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This is a text that is based on real events that I have experienced, or my friends have experienced, drawing on journals, conversations, and social media posts over the years. I have embellished the story here and there to craft the narrative. My goal is to post every four days till the story is complete.
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Southern Chastity
Chapter 22: Summer in the City
I awoke early the following Tuesday morning. The longer days meant even at 6:30 am there was some light coming in through the curtains already. I pulled off my CPAP mask and pulled off the top sheet that was over me and stretched. My nub had been leaking overnight and I noticed some crust on the sheets.
I was about ten weeks into my three-month chastity session. I was due to be released on September 6, the day after Jay graduated, which was still a few weeks away and I was feeling it deep in my balls. Rick said I was `in heat' when I mentioned it to him a few days prior and I wasn't going to argue with him.
I was walking to the bathroom to piss when my phone buzzed. I looked down to see that it was a direct message from a follower on my Tumblr page.
"Big fan of your blog!" it read.
I had been keeping an almost daily journal of how my lockup was going and the different experiences I had encountered along the way. Although John got me started, I had gotten into it and had been offering advice to others that were looking at chastity or sub space as well.
"Thanks!" I replied.
I had posted the night before about how horny I had been lately and that it had been a few days since I had the opportunity to service any doms other than John.
"Do you provide morning blowjobs?" he asked.
"I do," I replied. "It just depends on if I am running late to work. Are you interested?"
"Yes. My wife has not been in the mood lately and I need my balls drained," he replied. "Do you live anywhere near Smyrna?"
"Yes," I said. "Not far at all."
"Can you be here at 7:15 am?" he asked.
He provided me an address and I noticed it was only about ten minutes away.
"Sure," I replied. "Let me get cleaned up quick and I will be there."
"Perfect," he said. "Park in the street."
I put my phone down and jumped in the shower and washed down well. My nub was straining in my cage at the thought of getting to blow off some horny energy. After drying off and grabbing a quick breakfast, I put my clothes on and headed out the door.
The address he gave me was in an older neighborhood and there were a lot of trees that blocked the view of the houses. I finally found the correct address and parked in the street. I was sitting there for about a minute when I saw someone appear behind a tree where the driveway to his house bent down a hill into a secluded lot.
He was an older man, clean-shaven with light brown hair that was graying at the temples. He waved at me and walked over to my side door and I rolled down the window.
"Thanks for coming over," he said as he leaned on the window frame. "My wife is still asleep. Do you think you can just blow me here beside the car?"
"Sure," I said.
I got out and came around and opened the back door and sat down on the floorboard and he came in front of me.
"You think I can see your cage?" he said. "I've been a big fan."
"Sure," I said with a smile.
I undid my belt and pulled my pants and underwear down and then sat down in front of him again. He unzipped his pants and pulled out his hardening cock and then reached down and felt my cage.
"I love it," he said.
His cock was at full mast pretty quickly and I grabbed it with one hand near the root and started to slowly take it into my mouth. He groaned and put his hands on the door frame and looked down to watch.
As I started to move up and down his shaft, I ran my fingers over his balls lightly and then started to grope them a bit. His cock responded by producing precum which I lapped up quickly. He adjusted his stance a bit and reached down with one hand to put it behind my head and guide me back and forth on him.
"I needed this so bad," he whispered to me.
I started using my hand to work his cock and started to suck on him harder. He began to move his hips and force his cock deeper and deeper into my mouth. I was proud that I was able to take him as well as I was doing. My deep-throating skills were improving.
My nub was straining again, and I felt some precum start to leak out and drip down my balls and land on the street below. He looked down and saw this.
"You were not kidding when you said you were horny," he said with a grin.
I smiled and then started to work his shaft. He grabbed onto the frame again tightly and started to groan more. I felt his balls jump in my hand just as his cock started to pulse and streams of cum hit the back of my throat.
"Fuck," he groaned as he put his face over his arm.
His legs started to shake, and his ass clenched as his balls finished emptying in my mouth. When he was done, he looked down again and I pulled off him and licked the head of his dick a few times and then smiled at him. He reached down and pulled his pants up after.
"Thanks again," he said, and he turned to leave.
I watched him return around the tree and down the driveway and I reached down and went to pull my pants up. My nub was covered in precum, but fortunately, I had some extra napkins in the car from a meal I had brought home a few days ago, so I wiped myself down before dressing and returning to the front of the car.
I was checking my face in the mirror to make sure I did not have any cum in my beard when a car drove by on the street.
"Well, they missed seeing a show by minutes," I said to myself with a nervous laugh.
On Wednesday I was cleaning with my sub brothers as usual at John's house. When we had finished, we went downstairs to put the cleaning supplies away and when we came back into the dungeon, John was standing there.
"Well done with the house as usual boys," he said. "I have a treat for y'all. Once a year in the summer, I set aside a day for my boys to use the pool and backyard and bond a little bit. With Jay's upcoming graduation, I have decided that this Saturday will be set aside for you three. I will be out of town for the day, so you can use the grounds as you see fit. My only request is that you clean up after yourself."
"Thanks, Sir!" Bo said with a big smile.
"That sounds awesome," Jay said.
"Agreed," I replied with a grin.
"Very well," John continued. "Bo, I will see you for your one-on-one visit tomorrow and the rest of you have a good evening and drive safe."
"Thank you Sir!" we replied.
"Please tell me you both are coming," Bo exclaimed after John left.
Jay laughed and put his hand on Bo's shoulder. "I'll be here brother."
"I'll be here as well," I said.
"Cool," Bo said. "I'll bring some things to grill out if someone can bring some drinks and sides."
"I can get the drinks," I said.
"I'll handle the side foods then," Jay said.
"Ok, so we meet here by noon Saturday then?" Bo asked.
"Sure," Jay said. "I might even get here a bit before that. It depends on how late I stay up the night before and when I roll out of bed."
"Sounds good to me," I said with a laugh.
Saturday was another hot day in the South. There was not a cloud in the sky but at least the humidity level was not as oppressive as it usually was. I pulled up to John's house at about 11:45 am and came through the side door with the drinks and put them down to strip and put my clothes away before continuing into the dungeon. Jay was already inside and had the music going and set out some coolers.
"Well, you did get here early!" I replied.
"Yeah," Jay said. "Decided to get things set up."
"Hey bro!" Bo said as he walked in from the pool area. "I have the grill all set up and ready to go."
"Well, here are the drinks," I said. "I brought some beer and soda, so you have your pick."
We put the cans in the coolers and Jay opened some bags of chips to snack on while Bo put on an apron to grill up some hamburgers and hotdogs. After everything was plated, we sat at a table under an umbrella and ate.
"Are you excited about your upcoming graduation Jay?" Bo asked.
"Very much so," Jay replied. "Hard to believe it's already been a year. My sub brothers Johnny and Nick both messaged me this week to check in on me."
"How's Nick doing out in Seattle?" Bo asked.
"He loves it," Jay replied. "He told me his master, Adam, is dating another hot daddy bear, and it is looking like he will be moving in with them."
"Sounds like he will be busy!" I chuckled.
"For sure," Jay replied with a smile. "I'm hoping I get a chance to go out and see him again at some point."
"And how are Johnny and Ryan?" I asked. "I have not seen them out at the Eagle lately."
"Johnny said they have been busy," Jay replied. "They have some sort of business they are running. I don't know the details, but I do know that it's been taking up most of their time lately."
"I was going to say that I will be sad to see you go, but I guess change is part of the program," I replied.
"Oh, I will miss you both a lot, but we will still keep in touch and I am sure I'll see you around," Jay said. "But you are right. First Nick and Johnny leave, and then you two come in, and then I leave y'all behind. It goes by way too quickly."
"How's Master Jeff doing?" I asked.
Jay smiled. "He's great. We talked about him collaring me and moving me down to Savannah. Still working out the details, but it's looking good. So, fingers crossed, I might have his name on my collar."
"From the sound of it, Bo might have one come December as well," I said with a wink.
"Oh?" Johnny questioned with an eyebrow raised. "Is this Master Todd?"
"Yeah," Bo said. "Could work out. I have seen him a few times and he has been showing interest in me."
"Nice!" Jay said. "He's a hot daddy bear."
"For sure," Bo said, turning to look at me. "But, he has been eyeing Matt here as well."
"Well," I said with a laugh, "I think you might have a leg up on me since you are graduating first."
"Well boys," Jay said, "shall we take a dip in the pool for a while?"
"Right behind you," Bo said.
Jay got up and dived in the pool and Bo was right behind him jumping in cannonball-style and making a huge splash. I opened to walk in on the shallow side and work my way in.
"What is the matter," asked Jay jokingly, "afraid to get your hair wet?"
"No," I replied with a grin, "I just wanted to wade in."
"Whatever," I heard Bo say before he dove under the water and in-between my legs to knock me off balance and send me under.
"Bo!" I exclaimed as I stood back up and blew out some water I swallowed.
"Be careful there Bo," Jay said. "It is better to do it this way."
Jay grabbed me sideways and pulled me over and under again and I came up and pulled him under immediately after.
"Now he's moving!" Jay said with a laugh.
I grinned back and ran my hands through my wet hair. "It's a good thing I like both of you."
Bo was still laughing and came behind me and hugged my waist and put his head on my shoulder.
"I'm just glad we have some time to blow off steam," Bo said. "I've been horny as fuck lately."
"Oh, me too," I replied.
"I don't know Matt," Jay said with a grin as he swam over in front of me. "I've been reading your blog. You seem to be getting some opportunities to burn energy off."
I blushed a bit and Bo playfully bit my shoulder.
"Hey!" I exclaimed, looking back at him.
"So, when was the last time you got to service anyone?" Bo asked.
I told him about my encounter with the older man on the way to work on Tuesday and followed up with how close I had come to getting caught.
"Oh, that's nothing," Bo said. "I remember back last fall when a guy wanted me to come over and let him use my ass. When I got there, it turned out he was 19 years old and living with his parents. He made me lay down behind a hill near their house while he fucked me. After he loaded my ass up, he went back inside, and as I was walking around to get back to my car his father showed up."
"Oh shit!" Jay said.
"What happened?" I asked.
"He said he watched his son fuck me from the second-floor window of their house and asked me if I would be willing to take his load too," Bo continued. "So, we walked over in the woods a bit and he bent me over a log and fucked a load in me as well."
"Ok, that is fucking hot," Jay replied.
"You're a mess Bo," I replied as I reached back and tousled his hair.
Bo wrapped his legs around me and I felt his cage push into my ass crack. He then squeezed his arms around me tighter and put his head next to mine.
"You know your nub is caged right?" I asked jokingly. "It isn't going in my ass."
"Oh, hush you," Bo said. "I just like hugging you."
Jay smiled and came in front of me and wrapped his arms around my waist as well and put his legs around Bo. He squeezed as well, and I was stuck in the middle.
"It's a Matt sandwich now!" Jay said and gave me a peck on the lips.
"Ugh, you two are a handful," I said rolling my eyes and laughing.
We waded around a bit and then grabbed some beers and drank and talked. It reminded me a lot of our trip with Chris and Rick up to the mountains. We were able to let our guards down and just talk and grow closer.
As the shadows started to creep over the pool in the late afternoon, Jay started to move towards the stairs to get out.
"Well guys, I think I am going to get out and dry off," he said.
"Oh boo!" Bo replied. "Damn this day has flown by."
We followed Jay out and dried off and then sat for a few minutes to finish off the rest of our drinks.
"You don't have to stay and help clean up Jay," I said.
"Yeah, Matt and I agreed to take care of it if you want to head out," Bo said. "It's not much to do anyway."
"Thanks, guys!" Jay said getting up.
He came behind us and gave us each hugs around our necks and then headed into the dungeon to get dressed and leave.
"You up for going out to the bar tonight Matt?" Bo asked.
"Sure!" I replied. "You want to follow me over to my place and we can get a car to take us in from there?"
"Deal," Bo said with a wink.
So, we threw away our trash, cleaned up the pool area, replaced the solar cover, and then cleaned out the coolers. After everything was put away, we got dressed and headed over to my place, and got a car to take us into town.
Bo and I got to Woofs, the bear sports bar, about 6 pm. It was a little early, but the crowd was still decent. We ordered a pitcher of beer to split and headed back to the back tables to sit down for a while. After about thirty minutes, I felt a tap on my shoulder, and I turned around to see Max standing behind me.
"Hey, bud!" I said. "How have you been?"
"Not bad," Max replied. "You got an extra seat?"
"Feel free to pull up a chair!" Bo said with a smile.
"Sir Kenny is meeting me here, but I got here early," Max said.
"Nice!" I replied.
"Have you made a decision yet on joining the program?" Bo asked.
"Well, I had dinner with him and Sir Kenny on Thursday," Max said. "It gave me a chance to meet him informally. He had me wear a chastity cage overnight and I had to freeze the keys in the freezer. It was maddening!"
I grinned, "I remember doing that the first time with him."
"Me too!" Bo replied with a grin as well.
"Well, he said that since I made it overnight that I could meet with him tomorrow evening for dinner and we would talk more," Mac said. "He gave me an assignment to work on today to think about what I would be interested in exploring and how this might help me grow closer to Sir Kenny."
"It sounds like he is interested," I replied. "I had to do something similar when I was going through my initial interviews with him and thinking about it."
"Yeah," Bo said. "He usually has some tasks for you to do that allows him to size you up and determine if you will be a good fit."
"Ok," Max said. "He told me to bring my chastity cage with me in the car to dinner tomorrow, so I am assuming that more sessions are in store."
"Yeah," I replied. "Just be sure to be open and honest with him."
"Hey boys!" came a voice from behind me. I turned around and saw Kenny smiling and moving to stand behind Max.
"Hello, Sir!" Max replied and he bowed his head and Kenny kissed his forehead and hugged him.
"Nice to see you out and about," I replied with a smile.
"Yeah," Kenny said. "The boy and I haven't had a chance to get out much, so we figured we would have a few drinks here before dinner. What have you all been up to?"
"Not much," I replied. "Bo and Jay and I had some bonding time at Sir's house but other than that it's been pretty uneventful as far as the week goes."
"Has the boy told you he and I met with John this week?"
"He did!" Bo said. "Sounds like he might be our sub-brother soon!"
"I hope so," Bo said, gripping Max's shoulders. "I would love for him to be as well trained as you two are."
"Thank you, Sir!" Max said with a smile looking back at Kenny.
"I don't want to be rude boys, but I have a friend here that I met on the way in and I wanted to introduce Max to him," Kenny said.
"No worries!" I replied. "It was good to see you!"
"You ready boy?" Kenny asked Max.
"Right behind you Sir!" Max replied as he got up and followed Kenny over to another table.
"I still remember freezing my key for Sir that first time," I said to Bo. "It seems like a lifetime ago."
Bo smiled and tapped his glass of beer against mine. "You made the right choice."