The Leather Tailor

This story is purely fictional. All characters are consenting adults over the age of 18.

I had decided I needed to have someone tailor my chaps and long sleeve shirt so they fit me better.

I found a local place to have it done, so away I went.

He had me put them on of course and went about adjusting the legs and pulling them tighter, asking me questions where you could tell he thought I actually rode, which I did not.

He did the same with the shirt and when he was finished, I went on my merry way.

He called me later that afternoon.

"Hello" I answered.

"Hey, this is Alex down at the shop, I need you to come in in the morning and put this stuff back on for me, some of my measurements smudged and I want to get these right."

"Sure, I can come now if you want."

"No that's okay, I'm about to close up and go home. Tomorrow morning works better, okay? Have a good night".

He hung up the phone before I could answer. Okay, I thought, whatever.

I went in the next morning and he was there and when I walked in, he motioned for me to come in the back.

He had me put my chaps and shirt back on, while he was measuring the materials and marking them he asked, "you don't ride do you?"

"No Sir, I do not."

"Ah, I could tell as much yesterday. If you want these to fit better, you need to put them on as you wear them normally."

"Um, I typically don't wear anything under either of them."

"Alright, strip."

So I did, I wasn't terribly ashamed of my body. Once down to my underwear, I put the chaps and shirt back on.

"That's better," he said, "I can make these all tighter for you."

"Perfect."

He finished his measurements, and shook my hand, "I'll be in touch, they should be done in a few days."

"Thanks!"

So I left.

A few days later, he called to say my stuff was ready, could I come at the end of the day, just before closing. I obliged, it didn't matter much to me when I picked them up.

I arrived and the last customer was walking out the door, some guy buying new boots I guess.

"Hey there, come in the back and I'll get you set up."

He locked the front doors and motioned for me to go in the back, which I did. He pointed towards a leather couch in the corner and I went and sat down.

"I have to go get your stuff, why don't you get out of those clothes so you can try these on when I return?"

"Sure," I said, standing up and removing my clothes.

He took a long time to come back, but when he did, I was kind of surprised.

He was wearing his own leather chaps, a vest, and his cock and balls just dangled from his body. He was holding my chaps and shirt.

"Hope you don't mind me getting comfortable."

"Not at all, it's your store."

He threw my chaps and shirt towards me, sat on the couch, and started to stroke his cock. His balls had a thick leather strap around them, and a thick cock ring around all of him.

"Why don't you take that sexy ass, take off those boxers, and put that on for me?"

"Sure."

I pulled the boxers down, and pulled the chaps up, and put the shirt on. I still had my boots on, but I started to get hard, and more embarrassed.

"Don't be shy, I'm obviously giving you more than some alterations today. Come over here."

I walked towards him, he reached out, feeling the leather, making sure everything fit, and tugged on my balls while he was at it.

"That all fits like I want to, unbutton that shirt, get down here, and get Daddy's nuts in your mouth."

He pulled me down by my balls until he could reach my head, he pushed it down and I didn't resist. I was down for a good time like the next guy.

I sucked on the end of his nut sack, "that's right, suck on Daddy's sack. Fuck, that's good."

I leaned up with both hands and began to work his nipples. Tugging on both of them, while sucking on his nuts.

"Fuck, that's good. I want that ass now. Bend over this couch."

I dropped his nuts from my mouth and could see his cock, a thick 7 inches standing straight up. There was a glisten of precum on the head so I quickly licked it up.

He stood up, as did I, and he pushed me over the couch, pushing my head over the back of it.

He mounted in between my legs, "do you have a condom," I asked?

"Sure," he said as he reached into the pocket on his vest, produced a foil wrapper, and gloved up.

He spit in his cock a few times, spit on my backside and rubbed his head against my hole, "you ready?"

"Yes, please, give it to me."

He shoved his cock into my hole, that searing pain quickly came, but once all the way in, he rested here, waiting for my hole to loosen a little.

He put both hands on my shoulders, pulled his hips back, and began his fucking of my hole.

He was good, thrusting back and forth, in and out, for at least 30 minutes.

"Damn that's a fucking tight hole son."

"Thank you Daddy. I love feeling your thick cock inside me."

"Yeah? Where do you want Daddy's load?"

"In my mouth Daddy, let me swallow your seed."

"You got it," as he kept thrusting.

He kept fucking for another 20 minutes.

With a grunt, he pulled out from me, got off the couch, and pulled my arm to spin me around. I landed on the couch and he mounted me in the front, jerking his cock, he was close.

He started shooting his cum, and the first bit went right in my mouth, but the rest sort of shot out, spilling over my shirt, my chaps, and my cock.

"Oh shit!" He shouted as he came.

I was stroking my cock and started to cum after he started, shooting my load on my own leather too.

Covered in cum, he fell into the couch next to me, breathing heavily he said, "Damn son. That fucking hole is good. If you leave those here, I'll clean them and you can come back in a couple days to pick them up." Winking at me as he finished his statement.

I got up, stripped the leather, putting it gently on the table, trying not to spill the cum, I put on my clothes, and as I waited for him to unlock the back door, he smacked my ass, and said, "Daddy will be waiting next time. I can't wait to really plow that ass."

I smiled and walked to my car. That was fun. I'll bring some more clothes to be cleaned or altered.

..................................

Just a few days later, I received a call that my clothes were clean and to come by on Friday at 6:45 PM, closing time was at 7.

I arrived as instructed and he was there, cleaning up the store, wearing regular clothing. When I walked in, the bell rang, and he looked up, smiled at me and gave a wink.

I walked towards him, he motioned for me to go in the back, which I did. He came back shortly, and handed me a bag of what appeared to be leather clothing.

"Put these on, I'll be right back."

He disappeared into the back and I began to undress. I opened the bag and inside were my chaps, my shirt, but also a pair of leather shorts that had a codpiece on it, and an x harness.

I put on the shorts, the harness, the shirt, the chaps, and slipped on my boots. I found the mirror nearby and admired what I looked like. Alex quickly appeared behind me, wrapped his arm around me, "sexy looking, isn't it?"

"Yes, it certainly is." I replied quite confidently.

He held up a helmet and something else in his other hand, "I have a gift for you. I want you to put this on and we will ride to my cabin that's about ten minutes from here and we can have some fun tonight."

I hesitated, looking into his eyes, unsure if I could trust him or not.

"Look, you have two options. You can take off all this leather, take your chaps and shirt, get the fuck out of my store and never to return, or you can put the helmet on, ride bitch to my cabin and take as many loads from this Daddy dick that I can produce. Your call."

He walked away from me and sat on the couch, he set the helmet down on the couch and I could tell now that what he was holding was a thick leather collar with a tag dangling on it.

"I'm waiting, and I'm quite inpatient."

"Okay, let's go then. What about my car?" I asked.

"Your car will be fine here in the back parking lot of my shop, I'll put a tag in the window giving permission to park here. Now, come over here, get on your fucking knees, and take my collar. Once I put this on, it's not coming off until I decide to. This also means that you're my fucking bitch for the night. I will do whatever I want with you and your body. Understand?"

"Yes Daddy."

He slipped the collar around my neck, tightened it, and I heard something click. He held up a key to my face, and slipped into his jacket pocket, "there, now my bitch is locked in for the night. Put the helmet on and go out back and wait for me by my bike,"

"Yes Daddy."

I walked out the door, found his bike right by the door and stood against the wall. I looked around and quickly slipped on the helmet. He came out a few minutes later, locked the back door and unlocked my car, I guess he grabbed my keys. He locked my car after putting the tag in the front window, came over, mounted his bike and tapped the seat behind him.

"Let's go bitch. I'm fucking horny."

I got on the back of his bike and wrapped my arms around his waist, he fired it up and we headed down the road.