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

Chapter 21

Eventually Morning

All tortures come to an end, if only to get you ready for the next one.  My second night in the hole came to an end.  I was humming to myself again when I heard metallic clanking on the cell’s door.  Someone was fiddling with the lock.  Yeah!  Then the sound of the latch sliding over and – FINALLY – the door above me was slowly opened.  Room light flooded my cell and I squinted from the brightness.

When I could finally focus, I saw Sir standing over me, dressed in a suit and tie for work.  Terry was off to the side, naked, of course, except for his collar, cock cage, and boots.  Sir ordered me to stand up.  Terry got down on his knees and reached down into the cell to help me.  At least the angry redness on his torso had vanished overnight.  He still winced a bit when he moved. 

I groaned from the pain as all my joints and muscles protested.  They were stiff from the hours in the cramped position.  The full weight of that damned collar was once again on my shoulders and I had to watch my balance as I painfully stood up. 

Terry inserted the lifting fork under my arms and attached it to the hoist hook.  I was slowly lifted out of that damned cell.  When my feet cleared the opening, he grabbed me by the chain between the collar and waist, pulled me off to the side, and then lowered me to the floor.  I was very unsteady finally standing.  He unhooked the lifting fork and sent the hoist hook to the ceiling with the lift button on the control box.   Then he removed the fork from under my shoulders.  That felt good. 

Sir stood there watching all this until Terry was finished.  “You stink, boy.  Looks like our little slave boy wet the bed!  How naughty!  Terry-boy, hose him down and finish up here.  Then both of you get into Slave A until I’m ready to leave.”

“Sir, yes, Sir” Terry said. 

I missed my cue.  Sir unhitched his whip, went behind me, and delivered two more slashes on my back.  I yelled from the flash of pain and was a little confused as to why I was whipped.

“When I give an order, you will answer properly.  Now, do it!” He said.  “You were told to get into slave A after getting cleaned up.  Will you never learn?”

OK, OK, I thought.  That was my fault.  I presumed his question was rhetorical and didn’t answer.  It wasn’t.

He hit me twice again and I yelled again.  Then I stammered:  “Yes, Sir, I’ll learn, Sir.”

“Not right” He yelled.  “Good God, you’re slow.  I don’t know how you do your job.”

I realized I had left off the first ‘Sir.’  This Guy was really touchy.  “Sir, yes, Sir!  Sir, I will learn, Sir!” I said loudly, trying to placate Him.

“That’s better, boy,” He replied, hitching the whip back to his chaps belt.  He turned and abruptly left.

“Come on,” Terry said.  “We don’t have too much time.”

I followed him through a door I hadn’t noticed before off in another corner of the dungeon.  It led to a room with a tiled area on the far wall. 

“Stand on the tiles while I hose you down,” Terry told me as he uncoiled a garden hose from a bracket on the wall.  He turned on the cold water and sprayed it all over me.  It felt good at first to rinse the dried sweat and urine off, but then the stream stung when I turned around and he hosed my welted back.  He worked as quickly as he could.

“OK, sport, now the chains come off,” he said.  “Sir has loaned me the key.”

It was the greatest relief in the word to be out of the chains and have that ridiculously heavy collar off my shoulders.  “Oh, man,” I said to him.  “That feels wonderful.”

“Good, good.  I have to tell you that Sir is furious with you over your cursing him out last night.” He added.  “That’s why Sir activated your remote shocker.  He laughed when you screamed from the pain.”

“I sort of thought so and I certainly regretted it as soon as it happened,” I replied.  “Is that why He’s in such a touch mood?”

“His moods are unpredictable.  You have to get used to that.  Look, we have to hurry and get dressed for work,” he said with urgency in his voice. 

I followed him upstairs, still dripping wet.  We went into the small changing room we had first visited yesterday and put on the same clothes we had worn then, although Terry instructed me to go commando today. 

Then we went back to the foyer and got into slave A on the floor as we waited for Sir.

NEXT: Ch 22, Two Projects

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

  1. Whenever he is pulled up with those hook chains from his armpits it just turns me so much omg. I can just imagine the groan and grunt he makes while he’s being strung up like that so sexy 😍🥵
    ~Anupama

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