Damn, I slept well but really had to piss, I looked at the clock and decided I had time for a run before my call to Ray. I dressed for my run and went down stairs and found dad in the kitchen reading the paper and drinking coffee. I thought what the hell and poured my self a coffee and sat down. Dad looked up and said coffee and no run, what's up? Nothing I just thought we could spend some time together and I can always run. Ok, what you doing today, I said Ray and I are working out then some reading and hopefully hanging out with Carrie. What you doing, dad? He said lazy morning, meeting at the office and then nothing. What is the meeting about? He replied routine stuff with a team working on a new project, nothing special. I put some toast in and sat back down, dad, I had a good time last night and was glad you let me have drinks - one benefit of the club I guess. He looked up smiled and said, I enjoyed you company. It was nice to relax and have you leave your guard down some. I replied, get used to that, I need a friend with no agenda. What about Ray he said. I replied things are evolving and we are pulling apart. So the bets are to the point where the friendship is becoming all about the bets. So how do you know that, I asked. Let's just say, I get that and leave it alone for a while. I got up went to the bathroom, coffee makes me piss and called Ray.
Ray answered and asked, you ready to pay up or are there more excuses? I am ready, where and when, he replied my place in an hour, fine I replied. I went back to the kitchen and found dad on the phone, I waited till he hung up and said I am going over to Ray's in a little while. So a bet is due to be due to be collected he said, I just said yup. He paused for a few seconds, by the way the papers you requested will be delivered this afternoon you will have to sign for them. So pay off your bet, work out and be home before 1:00. Sure dad and thanks.
I went up stairs stripped and laid on my bed thinking about Ray and what would my afternoon reading entail. I pulled on a pair of old basketball shorts, no boxers and a loose tee shirt. When I went down stairs dad was working in this office so I just left for Ray's. Ray was in the kitchen drinking a beer and I flipped, dude it is 9:00 and you are drinking. He looked at me and said shut the fuck up and get upstairs and take that ugly shirt and shoes off and kneel in my room. I shook my head and went upstairs and did as requested.
Ray, finally came in holding another beer and I got up and said I'm not doing this with a drunk. He walked up to me put his arms around me gave me a big hug, looked me in the eye and said yes you are and 2 beers even in the morning don't make me drunk, so shut the fuck up and either enjoy this or don't it does not matter to me. He knelt down grappled the waistband of my shorts and pulled them Dow. Damn you are commando and semi hard. I guess you are looking forward to this? So dude, have you shit yet this morning, I replied that I had not. He said good first an enema. He went into the bathroom and produced a filled enema bag that I had not seen before. He said lay down, you know the position. When I was in position he shoved the tip in my ass no lube, stretched the hose as far up released the clamp and warm water started filling my gut at a rapid pace. I was struggling from the start. The bag emptied quickly he pulled the tip out and said commode and don't let it out. That made it harder, I was sitting there when he came back in nude turned around bent over and said eat my ass. He said if you do what I say you can release the enema. I reached up grabbed his hips pulled his ass to my face and started to lick, he said the hole dude use you tongue, I did and damn it could have been cleaner, no shit but lots of sweat and obviously he had not showered. I started to lick and release the enema. Ray straightened up turned around and said now my cock and finish releasing the enema. There is more I have planned for you. I sucked for a while and finished my business and he said clean up, no shower and get on your knees in my room.
I did as requested and Ray was waiting for me. Dude, you want a beer, I simply shook my head no. He got behind me, place a white strip of fabric over my eyes and tied it behind my head blindfolding me. He then leaned in and kissed me using his tongue then broke off the kiss? You have this figured out yet, I shook my head and he punched me in the stomach and I doubled over as I was unprepared for that. He kiss me again and said, you get it now, I shook my head again and immediately he grabbed my nips and pinched, I screamed and he kissed me again. He asked again and I replied no and was kissed again. Finally, he said you are such a fucking ass. The point is I can be nice or nasty and you have no say. Get on all fours and if you move I'll restrain you, your choice. He went somewhere knelt by my ass and I felt lube being put on my hole. I wanted you cleaned for a reason and he inserted a finger, it was different but pleasant but that was short lived as he inserted a second finger and started to finger fuck me. But damn that was starting to feel good when he put a third finger in and started working my hole. Damn that hurt and he kept it up but it never got comfortable and then I screamed as he shoved a fourth finger in. I was grunting and begging for relief. Ray responded by working my ass faster. I put my head down which raised my ass and he said thanks dude, that makes it bette for me. After what I would say was five minutes he stopped and helped me to my feet. I was hard and leaking pre-cum. That's unacceptable he said and kissed me and damn that did not help. While kiss me he reached for my balls and squeeze, I screamed and yelled stop please, that hurts. I do t care, he said get on your knees. Now that was fun, get on your back and give me 50 sit-ups. That was easily accomplished. I finished and he said 50 push-ups that was more difficult but easily in my range. Then he said get on your hands and knees and when I did he started with 3 fingers but no lube and he said he was using sweat for lube. Then It got real again as the fourth finger was forced in and I screamed fuck dude, go easy. There was no reply but a big glob of lube. Ray then said your choice my thumb and 4 fingers or 20 swats with my belt. I replied belt. He pulled his hand out of my ass and shoved his cock in and fucked my ass hard and fast till he shot in my ass.
Damn, now I had 20 swats to deal with. Get up and put your stomach on the seat of my chair. I did he removed the blindfold. He then said we could reduce the swats if I agreed to shit his cum out of my ass and eat it. I replied swats. Ok no counting no shit and he swung and I was counting in my head. I was determined to take it with no noise and as little reaction as possible. The first 10 were hard and fast the second 10 were slower and harder, at 15 he said damn, I'm going to get a reaction out of you yet. He swung and I jumped a little and by the end I had tears in my eyes but he was pissed at my taking his best so well. Ok, dude tell me how you going to work out today with that bruised ass, in fact it might be a few days. You want a beer?
I went over to him and grabbed him in a hug and kissed him deeply, then said thanks dude, I had fun, but I am not drinking and I am going to school and workout. Want to come? He just shook his head and said fuck no, I'm not doing that, I don't care what you think and the next time I win a bet this will be like child's play. Get the hell out of here. So I left for school and a workout.
I went in to the workout room and started working out and Jeff came over and was obviously pissed. Nice to see you Mike, where the fuck hav enough been? I thought we were to talk yesterday. Shit, I'm sorry, I totally forgot. There has been a lot of crap going on in my life. Ok, can we talk now, this is important? Jeff, I need to work out and home before 1:00 for something important, family related. How about I finish here, get home and you stop over my place at 3:00. Jeff, replied sure I'll be there. I went back to work and finished started out when coach said, Mike can I see you for a minute? Sure coach what's up, I replied. Practice starts in a few day and then a scrimmage at the end of the week. Have you given any thought to playing defense as linebacker? Not really I'll do whatever you think wins games. Well, I'm not ready to make that decision so I will be asking you to work on both positions. I just wanted to let you know. Thanks coach, but I have to run. I drove straight home, jumped in the shower and inspected my bruised ass. Damn it was swollen and red. Nothing to do but wait for package and then deal with Jeff.
About 2:30 the door bell rang and it was a delivery service, the guy said sign here. I did as requested, took the package and closed the door. I open the box and there were 3 folders with varying amounts of paper in each. I looked and the folders were labeled divorce settlement, will and trust. I thought, shit what have I gotten my self into. Then there was a knock on the door and it was Jeff. I put the papers out of sight and welcomed Jeff, saying let's go to the game room. We started chatting about things in general and it was pretty relaxed. I let it go on like that for a while and finally said, Jeff enough of this we need to get serious, about what he replied. I said Jeff I like you and I hope we can become friends but we are pretty different. I am more intense and conservative and you are care free and will fuck anyone walking. He laughed and replied, that's about right. Jeff, I said, we need to find common ground about drinking, sex, and drugs. Mike, he said, I'm not changing, football is important to me on many levels, but the other things are part of the package and my image. So Jeff, I asked, that image go to the college coaches as well? He replied, sure it does. On that level it is only about production, they don't care about the baggage. Jeff, thanks for the honesty, but that's not me, so where do we go from here. He replied football buddies, off the field we respect each other and stay out of each other's way. Jeff, I'm not sure that's possible as some of the shit you are into will interfere with football. It might, he said and if it does grab my face mask so to speak and refocus me. Football is important to me very important. Ok, that sounds like a deal, so no what, you want to hang out a bit. He leaned in hugged me and said Mike what I really want is for you to fuck me. I looked at him and said as tempting as it might be, and you do have a hot ass, how would that be football buds? Actually me being me, you owe me a favor as Andy hasn't told anyone you had Ray answering you door nude, so let's just fuck one time, we can be football buddies once practice starts.
Just then my phone rang and it was dad. He asked if I got the package and I said that it came around 2:30 but I had not had a chance to look at it. He said ok, then added he would be working late and would not be home for dinner. Shit, I was hoping to use dad as an excuse to get rid of Jeff. I want back to the game room to find Jeff nude with his ass up in the air. I said Jeff it can't be like that, please get dressed. Let's just play some video games, please. He got dressed we started to play a game then he said since you won't fuck me can I have a beer at least. They are in the refrigerator and bring me one. He came back with 2 beers sat next to me put his arm around me said let's go upstairs, I said your choice beer or sex? He said I'll put these back, we doing it here or in your room, my room I replied.
We went to my room and Jeff locked the door and started to make out with me like a sex starved maniac. I have to admit I responded in kind, clothes were all over the place and we collapsed on the bed and he was kissing me, sucking my nips, balls and cock. I pulled him up to me and kissed him and said, hold on there tiger you have a condom? Dude, he replied I'm a Boy Scout always prepared, he found his pants produced a condom tore open the package and started on my cock and balls, when I was hard he slipped on the condom and said up to now I have been doing all the work, so fuck me hard. He got up and got on his hands and knees on the bed, I flipped him on his back and I said, I want to do it like this so I can see your smug face while I fuck you. I lifted his legs and said hold them up and I got some lube and went balls deep on the first thrust and I simply pounded him fast and hard. Jeff was moaning and I reached for his cock while I slowed to a steady pace. With that he was really moaning Nd he tensed and shot a load all over his chest. I whipped a glob of cum on my finger and put it to his lips and he licked them clean That was so hot it brought me to the point where I filled the condom still in his ass. I collapsed on Jeff and we just laid there till he kissed me and said, damn that was hot. I pinched one of his nips and said shower. We showered and I said, pizza? He said, I can't I have a date. I just laughed out loud. Iraq he noticed my red ass he didn't mention it.
With that, went to try to read the documents.