A Customized Jockstrap

By Derrick Sanders

Published on Apr 28, 2023

Gay

A Customized Jockstrap Part 5

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This story is partially fiction and partially fact. Play safe out there. Needy subs who get off on thinking about an alpha's jockstrap can contact me with their own needs and offers of submission or ideas for how the jockstrap can be used.

Or just let me know you enjoyed the story.

Thanks to US92 for a great chat that I've incorporated into this story. Always hot to chat with a horny and clever guy.

Jockstrap prep part 5

I was still awake as the cum seeped into the jockstrap I was prepping for my submissive bottom boy. I could feel the warm cum slightly ooze as I came off my orgasmic high. Then my phone alerted me that I had a message.

A message from the submissive for whom I was prepping the strap. The eager little bitch told me he could not wait to smell my jockstrap and rub it against his body and against his eager asshole that needed an alpha cock inside it. The pictures he attached were of his hairy hole that needed a good fucking and of his submissive cock in the cockcage I had told him to start using after he paid me to prepare the jockstrap for him. I sent him a quick message letting him know that the images had me aroused and showed his willingness to serve his master.

Thinking of ramming his hot hole while his own submissive dick was caged and restrained had my cock stiffening up again, pushing against the cum in my strap. It would make good lube, but another cum would have to wait. I needed to get to sleep. Tonight was not the night for extended jack off session after session.

I woke up with my morning boner straining the fabric of the jockstrap and the urgent need to piss. Even though it was something of a challenge, I pissed through the jockstrap as my rank morning piss was the most aromatic of the day. I laid the soaked strap on the counter, took a quick shower--while not using any soap on my crotch. I put on the strap, some sweats and a wifebeater and got ready for another day of working from home.

The submissive messaged me and I told him that he needed to leave the cage on and spend some time thinking about how horny he was. I sent him a picture of me in the nasty strap and decided to go about my day. I didn't have time today to constantly message him.

After making good headway on my work tasks, I took a mid-morning break and discovered an email from a submissive near me who I occasionally meet. The middle-aged faggot likes to be tied up, blindfolded, spanked, have his nipples tortured, and whatever else I can come up with before eventually he begs me to fuck him. Usually I do, but occasionally if he's pissed me off I just jack off on him and leave. He was hoping that I would be available for a session later in the day.

The pictures of my online jockstrap purchaser's caged cock had aroused some of my slightly sadistic tendencies. There would be no jacking off in the jock tonight. I was going to breed.

I emailed my local submissive in response to his message and told him that I could meet him at five. He needed to have his full gear ready for me to use. I got out my chaps, leather vest, and boots so that I could lay them on the bed. Then I went back to work--until these subs all start paying me I have to keep working. But the evening's activities, instead of being a distraction, motivated me to get all my tasks done so I could meet my real world submissive later that day.

After several hours of work, it was time for a break. I switched into a pair of nylon shorts and about half way through my walk, I stopped and pretended to be on my phone. I let myself piss like a race horse, drenching my jockstrap and leaving a puddle underneath me. When I returned home, the shorts were dry and I threw my socks and shoes on the cement by the back door. Maybe I'd find a submissive who would want to buy them from me. I went back to work and waited until it was time to get ready to meet my submissive. Then I drank nearly a liter of diet soda. My bladder was going to be full.

I didn't bother to shower--the submissive needed to smell a real man anyway. It didn't take me long to take off the wifebeater and sweats and put on my leather chaps, vest, boots, and hat. My ripe jockstrap was underneath it all. I grabbed my bag of gear, got in the car, and texted my real time submissive that I was on my way and that he should be prepared for me when I got there.

As usual, he had moved his car to the street and his garage door was open for me. I pulled in and as soon as the car motor died, the door started to shut. There were my usual two cans of beer in the fridge which I quickly opened and downed in short order. My cock was chubbing up already. I grabbed my bag of gear, gave a good tug on my stiffening dick, and went in the house.

He was there in his spare bedroom in the basement which he had made up as playroom of sorts although why he had it carpeted (except for a few select spots) was beyond me. He had his blindfold on and was wearing a gray jockstrap--the color I always told him to wear. He was standing facing the wall next to a table that had a bottle of poppers and a few other items on it. When I saw the dildo in his ass, my cock started to leak just a little in my jockstrap. It was so stiff I could have sworn I had taken Viagra.

I told him to turn around and then put my hands on his shoulders and pushed him to the ground. He knew I had to piss and he knew what to do. He pulled my jockstrap off to the side and my cock flopped out, half hard. He took it in his mouth and I took a long nice piss right down his throat. He took every drop without a spill.

"Good boy. You must have been thirsty."

He didn't say a word. He knew not to talk to me unless I actually asked him a question.

I maneuvered him back to where he was facing the wall and I put the cuffs on his wrists which I then attached to the hooks in the wall. The shackles were put on his ankles and then chained to the hooks in the floor for that purpose. He was locked in place, leaning against the wall. I abruptly pulled the dildo from his ass and started spanking his ass with my bare hand.

He yelped as I spanked him and I was left with no other choice but to gag him, which I did. After that I got the paddle and spanked him even harder. His ass was so red and it was clear he was in pain.

But when I looked, his cock was hard.

It was just as hard as mine. Mine was leaking precum in my jockstrap. I could feel the wetness.

I reached around him and put one hand on each nipple. I grabbed each tit and squeezed them as hard as I could. Then I grabbed nipples and pinched. I swear my cock twitched as I worked the nipples with my hands. My own nipples ached to be touched as well.

Hard.

I could heard some sounds through the gag. I reached for the alligator clamps and put one on each nipple. That would be easier than squeezing them manually. I guess my sub howled in pain, but the gag worked pretty well. He did squirm when I put the alligator clamps, but it was easier for me and offered more consistent pain. The chain I had put between them could be pulled when I needed to inflict a little more pain. I found the pair of smaller tit clamps and attached them to my own nipples. I moaned slightly. I would not work mine nearly as hard as his were being worked, but the pressure felt good and only served to increase my arousal.

I really wanted to grab his nuts, but the last time I saw him my nut-grabbing landed him in the emergency room, so I would have to be good about his nuts no matter how tempted I was to squeeze the hell out of them. Instead I found the handful of clothespins and attached them to his ballsack. He squirmed as I attached the first one.

"Don't move faggot."

I worked to attached the first pin on his nutsack again.

He squirmed.

"Don't fucking move. One more move and you will regret it."

As I attached the second pin on his balls, he moved.

"I told you faggot. No moving."

I got the paddle--the one with the small holes in it. As it swooshed through the air, my dick twitched. As it smacked against his already red ass, it oozed out a huge drop of precum. I could feel it and it felt so good to have an oozing cock and a bright red ass in front of me. Nine more smacks to his ass. His bright red ass. The precum was flowing out of my cock. I felt like I was sweating testosterone.

"Five more pins on your fagsack. Don't move bitch. I enjoy the spanking and would love to inflict more pain you."

He didn't move as I put pins on.

I was ready to fuck. My cock was hard and aching to bareback a hot hole.

I took the gag out of his mouth. I loved to hear a bitch moan and make noise when he's got my cock in his fuckhole. Few things arouse me more than to hear those noises a faggot makes when he's getting fucked. There are tops who don't want to hear a word out of their bitch. I want to hear it. I want to hear them as I bury myself balls deep in their hole, which I fully intended to do as soon as I had this bitch ready.

But I had to piss. The beers combined with what I drank before I left home meant that the piss I took in his mouth when I first got there had not emptied me. I had more and I needed to go bad. I climbed large stepstool and got my cock at the level of his mouth.

"Drink bitch. And don't spill a drop on this nice fucking carpet that you thought you had to put in here. Be a shame to get piss on it."

He opened his mouth. I pushed my hard cock inside.

"Get a good seal boy. I really have to to."

And I did. I pissed and I pissed and I pissed. I worked my nipples as my dick drained the beer piss into this human urinal restrained below me. Damn it felt good. Now I was ready to fuck.

I got down and went to his ass. I pulled the dildo out of his hole. I then rammed it back in and heard him groan. He squirmed and squirmed as I started to slowly fuck him with it. He would not talk because I had told him he was not to speak unless spoken to.

"Do you want a real cock bitch in that hole?" I pulled on the chain that was connected to the alligator clamps on his nipples and he screamed in pain.

"Well, do you?"

"Yes Master."

He kept squirming and squirming. He wasn't wiggling his ass like he needed a good fucking. That's when I realized something. He needed to piss. He would not ask me because I had made it clear to him that only I asked questions.

"Do you have to piss, bitch"

"Oh YES MASTER. OH YES MASTER. URGENT NEED."

"Too bad. Shouldn't have drank so much. You mean to delay my fucking of your hole by something so trivial as your need to piss?"

No answer. He squirmed.

"Well bitch?"

"No Sir. I would never delay your fucking me."

I put the tip of my dick at his hole. I put the bottle of poppers under his nose and told him to inhale and hold it. The moment I put the lid on the bottle, I rammed my engorged prick in his hole. This was going to be fun.

I was balls deep in him. He made a deep guttural noise like a sense of relief had come over him. And it had.

The faggot was pissing all over his carpet. He could not control himself. I just kept fucking him, plowing him, readying myself to breed him. His ass felt so good and I was so fucking horny and in need of a cum to get my nut into his hole.

"Feel good to piss bitch?"

"Yes sir."

I kept fucking him. His pissing himself had me so aroused that after five minutes of hard fucking, I shot my load deep in his hole. My dick had not felt so good in ages. There was a little bit of cum on my cock as I pulled out and I wiped it on the jockstrap I was preparing for my online submissive.

I was careful not to step on any of the pissed on carpet.

"Hope that piss was worth it boy. You made a fucking mess faggot."

I left him restrained. He knew I would. He knew why.

I messaged one of my top buds and gave him the address of the restrained bitch. "There's a pussy bottom in need of a fucking. Use my cum for lube. Watch out the piss on the floor. Have him lick it off your boots if necessary."

I drove home with a happy cock in my jockpouch. My preparation of the jockstrap for my online submissive was almost complete.

Feedback from readers is welcome at derrick1968mwm@gmail.com. We're about ready to wrap up this jockstrap preparation series.

Next: Chapter 6


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