“Executive Retreat, Part 2: Dickie-boy On the Job” – by Steve McHalperin (FINAL)

Chapter 39


Terry explained everything later in the hospital.  Sir had indeed had a stroke.  He was probably so hyped up from my torture that His blood pressure skyrocketed and something ruptured in his brain.  Terry actually saved my life.  The program was set to increase the voltage continuously.  I don’t know how high it would have gone if Terry had not intervened.  He said he was watching the torture on the house’s video system, something he was strictly forbidden to do, but luckily his curiosity made him do it.  He saw me thrashing and screaming, but had to stop watching to take a pee.  When he returned he noticed that Sir had slumped back in the chair.  Normally the video cams are placed to focus on the vic being tortured.  These were, too, except that one showed Sir on the side of one of the screens. 

Terry rushed down to the dungeon and turned the computer off, which shut down all the electricity.  He felt Sir’s pulse and realized he was dead.  Then he saw that I had passed out.  He was frozen with indecision, but finally realized he had to call 911 for me and the police for Sir’s cadaver. 

I was rushed to the hospital ER by two first responders who were astounded when they saw Sir’s dungeon and what had been done to me.  The police had to arrest Terry until they could sort out the incredible story he told them about slavery, torture, abuse . . . you name it.

Immediate attention focused on me in the ER.  Someone knew how devastating electro-torture could be even though it left almost no visible signs, unlike a whipping or caning.  My balls were all swollen up and my dick was red/pulple.  My nips and navel were also swollen, but that was it, no other signs of my torment.  I found out later they gave me a shitload of pain killers, which kept me spark out for a day.  When I did finally wake up, a policeman was in the room, eager to ask me what had happened.  I told him the whole freakin’ mess, from executive retreat to private torture from Mr. DieQual.  They told me he was indeed dead and quite beyond the law – at least him personally, but not his large estate.

My recovery was interesting.  They had to strap me to the hospital bed so I couldn’t touch my privates while they healed.  I was given a drug which would prevent erections, again in order to let the tissues heal.  The night staff had a lot of fun giving me enemas.  They had a vacuum-type machine which could pump liquids into your ass and then suck them out after they kept them in an hour or so, just to torment me.  Ever have hot suds up your ass?  Your gut insists it wants to crap, but the plug prevents it.  You want to scream from the pressure and the pain, but they often stuck a towel in my mouth to stifle the noise.  I did enjoy the beer enemas, which they treated me to every now and then, quite against hospital policy.  What a goofy way to get buzzed!  They also checked out my sex plumbing after the initial drug had cleared.  They treated me to copious cums even strapped to the bed – or maybe it was better because I was strapped down.  My cock was in good working order, no lasting harm from the electro, but they kept rechecking anyway.  The bastards played with my nips, too.   

Other cops came by periodically to double check my story.  Terry came to visit me twice after he was cleared of any involvement in my tortures.  He told me he stole all of Sir’s videos, his complete archive.  He thought we could sell them for a lot of money.  He quit the company so he could get away from all the other executives who had remote zappers.  I quit, too, of course.  Other than DieQual, we didn’t name any names so the pervy execs probably continued their “retreats’ and on-the-job tortures. 

Terry removed his zapper but kept the CD on.  It was a German model like mine and he said he didn’t want to take it off.  He had my CD and key back at the house and had removed the zapper also.  We had long talks about what we were going to do. 

After a week, I was feeling much better and the physicians were satisfied with my progress.  I was released in Terry’s care and we both went back to Sir’s house.  Terry informed me Sir had actually changed his will and had named each of us as heirs to the house, although Terry was at two thirds and I got one third.  I thought the split was fair enough, but the fact that Sir had done it amazed me.  Terry said that Sir, in his own crazy way, did love us both.  I could tell from his voice that Terry felt that way about his former Master.  Yeah, I know it does sound crazy but I was beginning to feel that way, too. 

So we split the money from selling the house, after we had all the dungeon stuff removed and donated to Larry’s, the leather bar in downtown Houston.  I did note that Terry kept the electro-torture system for himself.  He also got the big Mercedes.  He wanted to move to LA.  I wanted to stay in Texas, and I thought I’d move to Austin after I bought me a new F-150.  We set up our torture video sales business on the web and quickly make a fuckin’ fortune on the sales.  Must be a lot of Tops out there  just craving for the real action shown on the videos.  We didn’t even pixelate out our faces.  Maybe someone might recognize us.  Didn’t matter.

Terry found a new Master out West, pretty much as nasty/loving as Sir was.  I got a job at the Motorola chip factory in Austin and cruise leather/cowboy bars, looking for my own new Master.  I look good: shirtless, tight shorts, boots, and a chain locked around my neck for advertising.  And, yes, I still wear the German cock cage, although I do remove it once a week to shave my crotch and maybe sneak in a JO.  I tell you, once a slave, always a slave.  God, I love this stuff!  Bring it on, Sir!  I can take it!  You can’t break me, Sir!

Well, maybe you can, Sir.  Let’s find out.   

The End.   


“Executive Retreat, Part 2: Dickie-boy On the Job” – by Steve McHalperin

Chapter 38

Over the Top

I completely lost track of time.  My whole universe was an ocean of intense pain, screaming my guts out, struggling against leather straps, pissing myself, and drooling like a baby from the gag in my mouth.  There were brief moments of rest when the electricity was either turned off or applied as a tingle.  I knew the rests were limited and hopelessness washed over me as I waited full of dread for the next cycle of torture.  Sir continued to sit His wine and leer at me.  I was coated in sweat by now, rivulets running down my face from my hair, mixing with drool from my mouth as it dripped onto my chest.  My legs dripped sweat onto the floor. 

During one of the brief rests Sir said to me:  “You are making fabulous video!  OMG, we’re going to make thousands off this scene alone!  Thank you, dickie-boy, for screaming so loudly!  Ha!”  Then the program kicked in again and I was stunned by the force of the assault. 

Elector-torture is unique.  It’s scary, for one thing, because it’s your cock and balls under attack.  But the higher levels, I mean, not the tingle, are so strong and hit you so hard it’s like a tank is crushing you.  You can’t imagine the shear force smashing into your body.  When set on a constant zap, it’s so different from a whipping or a caning.  There is no drop from the peak of pain; you are held there for as long as the program is set.  Could be ten seconds, could be a whole minute or more.  You just don’t know when it will drop.  When the program is delivering pulses, you twitch and jump in the bondage like a drunken puppet.  You can’t help yourself.  All your muscles simply flex as tightly as they can and then cramp, adding to the torment. 

I did think the program was getting more vicious as the time went on.  The peaks were higher, the pain was even more intense, and you screamed even louder than before.  Then it stopped.

I looked over at Sir and was astonished to see His big body slumped back against the chair, his head way back, motionless.  The wine glass had slipped to the floor and shattered.  Did He pass out?  Who in the fuck would be monitoring me now?!  How bad would the electro get?! 

It was terrifying to realize that my torture was now totally on auto-pilot, controlled by a mindless computer program that would keep increasing the shock levels, slowly but unstoppably, to higher and higher levels.  How much abuse could my body take?!

I guess it was another hour, who knows?  The electricity shocks did get stronger and I thought I was going to die right there in that electric chair.  My mind was getting fuzzy, my attention dissolving.  I was drifting out of this world, still screaming my freakin’ guts out.  Then I did pass out. 

Blackness.  Silence.  No pain.

NEXT: Ch 39: Recovery


“Executive Retreat, Part 2: Dickie-boy On the Job” – by Steve McHalperin

Chapter 37

Real Electro-CBT

Sir stood in front of me and leered:  “This is our electric chair, boy, one of the most powerful tools I have  to train you.  Terry-boy here can attest to its power.  He spent many hours strapped in like you while I slowly changed his mind about serving me.  He broke in the end; they all do.  Soon you will be a willing slave just like he is.”

“So, let me enlighten you on this control box,” He said booting up the laptop.  The computer has a sophisticated program and will control all the relays in the interface.  There is a wide variety of pain programs in the computer, enough to keep you engaged for many hours.  The programs control the particular electrodes to be activated, the voltage, amperage, even the wave shape.  It can do agonizing pulses that will force your body to twitch, slowly rising steady shocks to a predetermined peak, and there’s even one that is voice actuated so the more you scream, the stronger the shocks will be.  Isn’t that just so clever?  I will hook up the cables to sensitive parts of your body and then we will show you what real pain is all about.  The control is simple:  I pick the program, step back, press ‘enter,’ and just watch you suffer.  The laptop screen will show which electrodes are active and what the shape and level of the shock is.  I will sip red wine and listen to your screams.  I might adjust the program depending on how loud you yell.  Ha!  Isn’t that an excellent way to train young men!”

I didn’t answer.  It didn’t matter.  My fate was set.  I was going to get electro-CBT, maybe the worst torture this side of castration.  Maybe my balls would get fried and it would be castration. 

Sir began to attach the cables to my body.  The first set went on my hurtin’ nipples.  There were alligator clips at the ends which he clamped on after rubbing some gel on my pecs.  The metal teeth of the jaws dug into my tenderized flesh and I grunted from the pain.  Then a large clip went on my navel.  He inserted a three-inch metal rod into my cock, pushing it all the way in.  Only the cable stuck out.  A black loop was put round the base of my cockhead and tightened up.  A cable was plugged into a connector under the chair’s seat.  I guess this connected up with the dildo electrode currently filling my lower gut.

“And now a surprise for your balls!” Sir announced with lustful glee.  He picked up a metal cylinder maybe four inches long by three inches wide.  The bottom had a cable attached to it.  The top was attached to the cylinder by two snaps.  Sir unsnapped the top and pushed my ball sack into the cylinder.  Then he reseated the cap and snapped it shut.  There was a slot in the side of the cap for my stretched out sack skin to go through. 

“This little gem is another product of our marvelous engineering department.  In the bottom is a small but powerful motor connected to a metal piston.  When activated, the piston is driven up the cylinder, trapping your balls against the top which I just snapped on.  The computer controls the crush strength and when it is applied.  It can also send electricity to the cylinder.  It will hurt a lot!” He leered. 

“Sir, Sir,” I started to plead.  “Sir, please don’t do this, Sir!  I’ll be a good slave, I promise, Sir!”

“Oh, I know you will,” Sir answered.  “This will guarantee it.  Terry-boy, get me the black rubber ball gag.”

“Sir, yes, Sir,” Terry replied getting the gag from the equipment wall.  Sir forced the large ball into my mouth and buckled off the strap at the side of my head.  Now all my pleading would be garbled.  Only my screams would be heard.  My stomach was now frozen ice with fear.  I knew the pain from the remote zapper, but all the new stuff He had attached to me, I couldn’t imagine the pain.  I only knew it would be agony and I was strapped in so tight I couldn’t move an inch.  Then again, you don’t need to move much in torture, only your lower jaw as you scream.  A ball gag still lets you scream. 

“Go upstairs, terry-boy,” Sir commanded.  “Work on that new project while I start dickie-boy’s training.”

“Sir, yes, Sir,” Terry replied as he turned to go up from the dungeon.  He gave me a sad look as he went up the stairs, his thick thigh muscles flexing at each step. 

Sir busied Himself with the computer, tapping in various commands.  ‘Everything we did before this was a test, boy,” He said.  “I needed to see how you reacted to pain and sexual abuse.  You passed all the tests, and I was eager to begin your real training.  You show great promise, let Me tell you, but I need a total commitment and that can only come from breaking your willfulness.  I don’t want to break your manly spirit.  You can see that my terry-boy still has a good personality, but I need to change your thinking.  Your every thought must be about Me.  Your every action directed by what I want.  Soon you will want only what I want.  That’s the purpose of the training.  You’ll certainly survive, but you’ll come out the other end a total slave to Me.  And that will make Me very happy!”

“But enough philosophy.  Let’s get down to the task at hand!”  He made a final entry on the keyboard and pressed ‘enter.”  The program He had selected immediately went to work.

All the electrodes were producing a tingling sensation, not unpleasant by any stretch.  The piston on my nut crept up until it was snug against them, pressing them against the metal top of the cylinder  There was a tingling there, too.  That didn’t last long.  There was an abrupt jump in the shock going to my nipples and I groaned from the sudden escalation in pain.  Then my navel, then my cock.  This hurt! 

Then the program backed off to the tingle level.  Just as I started to enjoy it, the electricity went back to genuine pain.  My cock reacted according to its wiring and started to get hard.  At last, I thought, my dick can get a hardon!  No cock cage!  Yeah!  The pain was real, but so was the pleasure from my boner. 

I was surprised when the voltage profile shocking my dick started to come in waves, rather pleasant waves.  Oh man, I was temporarily lost in the pleasure of my dick, and even felt like I could actually have a cum if this continued.  It did!  Although the other electrodes alternated between tingle and pain, the juice to my dick was absolutely wonderful.  I could feel myself cruising along the sex interstate.  I was doing eighty miles an hour and seconds away from a fantastic climax, having been denied a boner and a cum for so many days.  Then it happened.

The voltage shot up through all the cables and the ball piston brutally closed down on my nuts.  I screamed like a wildman.  I have never felt pain like this!  My whole body spazzed, every muscle flexed and pulling hard against the straps.  Lost in the overwhelming pain was the frustration of being denied a delicious cum at the very last minute.  I could hear myself:  “A-a-gh!  A-a-h!  A-a-a-a-a-g-g-h!” filled the dungeon. 

Then everything just stopped.  No electricity anywhere.  The piston backed off a few millimeters, removing the crushing force on my poor nuts.  Everything was quiet, except for my residual groans and heavy breathing.  I finally opened my eyes, stinging with sweat, and there was Sir, sitting on a folding chair directly in front of me, sipping wine and smiling lustily. 

He nodded a few times.  “That’s what real training feels like, boy.  And you’re going to get even more over the next few hours.”

Hours?!  I froze at the thought.  How could I take this for hours?  I’d go nuts!  But that’s what He said.  I knew my rest wouldn’t last long when I felt the tingle return to all the key spots on my body.      

NEXT: Ch 38, Over the Top


“Executive Retreat, Part 2: Dickie-boy On the Job” – by Steve McHalperin

Chapter  36

Testing One, Two

I hung in the frame for several hours.  I was in a daze of sexual confusion and nipple pain.  The confusion was the melding of two opposite forces:  very nice waves of sexual arousal from the vibrator and spikes of intense cock pain from the metal screw points.  And this was against an odd confusion from my chest:  the vacuum hurt like hell, but the pressure on my nips was also sort of sexy, like there was a set of nerves from my nips to my cock.  At the time I didn’t fully understand it, but later on in my servitude to Sir I realized it was the melding of pleasure and pain into pleasure/pain, the hallmark craving of a true slave.  And only Sir could meet that craving with His whip, disciplines, tortures, and sexual abuse. 

Well, Sir did finally return to the dungeon.  He was carrying the dreaded remote zapper and I realized it was time.  He had promised to attach it and here it was. 

He grinned as he wordlessly attached the remote receiver to the underside of my new cock cage.  It easily screwed on.  Then He shoved the large metal ball into my asshole.  I grunted at the invasion.  The ball was attached to a metal arm which slid into the receiver box.  Sir pulled in on the arm, stretching my asshole muscle and then secured the arm to the box in that position.  There was a constant tug on the ball up my ass due to the shortness of the arm.  Of course, that was the least terrifying aspect of the device.  I was dreading a test run.  Sir confirmed my dread.

“Let’s make sure the device is attached correctly, shall we?” He asked, pulling the remote controller out of his chaps pocket.  You’re nice and sweaty now and your muscles are all pumped and shiny, so the video of the test should be excellent.”  He held up the remote and make a show out of pressing the activation button. 

I screamed as the electric current shot through my cock cage and ass.  Even on the lowest setting, the damned thing was agony!  I pulled wildly against the chains holding me spread eagled and just screamed my freakin’ head off until he released the button.  This left me panting heavily for air and hanging like a dishrag from the chains on my wrists.  If I ever had the chance, I vowed to take a hammer to the shocking device and melt the remote controller in a small fire.  

Sir let me hang there a few minutes until Terry showed up.  Sweat was running down my body like crazy. 

“Good, I’m satisfied the remote works and the new cock cage fits well.  But it’s time to move on to your first real lesson in pain.  Yes, yes, I know you’ve been gut punched and whipped, but these are not enough to enforce the level of servitude I require.  I need to take the cock cage off, so I have access to your, or should I say, my slave’s junk.  Don’t worry, I’ll put it back on later.  We can’t have that big cock of yours running around wild around the countryside.” 

Then Sir addressed his #1 slave:  “Be so good, terry-boy, as to uncuff him from the frame after I remove the cock cage, vibrator, and the pec vacs.  Help him stand up if he needs it.  Take him over to the big chair.  I’ll strap him in,” Sir ordered His #1 slave.

“Sir, yes, Sir,” Terry replied as required.  Sir released the vacuum and pulled the cylinders off my chest and unstrapped the vibrator that had tormented me so much.  He backed out all the metal screw points, unlocked the new cock cage, and unshipped my dick from the confinement tube.  Again I felt the cooling effect on my crotch.  I looked down and saw the red imprints from the screw points.  Yikes!  It looked like my dick had the measles.  But, there was no bleeding.  My balls still ached from the stretch out to the sides of the cage. 

Then Terry uncuffed my ankles and my wrists, supporting me when I started to sag.  It did feel good to have his muscular body so close to mine, but I was not in the mood to further enjoy it.  My dick was still being assaulted by a dozen screw points and my pecs ached.   

Terry moved me in the direction of a large, wooden chair bolted to the floor in one corner of the dungeon.  The thing was bristling with thick straps like a prison electric chair.  That actually proved to be a good name for it. 

He helped me sit down in the chair, but first he had to position my ass directly over a large plastic dildo screwed to the wooden seat.  The end of the dildo was metallic.  It was already slippery with lube and I grunted and winced as I slowly lowered myself onto the seat, pushing the dildo up my ass.  It was a rough entry; the thing was long and wide.   

Sir began the elaborate process of strapping me in.  He started with one across my lower abs, just above my new cock cage.  Then He worked on my arms.  Straps were wound around my wrist and then buckled to the wood; it would be impossible to pull free of them.  Another set went on my forearms just below my elbows.  Yet a third set went across my upper arms, pulling in tightly on my biceps and triceps.  A similar set of multiple belts secured my legs to the heavy legs of the chair, pulling my knees far apart and putting my cock caged dick directly in harm’s way.  A belt across my waist was pulled in very tight, pushing my chest out.  Two belts went across my chest, one above and one below my hurtin’ nipples.  The straps bunched up my pec muscles.

I thought that was it, but a thick belt went across my slave collar and yet one more belt went across my forehead.  Once that one was tightened and buckled off I couldn’t move my head an inch.  I was as close to being immobilized as you can get in a chair.  So, why the elaborate bondage?  What was Sir going to do now to torture me?

The answer was simple when Terry pushed over a cart with a big black box on the top shelf:  more electricity.  There was also a laptop computer.  The bottom shelf had a bunch of color-coded cables and Terry began to sort them out in pairs.  There were large metal clips at the outboard ends of the cables.  All the cables led to jacks in the right side of the box.  Terry plugged a power cord into a wall outlet and the box came to life:  Two dials lit up and a red power-on light gleamed at the top.  There was a series of switches along the bottom and a large knob surrounded by numbers going from 1 to 10.  OK, classic electro-torture.

I started to sweat again.  The belts were so tight I couldn’t even squirm to relieve my dread.  Sir simply smiled at me.  There was a lusty look in His eyes.  He was really going to enjoy this. 

NEXT: Ch 37, Real Electro-CBT


“Executive Retreat, Part 2: Dickie-boy On the Job” – by Steve McHalperin

Chapter 35

New CD

“Today is your fitting out day, boy,” Sir said after breakfast.  Terry-boy had made him eggs and sausages; I had cold cereal from my bowl on the kitchen floor, but the coffee in my water bowl was good.

“Sir?” I asked, not completely sure of what he meant.

“Your fitting out day for your new cock cage.  The special one from Germany came yesterday and today’s the day we upgrade your device.  The one you have been wearing is good, but this one from Germany is truly wicked.  You’ll like it, I know!”

“Sir, yes, Sir,” was all I could think to say.  I had almost forgotten about the “upgrade.”  Even since Sir saw it on the net, he lusted after it.  Unfortunately, it took six weeks to get here after He had submitted my precise measurements.  It was to be a custom-made job and cost a lot of money.

After Terry and I cleaned up the breakfast dishes, Sir directed me down to the dungeon.  “Let’s get started!” He leered at me.  I followed Him down the stairs.

Continue reading

“Executive Retreat, Part 2: Dickie-boy On the Job” – by Steve McHalperin

Chapter 34

Back to Training

The coffee worked its magic.  I noticed that Terry was again cock caged.  My body hurt from some of the painful moves he had wrestled me into.  Some elements of wrestling, like arm or leg locks, really can hurt and are designed to wear the other guy down with pain.  A ref will stop the pair if the pain gets excessive and gets too close to damaging tendons and joints.  Sir, as judge of the match, had no such knowledge, so Terry was free to really put a hurtin’ on me – which he did.  I know he had to, he had no choice, but it still hurt like hell and I sort of resented it.  As I said earlier, he did apologize, but I started to see him as competition rather than a buddy.  Didn’t matter much.  He was a trained slave, Sir’s #1, and I wasn’t.  I got all the punishment unless he really did something wrong, which was rare.  The training of dickie-boy resumed that Saturday afternoon. 

“This afternoon we are going to pursue another hobby of mine, dog training,” Sir said to us without mentioning anything about last night.  Terry told me the Friday Night Specials were about once a month, sometimes stretching out to six weeks but never less than four.  I guess Masters only have so much magnanimity.  I was startled to hear of “dog training,” since I had no idea what the hell He was talking about.   

“The two of you are to go down to the dungeon and wait for me in the at-attention stance.  No talking or I’ll whip the two of you!”

“Sir, yes, Sir,” we both answered, not quite in unison.  Terry led the way down the stairs to the basement dungeon.  We stood at attention at the bottom of the stairs.

He had changed into a weird khaki outfit, tailored tightly of course, with a vest full of pockets, like he was going hunting or shooting.  It certainly wasn’t Sir Leather Master, but it also was not all that friendly either.  The short single-tail whip was coiled at his waist belt, ready to use for the slightest mistake.

NEXT: Ch 35, New CD


“Executive Retreat, Part 2: Dickie-boy On the Job” – by Steve McHalperin

Chapter 33

Submission Wrestling

“Terry and I have enjoyed these monthly evenings for a while now, but there was always something I wanted to do.  With the acquisition of dickie-boy here, we can finally proceed.”  He turned to me:  “You perhaps don’t know it, but Terry-boy here was a champion wrestler in college, almost all-state, right, boy?” He asked His #1 slave.

“Sir, yes, Sir,” Terry answered.  “Sir, I just missed it by two matches, Sir.”

“Well, dickie-boy here was also a wrestler, weren’t you boy?” He asked.

“Sir, yes, Sir,” I answered.  I was pretty good, got a varsity letter, but no where near all-state. 

“So, this evening’s special event will be a slave to slave wrestling competition.  It will be submission wrestling and I will be the judge of the winner,” He said, slightly slurring his words from the bourbon. 

OK, I thought, drunken submission wrestling.  Been there, done that in college.  But none of us were all-state like Terry, so I already could guess the outcome.  Then, again, Terry was a few years older than me, so maybe, just maybe, he was rusty in his grappling skills.  I don’t think he had wrestled since school and that was a plus. 

There was only one question in my mind:  if this was submission wrestling and I lost, would Terry have his way with my ass?  He couldn’t with the cock cage on.  That was for sure, and I didn’t know if Sir would release him for the event. 

Terry and I moved to the center of the room and took up standard positions.  Sir then said:  “Ding!  Start the bout!”  I thought this was kind of stupid, but Sir does whatever the hell Sir wants.  It felt like ol’ home week, standing there naked, opposite another naked guy, getting ready to “’rassle.”  What was different was that we were wearing metal cock cages. 

We were both a bit shaky from all the booze, but Terry lit into me with a knee roll, flipping me down to the floor and onto my back in one smooth move.  I was dumb not to expect an aggressive first move.  Terry dropped down onto my stomach, turned, and started to press my shoulders down, going for an early pin.  I tried to twist and turn, but his body held me down hard to the floor.  Then his hands slipped off my sweaty shoulders and he collapsed right onto me.  As I felt his weight shift, I managed to muster the strength to twist my body with some leg leverage, and in the process he slid off my slippery, sweaty skin.  Whoa!  This was my chance!  He was on his stomach on the floor and I pounced onto his back. 

Getting a guy on his stomach is actually not a good situation to be in.  For a pin, you have to get his shoulders to the floor, which means flipping him over.  I pulled his right arm way up behind his back and he yelped from the pain.  I tried to use his arm as a lever to twist him, but he was too strong.

I don’t know why at the moment Sir called for a break:  “Ding!  Round one over!”

We both got up and accepted another round of bourbon which we gulped shot-like.  Then He dinged again to begin the second round.

Terry again went for an aggressive opening and again I fell for it.  This time he changed his move, grabbed my left arm and spun me around.  Once my back was to him, he zoomed in close and as he did he slid his arms under mine.  His chest collided with my back, which threw me off a bit.  He took advantage of this to lift his arms, and my arms, way up high as he planted his interlocked palms at the back of my head.  I was stuck in a classic full nelson.  He pressed hard and my shoulders hurt like hell from the pressure.  I mean, they weren’t all that recovered from the earlier sessions this week.  Now it was my turn to yell. 

I sort of knew where this was going.  I’ve used this strategy myself.  It’s easy to transition from a full nelson to a pin.  You force the guy down, avoiding letting him bend his knees by dragging him back along the floor.  Once his legs are straight out, boom, you drop his torso to the floor, move your hands from behind his head, and pin his shoulders to the mat.  Which is exactly what Terry did.  He did the whole maneuver is just a few seconds.  My shoulders were easily pinned and Dir called it.

“Ding!  Ding!  Bout’s over.  Terry-boy has won!  Good work, boy!”

Terry helped me up from the floor and I nodded to him in concession.  “Sir, thank You, Sir!” he replied to his master.  He extended his hand and we shook on it.    

OK, I did lose and Sir did uncage his cock, and Terry did fuck my ass for a good hour.  We had another round of shots before we started.  By now we were both buzed.

I saw why his cock cage was larger than mine.  His dick was really big, thick and long when it rocked up hard.  He also was not gentle; it was rough man sex.  He apologized later, but I told him it was OK.  Sir would have punished him if he hadn’t performed for the cameras.  Yes, Sir videoed the whole thing, all the wrestling and all the sex.  I remember yelling a lot.  My ass was still hurting from the previous nights’ festivities.   After Terry was done, Sir took His leave and plowed me until my gut was full and leaking man cum.  I had been used, abused, and once again reduced to a cum dump slave meat thing.    

I was allowed to sleep in a medium sized dog cage that night instead of the discipline hole, but I still had to wear the friggin’ heavy chains.  All three of us slept in that Saturday.  I was allowed access to coffee in a civilized cup instead of a dog bowl, that and some aspirin.  We were all in Sir’s kitchen around a breakfast table.  Nobody spoke very much.  We all had a lot of coffee to clear the cotton from our heads.  Man O man, that was some Special Friday.   My ass hurt as I sat on the chair.  

NEXT: Ch 34. Back to Training


“Executive Retreat, Part 2: Dickie-boy On the Job” – by Steve McHalperin

Chapter 32

Special Friday

My days, or at least my mornings, were getting into a groove:  maybe be awake when they come for me, maybe asleep, but the opening of the metal door to the hole is my alarm clock.  Light floods into the hole, blinding me for a few seconds.  Terry reaches down and helps me stand up.  I groan from the pain of uncoiling from my cramped fetal position.  I’m hoisted out of the hole, hosed down, and then we get ready for work, holding slave A in the foyer until Sir comes for us. 

What really pissed me off was the 10 o’clock janitor closet visit was to become part of my daily routine.  Terry informed me of Sir’s directive, the same as yesterday:  closet, strip, wait for the zaps, scream and double over onto the floor.  This goes on for a half hour and then I’m expected to return to my cubicle and work as though nothing has happened.  I’m drenched in sweat, my face is red from screaming, and I have to be at my work station checking computer code like normal.  It’s nuts, I tell you!  I’m leading two lives:  one, a computer engineer; the other, sex slave to a bunch of perverted executives, and one in particular, my immediate boss, Sir Master DieQual, torturing the living piss out of me every night. 

It was Friday, normally a TGIF event, but I was filled with dread.  What would Sir do to me over a whole weekend?  How much pain would I be subjected to?  Terry had said to me I would eventually experience all the tools and toys in Sir’s dungeon, but I had barely cracked the inventory with the few pieces of bondage and beatings I had endured so far.  Would there be a change-up or more of the same?  My Friday afternoon was filled with a lot of fear and very little work. 

On the drive home Sir was in a good mood.  I guess the prospects of a weekend of S&M with a new slave was a TGIF event for Him.  He actually talked to me, asking about project work and all.  I had my normal dog food dinner and waited locked in slave A for Him to come down to the dungeon. 

Loud laughing surprised me when the kitchen door to the dungeon opened and Sir and Terry came down.  Sir was in a really good mood.

“Atten. . .tion!” He barked.  I jumped up from the floor and braced into the required military stance. 

“I know what you’re expecting for tonight, boy.  I could see it in your face at work.  Did I tell you I really enjoy seeing my boys in fear?  Keeps you on your toes, doesn’t it?”

“Sir, yes, Sir!” I replied honestly. 

“Good, good,” He said.  “Tonight, however, there is a change in schedule.  Terry may have mentioned this but once a month we have a relax night.  We will have some chicken wings together, some beer, and maybe some premium bourbon.  We will review some of your videos or maybe watch some of Terry’s training sessions.  It will be a sort of social night.  No topic is off the table, but you must continue to address me as ‘Sir.’  That never goes away.  Understood, boy?”

“Sir, yes, sir!” I yelled out.  “Sir, thank You, Sir!”

“it’s not completely social, but you’ll just have to wait and see,” He added.

“Sir, yes, Sir!” I answered again, realizing Sir always had an agenda.  Nothing could be completely casual.  What did He have in mind?  I liked the wings, beer, and bourbon, but something else was going to happen, of that I was sure. 

“So, dickie-boy, for now you can relax and join us upstairs in the den for our ‘special Friday,’ as we call it.”

“Sir, yes, Sir!” I enthused, my mood totally changed from the dread of the afternoon. 

We went upstairs to His den, which had very expensive leather furniture.  The sideboard was already set with a big plate of wings, paper plates, beer in a big ice bucket, and some Cajun hot sauce, always a treat.  They went over and started to serve themselves.  Terry beckoned with his hand for me to join them.  I was hesitant since this was already a strange change-up from my normal position in Sir’s household.  Of course, Terry and I were still naked except for collars, boots, and metal cock cages, but I was already used to that. 

I got myself a plate of wings, dosed them with sauce, and popped open a Corona.  Sir even had a small plate of lime slices.  I joined them on the sofa, Sir was in the middle, dressed in fine leathers, his two naked slaves to either side.  What a selfie that would have made!

We watched the local news for a bit, chomping away on the wings and downing several beers apiece.  I was really enjoying this Special Friday.  Then Sir changed the channel to His internal video system and up came several torture scenes of yours truly, right up there on the big screen, getting whipped by a sexy Sir in leather.  The screams were in perfect audio, but He did turn the volume down a tad so we weren’t deafened.  Nobody said a word as I got whipped to a frenzy of struggling and screaming.  I have to say, I looked pretty good on the video, I mean, my musculature was flexed and corded from all the struggling and my skin gleamed with sweat.  I also finally got a video view of my back as Sir lashed it.  There were vivid welts, initially light red but rapidly darkening to purple/red.  What blew me away was no blood!  I was sure my back was raw meat, but Sir’s control of the whip was perfect:  all pain, no damage. 

Sir was clearly aroused at the videos; He groped His bulging crotch several times, but said nothing as the torture video switched to some of Terry’s earlier sessions.  He was bigger than me, more muscular, and put on a fantastic “show” of a slave getting disciplined. 

Sir stopped the video and went over to the server.  He got a bottle of premium bourbon out of a cabinet, and returned to the couch with three shot glasses.  He gave us each a glass and filled it with bourbon, including one for Himself. 

By way of a toast, all He said was “Cheers!”  We clinked glasses and drank the very good whiskey.  I noticed that Sir downed His drink in one gulp.  I sipped mine a bit, enjoying the savory burn, but then I thought I should follow His lead so I chugged the bourbon in one gulp.  Oh my!  Did it burn.  Fantastic stuff, bourbon.  Smooth, powerful, very nice after-taste.  I was amazed when Sir refilled our glasses and we repeated the chug-a-lug.     

OK;, by now I had a good buzz on and I was sure the other two were in the same boat.  Sir turned the TV off.

“Now, here’s the surprise,” He began. 

‘Uh, oh,’ I thought.  ‘Here it comes.”

NEXT: Ch 33, Submission Wrestling


“Executive Retreat, Part 2: Dickie-boy On the Job” – by Steve McHalperin

Chapter 31

In the Hole with a Nasty Twist

Sir returned later with Terry in tow.  He ordered Terry to harness me into the heavy chain setup, starting with the very heavy metal collar.  I was weak from the evening’s festivities and Terry had to steady me a bit.  He locked on all the cuffs and chain attachment points and handed the keys to Sir who pocketed them in his leather vest. 

Terry helped me over to the hole and pulled the heavy door open.  While he was hooking up the lifting hook to the hoist hook, Sir came over with the nipple vacuum system.  He smiled at me.

“We have to work on those nips, boy,” He said.  “Terry-boy, show him your man nips.”

“Sir, yes, Sir” Terry said.  He stood in front of me so I could see his chest.  His nipples had been sculpted into true man pegs, almost a half inch long and perfectly cylindrical.  He had the tight nipple rubber bands on at their bases and each nip was pierced with a thick metal ring.  The rings glinted in the room lights.  It was quite impressive – and very manly and sexy.  The rings complemented his sculpted pecs, solid muscle under the tanned skin. 

“It’ll take a while, dickie-boy, before you will be as sexy as my Terry-boy here, but we will work on it.  He checked the rubber bands at the base of each of my nips.  They were still in place.  I had almost forgotten about them in the midst of all the tortures.  Sir attached the slender cylinders and then hand pumped the vacuum way up.  I granted from the pain as my pegs were stretched into the cylinders.  Two more pumps and the pain jumped up two notches. 

“That should hold you for the night,” Sir said, pretending benevolence but radiating evil.  “Hoist him over,” He ordered.

“Sir, yes, Sir” Terry responded dutifully as he hoisted me off the ground and over the hole.  He spread a fresh pad over the floor and then I was lowered to the standing position and he removed the hook from under my arms.  My wrists were still locked to my waist chain, leaving me helpless to do anything.

“Down you go, dick-head,” Sir then ordered me.

I almost fell getting down but Terry was there to steady me.  I curled up into the knees to chest position.  All the chains rattled as I did.  Then a surprise.

“Tighten up the curl, dickie-boy,” Sir said. 

I tried the best I could to compress myself even further even though my ab muscles were screaming in pain as I contracted them to curl up.  My back and ass were stinging wildly; the skin was being stretched as I arched my back.  Then Terry slowly inserted four-inch-thick, fake wooden walls into the hole, reducing its size considerably and confining me very tightly.  The walls fit together with no wiggle room between them.  OMG, this was going to be a very rough night.   The original hole was bad enough, cramping all your muscles and joints.  This was much worse.  I could hardly move an inch.  My head was forced partially between my knees, which thrust my collar right into my lower jaw, securing my tongue against the roof of my mouth like a gag.

With no further word the door to the hole was closed and I entered the world of total darkness and virtual silence.  My  body was already cramping.  My muscles hurt from struggling in the frame bondage earlier in the evening, but now my nipples were burning from the extraordinary stretch the vacuum was forcing. 

I went through my usual sequence of singing, talking, screaming a bit.  I did avoid cursing out Sir; that got me in trouble before.  Guess I was learning.  The hole seemed hotter than previous nights, which were indeed warm and stifling.  Terry told me later Sir had activated the in-hole heaters, which can turn the hole into a tiny sauna.  Already I was sweating my ass off. 

I was overcome with a surprising wave of claustrophobia.  I’m not prone to this, I mean, hoods and blindfolds don’t bother me, but the extreme cramping did something goofy to my brain and I had a panic attack which lasted a good half hour – although time gets distorted in the hole.  Didn’t matter.  I suffered thru it and the wave went away, allowing me sleep a bit, I guess.  Hard to tell in the hole.  Your brain gets all fuzzed up, something like getting delirious, I guess, without going truly nuts.  I was hoping to “check out,” but I didn’t, couldn’t, ‘cause I was too strong.  Big Fuck!  All I could do was take the pain, man up like Terry had said.  I was trapped in this whole mess and there was nothing I could do about it except take it.  Big, Big Fuck!



“Executive Retreat, Part 2: Dickie-boy On the Job” – by Steve McHalperin

Chapter 30

Dickie-boy Gets Plowed Proper

I hung in the bondage, trying to recuperate best I could.  I had just gone through one of the most severe beatings in my life.  My back and especially my ass still stung fiercely.  Every single muscle and joint in my body hurt from the insa ne struggling against the bondage.  I hung there, my head drooping to the extent my leather collar would allow.  My mouth was still open and drooling.  Sweat and drool was scattered on the platform under me.  I was surprised there was no blood.  It felt like my flesh had been sliced to raw meat, but there simply was no blood on the wooden platform.  I did see two small rivulets working down my calves, so there was bleeding, but it clearly was minor.  I didn’t understand this.  How could Someone be so good They could inflict that much agony on a vic without massive loss of blood?  I mean, like, you see fake whippings in the movies and often the guy’s back is raw and covered in red acrylic blood.  I was sure there were welts, but I was still mystified by the minimal amount of blood.

Some fifteen minutes later Sir returned.  Terry was not with Him.  He lost no time in getting down to plan.  He went behind me, popped His Big Dick from the leather jock, and simply raped me again, brutally, forcefully, and very painfully.  It especially hurt when His hips smashed into my ass cheeks, rubbing in sweat and, I guess, breaking open some wounds. 

This session wasn’t as long as last night’s.  Masters get pretty primed when They torture Their young men.  We both yelled when He came:  me in pain, Sir in pleasure.  I was again reduced to a cum dump, a piece of muscular service meat, a warm hole to be filled by Sir.  I was humiliated to feel His load in my gut.  When He pulled out, some of it dripped out, further humiliating me.  Welcome to sex slavery, dickie-boy. 

He swatted me on the right ass cheek and I yelped from the sharp sting.  He came around in front of me and smiled as He wiped his bloody hand across my chest.  His blood mingled with my sweat.  Now I was a dish towel. 

“We’re going to continue your tit work tonight, boy,” He said as He turned and went up the stairs.

I knew I was going to spend another night in the hole.  Now He was going to up the ante, make me suffer some more.  Probably some type of tit clamp. 

NEXT: Ch 31, In the Hole with a Nasty Twist