I saw Cole eating lunch and when I went over he said MJ please say yes. I laughed and asked, do you want to fly back with us. He said either that or I'm renting a car and driving back, I need a break from the rents and they are eating lunch somewhere. Cole, that's fine and we will be leaving for the airport as soon as we get packed and check out. He smiled and said great, I'm ready now and want to get back so I can see Jessica. I laughed and said remember we need to decide who is going to golf. Cole smiled and said well it really helps that the Major is taking the other jet. I just shook my head and found Winnie and went to our room to pack. JJ had simply vanished and I was worried about him. I just threw my shit in my bag and Winnie was much more careful but was very quickly done.

Back down in the lobby I checked out and saw Kathy standing alone and JJ was outside. Cole came up to me and asked what's with JJ and Kathy? Cole, they are done with each other and it's a long story. Cole laughed and said MJ, you and JJ are out of it she just fucks jocks and moves on. Thankfully she doesn't consider a golfer a jock. I laughed and we all went outside and waited for the shuttle. There was a bit of a wait and when it arrived we threw our bags in the back and Kathy just stood there, I was wondering if she was getting in. JJ jumped in up front then Cole asked, so you getting in or not but we are leaving. With that Kathy got in holding her bag. At the airport the jet was ready and JJ opened the cargo hatch and said all bags in there and he looked at Kathy nd said that includes yours. When we finished the pre check JJ closed the cargo department and jumped into the left seat as he was flying us home as we had agreed. I checked to make sure that everyone was buckled in and thought it was interesting that Kathy was sitting beside Cole but went to the cabin with JJ. Everything was going smooth and we were quickly cleared for takeoff. We were at cruising altitude and I heard Cole yess, get you fucking hands off me. I looked at JJ and he actually laughed and I got up and went back and Cole was changing seats. I looked at Kathy and said, if you cause one more issue I will land this fucking jet and put your ass on the tarmac and I won't give a shit about how you get home. She smiled and I did I'm serious and we will be at Harrisburg soon and that can easily be done. The other alternative is that I simply throw you out. Back up front JJ said, thanks and I promise to make better choices. I laughed and said JJ, it's cool.

At the Allegheny airport we were cleared to land and it had been an easy flight. JJ and I was working on the shutdown list and we heard Kathy yell, I need off this piece of shit. I shrugged and got up and opened the door and she hurried to get off. I motioned for the others to stay put and then I heard, I need my bag. I stuck my head out and said well when we are fucking ready and I hope you freeze you damn ass of as you are not getting back in and I closed the door. JJ and I took our time and when we were finished he opened the door and we all got off. I opened the cargo hatch and Kathy pushed right past Cole and grappled her bag. As she walked to her car she raised her right arm and shot us the finger. With that I went inside and left instructions about the jet and we loaded our bags in the Wrangler and Winnie was upfront and JJ and Cole were in the back. I dropped Cole and JJ at my place and told JJ to find a beer and that I would be right back. At Winnie's I walked her to the car and arrived her bag we kissed and I said I'll see you in school, I need to check on JJ.

I was back as quick as I could and was glad to see that my bag was tan to apartment. I opened the door and saw Cole and JJ and they were into a couple of beers each. JJ smiled and said MJ, catch up. I laughed nd grabbed a Bud Light and looked at Cole and asked, is Jessica on her way? He laughed and said I decide to drink. I took a big gulp of my beer and grappled Cole and gave him a kiss which he returned. When he pulled away he asked, what no bet. JJ laughed and said well Cole, I don't know about MJ but I want to see that sexy ass. Cole laughed asked, here or in the spare room. JJ stood up pulled Cole to his feet and said dude, there are 3 horny teens here, with three soon to be hard cocks and three assholes all of which will be dripping cum. Cole laughed and stripped putting on a little show while JJ and I sat on the loveseat kissing and drinking beer. Once he was nude he grabbed JJ and pulled him to his feet undid his belt, opened his Jeans then he laughed. Cole got on his knees and then slapped JJ cock and got up saying damn there is no need to do anything you are hard and leaking. With that he knelt on the seat of the loveseat and leaned over the back. JJ wasted no time and almost jumped out of his jeans. Then I was surprised when he got on his knees and started to eat Cole's ass and Cole was moaning and in heaven. I stood up and stripped and went around to the back of the loveseat I gently lifted lifted Cole's chin and said open. When he did I guided the tip of my cock so that it sat on his lips. Cole grabbed my ass and pulled me close and my cock slid in his mouth. I wanted to be careful and not shoot too soon. JJ stood up and positioned his cock at Cole's wet hole and gently pushed and he stopped when his balls hit Cole's ass. It was so hot, I almost lost it and then JJ grabbed my shoulders and pulled me close and he kissed me and his tongue was in my mouth. I was fighting hard not to shoot. Having no choice I broke off the kiss and pulled out of Cole's mouth and grabbed a beer and sat nd watch JJ fuck Cole's ass. When he saw me watching he picked up the pace and just pounded that smooth ass. It went on and on and as I watched JJ pounded Cole harder and faster and finally yelled fuck, I. Going to shoot and he lunged forward, deep inside Cole and stayed there and unloaded. JJ went to the refrigerator and grabbed two beers and handed one to Cole. I was amazed at how quickly he finished that beer, especially since it was his 4th beer. With the beer finished Cole got up and went to his jeans and pulled a coin out of the pocket and said, well it's my turn. He looked at the coin and said well heads I do JJ and tails I do MJ. He threw the coin high in the air it hit the hard floor and bounced in the air and then against the base of the island and laid still on the floor. Cole went over and looked at the coin and smiled. He came over and sat on my lap and said MJ, my magic coin never lets me down and I've wanted your ass for a long time and now it's all mine. JJ went over to the coin and said damn, I wanted Cole to do me. Cole got off my lap and said MJ, you know the position. Cole went to my room and came back with lube. He slapped my ass and said, what you waiting for, I'm hard and ready.

I assumed the position as requested and I immediately felt a cold glob which was followed by two fingers, then three. Cole worked them around and it felt awesome. Cole was pushing me to the edge again with all this ass play and we hadn't got to the main event. I knew I was being loosened up so I should take that thick 7 inches easily. I wasn't surprised when he stopped as I was expecting him to fill my ass but he came around and knelt on the floor and kissed me. It was an intense kiss and he broke it off and said MJ, I'm sorry it isn't more special and we kissed again and again. Then he smiled and said well a guy gotta do what a guys gotta do and he positioned his dripping cock at my hole and gently slid it in my hole. He started sold and with each thrust increased the pace an the force. He just kept at it and I finally yelled Cole, just shoot and fill me up. About a minute later he lunged hard and stayed there as he emptied his load deep in my ass and collapsed on to of me.

Cole was quickly off me and I stood and stretched then sat back down and Cole sat beside me and we started to make out and kiss intensely. JJ said hey guys it's my turn. Then he sat on the other side of me and we started to kiss and sCole and JJ fought for my lips and then Cole started to lick and suck my nips while JJ and I made out. I was hard as a fucking rock and knew I needed to be inside JJ soon or there would be cum all over the place. Without a word JJ stood up spread my legs and simply sat on my cock and it slid right in as he had lube it up really good. When I laughed he said well I was a Boy Scout so I'm always prepared. With that he started to ride my cock and I just closed my eyes and sat there. Cole stopped kissing me and when I opened my eyes he was on his knees sucking JJ's cock and the way JJ was riding me Cole was holding his head still and JJ was actually fucking his throat. Cole was gaging and his eyes were watering but he just let it happen. I wasn't able to hold off like Cole did and I shot inside JJ's ass.

With that Cole got up and went right to the shower and JJ and I just sat there nude and talked. It was a quick shower and Cole left saying he needed to get to the house before the rents sent someone looking for me and if wouldn't be good if they came up here. You two should get dress and considering airing this place out it smells of sex. I laughed and said well Cole don't spend much time with the rents as you have had a bit to drink. He laughed and said, later guys and I'm ready for the morning run. He was out the door and I locked the door and JJ told me all about Kathy. He said he was surprised that she did jocks and I'm betting it was half the team. Then he smiled and said well she can suck cock and her ass is really tight. I laughed and got up and went to the shower. I was quickly joined by JJ and we kissed some and cum was dripping out of both our asses. JJ said that he also needed to check in with the rents and look for a more serious girl. I laughed and said, happy hunting.

I decided that I needed to visit the rents and thank them for making the trip and I went to the house. There I found Megan lecturing Cole about his drinking and she looked at me and asked so how much did you and Cole have to drink? I smiled and said I had 3 beers and a sandwich and I have no idea what Cole or JJ had. None of us were driving and it was a drama filled flight back and Kathy hit on Cole. Megan laughed and said, so if I drag JJ here I'll get the same story? I shrugged and said mom, I have no idea. I came down here to thank you and dad for making the trip this weekend, please don't make it more than that. You know we drink and as I said no one was driving or even walking that far. Well now that I did what I came for have a good night and I started for the door. Just as I got to the door Megan said Mike, I'm sorry I didn't mean to put you in a tough spot. I turned and said Megan, you didn't but you put your son in a tough spot and he deserves better than that. He has great grades and works hard nd has achieved more at 17 than a lot of people have. We are brothers and understand we will always have each other's backs, good night and I went outside gently closing the door.

Back at my place I had to laugh as JJ was right the place smelled like a locker room and it did smell like cum as well. It was cold outside so opening the windows wasn't an option so I sprayed the room with air freshener and went to my room and closed the door. It was early but I was hoping for some extra rest as the week ahead was full. Tomorrow was school and the office and back to school as the Friday recognition was rescheduled. I really didn't want any part of school and I was guessing it was the time at VT, I simply just wanted to move on. Then I needed to make a decision on the buildings and there was the trip to the west coast for golf and that USGA meeting. Then I thought about tonight and the fun with Cole and wondered why that happened as we hadn't played around like in along time. Then he has said he was sorry it was like that as he wanted it more special. Finally there was Winnie and her reaction to us getting special treatment at the restaurant. I hadn't done anything, then there was my reaction as I got mad. Once we got to school I would be all football and classes. I knew there would be parties and girls would flirt with me and more and at some point I would react to that. There was no way Winnie would be around all the time and I was sure I didn't want that. I was thinking that it was drama I didn't need. Then I laughed as I thought about Sean's sister and every time I saw here we ended up naked. With that I fell asleep thinking about how many days I could miss at school and still run track.

HAPPY NEW YEAR

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Next: Chapter 360


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