Southern Chastity

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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 21: Kenny's Boy

I got off of work Thursday and headed out into the parking lot to find my car. It was the height of the summer in August, and while the temperature was not extreme, the humidity was making it oppressive. I got inside the oven that was my vehicle and turned on the air conditioning and sat there a bit till things cooled off. My phone buzzed at me and broke my train of thought and I looked down and it was a message from my brother.

"Are you all done with work?" he asked.

"Yeah," I replied. "Just about to head home now."

"Swing by my apartment if you can," he said. "I need to talk to you about a few things and I have a package for you from mom."

"Sounds good," I replied, and I headed over to his apartment.

Since I started my training with John five months ago, I had been over to my brother's house a few times. I had explained what was going on and he understood the protocols of no clothes in a home and such, but it was still awkward being naked in front of him. We are twins, so it's not like we had not seen each other naked growing up and as gay men, we were both comfortable with our bodies, but still, it was my brother.

I got to his apartment and walked in to find him in his hospital scrub bottoms and crocs. He was standing in the kitchen stirring a pot that had some noodles in it.

"Hey bro!" Steve said.

"Heya," I replied, closing the door behind me. "Ok to strip, yes?"

"You are fine," he replied. "No one here but us two."

I took off my clothes and folded them next to the door and walked over to the kitchen. Steve glanced my way and noticed the smaller cage I was in.

"That's shorter than the last time you were here," he replied.

"Yeah," I said, instinctively grabbing my cage. "Sir swapped it out back in June. I guess I have not been by here since then."

"Well, to be honest," Steve said, "it's been crazy busy with work, so don't worry about it. Would you like some spaghetti?"

"Sounds good!" I replied as I sat down at his kitchen table. "What did you need to talk to me about?"

"Oh," Steve replied, turning to put a tray in the oven that had garlic bread on it. "It is nothing serious. Uncle Bill is heading out of town for the weekend and needs someone to take care of the dogs and watch the house. I can probably swing it, but I wanted to see if you were free."

"Yeah, that's no problem," I replied.

Our Uncle lived in Marietta, not far from where we lived. He was a bachelor and had two older yellow labs that lived with him at his house. It was a nice place and had a big backyard with a nice pool. We usually house sit for him when he had to go somewhere and made sure the dogs were fed.

"Cool," Steve said as he grabbed a beer and turned to me. "I'm going to stop by Friday night and feed the dogs, but if you can handle their morning and evening meals on Saturday and the morning on Sunday, that would be helpful. Bill gets back in the afternoon Sunday."

"I'll take care of it," I replied.

"He said we are welcome to have a friend over if we want, but nothing crazy," Steve said.

"I don't plan on having an orgy there," I said with a laugh. "Don't worry."

Steve smiled and grabbed me a beer and then plated the food and sat down to eat with me.

When I got back to the apartment, I saw Kenny sitting in his car on the phone. As I got out, he hung up and waved at me.

"Hey, Matt!" he replied.

"How are you doing bubba?" I asked.

"Not bad," Kenny said with a smile as he walked over to me. "Listen, I have been talking to John a few times over the past week. I want to set up some time for my boy to meet up with you and some of your sub brothers if that is ok. Max seems interested but a bit nervous and I want him to go into this willingly as his decision."

"Oh, no worries at all!" I replied. "Let me talk to the boys and see what we can figure out. Is it ok if I call you later this evening?"

"Yeah," Kenny said. "I will just be sitting at home."

"Cool," I replied. "Talk to you soon."

Kenny smiled and waved to me and we parted ways. When I got back to my apartment and had stripped down, I texted Bo and Jay to see if they might be free to meet Max.

"I'm around all weekend," Bo replied first.

"I'm going to be in Savannah this weekend," Jay said, "but if it is later in the month we can figure something out."

"Sounds good guys," I replied. "Let me talk to Kenny and figure out the details."

I called Kenny next to see how soon he wanted things set up. Jay would be graduating in three weeks, so there was not much time left if we wanted to include him.

"Hey bud," Kenny replied as the line connected.

"Hey," I said. "So, I messaged Bo and Jay. Bo will be around this weekend, but Jay is out of town. He said we can do something later in the week or next week if you wanted him to be there."

"Well, Max is free this weekend," Kenny replied. "But we could push it off. What do you think?"

"Well, Jay is graduating soon, so if Max is considering taking his spot, sooner is probably better than later," I said.

"That is true," Kenny replied.

"Plus, we will be his brothers if he starts training under Sir, so it might not be a bad idea to meet informally to determine if this is right for him and we can work as a team."

"That is true," Kenny said. "So, this weekend then?"

"Yeah," I replied. "I will be at my Uncles watching his house, but he did say I could have friends over. Why don't you see if Max would be willing to drive over Saturday and spend an afternoon with us? There is a pool, and we can relax at a neutral spot and talk, and he can leave whenever he wants."

"Yeah, I like that idea," Kenny said. "I'll talk to him tonight and get back to you."

"Sounds good!" I replied. "Talk to you later."

Saturday morning, I was up early so I could head over to feed Bill's dogs. When I got to his place, it was about 9 am, and walking in the two dogs lumbered over wagging their tails in anticipation of their morning meal. I stripped down and put my clothes on the washing machine near the garage door and then walked into the kitchen and bent down to grab their bowls. As I was grabbing the second one, I felt a cold nose on my balls, and I jumped up.

"None of that Coop!" I replied, turning around.

I filled their bowls and then opened the back door. The storm door inside the frame had a flap on it to allow the dogs to go in and out, but you had to open the main door for them to access it. I went out through the second storm door and walked around the back patio.

It was a humid morning, but nice and sunny. The birds were chirping, and I heard a crow cawing in the distance as well. Bill's backyard was surrounded by trees and was completely private. I knelt by the pool and stuck my hands in, and the water felt nice and refreshing.

As I stood up, I heard the flap to the door make a sound and Alex and Coop came running out to do their business in the yard. After they were done, they came over to me and licked my legs and I picked up their ball from the yard and played catch with them for a bit before heading inside to grab a drink.

I had arranged for Bo to stop by in the morning. I figured we could hang out and chill for a while before Max arrived. He was due after lunch and Kenny said that he could be a bit shy at first and to be prepared.

It was about 10 am when I heard the doorbell ring, and I went and opened the door to let Bo in.

"Hey!" Bo exclaimed as he hugged me and came inside. "This is a nice house!"

"Yeah," I replied. "My Uncle does a lot of entertaining with his friends here, so it's a bit of a bachelor pad."

Alex and Coop heard someone at the door and bounded through the doggie door and hurried over with their tails wagging to greet Bo. He reached down and petted them both.

"Well, they are friendly," Bo said with a grin.

"They mostly lounge outside and sleep," I said with a chuckle. "But they love new people."

"Where should I put my clothes?" Bo asked.

"Come over here by the garage door," I said. "I undressed in the laundry room and put my clothes on top of the washer away from the dogs."

"Sounds good!" Bo replied.

After he got stripped down, we grabbed some drinks and went and laid out by the pool for a while to enjoy the morning sun. It was not too hot out yet, and there was a slight breeze from the east. The dogs sprawled out and napped in the grass and apart from the sound of the birds in the area and the tones of a wind chime Bill had on the back of the house, it was quiet and pleasant.

"I could get used to this," Bo said as he stretched out on the lounge chair on his back.

I had gotten up to turn some music on low and grab a refill. As I went to lay down next to Bo in another chair, I tossed him a washcloth.

"Put that over your nub," I said with a grin. "That metal will heat up in this sun and you don't want to burn your nether regions."

"Ha!" Bo said with a smile as he laid it over his nub. "Good point."

After we soaked up some rays for a bit, it was starting to get warm, so we headed inside, and I pulled out some sandwiches I had brought with me.

"Can you believe that Jay will be leaving in a few weeks?" I asked, opening a small bag of potato chips, and eating one.

"Time flies," Bo said as he bit into his sandwich and washed it down with a soda. "I am going to miss him, but it seems like he has found his new master."

"I like Jeff," I said. "He seems like a caring dom and let me tell you, he had a pretty big load that I swallowed from him at the pool party."

Bo chuckled. "I never got to service him, but I agree he seemed nice. What do you think of Master Todd?"

"I like him!" I replied. "That white fur on his chest and those deep blue eyes are a nice combo. Well, that and his cock and balls too."

Bo grinned. "Yeah, he is attractive. I was glad to get a chance to service him again at the party last month. He also messaged me a few times after and I got a chance to go to his house last night."

"Oh?" I said with a raised eye. "How did that go?"

"His place is gorgeous," Bo said, putting down his sandwich and leaning back to gesture with his hands. "He must be rather wealthy. I felt a little nervous walking inside."

"Nice!" I replied.

"He had a dungeon area in his basement as well," Bo continued. "Not as big and elaborate as Sir's but it was well equipped. He had a cross painted on the wall and eye hooks were secured to the studs where they would be if they were attached to a real one. There was a leather-covered fuck table, a cage on the floor, eye hooks in the ceiling for suspension play, and a wide variety of toys and bondage equipment on shelves."

"What all did you do?" I asked.

"Well," Bo said, "he first had me get on the floor and massage his feet. I got the impression he loves to have his legs and feet rubbed. He suspended my arms above my head to a ceiling hook and put some nipple clamps on me and then did some light flogging. That was followed by giving him some head for a while. He then blindfolded me and put me in the cage with some hypno tracks on some headphones over my ears and after I zoned out a bit, he came back and bent me over the fuck table and loaded me up."

"Sounds like a hot time!" I replied.

"Yeah," Bo said. "Afterwards, he got me up and just hugged on me for a while and rubbed my belly and shoulders. It was very erotic. My nub was straining the whole time."

"Sounds like you might have caught his eye," I replied with a grin.

"Maybe," Bo said, returning the smile. "I would not be upset if he did want to go further."

After we finished lunch and chatted a bit more, I cleaned up and threw away our trash and we headed back outside again. I helped Bo reapply some sunscreen and he did the same for me and we lounged a bit more and then swam a bit as well.

Around 1:30 pm, I heard the front doorbell chime. I grabbed my towel and dried off some and then hurried over to the front door. As I opened it, a younger man in his early twenties looked up at me and smiled.

"Hey, I am Max!" he said.

"Hey, Max!" I replied, opening the door fully. "I'm Matt."

Max was extending his hand to shake mine and he looked down and saw I was naked and in just my cage. Bo showed up behind me at the same time naked as well.

"Umm, wow," Max said with a stutter. "I did not expect everyone to be naked."

"Ha!" Bo laughed from behind me. "We don't bite. I promise. My name is Bo!"

Max came in and shook his hand as well and I shut the door behind him. He was about my height, 5' 10" (1.8 m), and looked to be about 195 lbs (88.5 kg) or so. He had dark hair on his head that was buzzed very short and dark green eyes. His beard had some red in it in addition to dark brown and was a medium length. He had on a t-shirt and you could see some tufts of chest hair sticking out and his legs were pretty hairy as well below his shorts. It even extended to his feet where there were tufts of dark hair showing on his toes poking out of his sandals.

"Umm," Max stuttered. "I'm a little nervous here, to be honest."

"Oh, please do not be," I said putting my hand around his shoulders and leading him into the living room. "You are among friends. Kenny has spoken very highly of you and was wanting us to meet you."

Max grinned. "Sir has been telling me a bit about you and Sir John. He thinks it would be a good experience for me to train as you have been, but I am a little unsure."

"Well, that is why you are here!" Bo said.

"We were going to go back out to the pool," I said. "Is that ok?"

"Yeah!" Max said. "Sir told me you had a pool here. I brought some swimming trunks."

"Well, feel free to wear them or go naked like us," I replied. "You do what makes you feel comfortable."

"Yeah," Bo said. "We want you to relax and have a good time."

"I'm fine being naked," Max said with a grin. "Where should I put my things?"

I showed him where the laundry room was, and we headed back outside. After Max had undressed, he came outside, and the dogs noticed him and ran up wagging their tails to get petted before returning to their shady spot under a tree to sleep.

Max was a furball. He had dark hair all down his chest and back and a furry ass, which Kenny had mentioned before. He had put on a ball cap to keep the sun out of his eyes and we helped him rub some sunblock on, though it took a while to get all absorbed with his hair in the way. He had a nice set of hairy balls and his cock started to swell a bit as we rubbed his skin.

"Sorry about the erection," Max said as he covered himself slightly embarrassed.

"No worries!" Bo laughed. "I almost have forgotten what it is like to randomly sport wood."

Max smiled and after all the lotion was applied he sat down with us in some chairs around a table.

"Well, I guess we better introduce ourselves," Bo said. "As I said earlier, my name is Bo, I am 30 years old and I have been training under Sir since December of last year. I am from Texas originally, but I have lived here in Atlanta for about five years now."

"And I am Matt," I replied. "I am 39 years old and originally from Tennessee, though I have lived all over the south. I have been here in Atlanta for eight years. I started training back in March."

"Nice to meet you both in person," Max said. "Sir has been telling me about you. I'm Max, as you know. I just turned 23 and I was born and raised here in Georgia in a little down south of Atlanta. I moved up here after college to get away from home and I am rooming with some friends. I've been seeing Sir Kenny since the end of February and have been interested in learning more about what being a good sub is all about."

"Well, you ended up with a hot boyfriend," I said with a grin.

"I do like him," Max beamed. "But he has been wanting to explore kinks with me that I don't have a lot of experience with, so I am hoping to learn more. We hope to move in together in the next year as well."

"Would you consider yourself top, bottom, or switch?" Bo asked. "Just out of curiosity."

"Oh, very much bottom," Max said. "I'm kind of an insatiable one. I love getting fucked and sucking loads out of guys."

"Well, that is a good skill to have!" I said with a laugh.

"What about chastity play?" Bo asked.

"That would be new to me," Max said. I have never done it, though Kenny and I have talked about getting me started wearing one."

"I was a newbie like you when I first met Sir John," I replied. "If you decide to train with him, chastity is a requirement, but you will be given time to adjust. It's not easy, but you adapt."

"I can see that!" Max said as he grinned and looked at our cages.

"Are they painful at all?" Max asked. "They look so small!"

"It's not bad," Bo said. "There is an adjustment period, but over time you will learn to live in it and sometimes forget it is there. Assuming that it is fitting well that is."

"Yeah," I added. "Sir makes sure that it's a good fit so that you don't have issues and he checks you periodically to make sure you are not developing any irritation or sores or anything."

"I'm in my final six-month session before going permanent now," Bo said.

"Permanent?" Max said wide-eyed.

"That is one thing that Sir works you up to," I replied. "You will start at a week and over time he will build you up to longer and longer periods locked up. The last session is six months and at the end, you will be permanently locked in your cage."

"Well," Bo said, "That is unless the man who collars you wants it otherwise, but the intent is that you could be permanent if your master wants."

"I haven't discussed that with Sir," Max said.

"Don't let it scare you, though," I said. "This is all consensual. If it's too much for you, you can leave the training program. The idea is that you push your limits, learn new skills and techniques, and find your true self in the process."

"Yeah," Bo said. "Believe me I was nervous going in, but I have not regretted one day since I started my training. I've also bonded with some great sub brothers like Matt here."

Bo and I grinned at each other and held up our drinks as a toast.

"Well, I am looking forward to learning more, but I'd like to take a dip in the pool if that is ok," Max said. "It's hot out here!"

"Let's jump in!" I said with a laugh and we all jumped in the water and cooled off a bit.

For the next couple of hours, Max started to relax a bit and was more comfortable around Bo and me. We talked more about the program, the different kinks we have been exposed to, and the parties as well. Max seemed most wide-eyed about the most recent party over the fourth of July. We had started to discuss that after we got out of the water and were sitting down having a beer. Max started to pop an erection as he was sitting in his chair as we told him about the men we serviced and what went on.

"Damn!" Max said not even trying to hide his hard cock. "That sounds so fucking hot. I would have loved to have been there with those hot guys."

"I can see that!" Bo said with a big grin looking at Max's dick.

"Sorry guys," Max said. "My hormones are raging."

I laughed. "You in a chastity cage will be an interesting thing to see with as much wood as you sport."

Max chuckled back. Bo got up and knelt in front of him. "You mind if I take care of that for you?"

"Umm, sure!" Max said as he moved forward in the chair a bit.

Bo reached up and put his hands under Max's balls and guided his hard cock into his mouth. As Bo moved down his shaft, Max let out a groan and leaned back a bit. I smiled and sat back and watched as my nub swelled in its cage.

It was well known between my sub brothers that Bo gave the best head. He had given me tips over the past few months but watching him in action was hot. He had just about lost his gag reflex and he could work up a nice amount of spit to help a man's dick slide in and out of his mouth with ease. The way he could wrap his tongue around the shaft helped as well. He had a lot of skills all around.

As Bo started bobbing up and down on Max's cock, he started to move his finger under his ass and play with his hole.

"Oh fuck!" Max said as he leaned back some more and put one leg on Bo's back to give him better access to his furry ass.

Bo got his finger in deeper and found his prostate gland and started to rub it gently as he picked up the pace and used his other hand to assist his mouth in working Max's shaft.

I saw Max's toes curl as they laid on Bo's back and he closed his eyes and bit his bottom lip. Bo started going hard at it and stimulating Max's prostate and it was not long before he lifted his ass a bit and yelled.

"Fuck!" he screamed as he came. Max grabbed the sides of the chair hard to steady himself and Bo lifted off and watched a few spurts of cum fly into the air and land back on his face and beard. He then went back on Max and swallowed the rest.

After he caught his breath, Max looked down at Bo who was smiling back at him licking the cum covering his mustache and cheeks.

"That was amazing!" Max said. "You need to teach me how to do that to Sir!"

I laughed. "I am quite sure Kenny would love for you to do that Bo."

Bo sat up and returned to his chair and used his fingers to collect the remaining cum and swallow it.

"You shoot a pretty big load there," Bo said with a grin.

"You definitely know what you are doing," Max said with a grin. "Well, this has been great guys. I have enjoyed getting to know you both and I will talk things over with Sir some more. He said I am probably going to meet with Sir John next week."

"That will be good," I said.

"Just be prepared," Bo said. "He will size you up at that first meeting. If he thinks you are a good candidate, he will give you some tasks to carry out. Just be honest with him and see how things go. But, we would love to have you as a brother as well."

"For sure," I added. "Maybe this time next month you will be part of the chastity club."

Max grinned. "I guess I better shoot a bunch of loads over the next few weeks then."

We all laughed and got in the pool and swam around a bit more before Max said he needed to leave, and we got out and went inside. After he was dressed, we all hugged, and I saw him out the front door.

"He seems like a nice guy," Bo said.

"Yeah," I replied. "Kenny likes him and thinks he would be a great fit as one of Sir's subs. But we will have to see what Sir thinks."

"He's tasty too!" Bo grinned.

I put my arm around Bo and pulled him close and rubbed his belly. "You are a little piggy."

"Oink, oink!" Bo replied with a snort.