Leather Sir Pt. 02

This story continues right from Part 1. You don't really need to read it, but it wouldn't hurt.

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As I'm ferociously tugging at my cock, I suddenly hear his voice in my head, "only I tell you when you get to cum".

I drop my cock, it stands straight up, leaking a small drop of precum, begging to be touched, begging to cum again.

I remember his rules. I remember that he needs to trust me, and I need to trust him.

I look over at the clock, and it's about the time I would get home if I actually lived three hours away.

I opened my app, sent a message that I arrived home safely.

His reply was quick, "Good boy. You made good time. Hope you didn't speed too much. Can't have my sexy leather boy getting into a car wreck."

"Yes Sir, I will be mindful of my speed next time."

"Good boy," he replied, "When can you submit to me again? I've thought about you since you left, and I haven't left my chair, or gotten my cock to go down."

"Well Sir, how about this next Saturday, I could drive over again."

"I like that boy, I sure wish you lived closer so I could see you more often, I need some release."

"Me too Sir. Me too. I'm going to head off to bed Sir. Good night."

"Good night boy."

The next several days went by about as slow as humanly possible. I couldn't wait for Friday to arrive to see him. I still needed to keep my distance before I let him in.

We've messaged with each other all week, some fetish talk, some regular talk. I wanted to touch myself every night, but have resisted the ure. I still need to remember to tell him about when I did touch myself. Honesty, I thought, is the best policy.

Friday night, and I was lying in bed, thinking of the next day. Thinking of the ways he was going to need me. He wasn't using me, at least that's not how I felt it. I was giving my submission, and he was enjoying the service.

I received a message, "Good evening boy, I can't wait to see you tomorrow. Arrive by 11:00 am, wear only a leather jockstrap under your sweat suit, the hood and the rest of your uniform will be waiting for you, and so will I. You might get to please this throbbing cock of mine tomorrow."

"Yes Sir. I will see you at 11:00 am."

I hardly slept again that night, and woke up early. I put on my favorite leather jockstrap with the red codpiece, jumped into the sweat suit, and drove to his house."

I arrived right at 10:45, I parked down the street, walked up to his house, and noticed a different car on the street than had been there last time. I hope they were visiting the neighbors.

I walked into the garage, shed my sweat suit, and placed the hood over my head, but left the strings. I walked to the garage door to the house, and there was a sign. "Enter when ready boy, then kneel on the floor in the kitchen, ring the bell when you're ready to present yourself to your Sir."

I opened the door, and heard multiple male voices, I slightly panicked, ran back through the door, stripped the hood, jumped into my sweatsuit and sprinted to my car. I was not ready for more than one person. I was not prepared to deal with this. Too much, too fast.

I opened my app and saw a message, "Was that you boy that ran out of here? What happened?"

I replied, "I heard another man's voice when I entered the kitchen, and I am not prepared for more than one man. It's too much for me Sir."

"Oh," he replied, "I understand, however, the man you heard was my tailor. He makes custom leather clothing for me and my boy using precise measurements. He's the best guy within 100 miles of here. When you're ready, please come back inside."

"Yes Sir."

I took several deep breaths, tried to calm my nerves. I needed to trust him. I had no reason not to. He has had great patience with me, had great gentleness with me, and it was time I let a wall down.

I got back into the garage, hood on, in just my jockstrap. I opened the kitchen door, and walked in. I got down on my knees, took a breath, and rang the bell.

I soon heard his leather boots thumping the floor as he walked near me. I kept my face aimed at the floor.

He reaches down and grabs my chin, pulling me up to my feet. He wrapped his arms around me, he was wearing chaps, a jock strap, boots, a full body harness, gloves, and his cap.

"I'm glad you came back in. Let's get you completely secure."

"Yes Sir. I...um... think I've used this guy to tailor some of my leather, he might recognize my tattoos on my body."

"Let's cover them then boy."

He grabs my shoulder, spins me around, and proceeds to tighten the strings in the back of the hood.

He then grabs soft black tape and covers each of my tattoos completely. He puts his arm around my waist and leads me into the living room.

"Mr. James, meet my latest boy. He needs some measurements taken for some special clothing that suit my tastes."

There's a short block in the middle of the living room where Mr. James motions for me to stand. I step up on the block, and he begins taking my measurements.

"Sir, may I ask a question?"

He sits on the leather reclining chair in the corner eyeing me, "you may ask it boy."

"What exactly is he measuring me for Sir?"

"Just a few items that I wish my boys to wear when I want them to. Some leather, some not."

"Respectfully Sir, I have my own leather clothes, and not leather clothes, you don't have to spend your money on things for me Sir."

"Okay boy, what do you have that's leather. I figured you had some regular clothes, I just wanted to have easier access here to those clothes if it was needed."

"Sir, I have several pairs of pants, two pairs of chaps, several button down shirts, long and short sleeves, jock straps, and two pairs of gloves."

"See boy, you don't have what I require my boys to wear in my home. Let him finish measuring you, he will make the shorts, and I will provide for my boy. It's my job as your dominant to make sure you have what I want and what I need for you to service me."

"Sir, what if we don't, I don't know, work out" I ask?

"Then we will have an option for you to purchase the clothing from me, or I will return them to Mr. James, he will clean them, and repurpose them or sell them himself. I get a partial refund if it comes to that."

He gets up from his chair, walks over to me, "But I hope we 'work out'. I rather enjoy getting to play with this body, and I can't wait to let you service me later. Let Mr. James finish, boy, and that's a command."

He walks back to his chair and sits down, Mr. James continues my measurements, and scribbles down in his notepad what he needs.

"I'm all set," he says.

"Thank you Mr. James, you can see yourself out if you don't mind. I have some business to attend to."

"No problem."

Mr. James leaves the house and Sir comes to me, puts his leather gloved hand on the nape of my neck, and leads me to the special room. I don't want to call it a dungeon, because it's not a dungeon, so I'm going to call it a special room.

Once in the room, he pushes down to my knees, gently, but commanding in that special touch he has.

"Okay boy. Time for your inspection. First we'll do an oral one, then a physical one. Tell me, how has your behavior been the last week?"

"Good Sir." I replied, shakily.

"Nothing you need to tell me? Remember boy, we need to be honest and trust each other, regardless of outcome."

"Well, Sir, I did play with myself when I got home last week Sir. I didn't cum, but I badly wanted to, but I did play with my cock when I got home."

"Okay boy. Anything else?"

"Oh, and I forgot the ball stretcher at my home on my nightstand Sir."

"Is that all boy?" The tone of disappointment in his voice was strong.

"That's all Sir."

"Well boy, I know you know what this means, tell me."

"I need to be punished for breaking the rules Sir."

"That's correct, and punishments are not meant to be enjoyable, so since pain is something you don't enjoy, a simple spanking will do. Stand boy."

I do, and he leads me to his chair, bends me over so that I'm lying across the arms. He walks to a corner of the room, and I know better than to look right now. I hate being a disappointment.

He comes back and stands in front of me, he holds a thin paddle in front of my eyes. It's made of leather with holes in it.

"This is going to hurt some boy, but not break you. I think five for each infraction this time will suffice, don't you?"

"Yes Sir," I said with a shaky voice.

He walks behind me and I wait for it, the first smack, left cheek, "Ouch Sir."

"Did I give you permission to speak? Did I tell you to count or respond boy? Accept your punishment quietly and think about what you did to have to be punished. I don't want you to forget, I will start again."

He smacks me again and this time it was the right cheek. He alternates cheeks, but they weren't light. They hurt, but not enough to use the safe words because I knew that I had broken the rules, and that this pain would soon be done and gone.

Once he finishes the now twelve smacks, I had made a noise after the second one, he grabs my arm and pulls me up to him. He pushes me in front of him, places both hands on my now sore cheeks, "I hope I don't have to do that again. I only like administering pain when it pleasures my boy, but you need to be reminded of my rules."

"Yes Sir," I whimper.

"Now boy, get down on your knees, and prepare to actually enjoy being in my house. I want you to get down on all fours and clean my boots."

"Yes Sir."

I drop to the floor, he sits down in his chair, and lights his cigar that's waiting for him. I immediately begin licking the left boot, cleaning the leather, inhaling the scent. As I'm getting every millimeter of leather to shine, he reaches down under my chin and pulls me to his face.

"I forgot my scotch, go into the kitchen boy and grab me a glass of it. Two ice cubes and fill it about half full."

"Yes Sir."

I wasn't sure if I'm allowed to get up and walk or crawl to the kitchen, I opt to crawl.

Once I reach the door and grab the handle, he speaks up, "You may get up and walk once you're in the hallway, but return to your knees after you've given my drink to me."

I open the door, and grab his drink.

I return to the room with it, hand it to him, and drop down to his boots again. This leather god in front of me smells amazing, I want nothing more than to find his cock in my mouth.

I began cleaning his right boot this time. Repeating the process now that I have time to get some saliva built up, I could hear his leather glove rubbing against his leather pouch and I begin to push mine out with my stiffening cock.

"Alright boy, that's enough. Time for your physical inspection. Stand up and present yourself."

I do, and step back from him. I spread my legs apart and put my hands up behind my head.

"Actually, boy, I want your hands behind your back, holding your wrists together. I don't care much for armpits."

I adjust my arms, and keep my eyes on the floor.

He gets up from his chair, walks over to something in the distance, comes back to me, and stands behind me. I can feel his breathing on the back of my neck.

He pulls up my arms so they're parallel to each other across my back, he then quickly ties my arms together with rope, then attaching that rope across my biceps. Once the rope is tight he grabs the rope in the middle of my back.

"Try and move boy, I need to see how these ropes are on you. I have to ensure you don't lose feeling in any limbs."

I shift around, nope, not going anywhere. He is slipping fingers between the ropes and my body in various places.

He puts his body up against mine, exploring the front of me with his gloved hands. He reaches up with his right hand and covers my mouth and nose. His left hand reaches down and grabs my junk through my codpiece.

"You feel that boy? I'm in control of your body, and soon, I will be in control of your mind, and I hope someday to be in control of everything about you boy. You serve me well, and so far, are exactly what I need in a boy. Let's not rush it though, I want you to drop down to your knees in front of the chair, and put your torso on the chair while I explore my tight little hole back here."

He releases me, and I step forward towards the chair. I slowly drop down to my knees and lean forward into the chair. My face is on the soft leather, and I can smell his musk. I can smell where he sat. I inhale deeply and the smell is intoxicating.

"That's it boy, take it in, you'll soon be needing that scent so much, you'll never want to leave."

He leans down, and rubs my ass cheeks, "the redness is beginning to fade boy, you should be fine by the time you leave today. Let's see this boy hole."

He spreads both of my cheeks apart and rubs a finger against my hole. It's been many many years since someone has been down there. I haven't even done anything to myself.

"Damn boy, that's a tight fucking hole. When's the last time you were properly fucked?"

"Honestly Sir, I don't even remember. It's been so long."

"Well boy, I'm going to have to stretch you out, I don't think you can take me yet. We'll have to work on this. I'm going to use my fingers, then put a plug in your hole. Every day, after you arrive home from work, you will go into the bathroom and insert this plug, and then attach my ball stretcher for these nuts. I want them to hang low for me. The stretcher must stay on for at least an hour, and the plug should stay in until the following morning when you get up. Understand boy?"

"Yes Sir."

"Good, now, when I put my finger in, you need to push out, don't clench."

He reaches around and shoves his leather finger in my mouth, "Give me some lube boy."

I suckle on his finger, getting it nice and wet with my spit. He pulls the finger back and I feel him push into my hole, "AAAARRGGGHH!"

"I told you not to clench, now you need to push out boy."

I attempt to push, like I'm trying to push his finger out of me and my hole begins to hurt less. He just waits behind me.

"That's better boy, keep doing that."

He begins to work his finger in and out of my hole, loosening me little by little.

He removes his finger, and walks away from me, when he returns, he squirts some liquid on my crack, which slowly drips down to my hole. He pushes his finger back in once it reaches my hole. It's very slick and makes it easier for his finger to go in and out of my hole. I then feel it stretching, I think he's got two fingers in there now.

I moan into his leather chair, "thank you Sir."

"I'll forgive that indiscretion of speaking, boy. Keep quiet, I'll give you permission to moan when I can get my cock in here."

He smacks my ass cheek with his free hand.

I don't dare make a noise, I remember how this works.

"Okay boy, now I'm going to work the plug into you. Pay attention how I do this because you're going to have to do this yourself."

He removes his fingers, then I feel something firm against my hole, then it enters me. This isn't bad, but as the plug gets further and further into me, it's getting tighter and tighter. I reach a point where I feel like I'm going to rip in half, and he pulls the plug back. I guess my writhing around gave him a clue. He pulls the plug back almost all the way out, then pushes it back in me.

It gets further, then that sensation returns and he pulls back again.

"You're almost there boy. Once the base is in, you'll relax around it."

He pushes the plug forward after another application of his liquid substance. The plug slides and slides, and then I feel a quick POP.

"There, all the way in. Very good boy."

He reaches his arms down under my stomach and pulls me upwards to my feet. He spins me around to face him. He plants his lips on mine, and pushes his tongue into my mouth. As he reaches his hands down my back side, he taps the end of the plug. I grunt into his mouth.

I can hear and feel him chuckle. He continues kissing me, tapping the plug repeatedly.

He pulls back just a bit, "Okay boy, are you ready to get those sexy lips around my cock? Sir desperately needs to release a load."

"Yes Sir."

"Remember your manners boy, you must ask permission to put your mouth on my cock. It's a privilege to serve me the way I want."

"Sir, may I please suck your cock? I want to take your load in my mouth Sir."

"Of course you do boy. A good little sub boy always wants a cock in his mouth, always needs a load in his throat. He truly isn't happy without it. Let's go to the bedroom."

He swiftly picks me up and throws me over his shoulder, which isn't an easy task because I'm not a small guy.

We walk through the hallway and into the bedroom, we reach the bed and he gently lays me on it. He then grabs both of my ankles, pulling me down towards the bottom of the bed. I'm in a nice four poster bed with a leather sheet on it.

He grabs some rope from under the bed and attaches the rope to each ankle, and ties it quickly to the corresponding post.

With my arms behind my back, and legs now secure, I am truly tied down. He reaches down and rips the codpiece off my jock and I spring free.

"There's that lovely set of boy cock and balls."

He reaches down, grabs my balls and cock in one hand and tugs gently.

"Are you comfortable boy? Does this feel good?"

"Yes Sir, thank you Sir."

"Good. I bet you're wondering how you're going to service my cock like this. Well, I'm going to sit up on your chest and feed you my cock that way. I love looking down and seeing a boy's mouth stretching around my fat cock."

He lets go of my cock and balls, and walks away. When he returns, I feel something being put around my balls, then a string is attached to the end of the stretcher and he pulls the rope on the left side to my left foot, securing it around my big toe. He does the same on the right, and my balls are pulled just the right amount of distance. Any further, and this would hurt. I guess I better not move my feet.

He reaches down and places a blindfold over my eyes, "You don't need to see anything."

I feel him grab my cock and start stroking me. I arch my back in response, which pulls my balls away from my feet, I grunt, groan, and moan at the same time.

He releases my cock and laughs, "There, now you really can't go anywhere."

I hear him walking around the room but can't tell what he's doing. I soon feel the side of the bed go down and feel his breath on my chest. He soon leans down and grabs my left nipple with his mouth and the right with his gloved hand. I do my best not to moan because I don't have permission.

He gets up and straddles me across my stomach and grabs both of my nipples with his hands and pulls.

"You know boy, these nipples would look much better with rings in them. Would you be opposed to eventually having them pierced?"

"I don't know Sir. Never really thought about it."

"Well, it's a quick pinch, and you have tattoos, so it's not bad. But the choice is yours."

"Yes Sir. I will think about it."

He then releases my nipples and scoots forward up to my chest, almost on my neck.

I feel his pouch against my mouth. I stick my tongue out and attempt to lick it clean.

"That's good boy, now, you should be able to reach an edge with your teeth, so, I want you to pull my pouch off if you want this cock in your mouth."

I reach around with my tongue looking for an edge, I find one, get my teeth around the edge, and pull my head back as hard as I can and the snap comes open. I use my tongue to find the other edge and remove that snap.

"Only eight more to go," I think to myself.

He reaches down and pulls the codpiece off, "You got most of it."