Leather Sir

Our First Meeting

I had a highly sensitive job which kept me from exploring my personal fetishes for years, but I couldn't take it anymore.

I changed careers and found something I could do that was much less public and could be free to explore.

I found myself on a fetish site, had an account, and took pictures of myself, no faces of course, in my favorite leather gear.

I soon had an instant message pop up.

"Hello boy, like your pics and you're only 3 hours from me. Maybe we could get to know one another."

I replied back, "thank you Sir."

So we went back and forth for a couple weeks, we had gotten to know each other well, he had sent me pictures of himself, dressed in leather and not. His face and all. He understood my hesitations, and respected those boundaries.

It was a long pattern that would be difficult to break.

Finally one Friday evening, as I'm sitting in my apartment, jerking my cock to leather porn and ready to cum, I got a message on my app for the site.

"Alright boy, I've seen enough chat. I want you over here to service me. What do you say boy?"

There was a picture attached of him in a full leather cop outfit, sitting on his motorcycle, and in front of him was a chain dangling from the ceiling, and an empty collar attached.

I pondered if I was really ready for this. Could I really trust him not to "out me" or whatever they say? We had been chatting for a while, but he was patient when it came to a response and me opening up to him, slowly.

I replied, "I don't know Sir. I don't know if I'm ready for that yet."

His ding was almost immediate, "tell you what, you drive here in the morning, and when you get to my block, park down the street and walk up to my home. There will be a garage door on the side of the house, you can enter there, and I will leave for you a leather hood you can slip on. Once you're ready, knock on the door in the garage and we'll start with that. What do you think boy?"

I thought, that's not bad. Assuming he doesn't have cameras outside his house, I could still be "unseen".

I replied, "I like that idea Sir. I will be there at 11:00 am Sir. Anything else I should wear?"

"Wear your favorite leather outfit boy. And I'll see you then."

He sent his address shortly after, and I realized that he lived a lot closer than he thought. I used the nearest large city as my home city, and he was only an hour and ten minutes from my apartment.

I could hardly sleep that night, I was excited and terrified at the same time. My first encounter with a man in almost ten years. I jumped off my bed at 7:30, took a shower, ate breakfast and went about some morning tasks at home.

At 9:15, I went back to the bathroom, and cleaned myself out, just in case. There hadn't been a whole lot discussed of what's going to happen, but we had talked limits and fantasies for many weeks.

I jumped in my car, and drove to his neighborhood. I parked my car at the beginning of a public street with public parking.

I was wearing my leather boots to the knee, leather pants, shirt, tie, and vest. I was wearing that under the sweat suit I had on though, boy was it toasty!

Once I walked up to his address, I found the side door and entered. Sure enough, I looked around first, and couldn't see any cameras outside the house and in the garage.

In the garage was a regular car, and there was a small table just to the left of the door, and beyond that was the Motorcycle and the chain.

I slipped the hood over my head, and attempted to tighten the rope in the back, then removed the jogging suit, and took a few deep breaths.

I could leave now and forget about it, hope I wasn't seen, or I could enjoy myself and my life.

I knocked on the door and waited for it to open.

After what felt like three hours, even though it was more like a minute, the door opened, and there he was.

In everything from his picture, tight leather uniform from top to bottom.

"Come in boy. I'm glad you came."

"Thank you Sir. I almost didn't."

"Well, I'm glad you did. Come with me to the living room, take a seat."

We walked through the house, and arrived to a pair of leather couches.

I sat down, and he sat next to me, threw his gloved hand on my thigh.

"Let's get down to business boy, I asked you here to serve me. I enjoy our chats, but it's high time you show your appreciation for my abundance of patience, don't you think?"

"Yes Sir, and thank you Sir."

"Of course. I want my boys to trust me, let me lead them, and they'll find their happiness in me finding ours. After today, should you choose to return, you will be wearing a lot less clothing than you are now, but I wanted to see my boy all dressed up.

I will leave your uniform on that table with the hood for next time, but for now, I need to inspect my new boy. Come with me."

I followed him back out to the garage, where he put his gloved hand on my neck, and led me to the chain. He unclipped the collar and put it on the table and came back with two leather cuffs.

"Rule Number One: I am in charge, you don't get to do anything unless I command it."

"Yes Sir," I replied as he tightens each cuff.

"Rule Number Two: Only speak when asked a question, or for a response, and always remember your manners here. I don't need repetitive Yes Sirs all the time."

He reaches both wrists up as high as I can reach, and attaches the clips to the hanging chain. It's just high enough that I am on my feet, but barely.

"Rule Number Three: You will always be in uniform. And, only I tell you when you get to cum. I trust you'll obey this one, and be honest if you don't, but I don't have time for little metal cages on cocks. I like playing with a boy's hard dick as much as I like him playing with mine. You'll need more willpower to resist playing with yourself.

Rule Number Four: Only make eye contact with me when I command it."

"Rule Number Five: Your safe words are yellow for slow down, and Red for stop immediately. If you use the safe word, all play will stop, we will return to the living room couches and engage in a conversation about why the safe word was used, and how we proceed further."

He spins me around, smacking my ass, then grabbing my crotch and squeezing my junk through my leather.

He's squeezing tightly and I'm in pain, "yellow Sir."

"Good boy, just wanted to test you, I know how you don't like pain and wanted to be sure you'd use the word if need be.

He stands behind me, presses my back to his chest, pushes his crotch forward against my ass. He puts both hands on my thighs, and leans his head close to my ear.

"Do you understand my rules boy? If you say yes, then you agree to stay and be my leather boy, and if you say no, I will let you down, I will leave the garage, you will remove the hood and leave my house."

I pondered for a moment the situation I was in and how rock solid I'd become and how gentle his voice was, yet, in total control. I was mesmerized, and I wanted nothing more than to continue.

"Yes Sir, I understand."

"That's a good boy."

He reaches up, and loosens the ties on the hood, and I start to panic, "Yellow Sir!"

"What's wrong?"

"Please don't remove the hood, I'm not ready yet."

"I'm not removing the hood, I'm adjusting the ties boy. You got them a little tangled when doing this yourself. From now on, I'll tie it, you just put it on. Okay boy?"

"Yes Sir."

He tightens the straps and I can tell it's better adjusted this way.

He begins rubbing his hands all over my body, over my face, around my neck, up and down my torso, down my legs.

"Damn boy. You've gotten me so hard. Won't take long for me to feed you a load."

He walks in front of me and continues his exploration of my back side. He grips both of my cheeks, pulling them apart.

He leans into my ear, "I can't wait to fuck this pretty ass of yours. Would you let your Sir fuck your ass boy?"

As this is a question, I reply, "yes Sir, if it pleases you Sir."

"Ahhhhh, I see you're falling into sub space, good. I like a nice subservient boy."

He then reaches up, lets my wrists go from the chain, and attaches them behind my back. He leads me by the back of neck, back through the house, we turn down the hall, and enter a room. It appears to be a fun room. Your typical bondage and leather items are in the room.

He leads me forward, "kneel boy."

I do so.

He walks in front of me, gently pushes my head down, and walks to his leather chair.

I hear him messing with something, and then I hear a lighter.

"I hope you don't mind my cigar smoke boy. I know we discussed it in previous chats. I like a good cigar and a hot leather boy. Come over here and lick this crotch."

I sort of crawl, on my knees, towards him. Once I'm close enough, I lean my head into his crotch and begin to use my tongue.

He's moaning lightly, and rubbing the back of my head with his free hand.

He reaches down, pushes my head up, and his mouth meets mine. His tongue pushes into my mouth, exploring every inch, in a swirl of smoke around us, he's got one hand under my chin, the other holding his cigar, and his face attached to mine. Pure Heaven.

He releases my head and leans back in his chair, "Keep licking my leather boy."

I do as instructed. This continues on for a while until his cigar is a stub and he smashes it out in the ashtray on the stand.

"Stand up boy."

I do and he unzips my pants in the front, pulls off the codpiece and my cock springs free. It's dripping with precum.

He reaches for it with his gloved hand and starts to stroke me.

"I'm close Sir."

"Good boy, I'm glad you remembered your manners. A boy will cum when I want him to."

He let go of my cock, and grabbed the leather ball strap off the table, and he grabs my balls and pulls them down.

He puts the two inch strap around my balls, pulling them from my body. He gently massages them as I've never had my balls pulled this far.

He leans forward, putting his mouth around my ball sack, sucking them gently, his facial stubble tickling the underside of my cock.

He reaches up and grabs the base of my cock and drops my balls from his mouth, "Alright boy. You're going to cum for me now. Any mess you make, you will clean. Understand boy?"

"Yes Sir, thank you Sir."

"For what boy?"

"For letting me service you, for allowing me to cum Sir."

"That's a good boy."

He put my balls back in his mouth, and began to stroke my cock. He's tugging on it like he wants to pull it off, and I'm close, "can I please cum Sir?"

He drops my balls, "yes boy. Cum for your new Sir."

He strokes me faster and I start to shoot, he catches some of my cum in his hand, but most shoots on his chest.

Once I finish my orgasm, I'm regaining my breath, and he pushes me down to my knees.

"You made a mess boy, time to clean."

He feeds me the cum in his hand first, I lap it up, and suck on each of his leather fingers, he then pulls my head towards him, and I find every spot of cum on his leather. Once it's all clean, he stands me up with him, and leads me by my neck back to the garage.

Once there, he removes the leather cuffs, and pulls me against his body and kisses me deeply. My now soft cock sitting atop my stretched balls, still with the stretcher on them.

He stops kissing me, "I had a good time boy, but our time is up for now. I will go back to the house and you can remove the hood and zip up. I only have one request. Leave the ball stretcher on until you get home, then return it to me the next time you're here."

"Sir, can I ask a question?"

"Yes boy."

"You didn't get off, don't you want me to suck your cocm or service you with my ass?"

He laughs, lightly smacks my face, "in time boy, you will do that, and more. For now, I'll let your imagination run around thinking about this cock. Drive safely boy, message me when you're home."

"Yes Sir."

With that, he leaves the garage, I remove the hood, attach the cod piece, zip myself up, throw back on my sweatsuit and head home.

As I drive home, I wonder what his cock looks like, what it tastes like, what it would feel like driving in and out of my hole. I'm instantly hard when I finally get back to my house, but I have to wait another hour and a half to message him.

I go off to my bedroom and play with my cock and stretched nuts, I can't wait to go to his house again and really give him some service.

To be continued...