Leather Sir

I woke up on Sunday, refreshed, well rested, and hornier than I felt in a long time. I got out of bed and walked to the kitchen for some much needed coffee. I very quickly remembered the plug still in my ass.

I smile and walk into the bathroom instead. Figured I would take it out, clean it, do my morning bathroom activities, and then put it back in.

While I was sipping coffee and listening to the news rant on about one thing or another, my phone dinged.

A message from Sir, "good morning my beautiful boy. I hope you slept well. I will be out of town this week until early Friday morning, I've got some business to tend to in Madison. I will still be checking in with you. Hope you're well, and that my plug and strap find their purposes this week."

I smiled, "good morning Sir, I slept wonderfully! Be safe on your trip, can't have my Sir getting into a wreck or anything. :)"

A quick ding came in, "don't you worry boy, Sir will be just fine. Enjoy your coffee and have a good breakfast."

"Yes Sir."

So I went about my morning, drinking coffee, took a shower, dropped my morning log, and grabbed the lube with the plug.

It didn't take as much to get it in, but it did sting when my hole popped around that large base on the ring. Once in, I grabbed the stretcher and got it around my balls. I started my timer for an hour and I lie there, fantasizing about him, thinking about what he could use me for, then my thoughts turned dark.

What if he's not as patient when it comes to the hood? What if he wants to see my face and I'm not ready? Is he gonna toss me out like trash he's tired of? How far does he go? What does he like that we haven't done yet? I wish he was home so I could go over and ask all these questions, but instead I can't.

A few days go by, normal boring routine, but I look forward to my messages with him that we exchange every evening. He tells me about his trip, I tell him that work stinks. Lots of lol and hahas, but it's nice conversation. All sex all the time can get repetitive and boring after a while.

It's Thursday at lunch before I realize it and work stinks, I'm so horny, and I still have to make it though today and tomorrow.

I disappear at 5:00 swiftly, and message him, "I can't wait for tomorrow Sir. I'll definitely be staying the night."

A short while later, there's the ding, "I'm ready too boy. I'm gotten myself off so many times this week thinking of how I'm going to plow that tight boy hole this weekend. I hope you're ready."

"I too have thought about it Sir, but I haven't gotten off to it. I'm being good and following the rules, though this plug and strap I've got on right now are making it difficult."

"Good boy. Save that load for me. Can we do what I call a trial run this weekend? Give you a taste of what I really like? We've been doing the 'hook-up' protocol in my book and I want to move to the next chapter, but you have to be ready and informed on what I like."

"Sure Sir, we can do that."

His reply was lengthy and detailed.

"Safe words still apply as always, and I will respect your decision to wear your hood as long as you wish to. However, when you come over tomorrow, I want you to bring the following items in a duffle bag with you.

Leather Jacket and Pants, the tightest ones you own.

Two regular t-shirts

One pair of regular jeans.

Two pairs of regular underwear.

Two pairs of socks.

My plug and ball stretcher.

A black button down shirt.

That sexy boy ass ready to get fucked.

As always, bring yourself through the garage, come in the kitchen and bring your bag in the house. I'll see you after work tomorrow boy."

I rummage through my closet hoping to find a duffle bag, which luckily I have a leather one I find tucked away.

I go to sleep after removing the stretcher and sleep well, and had some great dreams too

Friday came, work was the slowest ever, and I decide to leave from there and go straight to his house.

I arrive on the street at 6:15, check for any messages, there are none, and walk up to his house.

His car is actually in the driveway this time and the garage door wide open. I tuck into the side door, and grab the hood off the table and walk back to the walkway by the side of the garage.

I slip it on and walk through the garage. Once in front of the door, I slip out of my clothes and put on the leather shorts with a codpiece that were on the table. Once through the door, I kneel, placed my bag next to me and ring the bell on the counter.

I hear him walking and feel the slow rumble of those thick leather boots. When he appears in front of me, he grabs the bag off the floor and puts his hand under my chin, there's no gloves. He pulls my face upwards, and lifts me gently to my feet.

"There's my sexy boy. Sorry about the garage door, I just got home and forgot to close it. I have something I have to put away, but go into my play room and kneel in front of my chair, and here, take this bag with you."

I grab the bag and walk in front of him, I catch a glimpse that he's wearing his knee high leather lace up boots with the red strings and a tight pair of leather pants.

He smacks my ass, causing me to jump a little as I make my way towards the hallway and into his special room.

He comes in shortly after I kneel, rubs his hand on my leathered head, he put his gloves on. Damn my favorite.

He picks up my bag, and drops in front of me, "open it, take everything out and set it neatly on each of your sides, I want to see how well you followed directions."

I begin to lay everything out, and once I finish, I toss the bag off to the side and lower my head, placing my hands behind my back.

"That's a good boy. Presenting yourself like that makes me want to bend you over this chair and pound your brains out. Fucking hot leather boy. Get up here."

I scoot forward and he leans down to meet my face to his, grabbing my neck, he tightens his grip as he kisses my whole mouth. He's exploring with his tongue while he's got a good grip on me, I'm slowly losing air, but I trust him so I keep my hands behind my back.

He lets go as I start to struggle breathing, "in that closet there boy, there's hangers. Hang everything up nicely, and then come back here when you're finished."

I do as I'm told and when I return, he's got his paddle in his hand, I'm worried. I triple checked the list to make sure I had it all.

I bow my head in disappointment, "I'm sorry Sir."

"For what?"

"I must have forgotten something and you're going to have to punish me Sir."

He reaches his hand down, picks up my chin, "you forgot the butt plug boy."

I smile, "I'm wearing it Sir."

He reaches down, feels up my ass crack, finding the bottom of the plug and pushing on it.

"I guess my boy here is becoming an ass slut, you'll soon beg for me to fill you with my thick cock, plugs simply won't do. How's it felt all week boy?"

"Amazing Sir, I want the real thing though Sir. I'm ready to be your bottom leather boy. Please use me Sir."

"In time boy, remember when I said this was a trial run, well, when boys are owned and in my house, they must be collared. This will not come off unless I take it off. You will be MY boy when I put this on and your body will be mine to use. Do you understand boy?"

"Yes Sir."

He picks me up again by my chin, I can smell his leather, and he kisses me once more.

He wraps the leather collar around my neck, tightens it just right, and puts a little gold lock on it. He holds up the key to me, and then slips it away into his pocket.

"I'm going to pull out my cock now, and you're going to work it with that slut mouth you got. You have ten minutes to make me cum. If you don't, you will receive two swats to the ass for every minute longer it takes for me to cum. "

He unzips his pants, opens the fly and pulls out his dick. It's half hard and his balls flop out under it. He lights a cigar, looks down at me, "timers running boy."

I put my mouth on his whole cock and suck ferociously. It doesn't take long for him to get fully hard and I take as much of him as I can without choking.

He moans in between each puff of his cigar, resting his free hand on top of my head. He picks up both boots and places them on my lower back.

He scoots down in his chair a little and I about gag completely.

"That's it boy. Take that fucking cock, get your Master's load. I'm gonna be feeding you several loads tonight and tomorrow."

I pick up pace and he flashes his phone in my face. Shit, I only have four minutes left.

I'm sucking like my life depends on, I really don't want to be swatted, it's not my cup of tea.

I feel his hips rock and shake, he's close, BEEP BEEP BEEP, fuck, timers up.

I keep going, I know he's pushed start again and I need him to cum.

He uses his hand to push me down and thrust his hips, causing his thick cock to choke me and I feel his warm salty cum flowing down my throat. He grunts loudly, holding my head in place giving me every ounce of his delicious warm seed.

Once done, I suck him a little more to get the last bit out and I can feel him getting hard again.

He pushes my head up off him, "that's plenty for now you greedy little cock slut. I'm famished, lets get dinner."

"Permission to speak Sir."

"Yes boy."

"How much longer did I take Sir?"

"Two and a half minutes. That's five swats with my paddle. You want them now or later?"

"Um, when it pleases you Sir."

"Good answer, now I'll deliver them later. I want your ass nice and red when I shove my cock deep into that slutty hole you're hiding under those shorts. There's dinner to be made, let's get to it."