“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


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

  1. Man, this guy is getting slammed… way worse than Erik.
    Like, no break, I feel exhausted myself after every session!

  2. Sir Aethelstan, thanks for your kind words. I’m happy to get you exhausted! Imagine how I feel writing this stuff. Ha!

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