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."
