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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 13: My First Session
I woke up Sunday morning to the light streaming in between the curtains. I didn't really want to roll out of bed, but I needed to gather up all my laundry and get that done before lunch. I had to be at John's house by 2 pm, so I had planned my chores out ahead of time. By noon, I was sitting down to have an Asian chicken salad I got from a local restaurant down the street and by 12:30 pm I was in the bathroom getting cleaned up and cleaned out to be prepared for whatever John had in store for me.
I stared at myself in the mirror after my shower. So much has changed in the past couple of weeks. I was collared and caged and on my way to becoming a trained sub boy. I had met two new friends that I had quickly bonded with and I felt like I had more of a purpose in my life. I looked down at my phone at the picture I had taken last weekend before my cage was installed. It was true that I missed jacking off all the time, but now that I thought about it, the past week wasn't too bad. I got to service some pretty hot guys as well.
I returned to my bedroom to grab some jeans and shirt and a fresh pair of socks and put them out next to the door and then I went and sat on the couch and pulled out my laptop to check my email before I left.
While I was sitting there, my phone beeped, and I looked down to see a message from Bo.
"Had a lot of fun last night brother," he said. "Good luck at your session today and enjoy that orgasm!"
He followed that with a big smiling emoji.
He was right. It was the end of my week session in chastity, so while I would be training under John today, I would also be getting my cage off and a nice orgasm. That should really help the ache in my balls these days I thought.
"Thanks bubba," I replied.
I pulled into John's driveway about five minutes early. Better early than late I thought. I walked around to the side door and placed my clothes in my bin and latched it shut and then entered the dungeon area. The lights were off, but there was some light coming in from the bad glass doors which reflected off the mirrored wall, so you could still see. I took my place on my yellow square on the floor and knelt with my head bowed and waited.
About ten minutes later, I heard John coming down the staircase. The door opened and he turned on the lights to the room. I saw his bare feet pass by me and go into the room and heard some things moving about. A few minutes later he returned and stood in front of me.
"Rise boy and face me," he said.
I got on my feet and saw that he was in his black and blue leather jock again with a pair of leather gloves on and a black cap on backwards, but otherwise he was naked. He told me to recite the creed, which I did so and then he reached down and grabbed my cage and moved it from side to side.
"How was your week in chastity boy?" he asked.
"It was ok, Sir," I replied. "I have had a pretty bad case of the blue balls the past few days, but I have been managing."
"That is normal," he said. "You will find this next session likely more challenging. Most of my boys say the two-week session is the one they struggle the most with. I will milk you next week in our one-on-one session; however, so that should help you cope some."
"Thank you, Sir," I replied.
"How many men have you serviced this week?" he asked.
"Three, Sir," I replied. "Sir Greg had me swallow his load at my interview on Tuesday. I sucked a friend off on Wednesday and that same friend fucked and loaded me twice on Saturday morning. Saturday evening Bo and I allowed a dom at a bar to take us home and fuck us and Bo got the load. I got to clean his cock off."
"Very well," John said. "It sounds like you have a healthy sex life. I will ask that from now on whenever you service a man that you send me an email with what happened preferably at the end of the day, but the next morning will do if it is a late night. I want to be aware of what you are doing, what acts you are performing and how well you please the men you are with. Is that understood?"
"Yes, Sir," I replied.
"Do you have a regular doctor and are you on Prep?" he asked.
"Yes, Sir," I replied. "I have a gay doctor that I see, and I am on Prep and get tested every three months."
"That is good to hear," John said. "Who is your doctor?"
"I see Dr. Jim Cole downtown," I said.
"Oh, I know him well," he replied. "Several of my friends and my boys have used him in the past. He is very good. He also knows about my program, so you are not to hide your device when you have visits there. Be open and honest about your chastity and let him know what you have been doing."
"I will, Sir," I said.
"Very well," John said. "Today we are going to work on a few things. The first is flogging. I know you do not like extreme pain, but we are going to work on your tolerance a bit today. Many dominants like flogging their subs and you need to learn to work through some pain. As always, you have your safe word and I want you to use it if the session becomes too intense. However, I want you to really work with me today. Push your limits as far as you can go and communicate with me. Is that understood?"
"Yes, Sir," I said with a little nervousness in my voice.
"Very well," he said. "Follow me over to the cross."
John brought me over to the Saint Andrews Cross, which is basically an X of wood mounted on the wall with rings that you can restrain arms and legs to at the four ends. He attached restraints to my wrists and ankles and then attached them to the cross so that I was stretched on it with my back to him.
He reached over and rubbed my back with his gloved hands before reaching over and grabbing his black leather flogger. He moved one hand down its length completely before swinging it gently and the ends hit the small of my back. The next swing was stronger and made an audible smack when it connected with my upper butt. I jumped a bit as well.
The next eleven strokes were of the same low intensity. Enough to make a smacking sound, but not hard. They were delivered over the course of a minute, but even though it was not too hard, the cumulative effect was causing my lower back and ass to feel some heat and hurt a bit. I was jumping a bit forward by the time he got to the tenth and eleventh hit.
John paused for a moment and let me sit there for about ten seconds before lightly brushing the flogger across the same area again. He then proceeded to deliver eleven strokes over thirty seconds this time concentrating on both cheeks of my ass and the lower portion of my back. I was starting to jump more at this point.
Then came ten lashes at medium intensity over the course of thirty seconds. These started to hurt, and I was groaning a bit and moving around as well. At the completion of the last lash I cried out a bit and he reached down and rubbed my back.
"Boy, I want you to breath in deeply," he said. "Make the pain work for you. Embrace it and concentrate on where you are and the pleasure you are providing for me. You can do this."
John then took the flogger and moved it gently from my ass and up my back letting it lightly run against my skin. He then proceeded to deliver eleven strokes of low intensity to my upper and middle back over the course of a minute. This was followed by a pause and then eleven stroked over thirty seconds and then ten lashes at medium intensity over the next thirty seconds.
The heat was building across my entire back and the pain was coming as well. John picked up a different flogger that had thinner ends and started to deliver lashes to my back spaced by 1-2 seconds. I started to cry out a bit as the flogger hit my back and sent waves of energy though me. It was an intense experience and I tried to focus my mind and watch my breathing.
John then delivered long strong strokes to my back. These hurt. I winced and cried out and struggled against the restraints and debated yelling my safe word. At one particular hit, I twisted and yelled, and he stopped and gently rubbed my back with his gloved hand.
"Breathe for me boy," John said. "How are you doing?"
"I'm ok, Sir," I said as I caught my breath. "It just hurts."
"We will do this for two more minutes," John said. "Focus hard on your breathing. You can do this. I have faith in you."
John then took the larger flogger and delivered ten strokes of medium intensity to my butt and lower back and then the same over my upper back. Then over the next minute, he brought the flogger down with a medium to hard intensity on my ass.
The first stroke made me gutturally yell and I twisted to the side a bit. The pain shot through me and I felt the sting and burning sensation after.
"I can do this," I thought to myself.
But, as the lashes continued, I began to doubt my conviction. I was crying out after each hit and struggling against my restraints. I wanted this to end. I could not take it anymore. Just as I was about to yell my safe word, John stopped.
"And that is it boy," John said, reaching over to rub my back.
John came behind me and embraced me. He put his head behind mine and hugged me for several seconds. He then gently used his gloved hands to rub over my back very lightly. The redness of my skin was apparent and there was a gentle heat flowing as well.
"A good dominant always incorporates aftercare for his sub," John said. "You have taken the flogging well and I am very pleased. How do you feel?"
"It was intense, Sir," I said as a few tears ran down my cheek. "I almost reached my limit."
"But you stuck through it," he said. "That is what is important. Feel the burn and heat in your skin and feed off it. Breathe in and out and focus your mind."
As he spoke to me calmly, I started to feel better. I still felt the heat and tingling in my back and ass, but a new sensation, almost a wave of energy ran over me as he continued to lightly rub his gloved hands over me. It was not something I had experienced before.
John reached up and released my restraints from the cross but left the cuffs on my wrists and ankles.
He had me get up on the leather table face down and my nub was placed in the open slot in the middle so I could lay flat. He told me to put my arms by my side. He put a leather blindfold on me and then put a small soft pillow on my forehead for my head to rest on. He then put headphones on me and told me to relax.
I could hear nothing at first. The headphones were noise cancelling so it was dead quiet. I then heard John's voice coming through from a recording.
"I am a sub," it began. "I am an instrument of pleasure for men. I will open my mind to exploring new experiences that please men. Pain can be pleasure. I can endure it. I can transform it. I can overcome it."
This was repeated over and over. It was gentle and soothing. As I sat there listening, I started to zone out a bit. I have no idea how long I was there, but at some point, I felt my arms being moved and secured to the corners of the top of the table past my head and my legs were spread and secured to the corners as well.
The recording continued. A light sound in the background was playing as well. I could not make out what it was. It was a series of tones that I did not recognize. I zoned out again until I felt the first hit of the flogger again.
John had brought down the larger one against my ass. He delivered low intensity hits to my ass over the course of a minute and the same sequence to my upper back. I winced and jerked a bit.
"I am a sub. I am an instrument of pleasure for men. I will open my mind to exploring new experiences that please men. Pain can be pleasure. I can endure it. I can transform it. I can overcome it."
Ten more strokes came down on my ass over the course of 30 seconds and the same sequence to my upper back. I twisted and cried out, though I could barely hear my own voice.
"I am a sub. I am an instrument of pleasure for men. I will open my mind to exploring new experiences that please men. Pain can be pleasure. I can endure it. I can transform it. I can overcome it."
Three strong hits came on my ass and I cried out and screamed after the last one. The tears were flowing out of my blindfold and down my face and landing on the padding of the table below. It was then that John stopped the flogging.
I felt him gently rub my back. He moved slowly around my ass and up to my head and back again. He blew against my skin and the sensation sent a shiver up my spine.
"I am a sub. I am an instrument of pleasure for men. I will open my mind to exploring new experiences that please men. Pain can be pleasure. I can endure it. I can transform it. I can overcome it."
I took a deep breath in and then out again. I repeated this for about thirty seconds as the recording continued to play. I then felt the headphones come off.
"How do you feel boy?" John asked.
"Sore, Sir," I replied. "But I am ok."
"I am proud of you," he said.
John undid the restraints and told me to flip over. The heat on my back and ass were very present and it stung a bit when my care skin hit the leather table. He reattached my restraints again and then I felt him grab my chastity device and he removed the cage and base ring.
"Stay right there, boy," he said. "I am going to go wash this and give it a good cleaning."
I saw there on the table blindfolded and bound and felt the stinging sensation on my back and ass. I also felt the cool air on my nub. It was free of its confines and I felt myself getting slightly hard. My balls were lifting and shifting a bit as well. It was a pleasant feeling for once after a week of lockdown.
I heard John return to the room. He lifted my balls and checked under and around them for any sores or irritation. He inspected my half hard nub for the same as well. I then heard a clipper turn on and felt him run it over my groin and trim up some of the hair that had grown over the past week. I was not trimmed smooth, just enough so that it would not catch in the cage. When he was done, I felt him rub some lotion over my balls and nub and I enjoyed the sensation.
John then grabbed my nub with his gloved hand and started to move up and down my shaft. While he was doing this, I felt him insert something into my ass. It was not thick, but it felt like it was curved. It came to rest on my prostate, and I felt him rub it back and forth as he moved up and down on my shaft. It got me fully hard immediately and I groaned a bit.
He moved up and down with a steady motion on my fully hard nub and continued to rub my prostate with the device. About a minute into this, I felt my balls lift and an intense orgasm flowed over my body as my nub convulsed and streams of cum came gushing out.
"Oh fuck," I yelled as I writhed and pulled against the restraints.
"Quiet, boy," John said. "You are not to speak during your end of session emissions."
John pulled the device from my ass and pulled his hand off my nub. As I breathed in and out savoring the post orgasmic glow that was quickly leaving my body, I felt him use a cold washcloth to wipe down my nub and surrounding area. The coolness made me jump and my bin quickly shrank. I felt him put the cage back on again and reinstall the locking screw. I was in my cage again for my two-week session.
John removed my cuff restraints and my blindfold and helped me to the edge of the table.
"How are you feeling boy?" he asked.
"I am good, Sir," I said. "That felt great."
"We are not quite done," he replied.
John got me off the table and led me over to the fuck bench. He had me get on it and restrained my arms and legs using its attached straps. I then felt him stick a lubed finger up my ass and he started to open me up before moving to two then three fingers.
I heard the snaps of his jock click as he removed the front portion and released his engorged cock. He placed it on the entrance to my ass and gently started to push forward, its girth filling my insides.
"Remember, boy," he said, "remain quiet. This is for my pleasure."
Once he had reached the point that his balls were at my ass, he pulled back and started to fuck me slowly and then faster and faster. He built up a rhythm quickly and I grabbed on to the bench and gritted my teeth as his fat cock pummeled my ass.
He reached up and grabbed my side and arched his back so he could get the full length in me. I could not struggle if I wanted to. I was tied down firmly enough that my ass was going to take whatever he wanted to give it. The flogging earlier had left my skin red and warm and the smacking of his groin and occasional slaps from his hands brought the stinging sensation out again. I was doing my best not to groan or cry out, but it was taking every ounce of my concentration.
This was not going to be a short ride. John sped up and slowed down. He would pull out and then slam his fat cock deep into me causing me to involuntarily grunt. He would jackhammer me and let his balls slap against my ass at each thrust. My head was spinning.
Finally, I felt him grab my wait firmly and pound hard a few times and then stop. His cock was pulsing and filling me deeply with his seed. I felt his balls move a few times and he slowly pulled back and cum started falling in drips from my well-bred ass.
John came to the front of the bench and presented his cock to me to clean completely of the remaining cum from it and then he undid the straps and let me stand up, catching me a bit when I lost my balance at first.
"You did well, boy," he said. "Clean the dungeon and you may go. I will see you again tomorrow for cleaning day."
John then turned and went across the room and went back up the staircase closing the door behind him.
I went and got the cleaning supplies from the isolation room closet and wiped down the leather table, the fuck bench and the cross. I wiped up the remaining cum and lube from the floor and did a quick wet mop of the areas as well. Once I had gone to the bathroom to wipe my ass clean, I returned to the hallway to get dressed and headed home.