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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 14: Getting into the Routine
Monday started a new routine for me that would carry through the rest of the year. I had a busy day at work followed by a quick dinner and then cleaning day at John's. On Tuesday I would get an email in my inbox with a reflective exercise to talk about what happened in the Sunday session, how I felt, what I thought were opportunities of growth for me as a sub and any feedback I had. Wednesday would be another cleaning day and then the following day would be a `task day' as John called it.
My first task came in my email after work Thursday.
Boy:
As part of your training, it is important for you to keep track of what you are doing, where you have to grow and what successes and failures you experience. To that end, I want you to set up a Tumblr account and to start posting daily pictures. You do not have to show your face, but your nub should always be clearly visible. Along with the pictures, I want you to chronicle what you have done in the past 24 hours prior with emphasis on any training you have done, what your thoughts are and where you see opportunities for growth. If you provide any sexual services or favors for others, they should be documented as well.
If any follower of your blog asks you questions, I want you to post them and be detailed in your answers. You should also strive to seek out other subs and doms as well to build a community where you can learn what subs are expected to do and what other doms expect of subs.
I want you to have this set up tonight and have your first picture posted by 10 pm. You should document your training last Sunday and anything that has happened of note since then. Send me the link and I will be monitoring this as you continue your training.
Sir
Keeping a blog was something I had done in the past, but an erotic blog that included naked pictures of myself, let alone pictures of myself in chastity, was not something I had ever done or had thought about. But I did go through the process of getting things set up and posted my first picture and recount of my previous training night as well.
I started to look for others in chastity and found a ton of blogs of both subs and doms in the lifestyle. I had added about 100 blogs to my account by the time I signed off that evening and got ready for bed. By Friday morning, I had equally as many follower requests and started to get messages and questions in my inbox.
When I got off work Friday, I opened up my blog and had a private message waiting for me. It was from a guy that was visiting Atlanta for the weekend for work and he liked the picture and recap that I posted. We got to talking over an hour period while I ate my dinner at home. He was a dom from Minneapolis that was in the leather community and had been interested in chastity for one of his sub boys but wanted to know more about my experiences and how I got started, so I gave him the full rundown of the past few weeks.
As we talked, he eventually sent me a picture of himself and I sent him mine. He was a hot looking man. In his picture, he was sitting on a bench in what looked to be a bar of some sort. He was bare chested, and his dark skin was glistening from sweat. He had black chaps on over tight jeans that showed what looked to be a pretty massive package from the looks of the bulge. He had a boy on his knees polishing his boots and he held a flogger on one hand that was draped over the boys back. My nub was straining pretty quickly.
The picture I sent him was one where I was completely naked and kneeling with my hands behind my back and my head faced forward. My caged nub and collar were on full display. He was impressed immediately and asked if I would be interested in helping him drain his balls tonight. I told him I would be honored to service him, and he gave me directions to his hotel.
It was actually only about 15 minutes away, so I jumped in the shower to clean up a bit and then headed out. When I got close, he told me the room number and asked that I knock three times quickly and then wait. When the door finally opened, I saw him at the threshold in just his boxers.
"Strip boy," he said.
I went to walk in and do so and he held his hand out on my chest and stopped me from entering.
"Did you hear me?" he said. "I said strip! Right there."
I was a little bit nervous. There was no one in the hall, but the idea of stripping down in a public area was not something I had intended to do. He sat there and looked at me, though, so I started to pull my shirt off and slipped my shoes and socks off and then stripped off my pants and underwear till I was completely naked in the hallway. He held out a bag and told me to put my clothes in it, so I placed them inside and he put the bag next to the door just inside the threshold. My shoes were still in the hallway, though.
"You may come in now," he said.
As he shut the door and turned toward me and told me to go over to the window and kneel facing him in front of it. I did what he asked. The blinds to the floor to ceiling window were completely open, and it was nearly dark outside. If anyone wanted to watch, they would have seen my bare ass kneeling quite easily from the third floor with the light in the room as a contrast.
He walked over to me and dropped his boxers as he passed the bed. His dick was impressive. It had to be at least 8 inches long (20.32 cm) and had a slight curve to the left. He had a nice set of balls as well. He walked over until his package was eye level with me and he was stroking it. He let it fall and slap my face a few times and he looked down at me.
"Let's see how well you can suck a man's cock," he said.
I reached out with one hand to grab his root and started to lick and suck on his head. I would have no hope of deep throating this monster, but I did do my best to suck what I could and lick its entire length. I also paid attention to his balls and took one and then the other in my mouth.
He had a musk that got me straining in my cage. I could tell he was a little sweaty and he later told me he had been working out in the hotel gym earlier. I took his cock into my mouth again and started to move up and down on it and used my hands to work the lower shaft. He reached down and grabbed my head and forced me down more than I was wanting to go, causing me to choke on several occasions.
He moved a bit and had me shift as well so that my side was facing the outside window. From the parking lot you could have seen it all. Me on my knees taking his large cock in my mouth and his hands on my head guiding him. I think he had a bit of an exhibition streak.
After a few minutes he pulled me off and grabbed a chair and moved it right next to the window. He told me to get up on the chair and hang my ass off. I knew what was coming next. He went over to the bedside table and grabbed some lube and started to rub it on his long and thick member. I was trying to prepare myself for the onslaught that was coming.
He got behind me and started fingering my ass. When he got to the point that he was fucking me with three fingers, he pushed my ass down a bit with the palm of his hand and pointed his cock at my hole and moved in, and I let out an audible gasp as his long black cock moved inside me.
"Damn, boy," he said. "This ass is just what I needed."
"Thank you, Sir," I said. "I'm here to serve."
As he continued to enter me, I started to realize just how big his cock was and I clinched up a bit, which caused him to slap my ass in response.
"Breathe, boy," he said. "Don't clinch. Relax and take this cock!"
I groaned as he finally got all the way in and he slowly started to fuck my ass as he held tightly to my waist. It was honestly a bit painful, but I was determined to pleasure him well.
As he started to speed up his thrusts, he reached down and grabbed my shoulders and pulled me up some so my back arched a bit. This gave him a bit more access to fuck me deeply and I was starting to cry out a bit as he pounded all the way till his balls hit my ass.
"How does that feel, boy?"
"Your cock is massive, Sir," I said. "It's a privilege to take it."
"Good boy," he replied.
He pushed me back down on to the back of the chair again and started to pound me with a medium thrust and speed and smacked my ass while he was at it. First one cheek and then the other. At first, it was not too bad, but as he continued, the pain increased, and I could feel the heat building on my ass as they reddened.
"That ass is warming up nicely," he said.
I just grunted and tried to hold back crying out as he continued.
Once my ass had a light red glow, he reached back up to my shoulders to pull me up again and arch my back. He then started to pound me hard and I heard the smack of his low hanging balls as they hit me.
"It's a good thing you caged that pathetic thing between your legs boy," he said. "This ass is made for a man's pleasure."
"Thank you, Sir" I replied in between a grunt and a cry.
He then pushed my head down with one hand and grabbed my waist with the other and shoved his cock deep into my ass as his cum erupted from his balls and flooded my insides.
"Fuck!" he yelled. "Take that cum boy!"
I was biting the back of the chair and doing all I could not to scream out. His cock was pulsing so hard that I felt it as it moved inside me. He sat there for a moment and caught his breath and then pulled back and then stopped just before he was completely out. He then waited a further few seconds to make sure his cum was well planted before his cock slid completely out.
"Clean me, boy," he said.
I got off the chair and down on my knees and grabbed his cock in one hand and licked him completely clean of my ass and his remaining cum. He ran his hand through my hair and was groaning while I was doing it.
"Thank you, Sir," I said as I finished and looked up at him.
He grinned and told me to get up. He led me over to the door and opened it and picked up my bag of clothes.
"I'll be sure to let you know next time I am in town, boy," he said. He then tossed the bag into the hall and pushed me out and closed the door behind me.
I was in a state of shock for a moment. Cum was running down my leg from my overfilled ass and I was completely naked in the hotel hall. I bent down and grabbed the bag and quickly put my clothes on. As I bent down to put my shoes on, I felt the cum leak out and start to soak my underwear.
By the time I got home, a wet spot had soaked through to the back of my pants. I was happy to get inside my apartment and strip down and clean up a bit. I went to my computer after and typed up a rundown of the evening's adventures and posted it to my Tumblr account and then I emailed John to let him know how things went and that the details were posted.
Saturday morning, I spent the morning cleaning my apartment and after lunch got my laundry done. I dumped it all on my bed after and was starting to fold it all when my phone went off. It was from Jay.
"Hey bro," he said. "Are you busy today?"
"I am just folding laundry," I replied. "What's going on?"
"Can you meet me at my apartment at 3 pm?" he asked. "Bo will be here. We need to discuss a few things."
"Sure, I can be there," I replied.
"Great," Jay said. "I'm on the first floor. I'll send you the address."
As the address came in by text, I was a bit curious as to what was going on. But, as it was 2 pm at the moment, I needed to hurry up and finish getting things put away so I could head over.
Jay lived about 30 minutes away on the north side of the city. When I pulled into his complex, I drove around the side of one of the buildings and found his apartment. Bo was still in his car when I pulled up and parked next to him.
"Hey Bo," I said.
"Wassup Matt," he replied and came around to give me a hug.
"You know what this is all about?" I asked.
"Sir wants us to prepare for something at his house," Bo replied. "But Jay said he would give us more details when we arrived. As the senior sub, it's his job to coordinate for parties and special events and gatherings at Sir's."
"Ahh, ok," I replied.
We knocked on the door and Jay greeted us in just his cage and collar. We entered the room and stripped down to ours as well and folded out clothes next to the door.
"Thanks for coming over guys," he said. "Feel free to sit at the table here and I will grab y'all some drinks."
The kitchen table was to the left of the door and the living area was to the right. The kitchen was in the back left of the room and in the back right it led off to his bedroom and bathroom. Bo sat in the chair next to the door and I sat opposite of him. Jay joined us and sat in the chair on the side of the kitchen area and handed us some cokes.
"Sir has informed me that he will be having two old friends from New York staying with him next Friday and Saturday," Jay said. "They are a couple and have a collared sub of their own that was one of Sir's first graduates. He has informed me that he wants us to be available to cater to their needs while they are here."
"What all will this entail?" I asked.
"One or more of us will need to be around as long as they are here," Jay responded. "We will be expected to respond to any and all requests including any maid or sexual services they may desire. Additionally, Sir wants us all three of us at his house on Saturday from 12 pm to 1 pm to provide sexual services in the dungeon area."
"This happens from time to time," said Bo. "Sir likes to treat his guests like royalty. We get them food and drink, provide massages, provide blowjobs or let them have use of our ass, and things like that. But we also have to stay overnight and be available as well."
"Correct," said Jay. "This means we need to coordinate who will be there and when as one of us has to be awake and available from the time they get to Sir's to the time they leave."
"Ok," I said.
"I have already requested a day off from work so I can get to Sir's house at 9 am to prepare for their arrival at 10 am on Friday. Ideally, I would like to have one of you come over to relieve me at 7 pm that Friday evening. That second shift will be 7 pm to 5 am on Saturday morning and the third shift will be 5 am to 3 pm and will include the time we will be in the dungeon area. They will be leaving at 2 pm, so the one of you that takes the third shift will go with them and tend to any last-minute needs while the second shift person works with me on clean up duties in the dungeon area. After they leave, the third shift person will have to strip the beds, put the sheets in the wash and then clean the room thoroughly before leaving."
"I understand," I said.
"Bo is next in seniority among us, so which shift do you want?" Jay said.
"I'll take the second shift," he said. "I'm a night owl anyway and I can take a nap after in Sir's pool house and then join you at noon in the dungeon."
"Very well," Jay said. "That means you are on the third shift, Matt."
"Sounds good," I said.
"I figured Bo here would take the night shift," Jay replied to me. "I talked to Sir about you taking the morning shift and he let me know there are some things that his guests like in the morning, so he will be letting you know what those are and training you on a few things tomorrow during your on-on-one with him."
"Ok?" I asked curiously.
"You will have to wait to talk to Sir about that," Jay said. "He did not let me know any more than that."
For the next couple of hours, we hashed out how things had gone in the past when people visited so I knew what to expect. I would be kneeling in any room they were in and had to respond to any request they asked of me. We also discussed what areas needed to be cleaned afterwards and who was to do what. I almost wish I had taken notes, but Bo assured me he would make sure I was up to speed.
After we were done talking, Jay told us he had to get ready to meet some folks. I asked Bo if he wanted to go to Woofs, the bear sports bar, for some drinks and dinner. He said that would be great, so we both got dressed and headed out there.
We arrived at the bar about 6:30 pm. It was a decent crowd for a Saturday evening, and we got a table in the back and ordered a pitcher of beer to share between the two of us.
"So, Bo, how often does Sir host guests?" I asked.
"Well," he replied. I have only been in training since December. He had some guests at the end of January, but nothing since then."
"Ok," I said. "So, not too common."
"No," Bo said, "But, just be prepared to be on your toes as we said. Sir expects an immediate response to any request and if we do not meet the high standards, he places on us, we can be punished after they leave."
"Well, this should be interesting," I said.
Bo poured a glass of beer from the pitcher that arrived at the table and took a drink. He then took the second glass and poured one for me and handed it to me.
"You'll be ok," he said.
As I grabbed the glass and started to drink, I noticed Dan come in the bar and he saw and waved at us and came over to the table.
"How are you boys?" Dan asked.
I stood up and gave him a hug as did Bo.
"We are good," I replied.
"Is this seat taken?" he asked.
"No, feel free," Bo replied. "Is your master not with you?"
"No," Dan said. "Greg had to go out of town for the weekend. So, I decided to get out of the house for a bit."
Dan ordered a whiskey sour from our waiter and then asked us, "so, what is knew with y'all?"
"We were just discussing some guests Sir will have over next weekend," I said.
"Oh yeah?" Dan replied. "Where are they from?"
"Jay told us that they were from New York and had a sub that graduated from the program a while back," Bo said.
"That sounds like Wes and Bart," Dan said.
"Did they visit while you were in the training program?" I asked.
"Yes," Dan said. "They have known Sir John for a long time. They collared a sub named Drew and he went with them when they moved to New York several years ago."
"Anything we should know about them?" Bo asked.
"Just that they are very demanding with a sub," Dan said. "Be sure you are ready for anything and don't make them wait."
"Ok," I said. "That is good to know."
"Also," Dan said, "Bart loves to have his balls tugged on when he is getting a blowjob, so if you are asked to service him, keep that in mind. But Wes does not like his balls messed with, so you will need to remember who you are servicing and not mix it up."
"I am glad we talked to you then," Bo said.
"Which one of you will be around in the morning?" Dan asked.
"That would be me," I said.
"Humm," Dan replied with a concerned look. "How experienced are you at watersports?"
"Like drinking piss?" I asked.
"Exactly," Dan said.
"Well," I replied, "I mean I have played with people that have pissed on me before and I have had them piss in my mouth a bit, but not much experience."
"That might be an issue, then," Dan replied. "Bart expects the sub to take his morning piss when he wakes. You will be expected to be on your knees next to the bed and drink it all from the tap."
"Oh," I said with some concern. "I wonder if that is what Jay was referring to earlier. He told me Sir was going to have to work with me on some things specific to his guest's morning needs."
"It's possible," Dan said. "As the morning sub you will also preparing breakfast for them."
"What will I be preparing?" I asked.
"I was the morning sub when they visited during my training," Dan said. "I prepared scrambled eggs, bacon, sausage, hash browns and biscuits."
"Oh, that is not too bad," I said.
"No, you will just need to plan your time accordingly and be prepared to drop everything at a moment's notice if they call for you," Dan said.
"I guess I need to start flagging yellow quickly," I said.
"Just like your collar color!" Bo said with a laugh which Dan joined in with.
"You can train on your own," Dan said with a smile. "Just collect your piss in the morning in a class and learn to drink it all. It is usually stronger in taste in the morning and the warm temperature was something I had to get used to as well."
"That is good advice," I said.
"Sounds like you got homework to do Matt," Bo said as he took a drink and winked at me.
We all ordered some pub food and hung out for a few hours before Dan said he was getting tired and wanted to head home. Bo and I agreed to do the same, so we paid our tab and I ended up getting home about 10:30 pm.
I walked into my apartment and stripped down and started to head to the bathroom to drain my bladder as a result of the beer I had been drinking, but stopped myself when I remembered what Dan had suggested I do.
As I needed to piss bad and knew it would be a lot, I got a large water bottle from the kitchen and held it under my caged nub. I let the piss flow and it started to fill the bottle up. Sure enough, it was pretty much full to the brim by the time I was done.
I lifted the container to look at it and brought it to my lips.
"Well," I said to myself, "here goes nothing."
I tipped the container back and the warm beer piss filled my mouth. It did not have a strong taste and was more salty than anything else. The warm temperature was something that was making me gag a bit. I paused for a moment to swallow and then continued to drink till I had recycled it all.
"Ugh," I replied out loud. "That is going to take practice. Especially if I won't have the ability to pause and swallow."
I rinsed out the container and went to sit down and play some video games before heading to bed for the evening.