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Chastity and Service
New York Bound (Part 1)
In October, my boss had approached me to travel again to meet with some clients we had been working with and secure an additional contract with them for the coming year. I had dealt with them remotely for over a month, but the face-to-face meeting would be vital to secure the deal. Initially, the meeting was set to be held in New Jersey, but the clients decided to have me come up to visit their home office in Manhattan.
I had discussed the upcoming travel possibility with John one evening while we were waiting for Bo to arrive for a training session. John had suggested that it would be a good opportunity for me to meet up with his friends Bart and Wes again. I had not seen them since they had visited and stayed with John when I was training to be a sub. They were both hot, and it had been an intense session that left my ass well used and my belly full of piss.
John gave me Wes's contact information and when I reached out, he insisted that I stay with them, especially since the office I would be meeting at was near their apartment. After clearing the arrangement with my boss, plans were set for me to fly out there on a Wednesday afternoon and stay through Saturday.
"Are you excited about your trip?" Bo asked me at dinner the night before I left.
"Yes," I replied. "I have never been to New York before."
"It's a wild place," Todd interjected as he sliced his steak. "There is always something going on, and Bart and Wes live near Columbus Circle, so you will be right next to Central Park, too."
"Yeah," I replied. "Sir Wes gave me the lowdown on their area."
"Well, just be sure you are on your best behavior and you treat them as you would me, boy," Todd said as he pointed his knife at me. "I expect to hear glowing reviews."
"Yes, Sir," I replied with a smile.
"I'm kind of jealous," Bo said. "I would love to go myself."
"Well, I will take lots of pictures and get a souvenir for you," I replied.
"Great!" Bo said.
Todd had given me the key to remove the security screw to my cage in preparation for the flight. He set out a plastic cage with an integrated brass lock to make the TSA security check easier. The following day, Bo blindfolded me, removed my metal cage, and replaced it with the alternate one before he kissed me and left for work. I placed my metal one in my checked luggage to switch back into and then took care of a few last-minute things before heading to the airport.
As usual, the TSA line was long, and when I finally got to the screening area, I put all of my belongings, including my shoes and belt, in the bins to be scanned. I then stepped into the millimeter-wave scanner and held my breath that everything would be ok. As I stepped out the other side, I turned to see the result, and when I saw the big red box over my crotch, I groaned.
"Do you have any jewelry on, Sir?" a tall male agent asked me.
I pursed my lips and lowered my voice to reply.
"I'm wearing a chastity device. It is plastic and I have the key if I need to remove it."
A slight grin formed on the side of his mouth and he leaned closer to me.
"No worries. I keep my boyfriend in one too. But I will need to give you a quick pat-down."
I smiled and nodded, and he had me stand to the side. He ran his hands down one leg and then the other and then put the side of his palm up against my caged balls.
"You are good to go," the man said with a wink.
"Thanks," I replied with a smile and I moved on to grab my things.
The flight to the city was uneventful. I was stuck in a middle row between two young men who barely talked, and I watched a movie on the screen in front of me to pass most of the time. I grabbed my luggage and headed for the pickup area when we landed. Wes had told me that their sub would be waiting for me and when I saw a bearded guy holding a sign that said 'Matt', I walked over to him.
"Are you Drew?" I asked.
Drew smiled and held out his hand.
"That would be me. You must be Matt."
"Yup!" I replied as I shook his hand.
Drew was a pretty handsome sub. His upper arms and chest were firm and built, indicating he worked out, but he still had some fat around his waist which formed a cute belly. His red and black chain around his neck had a similar gold tag to my own and indicated he was the property of Bart and Wes.
"Red collar, eh?" I asked as I reached up and rubbed my yellow and black one.
"Yeah," Drew said with a chuckle. "My sub brother Theo was the yellow sub when I trained. He graduated six months before I did, though, and was replaced by Ryan."
"Oh, I know Ryan well!" I replied. "I've serviced his master, Sir Jack, before. He and Johnny are cute guys."
"Yup!" Drew said. "I miss him. I haven't seen him in ages."
"Well, it is always great to meet another of Sir John's subs," I said.
"Are you all ready to head into town?" Drew asked.
"Yes," I replied.
Drew smiled and led me over to the curb and we got a car to take us into the city. The drive over was enjoyable. I was amazed at all the buildings and how densely packed everything was. Drew was quiet and let me take in the scene, but he did point out a few landmarks as we went. When we pulled up in front of their apartment complex, Drew helped me get my luggage out of the back of the car, and then we went inside.
"This is a nice building," I said as we walked through the spacious lobby and towards the elevators.
"Yes," Drew replied. "And you can't beat the location. From the rooftop pool, you can look down the length of Central Park. I'm fortunate that my masters Bart and Wes are pretty well off and can afford it."
"They are lawyers like Sir John, right?" I asked.
"Yup," Drew replied. "I don't have a job myself. I am responsible for keeping the apartment clean, cooking all the meals, running errands, and of course, tending to their needs."
"They are pretty handsome men," I replied. "I had a wonderful time with them when they visited Sir John when I was training."
Drew laughed.
"They visited when I was training, too, and that is how I first met them. They both thought I was attractive and had me up staying with them very soon after. I was collared at my graduation and moved up here the next month."
Drew walked out first when the elevator doors opened, and I followed him down the hall to their door. When he opened it, I saw the light pouring in from the windows and into the living area. There was a small kitchen to my right and a large bedroom with a bathroom to my left.
"Very nice!" I replied as I walked over and admired the view.
I heard a zipper open, and when I turned, I saw Drew stripping his clothes off at the door.
"Oops!" I replied as I moved over to start undressing too. "I don't know where my mind was at."
Drew smiled as he pulled his pants off and folded them.
"It is ok," Drew replied. "But my masters have the same rules as Sir John. Subs are not allowed clothing indoors and are to be respectful to them at all times."
"No worries," I replied as I pulled off my shirt. "My master Todd is the same way."
Drew adjusted his small metal chastity cage after removing his underwear and turned to put his clothes to the side of the door as I finished undressing. When I dropped my boxers, he smiled when he saw the plastic cage.
"Is that your travel one or your main one?"
"Travel," I replied as I grabbed my crotch. "My metal one is in my checked luggage. Can you help me get it on?"
"Sure," Drew replied.
My regular metal cage was reinstalled ten minutes later, and I felt more at ease. Drew got me a bottled water, and we sat on the sofa and talked for a while.
"Is this your first time in New York?" Drew asked as he pulled up and crossed both legs and turned to face me.
"Yeah," I replied. "It is a little overwhelming."
Drew chuckled.
"I get that, but I enjoy it. I have made many friends around here, and there are lots of things to do when I am not on house duty."
"Do you get much free time?" I asked.
"Yeah," Drew replied. "I am usually up in the gym a few times a week in the morning, and when my masters go out on the weekends, I am given a choice to tag along or do my own thing unless there is a specific need for me to be with them."
"I remember them having pretty high sex drives the last time I met them," I said.
Drew laughed.
"Well, Sir Bart is the hornier of the two, but Sir Wes has his days. Our relationship has evolved over time."
"How so?" I asked.
"When I first was collared and brought up here, I was much more of a servant tending to their needs," Drew said. "I slept in the closet in their room on the floor, and I followed strict rules and procedures. However, over time, things changed. A lot of that had to do with Sir Wes. He pushed to have me more of a third in the relationship. Sir Bart took some time to come around, but I now sleep in the same bed with them, and while I am still their sub, I am given a lot more autonomy and freedom."
"And you said you are still happy with the arrangement?" I asked.
"Oh, very much so," Drew replied with a smile. "I love them both a lot. I am glad I met Sir John all those years ago. He changed my whole life."
"Did you hear he was moving?" I asked.
"Yeah," Drew replied. "Sir Bart was pleased. They are looking forward to hanging out with him again when he moves up here. They used to be roommates in Atlanta back in the nineties, you know."
"Oh, I know," I said. "Sir John gave me some backstory on them. I will be sorry to see him go, myself. He has been a great mentor to me, but I know that there are plenty of subs up here that will be able to take advantage of his program once he gets it up and running again."
"Well, listen," Drew interjected. "My masters do not get home for a while, and I had plans to meet up with a dom in the building that I regularly service. You are welcome to join me or stick around here."
"Who is this dom and what is he like?" I asked, intrigued.
Drew grinned.
"Sir Randy is an older, retired man that lives on the next floor down. He is a hot daddy bear. He has a bald head and a medium-length white beard with thick arms and legs. We often work out together, and he has been helping me tone up my body and build strength. When he has been sweating, he has this musk that makes my nub swell and drip, and his cock is nice. He has a large set of balls, and although it is of average length, the girth on his dick is very impressive."
"And you don't think he would mind me tagging along?" I asked.
Drew laughed.
"I am sure he would love to have two subs servicing him."
"Ok," I replied. "Count me in!"
"Do you want to clean up quickly before heading down there?" Drew asked.
"Yeah, better be safe than sorry," I replied.
"The shower is off our bedroom," Drew said as he stood and pointed into the other room. "We have a shower shot you can use to clean out."
"Perfect!" I replied as I walked past him.
It took about fifteen minutes for me to be sure I was ready and when I dried off, Drew and I dressed and walked down the stairs to the next floor. As we neared Randy's door, we could hear electronic music coming from the other side. Drew knocked twice, and when the door opened, Randy greeted us. He had his shirt off, and I saw the coat of fur that covered his muscled chest and his large, bulging arms. His shorts were tight, and I could see the framed package under them.
"Hey, boy," Randy said to Drew.
Drew smiled.
"Hello, Sir!"
"And who is this hottie?" Randy asked as he reached out and scratched my beard.
"This is Matt," Drew responded. "He is a sub. He is in town for work and is staying with us for a few days. He wanted to tag along with me today."
Randy smiled, looked me up and down, and then felt my crotch.
"Chastity boy, too, huh?"
I grinned.
"Yes, Sir! Trained by the same man as Drew here."
"Excellent," Randy said as he turned to the side. "Come on in and strip off your clothes."
We entered and Randy closed the door behind us. The apartment was identical in layout to Drew's, but there was a portable sling on one side of the room and an oversized chair on the other facing a TV. Two bins of unfolded clothes were on the floor next to the chair. Randy turned down the music while we took our clothes off, folded, and then placed them on a table next to the door. He then sat in the chair and moved the bins to the wall.
"I have been doing some chores today and just got done with my laundry, so I am sweaty, boys."
"You know I don't mind, Sir," Drew replied as he adjusted his cage and walked over.
I watched as Randy put his arm around Drew's waist and then moved down to push his middle finger into the boy's ass. Drew spread his legs and grunted as the man fingered him. Randy lifted his other arm to expose his pit, and the boy shoved his face in and licked it.
"That's a good boy," Randy growled.
I was standing near the door, still admiring the view, and felt a pain in my cage as my nub swelled against the bars. Randy moved his head back and smiled at me. He stretched his legs out and flexed his feet.
"How about you get on the floor and rub my paws, Matt?"
"Sure thing, Sir!" I replied as I moved around and sat in front of him.
His feet were large, and I had to use both hands to rub them. I felt some knots in his foot, and as I worked them out, Randy closed his eyes and grunted. I saw his crotch bulge and move at the same time. Drew was rubbing his face around the man's armpit as he licked, and Randy had his entire finger up the boy's ass as he was wiggling it.
"Fuck!" Drew grunted as a glob of precum fell from his cage. "You are in deep, Sir!"
"Not yet, but I soon will be," Randy replied with a grin.
The man's foot was flexing as I rubbed it, and I felt as he pushed down and hit my cage. I let go and leaned back and let him play with the bars with his toes as he continued to open Drew up. When I heard him slap Drew's ass, the boy lifted himself, and Randy pulled his foot from my lap. He grabbed both sides of the waistband on his shorts and lifted his ass from the chair as he took them off. As they slid down his legs, I saw his large balls emerge, and his cock bounce up above them. Drew had not been lying. The man was beer-can thick.
"How about you get up here and suck me for a moment, Matt," Randy said. "Get me good and wet for this boy's ass."
"Yes, Sir!" I replied as I moved to put my face in his crotch.
I could smell his scent, and, like Drew, my nub began to leak. I opened wide and let the head of his dick enter my mouth. It was on the upper limit of what I had taken before and it took me a while to get it back to my throat. I gagged a few times as I moved up and down on it but made sure to use plenty of spit as I did. Randy grunted and moaned as I worked him over, and when I looked up, I saw him making out with Drew.
When a spurt of precum came out of Randy's cock, I immediately tasted its saltiness. His balls lifted as another pulse came, and I pulled off him, spat on his shaft, and licked around it. Randy chuckled and looked down at me as I lifted my head to meet his gaze.
"I think you are ready, Sir," I replied.
Randy patted his lap and looked at Drew.
"Hop on, boy."