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

Chapter 19

Down the Rabbit Hole

Sir released Terry from the wall cuffs.  The poor guy almost fell over.  Sir ordered him to straighten up and with great effort Terry complied.  His stomach was still bright red and his face was slightly contorted in pain.

“Terry-boy, hoist him in.  And put the big ass plug in.”

“Sir, yes, Sir,” came the reply, a little weak this time, but still meeting the rule. 

Terry went to the equipment wall and returned with a monster of a dildo.  He lubed it up in front of me and then asked me to bend over.  I bent but immediately felt the full weight of the friggin’ metal collar almost making me lose my balance.  After I steadied myself, he very carefully inserted the dildo up my ass.  The stretch on my asshole muscle really hurt and I grunted from the pain.  He pushed it in until it closed down over the constriction at the end of the monster.  Man O man, this was going to be uncomfortable. 

Terry went over to the wall and picked up a small control box with three buttons on it.  He activated one and a metal hook was lowered from an electric hoist in the ceiling.  I had no idea what was going to happen.  When the hook had descended to shoulder level, he slid a metal fork under my arms and pulled it up to my arm pits.  Then I felt him attach the hoist hook to the back of the fork.  He pressed another button and the hoist started to pull up, pulling me along with it.  First I had to stand on the balls of my feet, then my toes, and then I was lifted off the ground.  Because the hoist was centered on the hole, I swung to the middle of the cell’s opening, slowly bobbing back and forth like a pendulum.  Terry reached out and stopped my swinging.  He grunted from the pain in his own body as he moved.

Then he dropped a large white pad down into the hole and spread it out with a stick so it covered the floor.  Well then, I thought, here we go.  He pressed another button and I was slowly lowered into the hole until I was standing on its floor.  Once the tension was off the listing fork, Terry unhitched it from the hoist hook.  

I realized that when the door was closed, I’d be squeezed into that tiny space for the whole freakin’ night.  “Wait, Sir, you arent’ going to put me in this box, are you, Sir?” I asked in panic.

“Yes, I am!” He yelled at me.  He unhitched his whip from His chaps belt and slashed me across the back twice. ‘

“Yowl!” I howled at the sudden pain.  The two slashes really hurt. 

“Don’t you dare  tell me what I can and cannot do with my property!” He said loudly and angrily.  “You’re my property, a thing I now own, and I’ll very well do anything I wish!” He added. 

Oops, a big oops, I realized.  OK, so I was going to spend the night in the floor cell, the rabbit hole, the discipline hole. 

“Now, get your ass down into that cell and curl up with your knees to your chest and do it right now!” He ordered. 

I slowly lowered myself into the tiny cell and followed his orders, curling up into a fetal position, knees pressed to my chest.  At least it felt better to have the weight of my heavy neck collar finally off my shoulders.  The chains all rattled as I curled up.

“You’ll spend the next few nights in here, boy, so get used to it.  Feel free to scream.  There’s an infrared videocam in one of the walls.  Everything you do or say will be recorded.  I have two customers who enjoy this kind of torture.  Oh, and also feel free to piss.  The absorbent pad will soak it up.  Little boys are allowed to wet the bed here,” He added with a sneer.

Terry slowly closed the metal door and I was put into total darkness.  I heard the latch being slid over and the clanking of the big lock being hooked through the latch.  Then silence.  Darkness and silence.

This was going to be rough 

NEXT: Ch 20, A Night in the Hole


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

  1. When the hooks were under his armpits and pulling him up, how were his hands? Were they tied behind his back or above his head? Just curious!

    • I envision the hooks under his armpits with his hands chained at waist level to a chain circling his waist. He couldn’t move his hands up or down, so the hook stayed pinned under his arms. I usually don’t supply pictures with my stories, but check out the previous chapter and tell me if the guy’s not hot! I get all my inspiration from pics, but I’m always concerned about copyrights and stuff like that so I don’t post many. Imagination is often stronger.

      • Oh that’s so hot, love to imagine that. Another thing is, if possible, can you also make the guy Indian as well. A lot of the audience here likes Indian guys in peril or bandage it’s equally sexy. I’d love to talk to you about this can you contact me on IG: anupama654sri

Leave a Reply.

Fill in your details below or click an icon to log in:

WordPress.com Logo

You are commenting using your WordPress.com account. Log Out /  Change )

Google photo

You are commenting using your Google account. Log Out /  Change )

Twitter picture

You are commenting using your Twitter account. Log Out /  Change )

Facebook photo

You are commenting using your Facebook account. Log Out /  Change )

Connecting to %s