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

Chapter 17

The Drill Goes On, Tyler Too

So, I knelt there for over an hour while Sir and, presumably, Tyler had their dinner.  I did make one mistake:  My right thigh was cramping and had started to twitch and throb.  I move my knee a few inches in to relieve the pressure on my upper leg.  I screamed into the hood cock gag as my ass, cock, and balls were shocked with electricity.  I almost toppled over from the pain, but after a few seconds of agony it stopped.  The training tape temporarily stopped and Sir’s voice boomed into my head:  “I told you I was watching you.  I saw you break the position and you got punished.  That will happen every time you disobey.”

He stopped talking and the training drone resumed.  I was shaking from the discipline, but I managed a superhuman effort to get back into slave B and get my body back under control.  It was all I could do not to jump off the platform and run upstairs.  That would have been realty stupid, of course.  My junk would probably have been fried by the remote controller and God knows what kind of punishment tortures I would have been subjected to. 

So, I held the slave B position and knelt there mindlessly listening to the drone of the tape.   

He did return after, what, maybe two hours?  Seemed longer, but the tape suddenly stopped in my head.  I was starting to get hypnotized by the endless repetition and the “message” of the tape was sinking in. 

There was a short period of tremendous relief when Sir took of the hood.  The tape drone stopped, I could move my tongue and swallow again, and finally had vision restored, although I did wince from the bright lights focused on the platform. 

Sir was still stunning in His leathers, Tyler a naked, handsome hunk.  I thought I was going to be released and maybe subjected to some other torture, but Sir came over and pumped the suction handle a few times, increasing the vacuum on my nips.  I winced at the increase in pain and struggled to hold slave B the best I could.  I had a chance to look down at my chest while Sir was removing the hood.  My pec pegs were indeed pegs, elongated through the narrow suction cylinders and bright red from engorged blood.  There was some minor bleeding at the tips.  

Sir and Tyler went over to one of the walls.  I dared to look over since Sir couldn’t see my eyes while He was with Tyler.  He fastened Tyler to the stone wall with two metal wrist cuffs and two metal ankle cuffs, spreading his arms and legs widely apart in a classic spread eagle.  Then Sir put a thick muzzle gag on him, strapping it in back.  Tyler told me later the inside of the muzzle had a large cock piece which filled his mouth, just like the discipline hood.  He said Sir left him chained up on the wall for hours, often in complete darkness.  He had headphones on, too, with the endless drone.

Sir went over to the equipment wall and picked up an odd paddle.  It was a long piece of wood, maybe three feet, cylindrical, a club actually.  It had a large bulb of white material at one end.  Tyler said it was a solid rubber bulb covered in layers of cotton.  The material was stained in spots.

Sir returned to his spread eagled slave and pushed the bulbous end of the paddle into Tyler’s stomach.  He grunted into the gag.  The slave knew what was in store.

“This will be punishment for undercooking the pork.  I told you to always use the meat thermometer, but no, you knew better.  You are not paid to think, just to serve.” Sir said to his #1 slave.  Then he moved to the side and started swinging the padded bulb strongly into Tyler’s stomach.  Tyler screamed into the muzzle gag and every muscle in his body contracted.

Tyler told me later that Sir did not know how to box or punch well.  The bulbed paddle was Sir’s answer to this and allowed Him to gut punch very effectively, swinging the paddle like a club.  There were no jabs or upper cuts, just flat-on thunks of the bulb into Tyler’s ridged abs.  The rubber bulb was solid rubber and its impact was like a sledge hammer.      

Tyler took quite a lickin’.  Sir simply flailed away at Tyler’s abs, moving the target spot up and down, perilously close to Tyler’s cock cage.  A direct hit on that would have been excruciating.  I could hear his cries of agony, muffled by the muzzle gag.  There were intense red splotches where the bulb had hit.  He struggled like a madman in the spread eagle bondage, but there was no escape from the cuffs and chains.  There was no escape from the pounding of his abs and internal organs. 

Sir continued to brutalize Tyler’s abs for a good half hour.  There was a moment when the gut punching disturbed Tyler’s stomach.  He had likely also eaten with Sir, and getting gut punched right after a meal is never a good idea.  Sir saw Tyler’s abs start to flutter and twitch, a sign the stomach was not happy and getting ready to get rid of current contents.  Sir quickly removed Tyler’s muzzle gag.  Then he reached down, picked up a small, white plastic bucket and held under Tyler’s chin.

It didn’t take long for Tyler to lose the undercooked pork dinner.  Maybe just as well.  You’re supposed to thoroughly cook pork.  Sir held the bucket as Tyler progressed into the dry heaves.  Then He went over to a small sink in the corner and cleaned the bucket out.  He did bring it back with Him in case there might be another upchuck episode.

There was another round of gut punching.  With no gag in place, Tyler’s screams filled the stone dungeon.  “A-a-gh!  A-a-ah!” Tyler’s skin was blazing red from the blows; the angry splotches had merged into a red zone of abuse.  He struggled and thrashed as the punishment continued.  The metal cuffs scaped against the stone wall and the chain links ground loudly.  Every big muscle group on his body was now mounded and cramping.  Sweat poured down his chest and legs, dripping off his cock cage.  Even Sir was sweating from the exercise. 

In between screams, Tyler started to beg for Sir to stop:  “SIR!  PLEASE, SIR!  PLEASE STOP, SIR!!” followed by a shriek of agony as Sir hit him again.  I lost count of the number of blows to Tyler’s abs. 

It did stop.  Tyler collapsed in the bondage, his head drooping down as far as his leather collar would allow.  He continued to moan and groan from the residual pain in his muscles and gut.  This was quite an object lesson for me.  Don’t cross Sir in the slightest.  The Man was touchy and brutal when aroused.   

I immediately fixed my eyes forward, a requirement of slave B, so Sir wouldn’t have any reason to punish me more.  My plan didn’t work.  Sir never needed a reason to punish His slaves, especially the newbie, Sir’s #2 slave, poor ol’ Dickie-boy, poor me.  My self-indulgent pity-party didn’t last long. 

NEXT: Ch 18, The Chain Harness


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

  1. I can’t wait till he’s chained up eaglespread as well. Make him hang from the chains all night and beat his muscular abs and turn on the heater while he’s tied so he’s continously sweating

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