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M, MM, anal, BD, Exhib, WS
Chapter 13 I Lost a Bet - Weekend Away with Sir and Craig
Sir buzzed the intercom and I let him in and I was waiting for him at the door naked of course.
We hugged and kissed like we hadn't seen each other in months. He asked if I was ready and said yes. He handed me a wrap around towel that attached with Velcro. He handed one to Craig as well. Craig looked dumbfounded and Sir wrapped it around him. I went into the bathroom and put all of our things into a kit and said we're ready. Sir grabbed one of Craig's hands and I grabbed the other one and we left the apartment. Sir opened the door for Craig to climb into the back seat and at the same time tore off his towel. Craig sat down immediately. I handed mine to Sir and he threw them into the trunk.
Sir was pulling out of the parking lot and all Craig could say was "what the fuck" and kept repeating it. I sat sideways in the front seat and explained that we were going away for the weekend to a county retreat. I reminded him of Jack from the campground and at the dinner party. I said we were going to his home for the weekend since he was away. Craig asked about clothes, neighbors, driving there and just rambling on. I told him the house was way in the woods and wasn't visible from any roads and no neighbors were within miles. It would be just the three of us out enjoying nature and by the way without clothes for us. He still couldn't wrap his head around it, I said to just trust Sir, I had learned that.
I asked Sir if we passed a coffee shop I'd like one for the drive and turned and asked Craig and he replied "wtf" sure. Not too far up the road we saw the familiar sign and Sir pulled in and ordered for us. When we got to the window Sir paid and passed the drinks to me and I gave one to Craig. He was just shaking his head and took a sip. Back on the road Craig finally asked if this was a normal routine for us and I said that we don't have a normal or a routine. Sir pulled off the road and onto a gravel drive and said we are entering Jack's property. It must have been 10 minutes and we finally stopped at his house. It was a huge log cabin place with a wraparound porch. It had a big garage building and a hot tub nearby. I said I'll carry our luggage and Craig hit me on the back of the head. Sir said he did have a small bag that Craig could carry for him.
When he exited the car Craig's rock hard cock was leaking pre cum. I said look who is happy to get here. Craig gave me the evil eye and said he has been hard the whole drive.
Sir unlocked the cabin and we saw a big fireplace, modern kitchen and several rooms, searching for the one's we'd use this weekend. We looked and saw Jack's large bedroom and moved on until we saw two guest rooms, each had their own bathroom.
In the kitchen we read a note from Jack which said he had stocked the fridge with plenty of food and beverages so we should have enough for the weekend. Sir pulled out some food and asked who wanted to grill it. I said Craig and I would handle that. First he said he had a pair of hand cuffs to put on me for the weekend. Locked in place Craig and I searched for the grill then got it going. I told Craig to go get us a couple of beers and to ask Sir if he wanted one. Craig returned and he said Sir was busy but would join us in a while. We sat down and Craig asked how long I had known about the weekend plans and I admitted I found out only this morning.
He asked how we knew he would join us and I said you would, period.
He asked what we would be doing all weekend here in the country and I said that was up to Sir and he had never let me down yet. I've learned to trust him. Craig admitted it would take him a while but since he hadn't been arrested yet that was a good first step. I told Craig that he needed to learn from his experiences with Joe and to move on to better things. I said Sir had pushed my limits and made me comfortable with who I am. He would never intentionally hurt me. He said I'm glad for you and that we deserved each other. I told him his knight in shining armor would come along if he was ready for it.
I told Craig to get us another beer and to tell Sir the fire was ready. Craig brought out the meat, a beer and a special drink for me. He had to go back inside to help Sir with the rest of the meal. I put the meat on and sat back down in the rocking chair. It was doing wonders with the plug, nearly as good as Sir's cock. I'd finished both beverages and brought the meat in. I asked Sir if I could pee and was told that I had an empty cup and that would suffice. We sat down to a great meal and discussed various things. Sir asked Craig if he wanted to do anything special this weekend and he said not getting arrested would be top on his list. Sir smiled and said that was part of his plans. Sir asked if there was anything else and he said he would join in with whatever we would be doing as long as he wasn't going to be a third wheel. Sir said I guess that leaves things wide open. Sir looked at me a winked and I knew the wheels were turning in his head.
Once dinner had been cleared and the dished cleaned up Sir asked Craig if he knew how the hot tub worked and he said yes and went and got it ready. Sir asked me if I thought Craig was up for some experiences this weekend and I said we needed to push him gently but he would do ok with me around him to help. He said ok we'll have some fun tomorrow morning and see how that goes then play it by ear the rest of the weekend.
We joined Craig who said the temp was almost correct. I handed him his beer and reminded him that he was to keep my mug filled as needed. We all got in and the tensions left our bodies.
Sitting under the stars and talking just among ourselves was good. We got to see where Craig stood on his changing life. He said he wasn't ready to jump into another relationship but did want to play the field. Sir said that next weekend was the leather event at the campground and wondered if he would like to join us. Sir had already booked a cabin before we won the free one and Craig was welcome to use it. He said he really would like that but he knew Joe was planning on driving up for the leather contest and he wouldn't feel comfortable with Joe being there. Sir said I don't think that will be a problem since Joe was banned for six months because of his behavior the last time he was there. Sir said no Joe so no problem right? Craig said he would think about it but he was inclined to join us. Sir reminded him that I was to be a celebrity judge for the contest and he would want to be there for that.
Craig said he thought he would go to bed as it had been an unnerving beginning to the weekend but he did say he was glad he joined us. He kissed the two of us and went to bed.
I finally moved close to Sir and thanked him. He said just wait for a couple of minutes and I'd really have something to thank him for. I realized he removed the plug and then pulled me onto his cock. This felt so wonderful as I rode him. Sir pushed me off and laid down the towels on the edge of the hot tub and then he reentered me. I was looking into his eyes as he pounded me. I ran my cuffed hands all over his body. Sir found that wonderful spot and I was getting hard and straining at my bindings. I was breathing heavy and finally came all over our bodies. Sir continued to fuck me. His eyes mesmerized me. I was getting that feeling again in my cock thanks to Sir. I wrapped my legs tight around his body. Sir was able to vary the speed in which he fucked me. Whatever he was doing it was working again. I rubbed his hard nipples as he kissed me. That was all it took and I was shooting again. I threw my head back and clamped down tightly on him. He was grinning and then I felt him fill me up. He didn't stop until his soft cock slide out of me. He rolled over onto his side and held me close. He ran his hands over the cum on my body and fed it to me. I licked his fingers clean. Before anything could escape my plug was back in. We fell into bed and Sir held me close to him as we fell asleep. I don't think I moved all night.
I woke when I felt something wet and hard poking between my legs. Sir said he didn't want to waste anything so I'd better hurry up. One taste was followed by another and Sir said he was ready for the day. He said he wanted to try and put a small plug up Craig's ass but that I'd need to help him clean out. I said I'd do that and felt he was ready for the experience.
I found Craig sitting outside with a cup of coffee. I told him we had a surprise for him. I pulled him into the bathroom and said I was going to help him clean himself out. He looked at me strangely but said ok. In ten minutes he was ready for Sir. I told him to get down on all fours and Sir entered with a lubed small butt plug. Sir put some lube in his ass and then gently pushed the plug into place. I asked if he was all right and starting to breathe again he said yes. I helped him stand up and he said ohhhhh. I figured it had found that wonderful spot. His cock was standing at attention again.
I brought him out to the kitchen and asked if he wanted to help with breakfast. We rummaged around and get it all set. We carried it out onto the porch and first gave Sir his helping. I told Craig to sit down and he did so with a wide eyed expression. I served him then myself. After we finished I picked up the plates and said I'd do the dishes and for the two of them to just sit and relax. I did hint that I was a little thirsty.
I had a drink waiting for me when I rejoined them. I said why don't we spend a little time exploring the property. I saw a trail heading out into the woods. Sir said that was a great idea and he had another one as he thought that Craig should get the opportunity to experience hand cuffs. He pulled out a pair and now Craig and I were almost twins only he still had hair on his body and I didn't.
Craig was having a little difficulty walking barefoot thru the woods besides the fact he had a butt plug up his ass for the first time and his hands were cuffed making it all a little awkward.
After about a 1/2 hour we came to a log and sat down. I was the only one who brought along a mug so I was staying hydrated. Both Sir and Craig filled my mug as we trudged along. We reached the top of a hill and stopped to take in the view. Sir told me it was time to take care of him. Sir told Craig to watch and j/o. Craig was ready to shoot in no time and Sir pulled him close so I'd be covered in his cum. That sent Sir over the edge and he was shooting and most of it hit my face. Sir fed the rest to me with his hand and also shared some with Craig. After a couple of deep breaths we started to head back. Craig was stunned but I was ecstatic.
By the time we had returned back to the cabin most of the cum had dried. Sir went inside and made a phone call. I talked to Craig and said for him to not put any labels on what had just happened and just to take each experience for what they were. He nodded but still somewhat foggy.
Sir reappeared and said it is time to go. We pulled Craig over to the car and put him in the back seat. I climbed into the back seat with him and Sir drove off. Craig was holding my hand looking every bit as scared as I was when Sir took me out for a drive the first time. I rubbed Craig's leg trying to reassure him. I saw the familiar barn as we drove in. We parked and got out of the car.
Sir locked our cuffs on each of our right wrists and he said to follow him. Craig's feet failed to move, I had to encourage him to follow quietly saying he didn't want to be left behind.
We stepped into the barn and I saw George Sr. and greeted him warmly as did Sir. Craig was introduced and he shook George's hand while using the other to hide his cock. George asked Craig if he had ever ridden a horse before and he mumbled that he had ridden a lot as a youth but it had been a while. Just then little Sasha came running toward us screaming that yeah he could get naked too. He was naked by the time he jumped up into Sir's arms. Then he hugged me saying how good it was that his Uncle boy was here and naked. I introduced him to Craig and he said hi and thanks for allowing him to be naked. Sasha climbed down and went running out of the barn to enjoy his time being naked. George said that darn kid has so much energy.
Three horses were waiting for us. Sir helped me climb onto mine while he and Craig hopped up rather professionally. Sir hollered to George we'll be back in a while. I could tell that the plug was having the same effect on Craig as mine was on me. Craig's cock was standing straight up while mine was straining. We found that same place that we had rested last time.
Sir spread the blanket out and handed us a piece of fruit. Sir and Craig got a bottle of water and I got my recycled drink. We lay down and talked while staring at the trees. Craig said he was still in shock and didn't know how he was doing all of these things. Sir told him to just relax and to try and not over think everything. He said he would try.
Craig jumped when he heard the footsteps. He saw the guy approaching. Sir and I were lying still. He said I thought that I had scared you two off last time you were here but I guess you are back for more. He said it looks like I'll get to try the hairy one this time. Craig was petrified. I leaned over and said I just had to give him a blow job and he'll let us go on our way. I said he'd better do it so we can leave. Craig crawled over and started sucking on his cock. I leaned down and started to suck Sir. Both men were breathing heavy and came at nearly the same time. Craig looked up at him and said, "Can we go now mister"? He was told that we could leave only when Sir had finished his blow job and then he started laughing. We introduced Craig to Sasha's father George Jr. Craig sat down, but a little too hard as it caused him to moan. I leaned over and gave Craig a kiss and said the same thing happened to me a couple of weeks ago when Sir brought me here.
Craig looked at me and said this whole thing had been set up? We nodded our heads yes. Craig then laid down but Jr. told him that was the second best b/j he had ever received. He asked if Craig and I would show his wife how it was done. Craig finally had a smile on his face as he slapped my ass. Jr. said oh you two are into that too! He'd love to have the two of us over his knee just as his father had done to him many a times.
Jr. helped me stand up and we hugged as did Sir and Jr. I helped Craig stand up and he just shook hand with Jr. and smiled. We got back up on our horses and headed back. Sir got a slight gallop on the way back and that had created at least two extremely hard cocks. George Sr. met us outside of the barn. After we dismounted Sir looked at the two of us and said we must have enjoyed the ride. I hit his arm and Craig hit the other one. As if on cue, Sasha came running to us. He asked if we got that way from riding the horses and we all said yes. Sasha grabbed me in one hand and Craig in the other and told Craig his was bigger. We looked at each other smiling.
We all thanked George Sr. and said we had to be going. Sr. said it was good to see us and to stop back anytime. With that we piled into Sir's car and headed out. Sir asked if we wanted anything and I suggested we should get a few groceries to replace what we were using of Jack's.
He said that was a good idea and maybe we would want some extra wine with dinner. Craig was getting nervous. He didn't understand Sir as I did. We pulled into the same grocery store and parked away from the other cars. Sir left the two of us alone in the convertible. Craig couldn't stop looking around watching for anyone who might be headed our way. Soon the teenager from last time was headed over our way. Craig said what are we going to do. I encouraged him to just be calm. When he got to us he said hello and I remember you from last time. He asked how we were doing and I pointed to my hard cock and said everything was fine. He asked for my mug and slid it underneath his apron and we could hear him pissing in it. He handed it back and I toasted him taking a big long gulp. Craig grabbed my hand and said he didn't set this up did he? I said we would need to wait to find out. The teen walked over to Craig's side and asked to see his cock. Craig's cock was standing straight up and leaking all over. The kid touched it and Craig nearly exploded.
We saw Sir approaching and Craig started hyperventilating. I told him to relax and try to image doing this without knowing Sir had set it up and I was by myself last time. He looked at me with his eyes wide open and tried to breathe normally. Sir handed the kid some money and then we were off. Sir asked what we talked about and I said the usual. What would you talk to a teenager about if he found you naked? And I mentioned that today he filled up my mug. All Sir said was great.
On the way back we were stopped at a light and the truck next to us could see Craig and me sitting naked in the backseat. All the guy said was way to go; he could remember when he did that as a kid.
When we got out of the car at Jack's, Sir reattached our hand cuffs as they were meant to be used. Craig and I carried the groceries in and put them away. Sir said he needed to check his computer and for the two of us to sit outside and relax.
Craig said this weekend had been too fucking wild. He didn't know if he could ever remember something so fun. I told him to take it one step at a time. He should realize that relationships can be fun and exciting. He confided that he was looking forward to next weekend at the campground. While he didn't know too much about the leather lifestyle he was curious. I said it would be great to have a friend along. But I reminded him he should seek out his own fun as well. He said he would be sure to do that and give Sir and me some space. I told him that I hoped that this weekend wouldn't change the friendship we had developed over the last week.
Craig said it wouldn't and that this weekend was about some self discovery for him. He thought he might be more relaxed around Sam next time he stopped by. I said great, one step at a time.
Sir asked the two of us to get him a drink and follow him on the trail behind the house. Craig held his beer as we followed behind. Sir took a different turn along the trails than we had earlier today. I held out my mug as we stopped and looked around. Sir filled it up and we were on our way again. Finally we came to a clearing that had a sling attached to a tree. I was ordered into the sling and Sir pulled out my plug. Craig was told to get Sir's cock nice and wet for my ass. He did the best job he could. Sir was pounding my ass as I loved. Craig was told to j/o and he was pounding his cock like there was no tomorrow. Soon he was moaning and shot his cum all over my cock as Sir told him to do. Sir continued pounding my ass. I knew he wanted something else.
I could feel it as he tried to fill me. He told Craig to cum again. Craig pleaded that he couldn't since he just came.
Sir told him to find another way to cum he needed to use his mind. Craig realized if he could play with the plug in his ass that might get him aroused. Craig pulled and pushed the plug and he started to get hard again. Soon he was able to pound away at his cock and he was moaning again.
Sir told him to cum all over my face and body. When Craig shot again Sir hit that spot in me and I shot a load as well. Craig and I were both breathing heavily while Sir continued to fuck my ass.
Sir told Craig that he wanted to see him shot one more time. Craig was in a daze and didn't know what to do. I finally helped him and guided his cock into my mouth. While Sir was pounding my ass I was sucking on Craig. His sensitive cock was slowly responding to my mouth.
Craig couldn't believe that he could get hard again but it was happening. When he started moaning again I realized that he was again close to cumming. I clamped down on Sir's cock and when he heard Craig cumming Sir began to fill my ass. I was getting filled at both ends. Craig didn't have much left but Sir seemed be filling me like never before.
Sir pulled out a cock cage to place on Craig. It was like an egg but it was made out of wires and attached to a cock ring. Sir locked it into place and now Craig's cock was locked as mine was.
Craig's cage was a large egg shaped cage that put his cock and balls into one confinement. I was re-plugged before Sir helped me down from the sling and said we needed to get back to the cabin for dinner.
I led the way with Craig following me. Sir followed both of us as we walked. Sir asked for a beer and said to get one for Craig. We all sat on the porch. Sir said god that was fun. He looked at the two of us and said he was worried that we would try to have fun without him so it was time he confined Craig. He said Craig could earn his way out of the cage next weekend if he could be trusted. Craig was dumbfounded but mumbled he was sure he could be trusted. Sir said with the two of us sharing a bed he didn't want us to be fumbling into having sex without him there. He admitted it would be fun but he was in charge and that it wouldn't happen without him. I said I understood and thanked Sir for his foresight. Craig thanked Sir as well. He asked Sir if he had any suggestions about wearing this cock cage. Sir said yes he did. He said he never put something on a boy without wearing it himself. He suggested that Craig get used to sitting down to pee unless he held my mug close to himself to give me something to drink.
Sir said he hoped that we would behave during the week and I replied we didn't have much choice. Sir said it was not uncommon for to bottoms to fuck each other with a double headed dildo but he hoped that wasn't the case until at least next weekend.
Sir said it was time for dinner, pasta and sauce was in the kitchen and for us to get it ready. One of us was to bring Sir out a glass of red wine while dinner was prepared. I sent Craig out; he was on pins and needles. He nearly spilled Sir's glass of wine but returned ok. When he did I said wasn't that fun. How many times have you cum twice let alone three times in one scene? He admitted it was the first time but now he couldn't play with himself until Sir allowed it. He confided to me he was worried about his confinement.
I told him to get the garlic bread in the oven while I finished the pasta dish. I suggested that he go fill Sir's glass again with wine and then return. He said that Sir kissed him and played with his nipples before he sent me back in. He said that Sir had him sit in his lap while he felt his body. I said that was a good sign. I thought that this was another game and we should keep playing. I made a bet that the first one to sit on his cock would get a prize. We finished dinner and brought it out. Craig served Sir his plate and filled his glass and then sat at Sir's feet. I gave Craig his plate and sat next to him.
Sir wrapped his legs around the two of us and said what a wonderful night this was. His boys served him a great dinner and kept his glass full. He wondered out loud who would be sucking his cock tonight.
I nudged Craig and we gathered the plates. I asked Sir if he needed anything else and he said no, but later he thought someone could think of something.
I asked if Craig and I could have one of his cigarettes and Sir said yes as long as we shared it in front of him. I thanked Sir and we retreated to Craig's room and got a smoke. We returned and sat at Sir's feet and shared the smoke. Sir was rubbing both of our heads. He said he was in heaven being with the two of us. He thanked us for keeping him happy. I suggested that we get the hot tub going so we could relax after dinner and Sir said that was a great idea.
Craig went to get the hot tub ready. Sir filled my mug for me. He asked how Craig was doing and I suggested that he was very nervous. I said that the rest of the evening we should take it slow and Sir thanked me for my honesty. Craig returned and we finished his cigarette. I grabbed his hand and Sir's and we walked over to the hot tub.
Sir sat between us, with an arm around each. He found a way to play with a nipple on each of us.
Soon Craig was moaning. Sir had Craig stand up in front of us. We could both see that Craig's cock was hard and bulging against his cage. Sir said he thought the fit was just right to keep Craig from having any fun until next weekend. I said it looked like it was better fitting than my cage.
Sir reached down beneath the two of us and began to play with our plugs. Since both of our wrists were cuffed we didn't have any choice. He told us to lean over the edge of the hot tub and he massaged both of our asses. He would pull them both out and then shove them back in.
We were moaning in ecstasy. Sir said for us to get out of the tub and to dry each other off. He watched as we did so. He wanted to see how we took care of each other without arousing each other. Sir said we were all to sleep together tonight. He led us to our bedroom and crawled between us. I wanted to suck Sir's cock but was denied. He pulled up the covers and waited for the first of us to squirm. He was between us and rubbing each body with a hand. He was doing this to see who got hard, erect and painful the first. I guess that I was the winner. My cock was straining first. Sir played more attention to me once he had me going. It was no use denying that I was the loser or winner however you played the game. He wouldn't let up until I begged him to stop or until I came all over us. I won as I was the first to cum.
Sir woke me and said he was ready. I knew what to do. I watched as he held Craig in his arms and I got to satisfy him. It was a special reward for me. Craig moaned while he watched. I saw his cock trying to get its release against the wire cage.
Sir said for the two of us to go clean each other out. Craig thought this was gross but we did it anyway. Once we were cleaned out, Sir said that Craig was to take me out onto the porch and to shave me with the razor. It was to be a learning experience for him and that I might request the same next weekend. I took Craig to the bathroom and then out onto the porch and showed him how the razor worked. He fumbled around my groin while I tried to help him. I said maybe this week we could practice some more.
We went back into the bedroom and Sir had another hard cock. I said I would take care of this and told Craig to make breakfast. I took the opportunity to make love to Sir. It was my turn to show him how much I appreciated his care for me. I sucked his cock like I never had. I went down and had it into my throat, massaging it with my throat muscles. I had him moaning and soon I was rewarded. He filled me up. I said thank you, I needed that.
I suggested that we go easy on Craig. He was worried about his cock cage. Sir said he would get over it in no time. I agreed but again said to go easy on him. Sir did so and we had a relaxing Sunday morning. Craig didn't strain too much against his cage. I made sure to admire his addition and asked what Sam would say about it. We laughed and went on our business. I took Craig for a walk around the property. I told him that whatever happened was between us. He should never think that what happened was anything more than sex. Although sex was great, sex could be just for fun. I said I was looking forward to our next bike ride and then what happened when Sam joined us. Craig said he wouldn't have to hide his hard on any more. We hugged and said we were both looking forward to next weekend.
Sir had us ready after lunch. We had packed all of our belongings; yeah it was two tooth brushes and other personal hygiene products. With only one stop for a coffee we were back at my apartment within the hour. Sir said he wished he had time to spend with Sam and we said that we would be sure to send pics of us with him.
Sir took me into the bedroom for one last fuck until next weekend. We laid in bed afterword and talked about Craig and how he would be this week. I assured Sir that I would keep Craig moving forward and not let him get depressed. Sir got dressed and we rejoined Craig in the living room.
Sir removed our handcuffs and hugged the two of us together. He wanted to make sure that we were fine and said to call him if either of us needed to talk.
I wished Sir the best for the week and said I couldn't wait for his return next weekend. Craig hugged Sir and said the same. He was indeed looking forward to next weekend.