It was three years ago this month when I met Daddy Jerry on a random night at the bar. We acknowledged my submissive tendencies and his dominance. Within a week of that meeting we met at his place where I learned exactly what a devil’s tale whip could do. I couldn’t sit down for a few days afterwards and Daddy Jerry left me with a gaping butt hole after a good fisting.
We’d texted a few times after that and just never found an available time to meet. After that, life just happened and we gave up.
Three years later, I was at the very same bar where I’d met Daddy Jerry and within thirty minutes of my arrival, he walked in with a buddy. I had to look twice, he’d lost some weight in the three years and he looked taller and more confident in his black leather jacket. His beard looked trimmed, his jaw more square. His buddy was a Black man, grey beard, also 6’3”, looked pretty buff himself in a black leather jacket, a chest harness underneath. They both wore black leather Garrison caps.
They walked up to the bar and ordered a couple of beers. For some reason I became very nervous seeing Daddy Jerry there and I felt my body tremble and I began to sweat. I was there all alone sipping a rum & Coke.
I kind of hoped Daddy Jerry wouldn’t notice me as I was sitting at the corner and wasn’t very visible from where he and his buddy were sitting.
It appeared they were engrossed in conversation and then Daddy Jerry got up and walked towards the men’s room. That’s when I was spotted.
“Well I’ll be damned, how’s it goin’, boy? What’s it been now two, three years?”
“Three I think, Daddy. It’s going ok, I guess.”
“It’s great to see you, boy. You here alone tonight?”
“Yes Daddy”
“You still being a good boy?”
“Yes Daddy”
“I was just about to take a leak…if you wanted to drink straight from the tap?”
“Oh, I guess I wasn’t expecting that, Daddy?”
“Oh, but a good boy like you, I’m sure you’d do anything I ask if I remember correctly.”
“Yes Daddy”, I said bashfully.
“So why are you still sitting on that stool? Do you want Daddy to punish you?”
“No Daddy”
“Yeah, I don’t believe that for a minute. I remember how you took that devil’s tail so well. Now follow me, and if you are a good boy, I’ll introduce you to my fiancé. I bet he’d have a good time with you, boy.”
Daddy Jerry tapped his foot impatiently and I pried myself off the stool and he grabbed me by the wrist and pulled me into the toilets.
There were three urinals on the wall. The one furthest was in use, Daddy Jerry pushed me between the available ones and pointed to the gross tile floor.
I knew what he wanted, I kneeled and watched Daddy Jerry fish his big stick from his jeans. It was nearly as thick as a beer can and just as long. I opened my mouth and Daddy placed the head of his cock into my mouth, and then an inch or so more. I wrapped my lips around it and Daddy started to fill my throat with the most acrid, putrid fluid I’d ever tasted. Sensing I was either going to gag or pull off, Daddy Jerry pushed my head down further and held the back of my head firmly.
“It’s either going down your throat or all over you, boy! Take a pick!”
I did my best to swallow as much as I could with some dripping down my chin and the sides of my cheeks, but overall, I was pretty successful. It was a heavy flow that left such a bitter aftertaste I couldn’t wait to drink some water or my cocktail to get rid of it.
“I knew you’d be a good boy. I promised you a reward. Get up., boy.”
I followed him like a puppy out of the toilets and back to the bar. At least he let me pick up my drink along the way.
“Boy, this is my fiancé. You can call him MasterJerrell.”
“Hello Master Jerrell”, I said timidly.
“I met this boy here three years ago and introduced him to my devil’s tail, didn’t I, boy?”
“Yes Daddy.”
“Tell Master Jerrell what you just did for me, boy.”
“I drank your piss, Daddy”
“No, tell Master Jerrell, not me. I know exactly what you did, boy”
“I drank Daddy Jerry’s piss, Master
Jerrell.”
“And did you enjoy it, boy?”, Master Jerrell asked.
“No, I mean yes, Sir.”
“Which one is it? Yes or no? And I’m not your Sir, never call me that, understand, boy?”
“I enjoyed it, Master Jerrell. Yes, understood.”, I wasn’t being honest.
“I don’t think you’re telling me the truth, but I just met you so I’ll let it go, boy.”
“So you came here all alone, boy? Were you hoping I’d show up?”, Daddy Jerry asked.
“No Daddy, I was just out is all.”
“Before you left to come here, did you clean your boyhole out?”, he asked.
“Yes Daddy”
“So you were hoping to find someone to take your ass tonight, boy?”
“Yes Daddy”
“Finally, the boy is being honest”, Master Jerrell said.
“Boy, why don’t you tell Master Jerrell what I did to you when we played together?”
Daddy Jerry was deliberately humiliating me. I was turning crimson I was so embarrassed. My caged cock was yearning to brick. Blunted, my groin ached.
“Daddy, please, no.”
“Oh, come on boy. Don’t be bashful. Master Jerrell loves a good story. Don’t you want to please him, boy?”
“Yes Daddy”
“So take a sip of your drink, and do as I say.”
“Yes Daddy”
“Good boy”
“Daddy Jerry locked me into a stockade. I was blindfolded and my nipples were clamped. Daddy Jerry whipped me so many times and so hard with the devil’s tale, I couldn’t sit for days.”
“You’re leaving out some of the details. I know you didn’t forget them, boy.”
“Daddy Jerry inserted the devil’s tail handle inside my butt hole and fucked me with it. Then Daddy fisted me.”
“Fisted you, that’s great!”, Master Jerrell said excitedly.
“You left out something that I do recall, boy. Remember how I whipped your balls? You were screaming. It was delightful hearing you beg me for mercy!”
“I remember, Daddy. It did hurt a lot.”
“But you took it like a champ. All of it. You made me so proud, boy. Jerrell, this boy can take a good whipping, I have to give him credit. I didn’t go easy on him.”
“I’ve seen you in action, Jerry. I know what you’re capable of. Definitely not for beginners.”
“No, it was a good time. I’m just sorry I never got another chance to play with this boy again.”
“Well, maybe tonight’s the night then, Jerry. The boy doesn’t look like he’s got anything to do, do you, boy? And you did clean out your cunt for some action, didn’t you, boy?”
I took a huge gulp before I answered because I knew whatever I said next was pivotal.
“No Master, I have no plans, and yes, I was looking to find someone to hook up with.”
“Well, now you do have plans, boy. I think you’re coming home with us. Between the two of us, there’s plenty of dick just for you, and even more if you’re a good boy.”, Master Jerrell offered.
“Yes Master, yes Daddy.”
“Do you mind Jerry? I gotta piss from drinking all this beer.”
“Why would I mind? The boy likes being a piss bucket, don’t you, boy?”
I hesitated, because although I have dabbled in piss play, I don’t love it.
“Don’t you boy?”, he asked more firmly.
“Yes Daddy.”
“Yes Daddy what? And don’t tell me, tell Master Jerrell.
“I love being a piss bucket, Master Jerrell.”
“Well that’s good. Then show me, boy.”
I followed Master Jerrell to the toilets again.
“Where did Jerry have you earlier, boy?”
“Over there, Master James”, I said pointing to the spot.
“I can tell, there’s some piss on the floor. Did you miss some?”
“Yes Master Jerrell. It was a lot.”
“Let’s see if you can do better this time, boy. On your knees!”
When Master Jerrell pulled his huge cock from his pants I nearly passed out. It was a good seven inches soft! Thick as a baseball bat!
I had to open my jaw so wide I thought it would dislocate, just to take in the head and two inches!
Master Jerrell wasn’t playing. He pushed me over the urinal, my head horizontal to the urinal cake and he started to drown me. It was absolutely disgusting. His piss tasted like poison it was so bitter and so strong. When I started to spit it out, Master Jerrell desecrated my face covering me in his string scented piss.
“Open your mouth you filthy pig!”, he yelled.
I did as I was told and more urine made its way down my throat, burning my insides along the way. After he’d shaken his cock over my face, Master Jerrell pushed my face into the urinal cake and flushed. I was soaked.
“Come on, boy. Next time you’ll try harder, won’t you?”
“Yes Master”, I said sheepishly. My face and my hair were dripping.
“What happened, Jerrell?”
“The boy spit it out. I had to teach him a lesson, didn’t I?”
“Yes, of course.”, Daddy said.
“I thought you said this boy was obedient, Jerry. Should we even waste our time?”
“I am definitely disappointed, but I am sure he’ll make it up to, won’t you, boy?”, Daddy asked.
“Yes Daddy”, I said through clenched teeth looking like a horror show and probably smelling like one, too. Everyone was looking at me, it was so degrading, but yet I relished the attention.
Master Jerrell put some cash down on the bar.
“The boy better be worth my time, Jerry. Last time we took one of your boys home it didn’t go well.”
“I’m telling you, this one is different. You can really fuck him up, I promise.”
“There’s only one way to find out. Let’s go boy. Let’s see if you’re even worth my time!”
I walked between Master Jerrell and Daddy Jerry. I think Daddy wanted to be sure I didn’t get away.
“Dry your face, boy. I don’t want you dripping all over my seats.”, Master Jerrell said.
I looked confused. What was I to dry my face with?
“Use your shirt, boy! Take off your shirt and dry off your face. Jerry, you didn’t tell me the boy was dumb. You left that part out!”
“Jerrell, I’m telling you man, you’re gonna love whipping this boy. I know it.”
I pulled my shirt over my head and used it to wipe all of the moisture off my face and my hair. It smelled pretty bad.
We drove 15 minutes or so to their place. It wasn’t where we played before.
“Jerrell and I moved here a couple of months ago”, Master Jerry said.
“Wait until you see our dungeon, you’re going to love it.”
I found myself so confused. On one hand I was so excited and in the other I was very scared and nervous, I hadn’t set out for this when I left my apartment. I thought I’d get a vanilla hook up, a pump-n-dump, nothing more.
When we pulled in to the garage and parked, I stepped out of the car.
“Everything off”, Master Jerrell barked. “Only real men wear clothes in this house!”
First I pulled off my shoes and socks, then my jeans. I wore a royal blue Gym jock with a two inch waistband, very classic, it was tight enough to display the ridges and curves of my Cobra cage underneath.
“Jerry, you didn’t tell me the boy was locked. How intriguing!”
“He wasn’t when I met him, Jerrell. Who holds the key, boy, or are you self-locked?”
“No, a fuck buddy of mine has the key, Daddy.”, I whispered due to dry mouth.
“Say what? Speak up boy!”, Master Jerrell yelled.
“A fuck buddy of mine holds the key, Daddy and Master!”
“How long have you been locked up, boy?”
“Thirteen months, Daddy!”
“Holy shit, Jerry. That takes some real discipline and obedience. Maybe this boy will redeem himself after all. Not much of a piss bucket, but has potential. Let’s get inside, I’m feeling like I need to try this boy on for size.” Master Jerrell said miscieviously.
I followed the two men downstairs and was amazed by the space. A large room completely fitted out with a sling, fuck bench, the stockade I’d been in before, a St. Andrew’s cross secured to a wall. It even looked like there were hooks on the ceiling and in the cement floor. There was a large steel cage in one corner and shelves of toys and lubes, hooks filled with whips, paddles, straps…whatever you could think of, they had it in multitudes.
I was really wide eyed looking at all of this and once again my body started to shake. I was cold, too.
Daddy Jerry was next to me and wrapped me in his arms.
“It’s ok boy, we won’t let anything happen to you. We’re just going to have some fun. You want to make us happy don’t you, boy?”
“Yes Daddy”
“I know you do. I know you like to have fun, too. I remember it quite well. How about we get you warmed up, boy. Would you like that?”
“Yes Daddy”
“Good boy.”
I felt a little better after Daddy Jerry reassured me.
“Hey Jerry, quit coddling the boy. It’s time to get things going down here. How about we hang him upside down?”
“Jerrell, there’s plenty of time for that. Let’s do something a little less ambitious first. Bring me the spreader.”
Master Jerrell brought a black iron ankle spreader over and Daddy Jerry secured me to it, at the same time had zip tied the spreader bar to the eye hooks that were secured into the floor. My feet were flush to the ground, my legs spread open fairly wide and unable to move not even a centimeter.
Master Jerrell turned a switch on the wall and a bar was lowered a few inches.
Daddy Jerry took each of my wrists and handcuffed them to one hook that hung over my head. My pits smelled rank from nervousness.
Daddy Jerry put his nose to one of them.
“Jerrell, come over here and take a whiff. This boy smells like fear.”
Master Jerrell and Daddy Jerry were each sniffing into my exposed and stretched pits, and then they started to tickle me. I was trying to stifle my giggles and I hated that I was unable to move very much.
“I think this boy is ready, Jerry. Can I go first?”
“Be my guest. What are you thinking?”
“I’m thinking the flogger. That should warm him up before we go harder.”
“Yes, good idea.”
Daddy Jerry brought a heavy duty mean looking flogger over to Master Jerrell who removed his leather jacket and was now wearing only the harness. He was definitely more cut and defined than I expected, and his chest was covered in thick white curly hairs.
His face had the most sinister look I’d ever seen.
Master Jerrell stood next to me, his hand caressed my chest, my thighs, then my back and my butt.
“Yes, yes…this is perfect. This creamy white boy is going to be colored red by the time I’m done with him, Jerry.”
Then he unexpectedly kissed me full on the lips before taking a few steps back, straight and to my left. He whipped the flogger around with his wrist, I could hear it whirling through the air before it struck me right across the chest.
“Owwww”, I yelped.
That didn’t seem to phase Master Jerrell.
He cut across my abdomen with five successive blows one after the other, the fifth with great emphasis.
That woke me up and I yowled.
“This won’t do, Jerry. Get the ball gag!”
Daddy Jerry secured a ball gag between my jaw and it was tight.
Before starting up again, Master Jerrell fastened clothespins on my balls and then all over my torso, including my nipples. They were biting into my skin as they were metallic, not wooden.
Now satisfied, MasterJerrell went for my upper back and the backs of my thighs before wailing on my ass.
“Put your hips back boy, show me that white ass!”
Master Jerrell went apeshit on it. I couldn’t jump forward, but I sure did try.
“Grab a flogger, Jerry, you get the back and I’ll get his front.”
The two men found a rhythm and took those floggers to me like masters of their craft. There was no reprieve, my hide was stinging fiercely.
At one point I closed my eyes and took deep meditative breaths. The transformation was gradual, the fine line from pain to pleasure, and once I’d crossed over, I felt like I was levitating, each blow brought a level of euphoria I hadn’t experienced in many months.
I wanted more, but I was gagged so I couldn’t exactly ask for it. As much as I could do I stuck my ass out and my chest, too, accepting what I was given so willingly.
I don’t know how much time passed when the beating stopped. Master Jerrell had cracked the clothes pins off of my body long ago, as each one tore off, it felt like an inferno rising in my soul. The remaining clothespins were still gangling from the skin of my scrotum.
They both roamed their hands all over my body.
“You want to do the honors or shall I, Jerry?”
“Be my guest.”
One by one Master Jerrell removed each of this clothes pins from my balls and they ached so beautifully.
When Daddy Jerry removed the cuffs from my wrists, Master Jerrell caught me.
“You did well, boy”, he said.
Daddy Jerry took the ankle spreader off.
“You ok, boy?”, he asked while I shook my legs back to life.
“Mmm hmmm”, I said through the gag.
I was still feeling the rush, the endorphins flying through my veins. It felt like I was on speed.
“Want more boy?”, Master Jerrell asked hopefully.
“Mmm hmm”, I mumbled.
“Excellent! Jerry let’s try the cross. You get him settled and I’ll get the whip.”
Daddy had me face the wall, my already pink bottom and back we’re going to be striped by the time this was over.
Master Jerrell cracked the whip on the cement floor a few times to intimidate me, and it almost worked. I’d somehow put myself into a very calm hypnotic trance. I was ready for it.
And it came. The hard sting right across my upper back. I barely flinched, and it cut into my flesh. I grunted almost like I was getting my ass fucked.
“I told you, Jerrell, the boy can take it. Go harder.”
This time I heard Jerrell grunt, putting his full body into it as it cracked across my ass, two, three, four times in a row. Each one landing right across my globes. The searing burn was fantastic.
I stuck my ass out for Master Jerrell.
“Ohhh you see this, Jerry? This boy is eager for it. You want more do you, boy?”
“Pllleeathe!” I mumbled through the gag.
“Fuck Jerry! Where’d you find this boy?”
This time Master Jerrell went for the backs of my thighs and ankles. I leaned into it, shaking my ass, I wanted more on my ass!
Master Jerrell made my butt sing with absolute venom I could feel myself being reborn, coming alive, every nerve ending in my body was in sensory overload.
More blows, and then I was turned around for some torso and front thigh work. Each stinging blow made me edge closer and closer to orgasm. I felt like I was either going to jizz or cry.
Just when I was there, on the brink of something, it stopped.
But Daddy Jerry saw what was happening, the way my body had reacted, and knew I needed just something more to take me to rapture. He began to beat my balls with a leather strap, harder and harder until my entire body convulsed and cum dribbled right down my cage into my jock. I was shaking and when it was over I went limp and it it wasn’t for the shackles I would have fallen. I’d gone limp and started to sob uncontrollably.
Daddy Jerry dropped the strap and removed the gag, and the shackles and hugged me. My entire body was on fire. I’d taken a hard whipping. Broken skin on my chest and my abs, my thighs, I was sure my butt and back were even worse.
Daddy and Jerrell were great at providing me with physical and emotional aftercare and ensuring I was ok.
Once they were certain I was strong enough to continue on, they asked if I was up for some butt play.
“Yes”, I said rather quickly.
“Good boy”, Daddy Jerry said.
“How about we get you in the sling?”, Master Jerrell offered.
He carried me like a sack of potatoes over his shoulder and the two men made me comfortable in the sling and placed my wrists and ankles in the stirrups. I wasn’t going to admit it, but lying back in that sling did nothing to soothe the wounds on my back, but I was too hyped up to care about that in the moment.
“You want to open him up for me Jerry?”
“Yeah, I’d love to.”
Master Jerrell stood behind me and had me sniff some poppers while Daddy Jerry put his hard beer can cock in my ass. Damn, I’d forgotten how thick that fuck stick was, and I was dilating quickly from the chemicals.
Daddy Jerry went slow at first, but Master Jerrell pushed the sling forward and I was soon plunging down over it, swinging wildly as it plugged and unplugged me, I was very loose in no time.
“My turn”, Master Jerrell insisted.
The two men switched places. Now Daddy was feeding me a steady stream of the brown bottle while that wrist-thick dick was dicking my poor hole. It felt as long as a flag pole and as thick as a tennis ball can. I was losing my shit, my hole was being annihilated.
After taking turns fucking my ass, neither of them came just yet. They had stripped my cum soaked jock off of me before getting me in the sling. I could see more clear fluid continuously dripping down the side of my cage.
“You smoke weed, boy?”
“Yes Daddy”
“You want some before we fist you?”
“Yes Daddy”
Daddy Jerry walked away while Master Jerrell played in my hole with some lubed up fingers.
“I can’t wait to open up this cunt boy!”, he said.
Daddy Jerry returned with a lit joint. Given my hands were tied, he placed the joint between my lips. Between the three of us, we each took three tokes. In just a few minutes, with the added poppers, my hole was loosening up. My head was spinning out and there was a hunger building in my cunt.
Master Jerry put the bottle of x-lube inside my butthole and squeezed, then coated both his hands with it.
“Please”, I begged.
I wanted it. I needed a fist.
Master Jerrell corkscrewed his duckbilled fingers inside me, twisting slowly back and forth, easing my hole open. I somehow managed to push my legs back more, inviting Master to go further. And with a third hit of poppers and a last hit off the joint, the fist was inside me wrist deep.
Daddy held my feet back, exposing my gaping pucker.
“Oh yeah. Look at that. His cunt swallowed your fist, Jerrell.”
Master slowly turned his wrist from side to side, working the perimeter of my chute open, corkscrewing his was into me, opening me wider and little deeper, worming his way through.
I was loving it. Noises escaped me in high octaves and I saw clouds of color and light under my eyelids. It was marvelous.
And when Master began to slowly punch my pussy lips out, i started to piss a little bit.
“Look at him squirting, Jerry!”
“Fuck, he loves it. Let me get in there, too!”
Daddy Jerry lubed up his left hand and pried some fingers along side Master Jerrell’s. They worked as a team, slowly prying my ditch open wider, until Daddy’s thumb tucked inside and I now had taken both men’s fists. Daddy Jerry added more lube and slowly pushed the sling up and back, each time I felt my cunt lips open wider and swell more.
Master Jerrell undid the wrist cuffs so I could popper up on my own. Once I did, I felt my cunt loosen even more as it ravenously took double barrel punches. I had an out of body climax, my entire body shook as more semen seeped down my cage.
Daddy Jerry pulled his hand out and it was replaced by Master Jerrell’s hard cock. Master stroked his cock off inside my wrecked pussy, flooding it was his ball juice.
Daddy Jerry followed. My cunt was made into a sloppy pig trough.
The two men were exhausted, as was I.
It was now almost 2 am. We’d been at it for nearly four hours.
“Boy, you need to go home now?”, Daddy Jerry asked.
“No, but I don’t mind calling a Lyft.”
“No, you will stay with us tonight. I don’t think it’s a good idea for you to be alone. We put you through it tonight, didn’t we Jerrell?”
“Fuck yeah. Boy, I gotta give it to you. I really thought Jerry was full of shit, but you did better than most.”
“How about we all take a quick shower and get some sleep”, Daddy Jerry said like a true daddy.
“Yes Daddy.”
One by one we took showers. I especially made sure to clean out my cunt cave as it truly was a pigsty back there.
Daddy Jerry had me sleep between them on their king bed and he cuddled me.
“Good night, boy.”, he said as he stroked my hair until I fell asleep.
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