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

Chapter 20

A Night in the Hole

It was hot in the little cell and I started to sweat.  I was tightly cramped into the tiny cell and already I could feel my joints protesting.  Wasn’t much I could do about it, so I started to hum a song to break the silence.  I don’t even remember what song it was.  My back still stung from the two lashes Sir had given me.  I blamed myself for the punishment.  When would I learn to keep my mouth shut and just do what He wanted? 

One plus, if there was a plus, was that I didn’t have to listen to the obedience drone tape.  Any sound in the cell would be from me, not imposed by Sir.  I enjoyed the sound of the metal clinking as I moved the few inches I could and the chains clanked against the side walls, which were all cement.  The pad on the floor muffled most of the sounds, however.  Because of my new neural wiring, my cock wanted to get hard.  Being chained up in a punishment hole was sort of sexy.  The cock cage short circuited any pleasure in that department.  Not only that, it hurt.  Any erection in a cock cage is mighty painful, both the frustration part and the physical pain part.  What a waste of a sexy moment

Then I remembered that my new cock cage was a remote zapping device and Sir had the controller.  I had gotten a few shocks at the office earlier in the day, nothing I couldn’t handle without screaming.  I did jump in my chair, however, and got some strange looks from my comrades. 

Then I got mad.  I was NOT someone’s property, like He had said, a thing, a piece of muscle meat!  I had been forced into this absolutely against my will.  He had me trapped three ways from Sunday and I had no choice at all.  I needed His good will to continue to run my company and He had enough video evidence of me begging to be tortured that my reputation couldn’t possible survive unless I moved to Mars. 

Still in all, there was that flicker of defiance deep in me, that little spark of resistance that said:  ‘You can’t break me!  I can take anything you dish out!’  I don’t know where it came from, but every time I started to feel trapped, the flame was ignited and I felt better for it.  It was probably futile, but it did help.  Of course, my back still stung, a reminder of my true status, Sir’s property. 

Out of total boredom I started to song louder and then I yelled out a few times, I don’t know why.  The darkness and silence were unnerving.  The only sensory input I had was from myself.  The heat and confinement was making me dizzy and a little delirious after several hours.  Did I sleep?  I guess so.  I did wake up started to be confined, chained, alone in total silence and blackness. 

I am embarrassed to say I had to pee, and it got so bad I had to just let loose.  The pad absorbed all the piss, but I was mortified.  I really did feel like a little boy who just wet the bed, exactly as Sir had described.  Terry told me later that everyone pisses in the rabbit hole.  It’s part of Sir’s diabolical training program, part of His effort to dampen your willfulness and submit to His control.  Well, it was working.

After I pissed, I got mad again and started to shout some more:  “Fuck this!  Let me out!  Fuck You, Sir!  Fuck everything!”  It felt good to curse Him, but then the thought crossed my mind that I might have merite3d more discipline.  Maybe He would whip me for my defiance.  OMG, I shut up immediately.

Then I was startled with a strong zap to my cock cage.  I screamed at the burst of pain.  “A-a-gh!” was deafening in the confined space.  The shock lasted maybe four or five seconds.  It was agonizing and all my muscles flexed, bashing my feet and knees against the close cement walls.  I was left panting hard in recovery.  I thought it better not to curse at Him anymore, so I bit my tongue in defiance.  I also had to pee again, maybe from the shock, but this embarrassed me further and demonstrated that maybe I was a piece of muscle meat existing only for His perverted pleasure.  I was so confused. 

Guess I went to sleep, after the anger drained out of me.  When I woke up my focus was wondering all over the place.  The heat and confinement were becoming a true torture.  I hoped Sir’s video fans would be enjoying this   All my big muscle groups were now cramping from the distorted position.  And, of course, the lashes on my back still stung.  OK, so this was what the discipline hole was all about.  I sort of wanted to do almost anything to avoid another night in the hole. 

Again I drifted off to sleep.  At least I didn’t have any nightmares.  The real nightmare was when I was awake.  Everything hurt.  I moaned a few times for the video.  

NEXT: Ch 21, Eventually Morning


Group Sharing for 4-10-21

Hi Guys,

An experiment to see if we can help each other expand our enjoyment of the Net and TV!

If you see something you think others on this site might like, please share it in the Comments to this weekly Saturday post (click balloon in upper right corner) .

Movies, episodes, stories, websites, your own sites, even pay sites, special sales, etc. – be as descriptive as you like. Be sure to include the URL or Network.

Sharing the fantasy,



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

Chapter 19

Down the Rabbit Hole

Sir released Terry from the wall cuffs.  The poor guy almost fell over.  Sir ordered him to straighten up and with great effort Terry complied.  His stomach was still bright red and his face was slightly contorted in pain.

“Terry-boy, hoist him in.  And put the big ass plug in.”

“Sir, yes, Sir,” came the reply, a little weak this time, but still meeting the rule. 

Terry went to the equipment wall and returned with a monster of a dildo.  He lubed it up in front of me and then asked me to bend over.  I bent but immediately felt the full weight of the friggin’ metal collar almost making me lose my balance.  After I steadied myself, he very carefully inserted the dildo up my ass.  The stretch on my asshole muscle really hurt and I grunted from the pain.  He pushed it in until it closed down over the constriction at the end of the monster.  Man O man, this was going to be uncomfortable. 

Terry went over to the wall and picked up a small control box with three buttons on it.  He activated one and a metal hook was lowered from an electric hoist in the ceiling.  I had no idea what was going to happen.  When the hook had descended to shoulder level, he slid a metal fork under my arms and pulled it up to my arm pits.  Then I felt him attach the hoist hook to the back of the fork.  He pressed another button and the hoist started to pull up, pulling me along with it.  First I had to stand on the balls of my feet, then my toes, and then I was lifted off the ground.  Because the hoist was centered on the hole, I swung to the middle of the cell’s opening, slowly bobbing back and forth like a pendulum.  Terry reached out and stopped my swinging.  He grunted from the pain in his own body as he moved.

Then he dropped a large white pad down into the hole and spread it out with a stick so it covered the floor.  Well then, I thought, here we go.  He pressed another button and I was slowly lowered into the hole until I was standing on its floor.  Once the tension was off the listing fork, Terry unhitched it from the hoist hook.  

I realized that when the door was closed, I’d be squeezed into that tiny space for the whole freakin’ night.  “Wait, Sir, you arent’ going to put me in this box, are you, Sir?” I asked in panic.

“Yes, I am!” He yelled at me.  He unhitched his whip from His chaps belt and slashed me across the back twice. ‘

“Yowl!” I howled at the sudden pain.  The two slashes really hurt. 

“Don’t you dare  tell me what I can and cannot do with my property!” He said loudly and angrily.  “You’re my property, a thing I now own, and I’ll very well do anything I wish!” He added. 

Oops, a big oops, I realized.  OK, so I was going to spend the night in the floor cell, the rabbit hole, the discipline hole. 

“Now, get your ass down into that cell and curl up with your knees to your chest and do it right now!” He ordered. 

I slowly lowered myself into the tiny cell and followed his orders, curling up into a fetal position, knees pressed to my chest.  At least it felt better to have the weight of my heavy neck collar finally off my shoulders.  The chains all rattled as I curled up.

“You’ll spend the next few nights in here, boy, so get used to it.  Feel free to scream.  There’s an infrared videocam in one of the walls.  Everything you do or say will be recorded.  I have two customers who enjoy this kind of torture.  Oh, and also feel free to piss.  The absorbent pad will soak it up.  Little boys are allowed to wet the bed here,” He added with a sneer.

Terry slowly closed the metal door and I was put into total darkness.  I heard the latch being slid over and the clanking of the big lock being hooked through the latch.  Then silence.  Darkness and silence.

This was going to be rough 

NEXT: Ch 20, A Night in the Hole


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

Chapter 18

The Chain Harness

Sir walked over to the center platform where I was still kneeling in slave position B.  I stiffened in the stance at His approach and dared not move my eyes from forward. 

He slowly ran the rubber bulb up and down my stomach:  “I hope you saw that discipline of Tyler-boy as a lesson for you, too,” Sir said to me. 

I was terrified!  The Man was totally unpredictable despite all his rules for behavior. 

“Have you ever been gut punched, boy?” He asked me, pushing the rubber bulb into my navel. 

“Sir, yes, Sir!” I answered immediately, struggling to hold the slave B position. 

“And where was that?  College?” He asked.

“Sir, yes, Sir!” I responded.  “Sir, it was part of submission wrestling, Sir!”

“Interesting,” He said.  “I’ve had a lot of boys down here who did submission wrestling.”

It was a statement, not a question, so I didn’t respond.

“And what did you think of gut punching, boy?” came the next question.

“Sir, it really hurt, Sir!” I said truthfully. 

“Were you tied up, boy?” He then asked.

“Sir, no, Sir,” I said.  “Sir, other guys held me, Sir.”

“Well, that’s even sexier,” He said.  “But down here there’s only me, so I use heavy bondage.  Despite all the training, there are few lads who can take discipline without bondage.  Anyway, bondage looks better on video,” He added.

OMG, I had forgotten about the friggin’ videocam facing me.  It wasn’t just so He could watch me. Like the executive retreat tortures, all the went into Their video business to finance the whole pervy operation. 

“And so we move on,” Sir said to me.  “Slave dickie-boy, atten…tion!”

I jumped up from the kneeling position as fast as I could.  My leg muscles and joints complained; they were cramped tightly.  Then I braced into the military position, eager to follow his command after His brutalization of Tyler.  Sir went to the equipment wall and returned with a complicated set of chains hanging from a very large, heavy metal collar.

He laughed a little as He said:  “This is the dress code for the discipline hole where you will spend the night,” 

Dress code, indeed.  It was a heavy chain harness.  He fitted the ridiculously thick metal collar around my neck, compressing my slave collar against my throat.  I could breath without effort, but swallowing was a tad hard.  He locked the front of the collar with a heavy padlock.  The collar must have weighed over twenty-five pounds alone, let alone the weight of the chains.  Then metal cuffs went on my wrists and ankles, all made of heavy metal.  They were all linked by thick metal chain.   The chain to my wrists was short and held my hands at waist level.

“Stand here while I release Terry-boy from the wall.  Then you go into the hole!” 

NEXT: Ch 19, Down the Rabbit Hole