The Devil’s Tail

Occasionally, i enjoy the afterburn and emotional ride and release of a sound flogging. Finding a dominant man willing to give me what i need and then some has always been a challenge, but on a recent nights out at a local bar, i met someone that fit the bill. He was a white bear, 58 or 59, thick head of salt & pepper hair with a thick graying beard, hairy leather daddy. He spotted me leaning against the bar and immediately had me pegged as a submissive. 

He strolled up next to me, his large and tall frame had me trembling as he snickered and said, “how’s it going, boy?” and after a long, flirty, conversation, i finally admitted to him that i would welcome the opportunity to submit fully to him, and soon. I showed him some of my past beatings and he was impressed. He and i made plans to meet after work during the week. And now…the story…

I neglected to share in my opening paragraphs that master jerry disclosed his preferred weapon of working boys over is a devil’s tail. He says it is great to serve not only as a whip, but also can be used to fuck a hot hole. I was intrigued and said i was anxious to have him show me. we both agreed then and there to meet during the week to ensure we were just talk and no action.

So i anxiously drive home from work to clean out and prep for this date with master jerry, wearing a new jock i purchased from daily jocks, pink pouch with blue waistband and piping. I thought it looked completely faggy and submissive which was the vibe i wanted to give off. satisfied i was primped and smooth in all the right places, i drove over to his place. 

Master jerry answered the door wearing a pair of leather chaps, and a leather vest, opened in the front showing off his hairy body. He wore a riding cap and in curled up in his hand was that devil’s tail. I noticed his furry ass when he turned around to close the front door. 

Master jerry had me follow him to his basement, in a small room, dimly lit was a fuck bench. There were straps, shackles, and a stockade hanging off it. master jerry asked me if i was ready and i nodded excitedly. As i stripped, he gathered some things, like lube, clamps, a small cat o nine tails, and a leather hood. He instructed me to mount the bench. My stomach flat on its surface, he raised it up a notch or two. then he shackled my ankles to the side, adjusting my position in the back so my ass was at the optimal height for maximum impact. Then he opened placed the hood over my head and locked it. other than nose holes, the room went completely dark, i saw nothing. He placed my head in the stockade and then my wrists and closed and secured it. i was completely immobile. 

Master jerry ran his hands over my back and caressed my ass and said my smooth skin will make a beautiful canvass. He said ever since i showed him my photos all he could think about was painting my body with his own strokes (or something along those lines, i was nervous as he spoke). I felt beads of sweat drip from my pits and then he paused. He pulled on my left tit and clamped it, it felt like alligator clamps with the sharp teeth. I moaned into the hood, and then the other tit was clamped. Although my torso was just about flat on the bench, the biting of the clamps was rough, but the saving grace was that the linking chain didn’t have much room to flail about. 

The anticipation was growing inside me. i tried not to tense as he moved that tail over my body from neck to foot. I knew what was coming, i just didn’t know when.  Then it happened, that first stroke, right across the middle of my back. “ohhh ohhh”, i cried out, not because it hurt so much, more because of the surprise element. I wasn’t ready. I was forcing myself to let my mind rest and let it happen rather than trying to anticipate when and where it would happen. It really is a mindfuck. 

Master jerry was very astute and said, “just relax. Let it happen. This is what you wanted…just let go.” his tone and words put me at ease and i fell into a meditative trance. Master jerry then used that tail on my back several blows in a row. he must have moved behind me now because the stings were hitting vertically, the first was horizontal. “mmmmm nice”, he said as i was riding the after shock endorphin rush. 

After admiring his handy work, the tail struck my across my ass, starting at the tailbone working repeatedly horizontal down to the bottom of my bottom. These blows were non-stop and rapid fire succession. My body jerked and i was paralyzed by my confines. The clamps were biting hard, too. 

I heard him drop the tail and he then reached under me and pulled the clamp chain, stretching my nips downward, really tugging on them. I couldn’t believe this was making my dick hard! Then he reached under me and pulled my balls out of the jockstrap and held them in his hand, using the small whip on them. Again my body tried to pull away but i was kept in place, and the more i struggled, the harder master jerry pulled on my nuts and beat them with the whip. He didn’t go lightly. It was glorious, excruciating pain, which is short-lived if you can make it to the other side and feel the sensations of the after burn and glow and the endorphins. I was truly flying now and master jerry knew it. 

Master picked up that devil’s tail and it danced all over my back, my backside, my thighs and ankles, even my feet. Like a masterful artist, i imagined master jerry behind me like a maestro, using the whip to make a beautiful piece of art, creating visible whip marks and turning my pale skin into shades of pink, red, and even blue/purple. I hadn’t been properly whipped in so long, i left forgotten what a release it can be. my eyes were tearing up but the emotional release is cathartic. It’s like the magic of the whip releases all out my anxiety, my stress, and allows me to release this. 

Once we stopped after a good hour or so, i’d lost track of time really, master jerry said i was such a good boy and rubbed my body down. He said my skin looked fantastic, especially the lines across my ass. he said asked if i enjoyed it and through the hood, my muffled mouth uttered, “oh yes, master, i did!”.

Then he said, just you wait to see what else this tail can do. he told me he was spraying it down to make sure it was clean and then he shoved a couple of lube fingers into my asshole. Next thing i know, the handle of the tail is inside me, it slipped right inside me. master jerry began to push it in further, and then, he paused, and i felt him insert the tail end, pushing inside along the base. I liked the way it felt, he began to slowly fuck me with the tail using the middle as a handle! 

I was moaning deliciously as i liked my hole being worked open with this thing! “you want more?” master jerry asked. “oh fuck yeah, give me more”!  My hole was growing hungrier and i was still running on the adrenaline of that whipping. I was ready for anything.  

Master jerry let go of the tail still inside me at both ends and then he pushed his hard cock in along side of it. oh that was sweet. Feeling the heat of his big dick along side the tail was truly exceptional. Then he began to thrust inside me, the tail and his cock at the same time. My eyes rolled back into my head, my cock was insanely hard, my shaft leaking on the bench, wedged between it and my pelvis.

When master jerry took the cat o nine tails to my ass as he fucked me with that devil’s tail, i couldn’t hold back a second longer. Each stroke of that whip caused my cock to jerk under me and the friction was enough to set my cock firing off and a glob of my cum pooled under me, causing the skin of my pelvis become very sticky, 

My orgasm prompted master jerry to cum as well, flooding my pried open hole with his daddy seed. He pulled out, pulled off my hood, and fed me his dick.  Oh man, that was fucking fantastic!  He asked if i liked toys in my ass and if i wanted more. I said definitely yes. i was glad to know we weren’t finished!

Again, the tail remained implanted on both ends inside my hole and then i felt more lube being pushed inside me, followed by an object of some sort. I’d soon learn it was a large butt plug, and i could feel the lips of my ass forming an “o” stretching over and around the widest part of this huge plug, master jerry punching the base through and my hole swallowed it up whole. With it now fully inserted, master jerry had manipulated the ends of the tail so they were at each side. When he began to fuck me with the tail, and that plug inside me fully, it took my breath away. Of course the tail end side was easy to handle, but the left side, where the tail’s handle was inserted was a challenge. That extra insertion took a minute or two to get used to, my hole spasmed until it crowned open more, and for someone like me who enjoys hole play as much as i do, i was on another planet!

Master jerry pulled the plug and the tail out at the same time. Then he reached over and removed the nipple clamps. The initial pain of the blood making their way back to them was hard to handle after being clamped up for so long. But i didn’t have too time to focus on that. Master jerry punched his lubed up fist right into my gaping hole. I yelped out, “oh yeah, ohhh fuck!” that plug was the perfect way to open my pig hole!

I really wasn’t expecting to be fisted that night, but i was helplessly locked up and my gaping hole must have been asking for it. in fact, master jerry would later share that he saw my hole “winking” at him, and he just couldn’t resist. Equipped with non-collapsible meaty paws, master jerry began to punch inside my rectum, only going wrist deep, i imagined my rosebud being beaten to a pulp and my pussy lips swelling as he punished me, now internally.  This was more than i could ask for. 

As his punches became more intense my cock once again grew hard and i had no chance to fight back the ultimate orgasm that followed sending even more cum into that puddle under me. i was now completely exhausted and spent. My body went limp, and my wrists and ankles were beginning to feel strained.

Master jerry wiped my hole down with a warm cloth and then he released me from the bench. He carried me in his arms to the sofa and told me to lie there as he got us some drinks. What i really enjoyed was the conversation after he let me sit for a few minutes. He wanted to know what i was thinking throughout the experience, he wanted to learn more about the emotional release, what felt good, etc. i also asked him to explain the pleasure he derives from inflicting the whip and fisting a hole. It was interesting for us to get into each others minds like that. 

As we talked, in began to feel the stinging marks all over the back of my body. I was anxious to see them. I picked up my things and we went upstairs to his bedroom where he had a full length mirror. I was able to see exactly what he had done, and i was proud of myself to withstand it long enough to reap this reward. I thanked him and hugged him and even joked that i couldn’t wait to get to the gym tomorrow so i could walk around naked!

I dressed and walked gingerly back to my car and tried to sit without too much weight on my butt! Once i was home, i stripped naked again and of course did a closet inspection of my body. Admiring the marks and bruises, no bleeding, but very visible marks and bruises. I’d been through it! I also noticed the alligator clamp bites around my still hard nipples. I began to place them in my fingers and the heightened sensitivity made my dick grow. 

The more i watched myself tweak my tits the more blood flowed down to my cock. I couldn’t resist and i jerked a load into the bathroom sink! 

It was late now so i slumbered into bed naked, closed my eyes, and passed out. i was emotionally and physically spent.