I Lost a Bet

By Gary Sechen

Published on Feb 17, 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 14 I Lost a Bet - Back Home with Craig

The two of us sat on the couch and said what should we do now. We looked at each other and said we should go for a walk. It would give us some down time while in clothes and a chance to speak to each other if we felt necessary. We went to the park and found a place to sit. Both of our shorts were bulging rather impressively. Craig was still getting used to the plug in his ass although he admitted it was keeping him aroused. He thanked me for being there for him this weekend. He thought he would have had a break down if I wasn't there.

I reassured him that Sir was trying to help him past his troubles and to realize he had a lot to offer to a special someone. What we did over the weekend was a big play time for adults. The sex was wonderful and being naked all the time with Sir was icing on the cake. If that was something that Craig desired he could pursue it and if not at least he had the experience. Craig agreed and said he should try something at least once to see if it appealed to him.

When we got back to the apartment we ran into Sam and his wife as they were leaving. We asked if we could go for another bike ride tomorrow night and Sam said he was looking forward to it. His wife waved to us and pulled Sam along. We had a laugh and wondered if his wife had a cock cage on him. It did appear she was leading him around with a leash.

Craig said he would fix dinner as I surfed the net. We got a text from Sir that he was home and the flowers and trees survived without me. He said he was looking forward to next weekend with us. We said the same.

Craig and I watched TV for a while and then I said I was going to bed. Craig joined me later and again thanked me for a great weekend. He didn't mention Joe all day which I thought was great.

I did hear Craig moaning a couple of times during the night as his cock tried to get hard. He would learn how to deal with it. I got up early and went for a ride. It was so good out this early in the morning. It freed my mind of any concerns. I realized I should do this every morning.

Craig had the coffee made and we talked a little. He said he didn't realize he got hard so much during the night. I said it was because he was thinking back over the weekend. He smiled and said he didn't think he would have any cum ready until next weekend. I said he would be surprised. I told him to go get ready first and I'd help him if he needed it. I asked how he would be with his plug while he worked. He said he would call me if he needed to. I followed Craig and then got dressed. Craig showed me the new bulge in his pants. He thought all the women would be chasing after him. I said even a few of the guys would be intrigued.

Sir called at 10 and I said Craig was doing fine. I told him about our walk last night. I said he got cleaned up fine this morning and was ok going to work. I'll update him tonight after we both got home. I told Sir that Sam was going for a bike ride with us tonight and that should be interesting. He encouraged me to get a picture of the three of us.

Craig was home and naked before me. As I was getting undressed I asked about his day. He told me about everything including his bathroom experiences. All was fine and even fun for Craig. I asked him if he was ok with our bike ride with Sam tonight and he confided he was a little nervous. I said to think that Sam really wanted to change places with us and how jealous he was of us. I picked out shorts and a tank top for Craig and pulled out my favorite singlet to wear.

Sure enough Sam was knocking on our door at 7 he stepped in as we got dressed. I whispered to Craig to be careful as this was his first bike ride while wearing his plug. He thanked me and we were off. It took Craig a while but he got comfortable. Sam slowed down so we could keep up with him. When we got back to the apartment he asked why we were so slow tonight. I said we were out of practice as I was getting undressed. I grabbed three beers and sat with Sam as we waited for Craig to come back from the bathroom. He called out and said "tad ah", and walked around the corner. Sam said what the fuck do you have on? Craig walked right over to him and showed him as he touched the cage and felt it. Craig sat down and took a long sip of his beer before telling the story. Sam was riveted to every word as Craig told him.

Sam said that he'd be concerned about meeting Sir; he said he didn't know how he would react.

I told him that Sir did want to meet him; I think he wants you to be our adult chaperone during the week when he is not around. Sam said something about the fox guarding the hen house. Sam admitted that we certainly led a fulfilling life and he would have to see if he could convince his wife to have sex outdoors. He shook his head and said I doubt that will ever happen and not once had she ever given him a b/j. Her phone call ruined the rest of our evening. Craig and I agreed that Sam would be a good partner for a weekend getaway but figured it would never happen.

The days were flying by as both Craig and I were anxious for the Leather Weekend at the camp ground. Sir suggested that we both take a vacation day on Friday so we could get to the campground early. That was arranged and Sir said he would pick us up at 10am. Further instructions would follow.

Craig was doing fine at work while wearing his two new additions. He even wondered what it would be like without them. Someday he was sure that Sir would take off the cage and that he would ask for his butt plug back. However I'm going to enjoy them until that day happens he told me.

Sam let us know that he was going to the game on Thursday night. He was happy for the time out of his apartment and his wife only talked on the phone anyway. He said he would stop by at 6 and then drive us over to the field. When we got to the softball diamond, Joe said something looks different about you Craig but I can't figure out what it is. Craig and I nearly busted out laughing. Sam asked one of our teammates to take a pic of the three of us and I passed my phone to him as well for a pic.

As usual Craig and I were not playing since we didn't get to practice last Saturday. I think we had a better time with Sir, I think we were riding horses at the time. The three of us rooted on our team but it was a boring game. Everyone on the team was depressed but also steered clear of Joe. Most teammates joined Craig, Sam and I at another bar for drinks and we had a good time.

Everyone agreed that we were glad the season would end next week and that we would try to form a team without Joe. I made our apologies and we left. I didn't want to stay too late since we were leaving in the morning.

Sam joined us in the apartment for a night cap - or until his wife called. We asked a favor of Sam, would he take a pic of us in the bathroom mirror like he had taken of me a few weeks ago.

He said sure and I got the pose just right hoping that Sam would appear in the mirror. Before we sat down Sam asked if he could touch our cages again. I looked at Craig and we said sure. He lifted both of them feeling their weight and how they were attached. He said I don't know how you guys do it. I said it just is that is all. He asked if we get hard and we both said yes and it hurts like hell until it goes away. I said that since I had mine on for nearly 4 weeks that I've had several orgasms. It is different; it makes me want to satisfy Sir even more. Craig said he had not cum yet while wearing it but that might happen this weekend. He didn't really know what was in store for him and right now he wasn't concerned at all. Sam was transfixed on our cocks and their status. I'm sure he would be thinking of us while he was fucking his wife or maybe even jacking off. Sadly, Sam had to leave but he said he wanted to hear all about our weekend. We assured him that he would be the first to know.

I checked e-mail and got final instructions from Sir. I was going as I was now, naked. Craig would be starting off totally naked but Sir had a few wardrobe additions for him. He would allow Craig some freedom especially if he met someone he wanted to play with. And if that was mutual he would remove Craig from his confinements if he so wanted. I replied to Sir that I was texting him a few photos from tonight but otherwise I couldn't wait to see him in the morning.

Next: Chapter 15


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