Cast of characters - it was always about the bets

By Mike Simmons

Published on Oct 3, 2019

Bisexual

I got up as usual, early and went for a run. I decided on an extra mile so it took longer. I got home and found Ray sitting at the kitchen bar, nude and drinking coffee. I grabbed some juice and went up for a shower and simply ignored Ray. I did not know what to do and decided I was hungry so went back downstairs, Ray was still there, I continued to ignore him making an omelet and toast and as it was another great day, I went outside to eat. Dad saw me and asked if I needed anything and I said coffee with a little cream would be great. He returned and handed me a mug of coffee. Then he asked, Mike how long has Ray been sitting at the kitchen bar? Dad I'm not sure he was there when I got back from my run. I did try to talk with him and he told me it was none of my fucking business. That's all I know. That's fine Mike, give him time, I was brutal on him last night and I hear from him you were tough on him the other night. Dad, that's not accurate it was a give and take talk that night I thought it set the tone for going forward. Mike, it might have resulted in more self evaluation than you think dad said. Then he said sometime tonight reconfigure his task, let him get dressed but add something else.

We just sat there enjoying the warm morning the dad said so have you been told what you and Carrie are doing today? I bit back a snide remark and said, dad I am about to call and at lease ask what the dress code is for today. When I find out I'll tell you even if we are going somewhere to fuck our brains out, I could not help my self. He started with Michael and I cut him off, I'm not Ray, I think with both my big and little heads and we are both all in to this relationship and things you don't like or don't approve of are going to happen, if you stop asking you won't know and I promise it will not end up on the evening news. I got up, went upstairs and called Carrie. When she answered I asked so what we doing today. She replied Michael stop being a pain in the ass and just get here for noon. Fine, but what should I wear? Oh, a reasonable question, very very casual shorts, tee shirt or my favorite nothing at all. Oh I promise you won't have to take anything off. I love you babe and she hung up. I went down stairs, dad was still on the patio but now he was talking with a very uncomfortable Ray. I did not even look at or acknowledge Ray and just stood there, dad looked at me and I said very casual shorts and a tee, dad laughed and said that helps a lot and I replied, I know. As I walked away dad said Michale, I do trust you. I said thanks and please cut the Michael shit, and I went back upstairs.

I was just laying on my bed thinking about the week ahead when there was a light tap on my door and Ray was standing there. Mike, your dad said you would like to talk with me, is that correct? I took a couple of very deep breaths and said nicely, I wanted to talk last night and you didn't, so yes I want to talk. Ray, Carrie and I have a date and I should be gone most of the day so this has to wait till I get back. In the meantime please get dressed, I want to modify the task, I think this is too uncomfortable for you. But you are not off the hook. In our tasks so far we have done a lot of nasty and humiliating things to and with each other, You will get to choose the replacement task, and it should be the most humiliating thing that either of us done during a task, I got up gave him a hug and said, Ray I really want us to get past this, I just don't want to feel that our friendship over the years was just not being always about the bets and that there was more. We are both growing up, maturing but doing that in very different ways, let's find a path to let this happen and yet stay close. At this point he hugged me and turned to walk away and I saw tears in his eyes, I said Ray by the way big girls do cry. He left closing my door.

I left for Carrie's wearing pair of semi old shorts, a tight tee shirt and sneakers. I rang the bell and she came to the door took one look at me and said did you paint that shirt on, damn you are sexy and added come with me. She opened the garage door and pointed to a cooler and blanket and some other stuff and said, Mike will you please put that stuff in the trunk of your car. In a testy tone I sad yes ma'am, She laughed. I loaded the car got in and waited, she climbed in and said no holding the door today, I replied we are not at the club, thinking it is going to be one of those days. So where we going, she said can you find the lake at North Park, I said absolutely but why up there we have a perfectly good park close and she said it does but doesn't have a lake. Once inside the park I got very specific directions to a grove, which was full of people, she said I don't want the grove drive down that path and I did for a few hundred feet and then it opened to this undeliverable view of the lake. We parked unloaded the car spread the blanket. I laid on the blanket kicked off my shoes, carrie joined me, I reached over pulled her towards me and said thanks babe this is almost as good as Friday night and I kissed her. We just laid there talking and making out for a long time, she reached down and started to feel me up and stopped, got up on one elbow and said, Michael is that always hard. I said around you it is and to be honest today it is annoying as it has been hard so much today it is uncomfortable. She smiled and said too bad for you because today it is not about that, it is about you and me and definitely not that. Babe I should call dad and tell him that he is all over me about sex mostly because of Ray. We are not talking about him or any of that drama, just you and me all day. Let's eat I'm starving, she opened the cooler pulled out a couple of sandwiches, cheese and crackers and two cans of Pepsi. We just talked about things in general, school and what we wanted to do next summer and college visits and the like. At one point I took her hand put it between my legs and said you have wanted to feel this while it was behaving and she squeezed my soft cock and it immediately started to grow she kept her hand there till I was totally hard and said damn that was amazing. I would love to see that happen, I pulled her hand away and said not today. She said, let's clean up and get this all back in the car, I said are we going home and she replied, silly boy. We are going to the lake and rent a boat I want to see you get sweaty so you will take that shirt off and I can put my ripped sexy boyfriend on display. I laughed and we went to the lake. She rented the boat and off we went with me doing all the rowing. After we were finished on the boat we went to the nearby ice cream stand got a cone and sat on the shore looking at the water. This was a great day?

As we sat there she looked over and said Mike I'm pregnant, I screamed what? She laughed and said you zoned out and I wanted to refocus you, I am not pregnant. I am on the pill and you insist on those damn condoms so pretty impossible. Mike you have that offer from Penn State, will you go there to play football. Carrie, I'm not sure if I'm playing college ball. I am all about a good education, I don't need the money, but if football helps with business connections, well that might influence my decision on that. Besides, I will want to be finished with school in three years and I want to take some time to travel, I'm thinking Europe and Australia. Wow, Mike do you have that type of money? I replied Carrie I do and a lot more that will be needed for that. She looked at me shook her head and said, ok I won't ask. I replied good and right now I'm not saying. I looked at her and said Carrie this is not a proposal but someday I am marrying you. We might break up, we might go our separate ways but eventually you are going to be the mother of my children. She was stunned, then kissed me and said damn, Michael I hope you are serious, I am so into you please make that happen. Carrie please look at me, take a long look because I will not always have a body like this. She said, I know that but hopefully you will always have that sharp mind, wit and caring nature and a part of you that gets hard at the mere sight of me. We just sat there in silence.

I broke the silence and said, so Carrie where do you want to go to school? She said somewhere away but not too far like Virginia Tech or PSU no farther. To study what, I asked. Business or something along those lines. She said we might both end up at the same school. I said Carrie even after what I just said we are not selecting schools based on where the other is going. Mike, I know and that's the hard part. You will go to PSU to play football work your ass off to do it in three years and every chick on campus will want in your pants. Carrie, you won't play sports but there will be a lot of horny undergrads that will be looking to get you naked. I'm actually sorry I let that entire subject slip but damn that's how I feel. With that I leaned over and kissed her and it must have been intense and someone yelled get a room you two. I laughed and said that's a great idea, you in? She blushed and said I would be but it's not a good time of the month. However I am counting on it next weekend, by the way can you actually get a room at 17? Well Mrs. Simmons I'm going to find out and she laughed out loud. Let's head back, tomorrow is going to be an ugly start at school, and I need to make this thing between my legs have a quiet night. She said Michael I love every inch of you. Carrie please stop with the Michael - Mike is good enough. We chatted about things and the money came up again with her asking Mike all this money is it yours personally? I said Carrie it is in a trust controlled by my attorney and me and he goes away as I get older. Please don't ask me he how much. We drove past a very big newer house and I said Carrie you see that house over there, what do you think that would cost, she said I have no idea, I said pick a number and she said, 200 thousand. I said bade that's a little low but I could buy 100 of those homes and pay cash and still have money left, please drop the subject. That's a lot more than I wanted you to know but I am a seriously rich kid and I don't want that to have anything to do with what we have going on. I am going to bust my fucking ass to prove to dad that all that trust he has shown is worth it. So if you think I am going to be a rich playboy with no responsibilities tell me now and I'll drop you off at home and one of those line will have been crossed and things will never be like this again. Mike pull over, please. I pulled into a parking lot parked away from the other cars. She looked and me and said Michael, and I'll call you that every time it is serious, I love the guy that was at the park with me all day not the jerk in the car on the way home. I don't care if you a dime, two dimes or a trillion dimes, I love the Mike I have gotten to know so cut the shirt and kiss me, I did and said I'm sorry but the money thing is hard for me and fuck just kiss me. We did and she reached between my legs and started to laugh, damn I wish I could have helped with that today. Mike, I hope we actually do what you said and get married some day. That's a long hard unsure road. I smiled and said Carrie it will be what it becomes, only this time I am determined to make it be.

We got home, we quickly kissed goodbye she felt be up again and remarked it was soft again and I slapped her hand playfully saying don't encourage it. We unpacked the car, kissed good night and I drove home. I went in and found dad and A fully clothed Ray on the patio, I said Ray can I please have dad alone for a while, he said sure and left. Dad what you drinking? He said Mike what you having and I said a scotch sounded good and he said ok. I got up brought back two large drinks and dad replied so the date was that good? Dad, we had a picnic at north park and both of us were completely dressed all day, you happy? He said yes. Dad I'm glad because I proposed and we are getting married. He screamed WHAT? Just kidding dad but if we were college juniors that would be happening. Damn you plan ahead. I laughed and asked, so how is Ray? Glad to have some clothes on, so what's the modified task? Dad I left it up to him but it is none of your business and it will be over tonight, I'm guessing you won't hear a thing. Mike, so tell me about the date. Dad, what's with the trust issues with me and Carrie? Mike you are too all in on this girl and I'm worried. Dad you are right I am all in and she is all in as well. Have you ever experience that and he said no, honestly I have never been, not even with your mom. Dad that's a shame because it is an awesome feeling. Dad, let me ask and please don't answer till I'm finished, he said sure Mike. So dad am I slacking in anything, football, schoolwork, college recruiting, Brian and Tim issues, being responsible around here, is my laundry done is my room clean and am I eating responsibly. Please now tell me one area where I am deficient? He thought for a minute and said Mike I can't honestly think of one area. I replied so will you please let up on Carrie? He said I'll try. Dad how about the three of us have dinner at the club some night? Mike this sounds a lot like I am meeting the future Mrs. Michael James Simmons, Jr.? Dad that is a work in progress and it will not be for at lease 4 years so relax, I'm just trying to make you relax. Ok, Mike no dinner, especially at the club that would be the talk of the area, just please be careful and I'll back off. Mike one question, does she know about your financial situation, I said dad she calls me her spoiled rich boyfriend, based on my car my life style, the shopping spree I went on for clothes and how I don't work, but she truly thinks you just spoil me. Don't ask that again, good night I need to talk with Ray.

I went upstairs and found Ray sitting on my bed nude. I said well that's a surprise, he said you and your dad were longer than I thought, how was your day? I said Ray I'll tell you all about it once we settle the bet. Have you made a decision? He said yes, the most embarrassing thing was being naked all day in your house with your dad home. Next was answering the door to get pizza nude with Andy delivering the pizza, those two things are out. So the task I am choosing is me being naked in the shower and you feeding me your piss and me swallowing it. Does that meet your requirements? Ray it does and after that I hope we can get back to being best buds. Well Mike no guarantees about the best bud thing but let's try. I replied Ray I don't piss on command let's hang out here and I'll get out of these clothes, just close the door. I stripped to get to his comfort level and ask so Ray how bad are things? He said the underage drinking is not serious, thankfully I'm not 18 and the nudity thing was dropped, thanks to your dad. So on a whole pretty good. Football is another issue, but that's for tomorrow, unless you know something? Ray, I know some and there will be an assembly first thing tomorrow and it will all be put on the table and I am assuming there will be media there, but that's all I got. Ray now I need your help, todays date was a lot of fun but I am incredibly horny, can we change the task to me fucking you? He said Mike as much as I dislike that it is better than drinking your piss. I went to my desk drawer, got a bottle of lube tossed it to him and said put a lot in that hole, I need this. As he was doing this I was thinking about Carrie and got immediately hard, he looked over and said damn that hard already? I said pick a position and he went over bent over my desk, I retrieved my under pants said open up, I promised dad no noise, I put them in his mouth got my tee shirt and put it in my mouth. I lined up with his hole and drove it balls deep, he tensed and moaned into the gag and I started to pound his ass hard and fast. I was close pulled out went and got a condom tore open the package put it on and went balls deep again. The break helped and I went for a while longer filling the condom to the point where it was almost spilling out. My rapidly softening cock slid out of his ass and I remove the condom, threw it in the wastebasket. Ray, I'm not done. He replied really and I answered just jack off and shoot on my feet. He started and it took a while but he finally shot a nice sized load on both my feet. He started to get up and I said dude, clean that mess up using your mouth. He looked up and said Mike that's really sick and I won't do that. I said that's fine Ray then it's nude the rest of the time you are here or get to work on my feet. He immediately started licking his cum off my feet and from between my toes. I know he hated it but fuck it turned me on. This punk ass dude sucking my toes was awesome. He looked up and I said keep going, he said why they are clean and I said because I am enjoying this. Then he grabbed my ankle and opened his mouth and started on each toe individually. It was when he got to my big toe and took it all the way in his mouth then a second toe and then, damn all of them that I almost lost it. I reached down and helped Ray stand us gave him a big hug, he hugged me back and said, from all that I know I will always be second team behind Carrie and I'm good with that. He started to leave turned and said I'm sleeping nude tonight, thankfully there is none of that massive load to leak onto the sheets. How about a long talk tomorrow after practice, I replied deal and good night. I took a deep breath and thought he was very comfortable servicing my feet, I guess that's where he belongs, damn that's a shame.

Comments are encouraged as this is my first story.

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.

Next: Chapter 33


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