I Lost a Bet

By Gary Sechen

Published on Jan 3, 2023

Gay

The following story is fiction. Any likeness to real persons is purely coincidental. If you are under 18 or if it is illegal for you to read this in your region, please leave now and only return when it is legal for you to read this material. Otherwise, I hope you enjoy. Any feedback would be greatly appreciated. I am also very open to new ideas, characters, places to take the story, etc. Any feedback can be sent to gswm@bellsouth.net.

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M, MM, anal, BD, Exhib, WS

Chapter 3 - Friday night

Our short nap did little to resolve the tension with my cock, Sir woke me and I still had a raging hard on.

I stood beside the bed and helped Sir dress for dinner. I was (and all weekend) would be dressed as nature intended. Sir decided that I should have the hand cuffs properly attached, one to each wrist, for dinner I was allowed to keep my hands locked in front of me. Sir had me hold a plastic cup so that he could piss in it; it was a strange feeling holding another man's piss in a warm cup. I was ordered to take a big gulp and we moved on to dinner. I eventually walked normally to the restaurant, getting used to the large butt plug I now had in me. I carried Sir's piss and when we were waiting to be seated, I finished the cup. I held onto it incase Sir needed to use it again. We met up with Jack and a few of his friends and Jack had a naked guy with him, it was the one who was trying to hit on Sir earlier. We were able to get a large table with Sir and his friends seated in chairs, I alone was seated on the floor behind Sir. I learned the other naked guy was named Michael and he was allowed to sit in a chair at the table. I was glad that I didn't have to eat with him. Whenever anyone from our table got up to use the restroom, Sir handed my plastic cup to them and asked if they could get me a refill. Of course the cup always came back full for me to drink. Dinner was actually quite good, getting used to eating in hand cuffs was a challenge.

The men at the table decided that we should all go for a walk to allow the food to settle and then we should get a drink and sit by the bonfire. Sir and I were the last of the crew on our walk. I could eye Michael who I thought was my competition for Sir's attention. He was younger, had a better body and was a smooth talker - three things that I was not. My mind was racing again, thinking only the negative thoughts of how wrong things were going to be. Just at the right moment, Sir put his arm around my shoulders and pulled me tight while we walked. He must have read my mind. Chairs were arranged around the fire and Michael and I were sent with money and the drink order. I carried four drinks back to our group and Michael had the other three. I had left my cup with Sir and sure enough by the time we had returned I had another drink waiting. Michael couldn't understand how I kept getting refill from all the guys. I sat in front of Sir; he wrapped his legs around me. I was able to rest my head on his legs and thoroughly was able to enjoy the fire and listen to the men converse. I discreetly asked Sir if I could be allowed to refill my cup with my own piss and Sir nodded I could. I left with an empty cup and returned with a full cup, it even had a head on it. I was beginning to be a connoisseur of piss; I could tell what someone had to drink before I had theirs. My piss tasted quite strong, but that was because I wasn't allowed to pee very frequently.

The guys started to disperse in various directions. I could see Michael was looking at me as if he could kill me, he was so obviously jealous. As he left, he pointedly said to Sir that he hoped he would see him later. Sir replied that might happen. Sir suggested that we take a tour of the dance bar and maybe even play another game of pool. I grinned back at him at the thought of where our journey began. The music was loud and not many guys were dancing yet. Of course my first concern was that I was the only naked guy again, but since Sir had his arm around my waist the tension was eased a little bit. My eyes locked on a couple across the dance floor, they were talking in a group and didn't notice us. I turned and faced Sir and said we needed to leave immediately. His concern was evident in his voice and he walked me back to the pool table area so we could talk. I told him that I saw someone that I knew from my home town. We played on the same softball team, I had no idea he was gay and the guy who I thought was just a roommate and also played on the team was here with him. I said Joe knew many of my co-workers and I was afraid of what he might do or say. I was desperate to leave and I pleaded with Sir that we do so at once. He made a deal with me. If we left right then through a side door, he could have a little more kinky fun with me over the weekend. I said to Sir I would do anything he wanted but we had to leave at once. He asked me to point them out so he would know who I was talking about. He said that he memorized their features and would do all he could to avoid contact. We left without them seeing me, I was hyperventilating as we walked back to our cabin. I thanked Sir for his compassion; he thanked me for giving him more opportunities for fun. Sir told me to go wait at our cabin and he would stop and get us a couple of beers while I calmed down. This little scare was the only thing that deflated my cock, all evening it was leaking and mostly hard. After seeing Joe and his roommate Craig, I think my cock nearly disappeared.

Sir had me sit on the floor while he rummaged thru his duffle bag. Sir asked me about Joe and Craig. I told him that Joe was always bragging about how good he was and that he was better than everyone else. Joe thought he could do no wrong, and even if he did it was always somebody else's fault. Sir said he had a plan to humiliate Joe and his friend Craig, but that I was to be an integral part of it. I looked very skeptical at Sir but he told me to listen to the full plan before deciding. Sir said he wouldn't go ahead with the plan unless I was totally comfortable with it. He said it involved me wearing one of his leather hoods so that Joe and Craig wouldn't know my identity. The rest of the plan involved conning them into Sir's plan and making it so public and challenging he couldn't back down from it. Sir seemed to have a little bit of a conniving, evil streak in him; I'd need to remember that. Sir told me the plan a second time and asked me to repeat it which I did. He asked if I was ready, I chugged the remainder of my beer and we returned to the dance bar. It was a little more crowded now and a couple other guys were naked but for some reason most stayed in their clothes. Sir led me by the leash and we had another beer. Sir waited until he noticed that Joe, Craig and the rest of their group noticed us, they even were pointing at us. I started to shake a little but Sir again put his arm around me and even toyed with the butt plug. This brought me back to my new normal and we headed for the pool table. Sir uncuffed my wrists and we set out to play a game of pool. Neither of us was playing any good, occasionally hitting a good shot but also missing some really easy shots.

It didn't take long for Joe & Craig and their crew to follow us into the back bar. They watched us play and chuckled when we missed, I overheard them say the stupid slave can't even shoot pool. They wondered out loud how a master could tolerate such behavior of his slave. Sir took a moment before my next shot to give me what appeared to be a few pointers, he actually was telling me to ignore what they were saying and they plan was working perfectly so far. After Sir slapped my ass I did make the shot. The obnoxious guys gave me a Bronx cheer - if Sir wasn't here I'd have left crying I'm sure. We were getting down to the last few balls left on the table and finally Joe confidently walked over and put some quarters down as a challenge. Sir missed his next shot but left me with a great shot which I made. Sir came over to me and was giving me instructions on how to shoot the angle so I wouldn't scratch with the cue ball. Of course I did not do it correctly and I did scratch so Sir won again. I went over to him and he grabbed my nipples and twisted, saying one of these days you'll learn but at least you keep trying. He continued rather loudly that since I lost, I'd be taking a pounding in the woods tonight. That got some chuckles from those watching.

Joe walked over and said to Sir that I guess it is my turn to win now, and perhaps he would be doing some pounding of his own along the trails tonight. Sir wished him well but inquired if Joe and his partner would like to play doubles against Sir and me. I was shaking my head no to Sir but he said let's see what the challenger would like. He looked at his partner Craig who shrugged his shoulders and Joe turned to Sir and said you're on. And Joe continued how about we make the game a little interesting.

Craig came over and tried to get Joe to stop but as usual Joe's mouth couldn't stop. Joe added that the winning pair should get their way with the losing pair on the trails tonight. Sir said that sounds like a fair wager but that the losing pair should strip naked and give their clothes to the winning pair for the duration of the night. Craig was not up for this part of the bet even though he was the better looking of the couple. He did all he could to stop his partner from agreeing to this but Joe knew he couldn't lose so Sir and Joe shook hands on the bet. Sir asked if he could get the two competitors a drink while he was at the bar and they said thanks and told Sir what they were drinking. The pool table was set when Sir returned giving them their drinks and handing me a beer. Sir broke the rack and made one in.

He missed his next shot but was able to bury the cue ball so Joe really didn't have a shot. It was my turn and I made a shot but couldn't make the next. We are ahead two to zero. Craig meekly walks up and badly misses his shot, I know his nerves are getting to him and Joe starts laying into him when he walks back. Sir is able to make a nice bank shot but can't get the next one in although he leaves it nicely for me next to a pocket. He comes back to me and massages my shoulders while we wait for Joe to shoot. He decides to make a big production out of this shot, walking twice around the table. Finally he shoots and he makes his ball but the cue ball also knocks in one of ours. He doesn't have a good shot and misses. I have a difficult shot to try and get the ball in that is by the pocket but I know I really can't make it. I see a shot that if I just barely touch it, the ball might roll into another pocket. I try, but miss, leaving the ball to block that pocket. It is now Craig's turn and Joe is admonishing him to not blow it. He is told time and time again that he needs to man up and make a shot. Of course with all of that positive coaching, Craig again misses. Sir has an easy shot, we are now up 4-1 and he makes the next shot so we have only two more balls to make and we'll be shooting for the 8 ball. Sir misses leaving Joe a difficult shot. Joe is nervously pacing the floor. He lines up his shot and he does make it but is not left with a good shot since we have blocked two of the pockets. It is now my turn, I take a deep breath and size up which of the two shots I'll do first. Sir does not interrupt my concentration and I shoot and make the shot. I see that Joe is arguing with Craig, Craig is giving it right back to Joe. In what should have been an easy shot for me, I miss but I do not mess up the table for Sir. Craig is at the table and he is visibly shaking. He badly hit the cue ball and their ball ends up along the side rail. Sir has an easy shot at the last ball I missed and of course makes it. It is now up to him to make the 8 ball and we'll win. He looks over at me and winks but he only moves the ball closer to the pocket missing badly. Joe walks up to the table and talks about running the table so "he" can win. He will need to make 5 of their balls in and then make the 8 ball. Sir has his arm around my shoulders, gently rubbing them as we watch Joe.

He does make the first one but the tension gets to him and he misses very badly. I'm left with a very long shot down the length of the table. I'm left with a somewhat tricky shot to hit the 8 but to leave the cue ball out of the pocket. Sir gives my butt plug a little pat and I up looking at the shot. I line it up, take a deep breath and shoot. I close my eyes only to hear some ruckus in the background. The room is applauding, Joe is blaming the loss on Craig, Craig is pointing his finger at Joe, but more importantly, Sir was walked up to me and given me a big hug. He told me he knew I could do it and slapped my butt a couple of times. Sir and I walk over to shake hands with Joe and Craig but they are still arguing. Sir politely says he is ready to take their cloths; Craig shakes our hands and says good game. He removes his clothes and asks if he can keep his flip flops, Sir says yes. Sir also admires his will toned and very hairy body. Joe is still fuming; I walk over to him and hold my hand out for his clothes. He says to give him a minute, he walks over to the corner removes his clothes, walks past me and hands them to Sir.

He tells Sir that lets go to the trails now but Sir says he wants to enjoy a celebratory cocktail with his boy. He hands Joe a twenty and says what we are having and to get Craig and himself one as well. Sir reattaches my hand cuffs and we go back out to the dance bar, carrying two extra pairs of clothes. Sir finds a bag to hold their clothes and I carry it. I recognize a few of Joe and Craig's friends and they come by to congratulate us for a good game and encourage us on our winnings. Craig comes by to bring us our drinks and apologizes for Joe's behavior. Craig toasts us with his drink and decides to stand next to me so he will be less noticed and outside of Joe's rants. Sir whispers in my ear and I nod enthusiastically back to him. I nudge Craig and we are off to find Joe and to claim our winnings.

We have entered the trails and walking in the dark is really difficult. Sir finds a big enough open area and tells Joe to get to his knees. Sir puts a blindfold on him and also puts one of Craig. Sir gets the lube out and pushes Joe down to all fours and starts lubing up his hole. Just to shut him up, Sir puts Joe's underwear into his mouth. Once enough lube has been used, I get to suck on Sir to get him hard. He is ready to give it to Joe and he does. He enters Joe and is doing a nice long slow fuck. Sir wants this to last. I now turn my attention to Craig. I lay him down on the ground and get between his legs and give him a blow job. He is quite shocked at this, I'm sure he thought that one of us would be fucking him as well. I've decided that Craig deserves a good blow job and since I need the practice why not. Craig really has a great cock to suck, not too big and his moaning lets me know I must be doing it right. I pull off his cock and blow on it and he moans again. I suck on his balls and he is nearly rolling around he is in such pleasure. I go back to tease the head of his cock and he can barely hold back. I lick his hole and he nearly shot. I grab his balls and dive on his cock one last time and he shoots in my mouth where I can taste it. I keep sucking even as it gets too sensitive. I finally stop when he is nearly crying. I climb up on top of him, lean down and give him a big kiss sharing his cum with him. Our tongues share it back and forth until none is left. I lick on his nipples and he is still in heaven, not what he really thought he would be in for tonight. I pull him up and grab his cock and tell him to pee. It takes a while but a small stream starts and finally it is going full blast. He doesn't realize that he is peeing on their clothes. I don't feel the need to tell him. I tell Craig to wait right there and I'll be back shortly.

Sir is still doing his nice slow long fuck on Joe. Both are moaning I'm not sure who will cum first. Sir motions for some of the guys watching over to jack off on Joe. It doesn't take long for the first shots to hit him on the back. Soon the rest of the crowd is following suit. Lastly Sir pulls back for one long stroke and buries his cock deep in Joe's ass. He is filling it up like it never has been in the past. Sir tells Joe not to move and he'll wipe off his back which he does with Joe's shirt. Sir tells Joe that he is to remain in the woods for one hour doing whatever he likes and at that time to find him in the bar for his clothes.

Lastly he tells Joe that Craig has been given the same instructions and not until they both show up in the bar will they get their clothes.

Sir, Craig and I walk back to the bar. Craig has not caught on as to who I am. Sir and Craig talk a little and I now understand that he is really a nice guy. Why he is with Joe I'll never figure out. A guy comes over to talk to Craig and Sir tells him to go on and enjoy himself. Sir attaches the leash to my collar; he pulls me in front of himself and wraps his arms around me while we both watch the crowd. So soon after he has finished fucking Joe I can feel Sir's cock knocking at my hole. He gently rubs my nipples and asks me how I'm doing. I tell him I can't wait to see Joe's face when he comes back and even more when he finds out the condition of his clothes. We've heard that the two of them are just there for the night and are driving back home as soon as their hour is up.

I see many guys staring at us; I realize it is not just me they are looking at. I feel good about this. I can be naked and enjoying myself at the same time. Sir asks me if I'm thirsty and I say yes. He gently slips away heading to the bar, I watch the crowd, some dancing some trying to pair off. A few are watching me; I stand up tall and proud. Eventually Sir returns, he has his drink and I see him hand me two drinks for me. I literally am a two fisted drinker and since I'm also cuffed I must bring both to my mouth to drink one of them. I quickly realize that they are both filled with piss. I turn towards Sir and he toasts both of my drinks, he says I get bonus points if I can tell which one he supplied and double points if I can tell who supplied the second glass. I taste one and then the other, back and forth between each one. They both taste familiar but I finally choose the one in my left hand as Sir's piss. He smiles, leans in and kisses me and says correct on the first account. Then he says I have until I finish the second cup to determine whose piss that one is. I search the crowd knowing that one of these guys is the donor.

My eyes connect with Craig, he smiles and now I know. Sir congratulates me and tells me I should go thank Craig. I walk up to him and say one naked guy to another, thank for the drink. He says to me thanks for the fantastic blow job, you could teach Joe a lot about taking care of a man. I just smile and say it was my pleasure. I comment that maybe we could do it again sometime and Craig says I hope so.

I notice a commotion and see that it is naked Joe looking for Craig so I hustle back to Sir. We watch the whirlwind that is Joe, sucking all the life out of the bar. Fortunately he is just in a rush to get his clothes and leave the campground; everyone is hoping he'll never return. Sir hands him the bag of clothes and he grabs it walking toward Craig. Finally he realizes that his clothes are cum and piss covered and he just blows up. He throws the bag at Craig and tells him they are leaving now and to get a move on. Sir hugs me and tells me he knows why I was concerned about running into him. I thank him for the evening. Sir says shall we go and I say I'd love to.

We are back at our cabin and Sir has undressed nearly matching my outfit. He unties the mask I've been wearing and he rubs my hair and face. He says to me why don't you see if you can bring me back to life, I don't need to be asked twice. I'm on my knees working on Sir's cock. I start by licking the head all around and next take each of his balls into my mouth. I ask Sir to lie down on the bed and lick between his balls and ass; I've found a pleasurable place on Sir's body. Next I lift Sir's legs and suck on his ass hole. Now I have him moaning. I return to the head of his cock and he is beginning to leak some of his juice for me. I have all of Sir in my mouth, working him down my throat. Sir has wrapped his legs around my head as I get Sir all the way in. Sir is now face fucking me using his legs for leverage. I'm able to control my breath and this is now as pleasurable for me as it is for Sir. I feel his cock swell and I know he is unloading down my throat. My cock is trying to burst out of its skin but I maintain my calm and this time do not explode. I try to work my tongue over the head of Sir's cock to coax a little more cum out but I think he has now been drained dry. Sir pulls me up into bed with him and up tight to his chest.

Next I feel the covers up around me followed by Sir's arm. My nipples are rubbed gently, next my belly and finally my cock and balls are felt by Sir's strong hands. I'm replaying the day in my mind trying to not fall asleep so I can enjoy everything again.

Next: Chapter 4


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