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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 27: Beach Bums
The following Friday I had taken the day off of work so I could join Bo and Master Todd for the weekend getaway to Florida. Bo had given me the directions to Todd's house and told me to be there by 9 am. As I pulled up to his place, I was impressed. Bo told me he was pretty well off, but the two-story house was gorgeous with a perfectly manicured lawn. I drove up the driveway and parked off to the side. Inside the open garage, I could see Bo putting some luggage in the back of Todd's car.
"Good morning!" I said as I walked up to him.
"Hey, Matt!" Bo replied as he turned and gave me a big hug and kiss. "I just put my things in the back here, go grab your stuff."
"Will do," I replied, and I went and grabbed my bag and put it in the back of the car as well.
"Welcome to my home, Matt," I heard the voice of Todd say.
I turned and saw him come around the car. He had a Hawaiian shirt on, and the top buttons were open showing off his white fur on his chest. He had some cargo shorts on and sandals. He looked like he was ready for vacation.
"Thank you, Sir," I replied. "I also appreciate you inviting me along."
"No problem," Todd said as he put his arm around Bo's shoulders. "The boy and I have been talking and I figured it would be a good chance to get to know you better and discuss some things as well."
"For sure," I replied with a smile.
"Boy, go inside and check my bedroom for anything we missed and then lock up the house and then get in the car," Todd said to Bo.
"Yes, Sir!" Bo replied as he went back inside.
"Matt," Todd said as he looked at me. "I have been talking to John and I have decided to collar Bo at his graduation ceremony in December. I have not told him this formally yet, but I think he has a good idea. I will be telling him of my decision this weekend."
"That's great to hear, Sir!" I replied.
"I picked up on the fact that you two were a bit close and he and I discussed the relationships a sub can have while collared," he continued. "I told him it was ok to spend time with you as long as John is ok with it as well, but we needed to have a more formal discussion in case he came into my home, as he will be soon."
"I understand, Sir," I replied.
"For the duration of this weekend, I want you to continue to follow John's protocols, but I also want you to feel free to speak up and voice your opinions and thoughts as we talk about various things," Todd said.
"Thanks, Sir," I replied. "I appreciate that."
Todd smiled and squeezed my shoulder and then turned as Bo came back into the garage.
"Everything is packed, and the house is locked up, Sir," Bo replied.
"Good deal," Todd said. "You two boys get in the back."
We climbed into the back seat as Todd got in the front and then he pulled the car out and down the driveway and we were off. Todd had a small plane that he was qualified to fly at the local public airport and that's where we headed next. When we pulled up to the hanger, a man came to greet us, and we grabbed our bags and he drove Todd's car off to park it.
We walked over to the small plane and looked inside. It had two seats in the front and four seats in the passenger area. It had two props and was white with some dark blue striping.
"This is my Beechcraft," Todd said. "It's a little older, but it's my baby and a reliable plane as well. Go ahead and stow your bags inside and get settled and I will be in shortly."
"Yes, Sir!" we replied, and Bo and I boarded the plane.
I had never been aboard a private plane before. It wasn't overly large but was comfortable to sit in. We put our bags in the back seats and then sat opposite one another.
Bo smiled at me. "Are you excited?"
"Yes!" I replied. "This is a new experience for me."
"Me too," Bo replied.
Todd came in and then made sure we were buckled in.
"It's about a three-and-a-half-hour flight down to the keys," he said. "It depends on the wind and how we are routed. There are some drinks there in the cooler. Just let me know if you have any issues or questions."
"Yes, Sir!" we replied.
Todd got into the pilot's seat and did his pre-check and start-up procedures and then we started moving and were off not too long after. The flight was pretty smooth. We flew lower than a normal commercial plane does, and you could see more of what was around you. As we neared the Gulf of Mexico, the blue water shined the sun back at us and I watched the coastline as we flew down.
It was a little after 1 pm when we started to make our descent down to the small airport on Marathon Key. After we pulled up to the hanger and the plane came to a stop, someone came over to help with getting the plane stored and brought over a car for us as well.
"You boys put our luggage in the back, and I will join you in a second," Todd replied.
After the car was packed, we got in the back seat and Todd got in the front soon after. He drove us around the island, and we ended up on a road that paralleled the water. As we neared the end of the road, we came upon a gate and Todd stopped the car to punch in a code and it swung open after. As the car pulled in the driveway, I saw a cute bungalow home appear that was surrounded by palm trees and bushes.
"This is my vacation home," Todd said. "It's called 'Point Comfort'. It's surrounded by a fence and my next-door neighbor is a friend of mine. He is not here this weekend, so the property and beach area will be private for us."
"That sounds awesome," I replied.
Todd stopped the car and we all got out and grabbed our things. When we walked up to the front door, he unlocked it and let us in. The living room was surrounded by windows and we could look back and see that at the far side, there was a wall of windows and some doors that led out to the private beach area. The kitchen was off to the side and there were three bedrooms and a bathroom as well.
"Strip down, boys," Todd said. "Unless we go anywhere, you will be naked the whole weekend."
"Yes, Sir," we replied and started to undress.
Todd went around and started to open the windows. The temperature was rather warm and the breeze off the water helped to cool down the place and air it out some.
"On your knees, boys," Todd said to us as he walked back over.
We got down on our knees next to one another and he stood in front of us.
"Here are the rules," Todd said. "First, in my home, wearing clothes and the use of furniture is a privilege for collared boys only. You two are neither. Second, I expect you to keep the house clean while we are here and follow any request I have of you. Finally, you are not allowed to leave the house without permission. There will be designated time for you to enjoy yourselves, but first and foremost, this is a vacation for me, and I will be using you to that end."
"Yes, Sir," we replied.
"Bo, please stand," Todd said.
Bo stood up and put his hands behind his back. Todd came over and stood in front of him and placed his hand on Bo's chest.
"Bo, I have been very impressed by your level of obedience and the skills you have shown me over the past couple of months," Todd said. "As we discussed last weekend, I have given serious consideration to collaring you when you graduate. I have made it clear I am not looking for a romantic partner at this time, though if something develops, that is fine. Have you thought more about this?"
"Yes, Sir," Bo replied. "I would be so honored to be your sub. I enjoy the time we spend together and pleasing you brings me a lot of pleasure."
"I am happy to hear that," Todd said. "I am letting you know, then, barring any issues over the next few weeks, you will be receiving my collar then."
I saw Bo's face beam and a huge smile appear. "Thank you so much, Sir!"
"We will use this weekend to talk more about this, but I want you to start the process of putting in your notice to leave your apartment as well," Todd said. "I expect you to move in with me in December."
"Yes, Sir!" Bo replied.
"Matt, please stand," Todd said.
As I got up, Todd moved over to stand in front of me.
"Matt, I know you and Bo have a close relationship," he said. "How would you describe it?"
I swallowed hard and looked at Bo and then Todd. "Well, Sir, Bo is my sub brother. I look at him first and foremost as my family and someone I want to look after and support as we do our duties. But, we have also discussed our feelings for one another. I am attracted to him and would consider him as a boyfriend if it were not for Sir John's program. I am nervous about exploring a deeper relationship with him until we can figure out where our lives will be headed. But I do care a lot for him."
Bo smiled and reached over and held my hand. Todd grinned back as well.
"Bo has stated similar feelings," Todd said. "I encouraged him to be honest with you and to talk to you about them. Has he done so?"
"Yes Sir, he has," I replied.
"As a collared boy, Bo will be part of my household in December," Todd said. "But, as long as John approves and is ok with it, I want you to feel free to continue to see him and spend time with him after this time. However, he will have dedicated responsibilities to me, and my needs will come first."
"I understand," I replied.
"Bo," Todd said as he turned to him. "What are your thoughts?"
"It's like what Matt said," Bo replied. "I like him a lot. I appreciate you allowing us to explore this more."
"Well, there are other aspects we need to talk about as well," Todd said. "A romantic relationship can be complicated for locked boys. I expect permanent chastity from my subs. That means you two will not be able to experience the intimacy that most males have when dating. However, I will be exploring some things with you this weekend that may offer some help in that regard."
"That sounds interesting, Sir," Bo said with an inquisitive look.
Todd smiled devilishly. "I am looking forward to seeing how it works myself. In the meantime, let's grab a late lunch."
We followed Todd back into the kitchen area and he microwaved some meals for us out of the freezer. We sat on the kitchen floor and ate while he ate at the table. After we were done, he showed us out the back doors. The beach extended from the waterline right up to the back of the house. There was a dock that extended out from the shore into the water and a boat was moored to it. There was a nice breeze blowing off the water and it felt wonderful outside.
Todd stripped naked and grabbed a lounge chair and walked out onto the beach.
"Grab three towels out of that box just inside the door there, Bo, and follow me out here," Todd said.
After grabbing the towels, we stepped out into the sand. It was a bit warm on our bare feet and we walked quickly over to where Todd had placed his chair. He took one of the towels and placed it on the lounge chair. He then placed the other two towels on either side of the chair and then laid down.
"You boys can sit beside me," Todd said as he pointed to the towels.
We sat cross-legged on either side of him and he laid back with his arms behind his head and closed his eyes. I looked out to the water in front of me. It was crystal clear near the shore and there were waves gently moving in that gave a soothing sound, in addition to the calls from seagulls flying around.
Todd started to snore a bit and we realized he had nodded off. Bo got up and came around and sat behind me. I felt his cage poke my ass as he leaned over on my shoulder.
"This is nice," Bo said. "I could get used to this quick."
I laughed a bit. "It is relaxing. I have not been down to Florida in quite a while."
"Me either," Bo said. "But it reminds me a bit of the beach back in Texas. Just not as hot here."
I laughed again and then brought my hands up over his and leaned my head back and he nibbled on my ear a bit. We sat there for about fifteen minutes and relaxed and I had just started to close my eyes when Todd spoke.
"You like my little hide-a-way, boys?" he said looking over at us.
"Yes, Sir," I replied. "It's very nice."
"How would you two like to join me in a swim?" Todd asked.
"That would be great," Bo replied.
"Come on, then," Todd said as he got up and walked over to the water.
We followed him in and waded out a bit. The ground was a mix of sand and some rock and we saw some fish move around as we moved.
"The boat that is docked there is mine as well," Todd said. "We will probably take that out tomorrow, as long as the weather holds."
"Do you fish much?" I asked.
"Some," Todd replied, "but I just like being out in the water."
After swimming for a bit, we got back out and dried off and Todd had us follow him back inside. Once we closed the door behind us, he directed us back into a bedroom in the corner of the home that also faced the beach. When we entered, we saw it was set up as a mini-dungeon area. There was a sling and fuck bench, as well as a small cross on the wall and various toys in shelving on one side. Todd opened the windows to let some air in and then turned to us.
"Now for some fun boys," Todd said. "Matt, I think it is about time you and Bo bonded a little bit more. Come over here and get on the bench."
"Yes, Sir," I replied, and I walked over and laid down on it. It was virtually identical to the one Sir had and he strapped my arms and legs down in it.
I turned my head and watched as Todd went over to the cabinet to the side and pulled out some items.
"Come over here, Bo," he said.
As Bo walked over, I saw what was in Todd's hand. It was a strap-on dildo harness. I watched as he buckled it around Bo's waist and then he lubed the dildo that was attached to it.
"How long has it been since you have fucked anyone, Bo?" Todd asked.
"Over a year, Sir," Bo replied.
"Well, this dildo is molded after my cock, so in a way, you will be fucking Matt with my dick," Todd said.
He got some lube and started to rub it over the dildo and then he brought Bo over behind me.
"Bend down and put your face in Matt's ass and get him loosened up Bo," Todd said. "Then I want you to fuck him good."
"Yes, Sir!" Bo said with a smile.
I felt him put his face in between my cheeks and his tongue started to dart over my hole. I moaned a bit and my nub started to leak. Bo is an expert rimmer and started to work me over pretty well and used lots of spit to get me lubed up too. When he was about ready to mount me, Todd came over and stood in front of me.
"Open up, boy," Todd said. "You're gonna get my dick in both ends."
As Todd pushed his hard cock into my mouth, I felt Bo slide the replica of Todd's cock in my ass. I groaned as I was penetrated from both ends and Todd reached down and held my head as he started to assault my throat. Bo started fucking me slowly as well and then with a moderate speed once he got used to the strap-on.
"You enjoy fucking Matt, Bo?" Todd asked as he looked over at him.
"Yes, Sir!" Bo replied.
"Good boy," Todd replied.
Todd started to fuck my face harder and was hitting the back of my throat more. I had gotten better, under Sir's training, at deep throating, but I still was gagging a bit, sending more spit out of my mouth and down my beard and onto the floor. He was not slowing down, though, so I concentrated on making sure my teeth did not get in the way. It was not long before he was grunting and breathing heavily.
"You want my load boy?" Todd asked.
I grunted as best I could as a way of saying yes and I felt him tense up and then his cock exploded cum down my throat. He pulled out a bit and it filled my mouth up and started to leak out and down my beard. He then shoved it in again and let me suck him off and swallow his load.
Todd held my head until he was done and then pulled back. Bo was still fucking my ass and he had just the right angle that it was hitting my prostate in a good way. I felt the sensation deep in my groin area and knew it would not be long until he would be fucking an orgasm out of me.
"Sir!" I yelled.
"Yes, boy?" Todd replied, looking down at me.
"May my nub have an orgasm?" I asked.
"Bo must be hitting the right spots," Todd said. "Will you agree to fuck him the same way and give him one too?"
"Yes Sir!" I replied.
"Then you have my permission," Todd replied.
Bo grinned and started to fuck me with Todd's cloned cock harder and the sensation started to build behind my balls. I squeezed my ass a bit and could hold it back no longer and I felt a wave of energy explode through my nub as the internal orgasm hit me. Cum started to dribble out of my cage and I groaned.
"Oh fuck!" I replied as I closed my eyes and gripped the bench. "Thank you, Bo!"
Bo slowed down and then brought the dildo completely inside me and leaned over me and embraced me and kissed my back. He then slid the dildo out and leaned down and licked my cage clean of the cum that was dangling from it.
"Don't forget what's on the floor, boy," Todd said, pointing at the puddle on the floor and Bo got down and licked that clean as well.
"Good boy," Todd replied. "Now it's time for Matt to repay you for that."
Todd came over and undid my restraints and helped me up and then took the harness off Bo and put it on me. He then tied Bo down and I got behind him and bent down and started to rim his ass.
Bo started to groan as I got my tongue deep in him and I used my fingers and some spit to start to open him up as well.
"Fuck me, Matt!" Bo shouted as I started to put three fingers into him.
I smiled and stood up and brought the dildo over to his ass. It was amazing how much it looked like Todd's cock. I watched as it started to enter his ass and Bo clenched the bench as it filled him.
Fucking him with the dildo was a new experience for me. I had never used one before. The last person I had fucked was Chris back in March. Over seven months later, I was trying to get back into the headspace and make sure I was hitting the right spots for Bo as well. As I worked the dildo in and out of his ass, Todd started to stroke his cock and it was getting hard again. He came up behind me and rubbed his cock over my ass.
"Hold still for a moment boy," Todd said as he slid his cock into my loosened ass.
I felt it enter me and I squeezed my ass a bit to grip it. Todd groaned in response and then put his arms around my upper chest.
"Now, use that clone of my cock to fuck a load out of Bo and use your ass to milk my cock dry," Todd said.
I started to move back and forth pushing the dildo into Bo as Todd's cock came out of mine and then as I pulled out, bringing Todd's cock back into me. It took a bit of work to get the rhythm right, but I eventually got to where Bo was getting a good fucking and so was I.
"How are we doing down there, Bo?" Todd asked.
"I'm getting there, Sir!" Bo replied.
"So am I," Todd growled into my ear.
Todd started to fuck me a bit and I slowed down and shoved the dildo deep into Bo. As I held it there, Todd started to piston fuck my ass and the force drove the dildo into Bo's ass a bit deeper as well and started to move it slowly back and forth. The sensation was just what Bo needed, because soon after he spoke up.
"Oh, my nub!" Bo shouted.
"You close, boy?" Todd asked as he continued to fuck me.
"Yes, Sir!" Bo replied.
"You have my permission to cum," Todd replied.
Bo started to groan loudly as his nub started to pulse in its cage and cum began to drop onto the floor. Todd growled as well and shoved his cock into me as it delivered its second load deep into my bowels.
"Fuck, boy!" Todd exclaimed as I felt his cock pulsing inside me.
After a few minutes, he pulled out and I gasped a bit. I then slowly pulled out the dildo from Bo's ass and then got down on my knees to clean his cage and nub off and then lick Bo's load off the floor. When I was done, Todd had me clean his cock off, and then he took the harness off me and let Bo up.
"I think you need to clean him again Bo," Todd said pointing at my cum covered ass.
"Gladly!" Bo smiled and I leaned over the bench so he could tongue me clean.
When he was done, I got up and we hugged each other and kissed and Bo licked some of the dried cum out of my beard.
"See boys?" Todd said as he grabbed a small towel to wipe his hands and forehead. "Chastity sub-boys can still find ways to be intimate. While you must follow John's protocols as his trainees, I believe that life is not all about service. You have to find your pleasure in it as well. But, if you want to do this again, you will have to do so under my supervision or permission."
"Yes, Sir!" we both replied.
"Bo, on your knees," Todd said. "I need to piss now."
After Bo took Todd's piss, we went back into the living room area and Todd laid down on the sofa to take a nap and we cleaned up the playroom before coming in and sitting down on the floor. Bo then laid down and put his head in my lap and rubbed my legs.
"I enjoyed that," Bo said as he looked up at me.
"Me too bubba," I replied, and I rubbed his chest as he started to doze off.
I had been leaning against the wall and had dozed off myself, so I was a bit out of it when I felt Todd's hand on my shoulder, waking me up. I opened my eyes and saw him looking down at me. Bo was nowhere to be found.
"I sent Bo down the road to the corner store for some food," Todd said. "We need to talk."
"Yes, Sir," I replied as I rubbed my eyes.
Todd sat in a chair in front of me and picked up a glass of whiskey he had poured and put it on a table. He took a few sips and then looked at me.
"Bo will be my collared boy very soon," Todd said. "As I have said, I am fine with you continuing a relationship with him; however, we need to talk about some ground rules."
"I understand, Sir," I replied as I brought my legs up and sat cross-legged.
"When do you complete your service with John?" Todd asked me.
"March of next year," I replied.
"So, you will be busy with him and your sub brothers and those responsibilities come first," Todd said. "When you have free time, though, you are welcome to come over to my house to see Bo but as a collared boy, he will have seniority over you in the house. In effect, you will be the beta boy in the house, and he will be the alpha sub when you are visiting."
"That makes sense," I replied.
"I have been seeing someone myself that may turn into something at some point," Todd replied. "If that is the case, then we may have to reevaluate things."
"Yes, Sir," I replied.
"I do not believe in 'owning' boys," Todd replied. "Bo will be my collared sub and will have duties and responsibilities, but I also will respect a certain amount of freedom on his part to develop his relationships. If you two continue and things get more serious, I am not opposed to possibly collaring you as well. How do you feel about that?"
I was a bit shocked as he took another sip and looked at me. I had not even considered being collared at this point, but the thought of being a sub with Bo under Todd was nice.
"I would be very honored, Sir," I replied. "You are a very kind dom and I have enjoyed being around you."
"I appreciate that boy," Todd said. "I will have to think more about this and see how things work out with Bo once he moves in with me, but I can see where having the two of you around would be nice. Plus, if I do end up in a relationship with Pat, the man I have been seeing, then it would be beneficial to have two subs around as well. We shall see, though."
"Thank you so much for considering it, Sir," I replied.
"Well, why don't you come over here and massage my feet while we wait on Bo to return," Todd said.
I crawled over in front of Todd and put his big feet into my lap and started to rub them. He leaned back and sipped on his drink and relaxed until Bo returned. We then put the food away that he had brought and went back out on the beach and relaxed until the sun started to set. As we watched the glowing orb on the horizon, Bo sat behind me on the towel and hugged me tightly, and lightly kissed my neck.