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

Chapter 31

In the Hole with a Nasty Twist

Sir returned later with Terry in tow.  He ordered Terry to harness me into the heavy chain setup, starting with the very heavy metal collar.  I was weak from the evening’s festivities and Terry had to steady me a bit.  He locked on all the cuffs and chain attachment points and handed the keys to Sir who pocketed them in his leather vest. 

Terry helped me over to the hole and pulled the heavy door open.  While he was hooking up the lifting hook to the hoist hook, Sir came over with the nipple vacuum system.  He smiled at me.

“We have to work on those nips, boy,” He said.  “Terry-boy, show him your man nips.”

“Sir, yes, Sir” Terry said.  He stood in front of me so I could see his chest.  His nipples had been sculpted into true man pegs, almost a half inch long and perfectly cylindrical.  He had the tight nipple rubber bands on at their bases and each nip was pierced with a thick metal ring.  The rings glinted in the room lights.  It was quite impressive – and very manly and sexy.  The rings complemented his sculpted pecs, solid muscle under the tanned skin. 

“It’ll take a while, dickie-boy, before you will be as sexy as my Terry-boy here, but we will work on it.  He checked the rubber bands at the base of each of my nips.  They were still in place.  I had almost forgotten about them in the midst of all the tortures.  Sir attached the slender cylinders and then hand pumped the vacuum way up.  I granted from the pain as my pegs were stretched into the cylinders.  Two more pumps and the pain jumped up two notches. 

“That should hold you for the night,” Sir said, pretending benevolence but radiating evil.  “Hoist him over,” He ordered.

“Sir, yes, Sir” Terry responded dutifully as he hoisted me off the ground and over the hole.  He spread a fresh pad over the floor and then I was lowered to the standing position and he removed the hook from under my arms.  My wrists were still locked to my waist chain, leaving me helpless to do anything.

“Down you go, dick-head,” Sir then ordered me.

I almost fell getting down but Terry was there to steady me.  I curled up into the knees to chest position.  All the chains rattled as I did.  Then a surprise.

“Tighten up the curl, dickie-boy,” Sir said. 

I tried the best I could to compress myself even further even though my ab muscles were screaming in pain as I contracted them to curl up.  My back and ass were stinging wildly; the skin was being stretched as I arched my back.  Then Terry slowly inserted four-inch-thick, fake wooden walls into the hole, reducing its size considerably and confining me very tightly.  The walls fit together with no wiggle room between them.  OMG, this was going to be a very rough night.   The original hole was bad enough, cramping all your muscles and joints.  This was much worse.  I could hardly move an inch.  My head was forced partially between my knees, which thrust my collar right into my lower jaw, securing my tongue against the roof of my mouth like a gag.

With no further word the door to the hole was closed and I entered the world of total darkness and virtual silence.  My  body was already cramping.  My muscles hurt from struggling in the frame bondage earlier in the evening, but now my nipples were burning from the extraordinary stretch the vacuum was forcing. 

I went through my usual sequence of singing, talking, screaming a bit.  I did avoid cursing out Sir; that got me in trouble before.  Guess I was learning.  The hole seemed hotter than previous nights, which were indeed warm and stifling.  Terry told me later Sir had activated the in-hole heaters, which can turn the hole into a tiny sauna.  Already I was sweating my ass off. 

I was overcome with a surprising wave of claustrophobia.  I’m not prone to this, I mean, hoods and blindfolds don’t bother me, but the extreme cramping did something goofy to my brain and I had a panic attack which lasted a good half hour – although time gets distorted in the hole.  Didn’t matter.  I suffered thru it and the wave went away, allowing me sleep a bit, I guess.  Hard to tell in the hole.  Your brain gets all fuzzed up, something like getting delirious, I guess, without going truly nuts.  I was hoping to “check out,” but I didn’t, couldn’t, ‘cause I was too strong.  Big Fuck!  All I could do was take the pain, man up like Terry had said.  I was trapped in this whole mess and there was nothing I could do about it except take it.  Big, Big Fuck!



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

  1. Funny how things work in your head but this chapter has stayed with me ever since I read it. Powerful imagery.

    • Yes. Same here. The lengths any kind of torture can go are unimaginable. I usually have fun and even get horny with fantasizing over other types of torments applied to hot men, however this I admit freaks me out a bit…

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