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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 28: Visiting Key West
I woke up Saturday in Todd's guest room. He had Bo spend the night with him in the master bedroom. The light was coming in from the window and I heard the sound of the surf out the open frame. I got out of bed to go to the bathroom and after I was done, I walked down the hall and noticed that Todd's door was open. When I started to peek in, I saw a cot at the foot of the bed with a pillow and sheet on it where Bo had been sleeping, but it was empty. Once I got to where I could see the bed itself, I saw Todd laying there with the sheets pulled back and Bo was in between his legs giving him a blowjob. Todd looked up and saw me in the hall.
"You sleep ok, boy?" Todd asked me as Bo continued to work his cock.
"Yes, Sir!" I replied with a smile.
"I'm glad," Todd said. "Why don't you get some breakfast started and I'll be in shortly after the boy drains me."
"Will do, Sir!" I replied and I continued into the living room and around to the kitchen.
I opened the refrigerator and scratched my belly as I determined what I could make. Bo had picked up some fresh eggs and sausage, so I pulled those out and I got out some bread for toast as well. I found an apron hanging on the wall to protect my nub and I started to scramble some eggs and fry up the sausage in a pan.
The smell of the sausage started wafting through the house and it was not long till Todd came around the corner into the kitchen. His balls were a little less heavy.
"Smells good, boy!" he said as he inspected everything and then started some coffee brewing.
"Did you sleep ok, Sir?" I asked as I turned the patties.
"I did," Todd said as he grabbed a coffee cup. "I always do here. I find the sound of the water soothing."
"I agree, Sir," I said as I moved the pan off the heat and finished scrambling the last of the eggs.
The toaster dinged and I pulled the last two slices out and put them on a plate with the others.
"I am almost done here," I replied.
"Good," Todd said as he put his cup down and turned to look at me.
After I had finished the eggs, I put the pan to the side and turned to get some silverware.
"Before you get to plating anything," Todd said, "how about you get on your knees and help me here. I need to piss."
"Absolutely, Sir!" I replied.
I took off the apron and got down in front of him and he placed his soft cock in my mouth. I looked up at him as he placed both hands back on the counter and I felt his warm stale piss start to flow into my mouth. I closed my eyes and concentrated on my breathing and swallowing and managed to get it all down without a drop spilled. When I felt the stream start to slow, I opened my eyes and saw that Todd was smiling at me.
"Very good job, boy," Todd said as he reached down and wiggled his cock in my mouth to get the last drops out.
Once he was done, I stood back up and he turned to fill his cup with coffee and then went and sat down at the table. I plated his food for him and brought it over just as Bo was coming into the kitchen.
"Morning, Bo," I replied with a smile as I laid the plates down and then turned around.
"Good morning, bro," Bo said as he came behind me and hugged me.
Bo followed me into the kitchen after and I gave him his plate and grabbed mine and we walked over next to Todd and sat on the floor to eat.
"I've decided to take the boat out today, boys," Todd said as he ate some of the eggs. "I can show you some interesting places around here and then after we can drive down to Key West. Have you two ever been there?"
"No, Sir," we replied.
"Good deal," Todd said as he took a drink of his coffee. "I have a friend that has a house just off Duval Street. I think he would like you two."
"That sounds like fun, Sir!" Bo replied as he finished his food.
"In that case, Matt, why don't you clean up the kitchen and I'll go take a shower," Todd said. "Bo, you can come join me as well."
"Will do, Sir!" I replied and I got up and started to take the plates into the kitchen as they left the room.
After I had finished washing all the dishes and drying and putting them away, I wiped down all the surfaces and then walked over to the back door and opened it to let in some fresh air. I was leaning against the threshold, enjoying the morning breeze, when Bo came behind me and put his arms around my waist.
"Todd said you could go take a shower now if you wanted," he said as he put his head on my shoulder.
I turned around and kissed him and then said, "sounds good."
After I had got cleaned up, we all put on some clothes and followed Todd out to the boat. He had us get on and threw off the lines and then started it up and drove us around the island. There were several places where the vegetation had overgrown and there were lots of birds nesting and flying about. He also showed us some good fishing spots and gave us a little history of the area as well. He had grown up here as a kid before moving away and the land the house was on had been his grandfather's. He had built the home there after he became a partner in the law firm in Atlanta.
We had packed some sandwiches before we left, and we got those out and ate on the boat near the shore as we watched some seagulls compete for some scraps of something on the beach.
"So, what do you boys think?" Todd asked as he took a bite of his sandwich.
"It's a neat area, Sir!" Bo said.
"I agree," I said. "I can see why you like coming here."
"It's a lot more enjoyable when you can share it," Todd said. "I am glad you could come with us, Matt."
After we had finished our lunch, Todd drove the boat over to a dock area to refill it with fuel and then we headed back to the house. We pulled in about 2 pm and after he tied the boat up, we walked back into the house.
"Keep your clothes on this time, boys," Todd said as he closed the door behind us and locked it. "I'm going to grab my keys and we can head down into the city."
It took us about an hour and a half to get down into the city, as we had to stop for gas along the way. As we got into Key West, I noticed how many people were wandering around.
"This is a tourist city," I said.
"Yeah," Todd replied, "it can be pretty hectic on the weekends. The home we are going to is a bit out of the high population area though."
We drove across Duval to Whitehead Street and he parked next to a corner home that was above a small shop.
"We are here, boys," Todd said as he got out.
He led us up some back stairs and knocked on the door and when it opened, an older man greeted us.
"Hey, Bill!" Todd said loudly as he leaned over and hugged the man. "How have you been?"
"Doing well, Todd!" Bill replied. "Are these the boys you told me about?"
"Yes, indeed," Todd said as he turned to the side and pointed at Bo. "This one here is Bo and the one that I plan on collaring in a few weeks. Next to him is his boyfriend and fellow sub, Matt."
I blushed a bit as Todd introduced us, as this was the first time someone had addressed me as Bo's boyfriend.
"Good to meet you both," Bill said as he extended his arm to us and shook our hands.
Bill was a little shorter than me and was bald, with blue eyes and a bright white beard. He did not have a shirt on, and he was covered in dense white fur. He had a nice belly and a large tattoo of an anchor on one arm. Below his cargo shorts, I saw more white hair running down his legs and on the top of his bare feet.
"Come on in!" Bill said.
Todd walked in and we followed him, and Bo closed the door behind us.
"Go ahead and strip, boys," Todd said, as he followed Bill over to a couch. "You will follow the same protocols as in my home."
"Yes, Sir," we replied, and Bo and I took off our clothes and folded them next to the door.
Todd had us come over and sit in front of them near the couch as the two men talked.
"Would you like a beer, Todd?" Bill asked.
"That would be nice," Todd replied.
"Bo, go into the kitchen there and get your Sir here a drink," Bill replied. "They are on the bottom shelf. If you two are thirsty, there is some bottled water in there as well."
"Yes, Sir!" Bo said as he got up and went into the kitchen.
Bo returned with a beer for Todd and some water for us and then sat down again and we watched quietly as the two men talked about what they had been up to lately and what was new with some of their friends. I got the impression that Bill was an old friend of Todd and that he had lived on the island for some time.
"I've got a guy coming over to give me a massage shortly," Bill said. "Would you like to have one too, Todd?"
"That would be wonderful," Todd said.
"Are you ok with the boys leaving for a while?" Bill asked. "It would be better if it was just the two of us here while the masseuse is doing his work."
"I'm sure they can find something to do," Todd said as he looked down at us. "Why don't you both get dressed and you can head into town and do some sightseeing."
"Thanks, Sir!" Bo replied.
"When should we be back?" I asked.
"Come back at 6 pm," Bill replied.
"Sounds good, Sir," I replied and we both got up and dressed and then headed outside.
As we walked down the stairs to the street, Bo turned to me and said, "where should we go first?"
"Why don't we go up to Duval and hang a left," I said. "That's where we saw everyone coming from."
"Following you!" Bo replied.
We headed down the street and followed the crowds as it started to get busier. After stopping to get a frozen margarita to sip on, we continued down till we got to Mallory Square. There weren't any cruise ships docked there, so there was a perfect view of the water and the sun that was starting to get low on the horizon. Some performers were starting to show up to get set up for the entertainment that they put on before sunset, but it otherwise was low-key.
Bo put his arm around my waist and leaned on my shoulder as he sipped his drink.
"So, did the whole boyfriend thing freak you out a little?" he asked. "You had this look on your face."
"Well, I was not expecting him to introduce me like that, but I didn't mind if that is what you were asking," I replied.
"I get that," Bo said as he moved up and kissed me on my cheek.
I turned and put my arm around him and started to kiss him on his mouth. We both closed our eyes and got lost in the moment as our tongues explored each other and we rubbed each other's backs. My nub started to swell, and I reached down to adjust my cage a bit.
"You know if we keep this up," I said as I backed away for a moment, "I'm going to have a serious wet spot on my pants."
"Me too," Bo said with a grin.
"It's been a while since I have dated anyone," I said. "And I sure have not done it in a cage. So, I suspect it might be a bit awkward at times."
"It's ok," Bo said. "I broke up with my last boyfriend last year and he never understood my interest in chastity. At least we have the same kinks and interests."
"And doms to explore them with," I replied with a smile.
"That felt so good when you were fucking me with that dildo, though," Bo said. "I am glad I got permission to cum. That helped my sore balls."
"Ugh, I know the feeling," I replied. "And I am only just about two months into my six-month lock session."
"Only a little over a month till I'll be given the choice to go permanent and have one last normal orgasm," Bo said.
"Are you nervous at all?" I asked.
"I mean, yeah, I am," Bo said. "But with you to support me and the encouragement of Sir John as well as the prospect of a collaring by Sir Todd, there is a lot to look forward to."
"And I'll be giving you your last blow job," I said with a grin.
Bo grinned back. "I know. Makes me look forward to graduation even more."
We kissed one more time and then decided to start to make our way back. We walked around to see some of the sights and also took a side street by the Hemingway House before getting back to Bill's house just before 6 pm. We knocked on the door and Todd let us in, and we started to undress again.
"Did you boys have a good time?" Todd asked.
Todd was naked but had a towel wrapped around him. Bill was the same way and was in the kitchen grabbing a beer.
"We did, Sir!" Bo replied. "Did you both have a good massage?"
"Indeed," Todd said. "But no happy ending."
"That's what you subs are for," Bill said with a smile as he took a sip of his beer.
Bill pulled open his towel and revealed a large, low-hanging set of balls. They could be door knockers I thought. I watched as he adjusted them a bit and started to grip his cock as it began to grow.
"You better get on that, Matt," Todd said to me. "Don't make him wait."
"Yes, Sir!" I replied and I moved over and knelt in front of him.
I took his cock into my hand and started to go down on him. Bill leaned back a bit and spread his legs more for me to get better access. As I started to work his shaft, Todd snapped his fingers at Bo, who came over and started to work his cock as well.
Bill's cock was a nice average size and fit perfectly into my mouth. I was able to give him some good deepthroating action as well and I fondled his large balls. That got a reaction from him and he stretched his legs out and groaned. I rolled his balls in my fingers gently as I started to swirl my tongue down his shaft, and he looked down at me and grinned.
"Someone has been teaching you well," Bill said.
"My friend John has both of these boys in his training program for subs," Todd said as Bo bobbed up and down on his cock.
"Remind me to thank him," Bill replied.
Bill reached down and put his hand on the back of my head and guided me down on his cock and forced me deeper on him. I moved my tongue from side to side as I went down and when my nose hit his bush, he held me there till I ran out of air and coughed, and he let me up. I went back down on him again and took in his scent from his crotch and my nub started to swell in its cage as a result.
I looked over and saw that Todd had gotten up and bent Bo over the side of the couch and was starting to fuck him. Bo looked up at me and smiled and then put his head down to concentrate on gripping Todd's cock as he pushed in and out.
Bill grabbed my head again and turned me back and forced me down on his cock again and I focused my attention on him as Bo started to grunt from the force of Todd's thrusts. I felt Bill's balls start to move a bit and knew he was close, so I increased my speed a bit and used my hands to jerk the bottom of his shaft as well. Bill stuck his legs out and groaned and I felt his balls lift in my hands as his cock exploded cum into my mouth, which I greedily swallowed. Bill reached down and held me on him till he stopped cumming and then collapsed a bit as I lifted off and licked him clean.
"Fucking hell, that was good," Bill said as he looked down at me.
I was smiling back as I heard Bo start to grunt harder and he started to grip tightly on the couch. Todd was fucking him hard and I could hear the smack of his groin as he made contact with Bo's ass. It was not long till Todd was blasting his load deep in Bo's ass and Bo squeezed down at the same time to milk his cock dry.
Once Todd had recovered from his orgasm, he pulled out of Bo and slapped his ass a few times and then came around and sat next to Bill again and grabbed a beer to take a few sips.
"Thank you, Sir," Bo replied as he fingered his ass.
"You are welcome, boy," Todd replied a bit out of breath.
I crawled around behind Bo and parted his ass with my hands and dove my head in to lick it clean. Cum was running out of his hole and I licked it up and then dove my tongue in a bit for good measure as well. Bo groaned in response and almost lost his balance.
"Looks like we got some piggy subs," Bill said with a laugh.
"Indeed," Todd replied. "I'm pretty happy with that."
The two men finished their beers and then Bill got up and said that he needed to run some errands, so Todd told him we would head out and we all got dressed and piled back into the car to head back to Todd's house.
"How did you enjoy your afternoon, boys?" Todd asked us from the front seat.
"It was a lot of fun!" Bo replied as he reached over and held my hand. "We toured around the city a bit by foot and went by the water as well. Seems like a neat place."
"Yeah," Todd said. "I'll probably take you down here for New Year's Bo. It's quite an experience and I have some fellow doms that would love to ring in the new year using you."
"Yes, Sir!" Bo said with a smile.
We picked some food up on the way home and ate it at the house, then packed up as we needed to fly back early to make it back to Atlanta by the afternoon. I still had my one-on-one with John and Todd had some things to do as well. After dinner we played some cards for a while and relaxed and then when it was time for bed, Todd brought Bo into his room and closed the door, and I went back into my bedroom and caught some sleep.
The next morning, I made breakfast again, and then after we cleaned up, we were out the door and headed to the airport. Some weather in the area delayed our take off for a bit, and I was nervous about missing my set time with John. I had neglected to tell him I was heading out of town so I texted him to let him know what was going on and I might be late.
"How late will you be, boy?" John replied.
"It looks like maybe thirty minutes, Sir," I said. "We are just about ready to take off."
"Ask Bo to come with you when you come over," John replied. "We need to talk."
"Yes, Sir," I replied.
I had a concerned look on my face and Bo looked over at me.
"What is wrong?" he asked.
"I forgot to tell Sir I was heading down here with you and I was letting him know we would be a little late coming back," I replied.
"Well, I did tell him you were invited," Bo said.
"I know, but I did not," I said.
"Oh," Bo replied with a worried look.
"He asked if you would come over to the house with me when we land," I said.
"I can do that," Bo replied. "I hope you are not in trouble. I would feel bad."
"Don't be," I said as I reached over to hold his hand. "It was my mistake."
Bo squeezed my hand back and then we sat back and prepared for takeoff. The flight back up to Atlanta was pretty smooth and we landed only a little late. Todd drove us back over to his house and then Bo followed me in his car as I drove over to John's.
When we arrived, we took our clothes off and put them in our bins and walked into the dungeon area. It was about 35 minutes later than I normally came. John was inside on a chair waiting for us. I was a little concerned as we moved to the side and knelt in our squares on the floor. After we sat there a moment in silence, John finally spoke.
"Stand up, Matt," he said firmly.
I got to my feet and faced him with my hands behind my back.
"Todd called me a bit ago, before you both arrived, to let me know what went on," John said. "I am glad you both were able to serve and please him, but I have some concerns. Do you know what they are?"
"I neglected to tell you I was going out of town and as a result, I was also late today," I replied.
"Those are transgressions we will address, but I am also concerned about the relationship you two have," John replied. "Bo, please stand."
Bo got to his feet and stood next to me with his hands behind his back as well.
"While I respect the views that Todd has, I would prefer that my subs not be romantically attached," John said. "You have a lot to learn and you will be relying on each other during the process. Relationships can be tricky and volatile at times and I don't want anything to impact your duties as subs under me. Do you understand this?"
"Yes, Sir," we replied.
"What you do on your own time is your business, but while you are a trainee of mine, you will put a halt to any relationship outside of the sub brother aesthetic," John said. "Do you both agree to this?"
"Yes, Sir," we replied.
I felt a pain in the pit of my chest as I said those words. I was worried about the dynamics of exploring a relationship with Bo and while I liked him, I was disappointed that I did not come to John first to discuss it and get his permission.
"Bo," John said as he looked at him. "You will be graduating soon, and should Todd follow through and give you his collar, you will be under his house and rules. If you two wish to pursue something at that time, you can do so as long as it does not infringe on Matt's duties and responsibilities with me. Is that understood?"
"Yes, Sir," Bo said.
I turned my head to where I could see him, and he was visibly a bit upset and a tear ran down his cheek.
"I am not trying to be heartless, boy," John said as he walked over to him and wiped his cheek. "But do you understand why this has to end at least until you graduate?"
"Yes, Sir," Bo replied.
"Matt, step forward," John said.
As I did so, I noticed the leather paddle sitting on the chair that he got up from. He grabbed it in one hand and looked at me.
"Bend over and touch your toes, boy," John said.
I swallowed hard and did as he asked. Bo held his breath as he watched John pull his arm back up into the air. The paddle then swung quickly down at me. The impact was hard and the sound of the smack on my ass echoed through the room. I grimaced at the intense pain as a result, but managed not to make much of a sound.
"That was for not informing me of your trip," John said loudly.
"Thank you, Sir!" I replied loudly.
A second impact hit my ass with the same force shortly after.
"That was for your tardiness today," John said.
"Thank you, Sir!" I replied.
Finally, a third swing came down on me and almost made me lose my balance due to the force of the blow.
"And that was for not telling me about your relationship," John said.
"Thank you, Sir!" I replied again.
My ass was on fire and I bit my bottom lip, trying not to cry out.
"Rise, boy," John said as I turned to face him.
I looked over and Bo had tears in his eyes, and I felt horrible. I wanted to rush over to him and hug him and tell him it would be ok, but I knew I had to stay still. John placed the paddle on the chair and told me to return to my spot next to Bo.
"Everyone makes mistakes, boys," John said. "The matter is closed, and we can move forward. Bo, you can leave now. I will see you tomorrow for cleaning day."
"Yes, Sir," Bo said with some cracking in his voice.
He turned and left the room and then John turned to me.
"You understand why that was necessary, right boy?" John asked.
"Yes, Sir," I replied. "I apologize."
"Apology accepted," John replied. "Go over to the cross and prepare yourself. I need to burn some energy off in our session today."
"Yes, Sir!" I said.
John was not kidding when he said he had to burn off some energy. After flogging me on the cross for a while, he pissed down my throat and then bent me over the fuck bench and loaded me up twice before he sent me home. As I walked into the apartment, I felt well-used. I closed the door behind me and was getting dressed when I heard a knock. I turned and opened it and saw Bo standing there.
"Do you mind if I come in for a moment?" Bo asked.
"Sure, bubba," I replied, and I let him in.
I finished pulling my clothes off and he undressed as well and then came over and embraced me.
"I am so sorry you had to get punished," he said as he started to sob a bit. "Right after I left, I drove over here and waited for you to get home so we could talk."
"It's ok bubba," I replied as I held him. "I made a mistake. I should have told him. He was completely correct. I also knew it would be complicated to become closer to you."
"I know," Bo said as he wiped his face.
I pulled him back and looked into his eyes.
"I do care a lot for you Bo," I replied. "But let's just be good friends and sub brothers for now and in December after you graduate, we can see what happens. You've been a great support and friend to me during my training and I don't want to ruin anything we have. I think we can wait a few weeks."
"I agree," Bo said with a smile.
I gave him a quick kiss and then rubbed his cheeks.
"Would you like to stay awhile and play some video games?" I asked. "I would love the company."
"Yeah," Bo said. "I'd like that a lot."