Leather Sir Pt. 06

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I arrive at home and walk into my apartment. I realize that I don’t have the butt plug, which sucks, but he’s closer now and I can probably go there tomorrow if I want to.

I fall into my bed, feeling a mix of emotions. I’ve really been enjoying our time together, but am I really ready to up and move with him to Madison, or stay here and lose him?

My job is generic enough, so I jump up from the bed, go to my kitchen island where my laptop sits, grab a drink and start looking up job openings in Madison.

Madison looks quite cold during winter months and would be perfect for leather clothing for most of the year.

I find a few jobs that I could easily apply for and qualify for. I could move across the country with him, start a new life, be anyone I want to be, which includes his leather boy.

I shut the lid and go to my couch. I fall onto my couch and flip on the television. Mindlessly I watch some program that I’m not really paying attention to and I fall asleep.

When I wake up, I have a missed call and a text from Sir.

“Hey Michael, I hope you got home safely. Since you’re a lot closer to me, I hope to see you more often.”

I text back, “yes Jamie, I made it home Sir. I was thinking that too. Maybe I’ll swing over tomorrow.”

“I’d like that. I’ll see you at 6:30.”

I drop my phone and hope the decision finds me easily.


I leave work the next day, head to his house, and when I arrive, I walk into the garage, and there’s nothing on the table for me, and when I get to the door, there’s a note, “Meet me in the back boy.”

I walk back through the door, and find him reading something on his phone. He looks like he’s just lit a cigar and he looks up at me.

He puts his cigar down, stands up, and grabs me with both arms. He plants his hands on my ass and his mouth on mine. He’s kissing me like he hasn’t seen me in three weeks.

Once he pulls from me, he speaks “I hope you’ve had time to think. I don’t want to talk about Madison until you’re ready. I got you a cold beer, take a seat with me.”

I sit down, he resumes his cigar, I sip my beer, and we sit there in silence.

“Tell me about your job boy,” finally something to break the silence.

I explain what I do, and I explain that it can be done almost anywhere. I talk for a few minutes and he just listens, puffing on his cigar.

Once I finish, he looks at my face and starts to rub his crotch. He’s smiling with his cigar in his mouth, “damn boy. You’re just so fucking hot, you get me hard and all I wanna do is fill those fucking holes with my cock.”

I slip out of my chair. I look around and don’t see anyone, so I crawl over to him, I unzip his shorts and pull his cock out. I take it in my mouth, and he begins to moan.

I’m bobbing up and down on him as his hand rests on my head. He’s gently pushing me down farther and farther until I take him entirely in my mouth.

He pushes out his cigar even though it’s only half gone. He then picks up my head and shoves his cock back into his shorts, “I don’t want to cum yet. Let’s go inside.”

We get into the living room, he yanks off my shirt, and he picks up the leather collar on the end table, “do you want this?” He says to me.

“Yes please Sir.”

He slips the collar on, and locks it in place. He grabs the ring and pulls me with him. We walk into the bedroom, he pushes me onto the bed and he straddles me. I see him reaching for the rope and he ties my wrists to the bed post.

He spins around on me and starts to remove my shorts and red briefs that I wore. altyazılı porno I didn’t even think to put on any leather. I lie there naked as the cool air conditioned air blows across my skin. He gets off the bed and reaches down for my nipples, which are both hard.

He pinches and pulls them, “someone’s excited.”

My throbbing cock agrees with him, he reaches down to push his finger against the head where a drip of precum is going to fall. He brings his finger up to my mouth, “open wide boy.”

I do and suck on his finger, “damn that mouth is hot,” he says.

He pulls his finger and begins to undress, he takes off his clothes and throws them in the corner. He then walks into the closet and pulls out some leather clothes. He pulls the pants up over his thick cock, which takes a second for him to pull through the zipper.

“That’s not getting tucked away.” He says.

He then grabs his bulldog harness and slips it on. Once he feels satisfied, he slides his legs into his pair of boots. He walks towards me while he puts on his gloves. He reaches the bed and grabs the end of his cock, pulling on it for a drop of his own precum. He pushes that into my mouth.

He gets on the bed and grabs both ankles and ties them up to the top of the bed, he always has ropes hanging at the points he likes. He slips them around and my legs are anchored above my head. He slides Two fingers in my mouth and I think I know where this is going.

“Get my fingers nice and wet boy, need plenty of that boy lube for your tight hole. You left the plug here so you’re gonna need some opening up.”

He pulls the fingers out and pushes them into my hole, I groan as they pop through the ring. He slowly starts pushing them in further and back out. He then pops them out and positions himself against me. He puts on the condom and adds a bit of actual lube and pushes his cock inside me. He slides in easily.

I moan in pleasure and he grabs my cock. He’s thrusting lightly back and forth, but stroking my cock hard.

“I’m close Sir.”

“Ask for it boy.”

“Can I cum please Sir.”


He stops stroking, holds the base of my cock tightly, and thrusts much harder than before. He continues fucking my hole and holding the base of my cock. I feel my almost orgasm fading.

He starts to stroke me and I start rolling my hips.

“Don’t forget to ask permission boy. If you cum without permission, you’ll earn yourself twenty smacks with my favorite paddle.”

“Can I please cum Sir? I’m close.”

“You may not.”

He grabs the base hard once more. He continues thrusting deep inside me and I can’t contain myself. I’ve got a mix of frustration and pleasure flowing through my body at the same time.

“Oh boy, I’m close to cumming. I’m gonna cum,” he shouts!

He pulls out of me and pulls off the condom. He strokes his cock with his free hand and starts squirting his cum all over my cock and stomach.

“Oh fuck! Aaarrrrggghhh.”

Once he’s done, he strokes my cock again, using his cum as lube. He’s not stroking fast enough to really get me there.

He stops stroking me and releases both of my ankles. He lays them on the bed and ties them to the posts again. I’m spread eagle on the bed.

He walks from the bed, picks up the condom off the floor, throws it away and grabs something. He comes back and he’s holding a ball gag. He leans on the bed, pushing the ball into my mouth and then tightens the straps around the back of my head.

He walks out of the room, “don’t go anywhere boy. I’ll be right back.”

I give him a look türkçe altyazılı porno that says, “oh yeah, because I’m oh so mobile.”

He laughs and leaves the room. When he returns, he’s got his cock shoved back in his pants, his cigar is in his mouth, lit and smoke follows him through the room.

He gets on the bed again, and starts to stroke my cock again. I look at him with panic. How am I supposed to ask permission or tell him I’m close. He looks down at me, and smiles.

“I hope you can control yourself. I will feel your body tense and will stop before you finish. You get to finish when my cigar is done.”

I nod my head and watch his cigar as he puffs on it, hoping it burns faster. He’s stroking my cock, I’m close, I roll my hips again, and he grabs the base.

“No no boy, I’m not done yet.”

He holds the base tightly. I groan in frustration.

He continues this as I watch his cigar burn down and down until I’m sure there’s nothing left. He gets off the bed and smashes it out.

He comes back and picks up my cock again. He’s stroking it as slow as humanly possible and I feel like I’m going to explode.

“Is my boy frustrated? Are you ready to cum boy? I bet you’re pretty desperate.”

I nod my head quickly, and grunt through the gag.

“Don’t take that tone with me boy. Remember, you’re tied down, gagged and your cock is in MY hand. I can just stop now and send you home frustrated.”

I shake my head no.

“Okay boy, that’s better. You have two minutes to cum. For every 30 seconds you take longer than that, you’ll get 5 swats. You need to learn to control your cock.”

I nod my head yes, he starts the timer on his phone. I close my eyes and urge my cock to cum. He strokes me hard and fast. His cum still a little wet, I’m close. I feel it.

“Oh by the way, you can cum boy.”

I rock my hips and start shooting. I feel drops on my chest, on my face, and it’s the most intense orgasm I’ve had. a few seconds after I finish, his phone goes off.

Once I’m done, I’m breathing heavily. He gets up, wipes his hand with a wet towel and leans over me. He cleans up all the spots on my body and face. I’m sure he’d be feeding it to me if I wasn’t gagged.

I’m cleaned up, he drops the rag into a nearby basket. He lies down in the bed next to me. He starts twirling his fingers around my nipples. I’m spent and still breathing heavy.

“So, I’m going to Madison this weekend to see a couple houses and to sign my contract. I want you to go with me and see the city. You don’t have to, again, this part is your free will. If you do decide to go with me, you’ll be going as my boy and will be collared the entire time.”

I look over at him with wide eyes, he knows what I’m thinking.

“No boy, you won’t be wearing this collar, this collar is for private use only, especially when I fuck that boy hole. I have a chain and lock that you’ll wear with my initials on it. You take a few minutes here to think. I’ll leave you be.”

Before he gets to the door, I grunt loudly, he stops and looks back at me, I nod my head yes. He smiles, “that’s a good boy. I’ll be back. Gotta piss.”

With that, he leaves the room and I’m just lying there, naked, spread eagle, and starting to get hard again at the smell of the room and the thoughts of hotel sex in Madison.

————- Lets fast forward, shall we? —————

I’m sitting next to the window with Sir to my right, I’m looking out over Madison’s night lights. Because I couldn’t get Friday off on short notice, we took a late flight in.

I’m playing with my new chain and hd altyazılı porno lock, Sirs reading some news on his tablet. He sets his hand on my knee and asks, “you okay?”

“Yea, I’m okay Sir.”

We touch down, get his rental car and drive off to the hotel. Once in the lobby, I drop our bags, which Sir just looks at me for. He refuses to let an employee carry them up to the room, smiling at me, “we, or rather, he can handle it.”

I pick back up the two bags, and grab the rolling suitcase and scowl at him. He finishes with the desk and we head towards the elevator. While we’re waiting for it, he leans over, “be careful boy, I packed my paddle and that scowl can earn you some swats. I’ll let that go for now.”

“Yes Sir.”

I didn’t know what he had packed, only what he told me to bring, which wasn’t much.

We arrive in the room, he shuts the door after letting me walk in first, and I set our bags down and he’s suddenly behind me ripping off my shirt. He spins me around, grabs my nipples and pulls me into him.

He’s got his leather gloves on, when the hell did this happen? He pulls me into him and I lay my head on his chest. His leather vest smells good. I’m wearing my leather jockstrap under my jeans but that’s it. He’s more comfortable wearing leather in public.

He lets go of my nipples, “strip boy.”

I step back and do so, he pulls down his jeans to reveal his jockstrap, he pulls off the vest and his shirt, revealing his harness underneath.

I’m standing in my jockstrap, looking at his magnificent body, he steps towards me after grabbing the leather collar from the bag. He places it around my neck, and locks it in place.

“Okay boy, in this room this weekend, you will be wearing the thick collar, and the chain collar will not come off, remember, I left that key at the house on my dresser, oops, silly me forgot it.”

He smiles, spins me around and walks me over to the couch. He pushes me against it, and grinds against my bare ass with his leather crotch. He pushes open the curtains and reveals the city line. We’re high enough up so that no one can really see us.

He pops off his pouch, and I hear the foil wrapper, the lube bottle and that familiar noise of him getting ready.

He pushes his cock forward against my hole. Once all the way inside, he pushes against my legs, I put them up on the couch, my top half leaning over the couch and almost face plant into the window. He grabs the back of the collar and begins his thrust. It’s late and we have a busy morning so this won’t take long.

“I wanted your first look at the city to be a good one. A look at the city while I pound your boy hole.”

He thrusts hard into me and as he’s been fucking me almost every night, it doesn’t really hurt anymore. Just feels amazing as he brushes against my prostate over and over again.

“You hungry boy? You want a midnight snack?”

He pulls from me, spins me around, takes off the condom, and strokes his cock right in my face. I look up into his eyes and open my mouth.

“That’s right cum boy, eat my fucking load.”

He shoves his cock in my mouth and starts his orgasm. He’s groaning and thrusting his cum deep in my throat. Once he’s done, I start rubbing my tongue around the head, getting all the cum off him.

“That’s right, fuck, clean my cock boy.”

He pulls from my mouth, picks me up off the couch, and leads me to the bed, I lie down in the bed, he gets in behind me and shuts off the light.

Whispering in my ear before I fall asleep, “I really hope you decide to move here with me. We’re gonna look at a few houses in the morning, and tomorrow night, we’re going to a leather bar. But what I am most ready for is to dive my cock deep in that hole, without a condom, and seed my slutty boy’s cum hole.”

I smile and drift off to sleep.

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