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

Chapter 27

A Vicious Night

Terry handcuffed my wrists behind my back, as instructed by Sir, and then I ate my “dinner” of dog food and washed it down with water I lapped from my water bowl.  Eating this way really makes you think you’re a dog, a pet to Someone, not worthy of eating at a table with other humans.  Terry told me it’s  part of Sir’s program of ego deconstruction,  That and the droning obedience tape are designed to reduce willfulness and refocus the slave’s mind on Sir.  It’s not mind destruction; that would be counter-productive and not make for a spunky slave boy.  It’s simply a refocusing of the slave’s mind so that Sir is the new center of its universe.  And there are two big parts to serving Sir:  taking any kind of pain or torture He might wish and total sexual servitude to Him.  It’s that simple. 

The only problem for any young man is that the training program takes a long time ‘cause us guys are pretty independent-minded.  It requires tremendous pain to enforce total obedience.  A really good potential slave already has the neural wiring for mixing pain and pleasure, so that intense pain also involves intense sexual pleasure.  I told you earlier that I had that.  I always got a boner when my step father whipped me and that was followed by a powerful JO session once he cut me down from the ropes.  In my senior year in high school, the pattern was so strong that sometimes I had a hands-free cum during the whipping.  This usually enraged my step father and he took out his anger on my back and ass.  I could still muster up a private JO session even after a whipping cum.   

After I ate I dropped into slave A the best I could in cuffs, planting my forehead to the cement floor of the dungeon.  I didn’t steel my eyes until I heard Him coming down the dungeon steps.  Guess I was still “willful,” as Sir put it.  This evening’s project was a big escalation in pain.

“Let’s call it Pain 202,” Sir laughed at me as He stood over me.  “OK, get up and go over to the frame!” he ordered.

This slave boy jumped up from the floor and trotted over to the big wooden frame on its platform in the center of the dungeon.  I stretched out my arms and legs without being bidden and Sir buckled the wrist and ankle cuffs on.  There was no need for locks; I couldn’t reach the cuffs with my fingers.  He had me in a tight spread eagle. 

“Two things tonight, dickie-boy,” Sir leered at me.  “The first is a good thrashing with my single tail on your back and ass, followed by a caning.  The whip will tenderize your flesh.  This makes the caning hurt more.  You need to feel the full fury of a sound beating,” he added.

Like I hadn’t had sound beatings from my step dad.  My stomach knotted again as fear took over.  My dick tingled in the cock cage.  It really wanted to go hard.  Not tonight, dickie-boy, I told it.  Maybe never.

Sir unhitched the whip from his leather chaps waist band and lashed it in the air a few times.  I jumped at the shark cracks, not knowing when the beating would start in earnest.  Then it started.

There was a big whooshing sound as the leather sliced the air.  Then the expected splatting noise as the braided leather sliced into my upper back.  Then the explosion of pain and a scream.  “A-a-a-h!  A-a-g-h!” echoed in the dungeon, as I guess it had many, many times in the past.  I pulled violently against the cuffs and chains holding me and every muscle in my body flexed and mounded.

Two lashes in quick succession.  Redoubled screaming and struggling.  Two more.  Two more!  I was screaming nonstop and having trouble getting air to breathe with the big bit gag strapped into my mouth.  You need air to scream, but I couldn’t get enough.  My body was on survival autopilot.  Somehow I didn’t suffocate and somehow I couldn’t stop screaming from the blinding pain in my back. 

Whosh/splat/scream/struggle/gasp.  Whosh/splat/scream/struggle/gasp for air.  On and on, up and down my back.  Then Sir switched to my ass, slicing the leather across my ass cheeks.  This was agony.  I couldn’t escape the bondage.  I was screaming like the primal trapped animal now, raw, full-throated yells of pain, struggling like a maniac to pull free of the chains and cuffs. 

I had no idea of how many lashes I took that night.  I saw Terry standing by but he had not been told to keep the count.  His face was white but he kept his cool.  He knew better than to do otherwise.  His face did twitch a few times.  He full well knew what I was going through from his own training sessions, including the most recent one two nights ago. 

The beating did stop.  I was covered in sweat and so was Sir.  He massaged his leather jock which was at total bulge.  Sir came over and stood directly in front of me.  He reached up and put His hand under my chin, forcing my head up.  The leather slave collar dug into the back of my head.  We locked eyes. 

“That’s what slave boys get when they disobey.  Remember this any time you want to disobey.” He said slowly as he closed his hand and pushed in my cheeks.  “I can still see the flame of defiance in your eyes, boy.  Masters are skilled in assessing the state of Their boys by their eyes.  I have only begun with you,” He said.

Guess He was right about defiance.  I couldn’t help myself.  The more He hurt me, the more that stupid little flame of rebellion was stoked.  I was determined He wouldn’t break me.  How dumb can you get!?

The next torture almost broke me. 

NEXT: Ch 28, The Cane

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

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