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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 25: My Work Trip
The week after Max was initiated, I was called into my boss's office. I was a little nervous as I did not talk to Richard a lot and he had a pretty stern demeanor.
"Come in, Matt," Richard said as I knocked on the side of his open door.
"What did you want to see me about?" I asked.
"We have a bit of an issue I am hoping you can help me with," he replied. "Jim was supposed to be flying to Denver this week to present the proposal you worked on for X Corp."
I knew Jim well. He and I worked on a team of individuals that had drafted a technology proposal for the start-up. We were bidding to handle their IT needs and support and we had been working on an analysis of their needs and how we could step in to help.
"Did something happen?" I asked.
"His wife just called me and told me that he had to be rushed in for an emergency appendectomy earlier today," Richard replied.
"Yikes!" I said. "Is he ok?"
"Well, they found out it had burst, and it was touch-and-go for a while there, but they think he will be ok," Richard replied. "The big issue is that he will not be able to present the proposal. Would you be able to step in and do it for us?"
"I'd be happy to," I replied.
"Good," Richard said. "You'll be flying out Thursday morning and coming back Saturday afternoon. They will expect you to have dinner Thursday night with a few of the X Corp team members and you will present on Friday. I'll have Betty arrange the travel for you. Please talk to your team and get up to speed on anything you might have questions about."
"Thanks, Sir!" I replied as I turned to leave.
As I was walking down the hall back to my office, I was going through a myriad of questions that I wanted to address to prepare. I reached down to scratch my leg and my hand hit my cage under my pants and then I panicked. How was I going to get on a plane with this metal cage?
When I got back to my office, I texted John and let him know what was going on. He told me not to worry and that we could discuss it when I was over for cleaning. He assured me that this was not something new for his subs and he had a solution.
So, on Wednesday, after I was done with my duties and my sub brothers had left, John came downstairs to the dungeon area to talk to me.
"So, where will you be going, boy?" he asked as he went over to a cabinet against the wall.
"Denver, Sir," I replied. "I'll be taking over for a colleague of mine that got sick."
"And I am assuming you have never flown with a chastity cage on," he said as he rummaged through some drawers.
"No, Sir," I said. "I was not aware you would be able to wear one, given security."
John found the item that he was looking for and turned around to look at me. "You will be fine. Chastity devices are considered 'religious and cultural wear' and the TSA should allow you through. However, you should be aware that you will likely set off the metal detector or show up on a scanner."
In his hand, John had a small plastic box. He took the key that would remove my security screw and placed it in the box. When the lid closed, there was a small opening that he put a plastic lock through that was numbered and he closed and locked it. He then handed it to me.
"This plastic lock is numbered and cannot be relocked if removed," John said. "In this way, I will know if you have tried to access the key within. You should pack this in your carry-on bag. If they require you to remove your device for any reason, break the plastic lock and remove the key to do so. However, you should immediately text me if this occurs."
"I understand," I replied.
"You may be required to have a pat-down and in rare instances, they may move you to a private room, but I have never had one of my subs told they needed to remove it," John said.
"Ok, Sir," I said.
"Text me when you land tomorrow and let me know if you ran into any issues," John added.
The next morning, I was rushing to get ready for my flight. I had packed the night before, but I still had some last-minute things to do. When I finally put my clothes on and headed out the door, I didn't have much time to spare.
The trip to the airport on the south side of the city took about thirty minutes to reach. I parked in the parking deck and headed into the airport a little nervous about how this was going to go with my cage. I got my luggage checked and then headed to the security checkpoint.
When it was my turn, I walked up to the TSA agent and he checked my ID and my ticket and then I went to the table to put my CPAP device through the x-ray machine as well as my carry-on bag. They were putting people through the body scanners, so after I removed my shoes and belt, I walked into the booth and raised my hands and the device scanned me.
When I walked through to the other side, the image on the screen showed my body and two large yellow squares over my crotch. A large man in a TSA uniform looked at me.
"Do you have any metal objects in your pockets or jewelry on, Sir?" he asked.
"I do have something on down there," I said quietly and pointed to my crotch.
"Come over here, Sir," he replied, and he got another man to come over.
"What are you wearing, Sir," the second man asked me as we moved off to the side.
"It's a chastity device," I said nervously.
"Very well," he said. "Stand and spread your legs."
I felt him pat down each leg and then he used the back of his hand to move up and it bumped the metal in the cage. He then stood up.
"You can move on through," he replied.
I took a giant breath in and let it out and then grabbed my things to head for the plane.
I landed in the early afternoon and after I got my things, I picked up my rental car and drove over to my hotel. It was a nice day out and the mountains were beautiful in the background. We have mountains in Georgia, but they would be little more than hills compared to the Rockies. After checking in, I put my things down and collapsed on the bed, and texted John to let him know that everything went well.
"Are you checked into your room?" he texted me back.
"Yes, Sir," I replied.
"No clothes allowed if you are there by yourself," he said.
"Understood, Sir," I texted back, and I got undressed and then sat back on the bed.
I had several hours to kill before I had to meet up with the potential clients for dinner, so I opened up a couple of cruising apps and browsed to see who was around. Anytime you are new in an area, you get a lot of attention. I was the 'new meat' as it were. Most of the guys that messaged me did not keep the conversation going or were not interested when they found out I was not a top. However, one man did catch my eye.
His profile picture was just his chest and I normally do not respond to headless profiles, but he quickly added a picture of himself after he initially messaged me. He was clean-shaven and slightly overweight. He had a receding hairline and ash-colored hair. But, what got my attention was his private pictures. His cock was massive. It looked to be as thick as a beer can and there was proof in a later picture where he had it next to a can of Coors.
"What brings you to town, boy?" he asked me.
"Work trip, Sir," I replied. "I am just in town tonight and tomorrow."
"Show me that ass," he said.
I sent him a picture of me kneeling on the floor with my ass up in the air. My cage was dangling prominently beneath me as well.
"I love a hairy ass, boy," he said. "How long have you been in chastity?"
"Since March," I replied. "I have been training under a dom and he has been working me up to longer and longer periods in the device."
"Are you wearing it now?" he asked.
"Yes Sir," I replied. "I flew with it on."
"That's hot," he said. "I would love for you to service me."
"When are you free," I asked.
"I am right now," he replied. "Are you in a hotel?"
"Yes Sir," I replied. "I would be honored to service you today if you want to come over."
"Send me the address, boy," he replied. "I'll be right over."
After texting the location of the hotel to him and my room number, I got into the shower and cleaned myself out with the travel douche that I had with me and then cleaned the rest of my body of the sweat I had built up from travel. I was just walking to the bed again when I heard a knock on the door.
I walked over and looked through the peephole and saw that it was him. When I opened the door, he looked me over from head to toe and then reached over and felt my cage.
"You've got some full balls there, boy," he replied in a deep voice as he closed the door behind him.
His eyes were dark blue, and he stared at me intensely for a moment before using his hands to push me to my knees. He then unbuckled his belt and his pants fell, revealing his stiffening cock under his belly. I reached out and took it in one hand and tried to get it into my mouth, but it was so thick that I could only get partway down it.
He reached around and grabbed my head and tried to force me down farther, but I could not take it and I started to choke. He pulled me off a bit, but then forced me down again till I gagged.
"You better get used to this cock, boy," he replied, looking down at me. "You got me over here, so I'm using you as I see fit."
He then continued to force his cock down my throat and the constant gagging and coughing were making me a bit nauseous. Spit was flowing out of my mouth and down my beard and was dripping on the floor as well.
He pulled his shirt off and rubbed his belly and then moved me over to the bed and bent me over it. He knelt and put his face in my ass, and I felt his tongue start to explore my hole. I was groaning in pleasure and my nub started to leak and it ran down the side of the bed sheets.
He pulled his face out and replaced it with his large finger and I felt him move in and out of my hole. My legs wobbled a bit as he forced it in and out and then moved to put two then three fingers in me. As he was doing so, he was stroking his fat cock with his other hand and preparing for his assault.
I felt him move up and start to mount me next. He placed both legs on either side of my body and pointed his cock towards my hole. When the head started to go in, I gasped loudly and clenched my ass shut. He smacked my ass hard with one hand in response.
"Open up, boy!" he replied forcefully.
I took a deep breath in and tried to relax, but as he started to enter me, it was taking all I could muster not to cry out. It felt like he was ripping me in two.
When he finally got all the way in, I felt like I was impaled by a tree trunk. I felt his belly on my ass and he leaned down a bit and rocked his cock back and forth a bit to let me try to adjust as much as I could.
"Here it comes, boy," he replied as he started to pull out and then push back in again.
As he started to fuck me, I grabbed the pillow in front of me and bit down hard on it. He reached down and grabbed my waist to hold me still and started to pick up the pace and use me for all I was worth.
I am not going to lie, it was painful. I was doing everything I could to not cry out and tell him to stop. I concentrated on my breathing and tried to think of anything other than the massive dick that was testing my limits.
He started to fuck faster, and the sensation overload kicked into me and the pain lessened. I started to feel his belly slide around on me as he began to sweat a bit and he gripped my waist hard and started to grunt louder and louder. The bed started to move and creek and he pounded away.
"Fuck, boy," he said as he breathed hard. "Are you ready for my load?"
"Fill me up, Sir!" I yelled.
He grunted loudly and shoved his cock deep inside me. I felt every pulse of his cock as it moved within me and he laid down on top of me and I felt his chest move up and down as he caught his breath. He nibbled my neck a bit and then lifted himself off me and slid out.
I felt like my hole was gaping. I felt his cum run down my leg and he smacked my ass a few times as he caught his footing.
"That's a well-fucked ass," he said, reaching down to put his thumb in my hole and feel his load.
He reached down and felt my cage and noticed that cum was running out of my nub as well.
"Looks like I fucked a load out of those full balls too!" he said with a laugh.
I was trying to move and get up and was concentrating on how sore my ass was and had not even noticed. When I got to my feet, I noticed the cum running out of my nub and that it was all over the side of the bed.
"That you did, Sir!" I said with a smile.
He grabbed a towel from my bathroom and wiped his sweat away and then tossed it on the bed. He had me get down on my knees and clean the cum and ass off his cock as well before he got dressed.
"Thanks for that, boy," he replied as he slid his shoes on to go. "Enjoy your trip here."
He waved at me as the door closed behind him and I smiled back. After he was gone, I reached around and felt my ass. Cum was still running down my leg and there was a little red in it as well. I decided to go take another shower and clean up again and then take a quick nap before dinner. I knew for sure I would be walking funny the rest of the night, though.
The dinner that evening went well, as did the presentation the next day. The clients were impressed with our services and cost analysis and I ended up securing the contract with them. I was exhausted after a long day and ended up going to bed early that night. The next day, I packed up and headed back to the airport to drop the car off and catch my flight home.
After I got my luggage checked, I headed back to the security checkpoint. As in Atlanta, I showed them my identification and ticket and then headed back to take my shoes and belt off before screening. This time, they were using a metal detector. As I went through, the device went off.
"Is there anything in your pockets, Sir?" the TSA agent asked me.
"No, Sir," I replied, and he waved me through again.
The device went off again and before I could explain, he had me move over to the side and another man came over.
"Is there anything in your pockets, Sir?" he asked me.
"No," I replied. "Though I am sure I know what is setting it off."
"What is that?" he asked.
"My chastity device," I replied.
"Your what?" he asked with an inquisitive look.
"I'm wearing a metal cage on my genitals," I replied, as my cheeks started to redden from embarrassment.
"Come with me," he replied.
He led me around to a private area and then told me to drop my pants. He patted around my socks and then moved up and let the back of his hand move around my crotch area.
"I'm afraid you will have to pull your waistband back and let me see the device," he said.
I was mortified at this point with my pants around my ankles, but I pulled the waistband to my underwear forward and he took a quick look at my cage.
"Are you wearing that of your own free will?" he asked.
"Yes, Sir," I replied.
He gave me a weird look and then waved his hands.
"You can dress and leave," he said.
I pulled my pants off and went back to the screening area to grab my things and then headed off to my gate. I was sure to text John when I had the chance to let him know how things went.