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

Chapter 35

New CD

“Today is your fitting out day, boy,” Sir said after breakfast.  Terry-boy had made him eggs and sausages; I had cold cereal from my bowl on the kitchen floor, but the coffee in my water bowl was good.

“Sir?” I asked, not completely sure of what he meant.

“Your fitting out day for your new cock cage.  The special one from Germany came yesterday and today’s the day we upgrade your device.  The one you have been wearing is good, but this one from Germany is truly wicked.  You’ll like it, I know!”

“Sir, yes, Sir,” was all I could think to say.  I had almost forgotten about the “upgrade.”  Even since Sir saw it on the net, he lusted after it.  Unfortunately, it took six weeks to get here after He had submitted my precise measurements.  It was to be a custom-made job and cost a lot of money.

After Terry and I cleaned up the breakfast dishes, Sir directed me down to the dungeon.  “Let’s get started!” He leered at me.  I followed Him down the stairs.

As usual, I was naked except for boots and a thick leather collar.  I don’t think you can count the cock cage as an article of clothing.  Sir made me do some situps and pushups; He like to watch Terry and me exercise. 

When I was all sweated up, He ordered me over to the frame in the middle of the dungeon, stretched out my arms and legs into a spread eagle and cuffed me in place.  Then he brought over the new device.  The metal cock tube gleamed in the dungeon lights and I could see that the base ring was much thicker than the metal CD I had on.  Sir unlocked my device and pulled it off my junk.  My crotch immediately felt cold without the metal cladding on my dick, but that didn’t last long. 

Sir circled the thick metal ring around the base of my ball sack and my cock.  It was indeed heftier than the previous one.  Plus, the opening for my plumbing was definitely tighter, a lot tighter.  I squirmed a bit as he clamped the base ring on.  This was going to get rough. 

“Yes, this model has some serious modifications, which you will have to deal with,” Sir said as he lubed my dick up for insertion into the confinement tube.  I did not even begin to get hard, even though the whole operation is rather sexy.  I was afraid!  This new device was not going to be easily tolerated like the last one. 

The cock tube had a long, metal urethral tube which he lubed with antimicrobial gel and then forced into my piss slit and up my urethra a good ten inches.  There was a metal ball at the working end and I could feel every inch of its penetration into my dick.  Even the urethral tube was thicker than what I had worn.  It immediately hurt. 

The cock tube itself enveloped my dick as he pushed and slightly rotated the metal tube.  I noticed some screw ends sticking out, a lot of them.  The screws ended in Allen wrench openings.  He maneuvered the base of the cock tube against the base ring.  The tube was a tad short and my dick was already pushing against the end of it when the tube mated to the base ring.  Then He quickly locked the whole thing up.  As with most CDs, the click of the lock is not very loud or dramatic, but what it signifies is mind-bending:  total control of your manhood by a Master.  It’s a strong message that your most intimate body parts are no longer yours, but belong to Him and are under His control.  Sir made a show of adding the keys to the new CD to the chain around His neck.  The keys to Terry’s cock cage were already there, plus a few other ones I didn’t recognize. 

 “There you go, dickie-boy, now you’re all fitted out and once again that wild cock of yours is under my complete control,” He said, smiling at me.  “I’ll attach the remote zapper later. 

“Sir, yes, Sir,” I answered.  “Sir, thank You, Sir,” I added for good measure.  Sir likes it when I thank Him for punishing me. 

“So, how does it feel, boy?” He asked.

“Whoa, it’s really tight, Sir.  Much tighter than the other one, Sir,” I answered truthfully.  “It really hurts, Sir!” I added. 

Sir unhitched the short whip from his chaps waist band, went behind me, and slashed the whip across my back four times.  I screamed at each blow.

“Sir, what’s wrong, Sir?” I asked in total confusion at the discipline.

“You are a slow learner, boy.  I don’t know if I’ll keep you.  What’s wrong?  Every sentence you say to Me must begin and end with My proper address, which is ‘Sir.’  That’s what’s wrong!” he added in anger.

OMG, He was right, of course.  “Sir, it really hurts, Sir!” I said, trying to placate him. 

“That’s better.  It’s supposed to hurt,” He said.  “The tight fit is not by accident.  That’s what $800 buys you, total customization.  They had your measurements, but I had ordered the tightest fit possible within those measurements.  So, it does hurt, boy?”

“Sir, yes, Sir!” I said. 

“Where, exactly?” He asked.

“Well, Sir, the tube inside hurts a lot, especially that metal ball at the end, Sir.  Sir, and my balls, Sir, are pushed out much farther with this one, Sor.  Sir, they’re starting to ache, Sir.  Sir, the tube fits tightly, too, Sir,” I added, hoping I complied with His speech code.

“There’s more, dickie-boy, another German innovation,” He said reaching into the pocket of his leather chaps. 

He withdrew an Allen wrench and went to work turning in the various screws which studded the cock tube.  I quickly got the picture:  the screws ended in points which were now slowly pushing into my cock flesh.  I grunted from the slowly increasing pain in my dick.  Even the slightest erection in this rig would be really bad.  I had more room before; this one had zero room. 

Then the ultimate terror:  He screwed in a half dozen or so pointed screws in a cluster right at the end of the tube, surrounding my cockhead.  I grunted and grimaced again as the metal points dug in.  The slightest beginning of a hardon was going to bad, real bad.

“To introduce you to the full power of this new cock cage, I’m going to leave you in the frame for a few hours.  But it wouldn’t be fun just having you hang there.  Let me give you something to think about.”

I knew this was going to get worse.  With that Sir went over to the equipment wall and came back with a white vibrator.  He had several models; this one had leather straps.  He fastened the damned thing to my left, upper thigh with the straps and adjusted the vibration head right against my new cock cage.  He plugged it in an outlet on the side of the central platform where I was spread out, and turned it on.  The reaction was immediate.

The buzzing pulses were transmitted through the metal cock cage directly to my dick.  There was no denying the pleasure.  It was very sensual and, unfortunately, very arousing.  The last thing I needed was a hard on with a dozen or more metal points sticking into my poor dick.  Well, it happened.  The stimulation from the vibrations was just too juicy to ignore and my traitorous dick started to get hard.  I screamed from the pain:  “A-g-h!  No-o-o!  Stop!  A-a-h!” 

On the plus side, the pain did short-circuit the whole arousal cycle and my dick went flat, giving me some relief.  But the vibrator was insistent and the cycle started over again.  More screaming, more deflation, rinse and repeat.  Sir was laughing at my torment as well as mashing the huge bulge in His leather jock. 

I thought He was done, but He went back to the equipment wall and returned with the pec peg pump.  He lubed up the two cylinders and attached them one by one as He squeezed the handle on the hand pump.  My nips were drawn into the narrow tubes and the vacuum pulled them out to the point of pain.  I groaned at the additional torment.  He just stood there for another five minutes or so, relishing His suffering muscle slave’s torment.  Then He turned and went upstairs.

I was left chained in the frame while my cock went through cycle after cycle:  sensual arousal/pain/scream/go flat.  It was maddening and very painful.  I looked down expecting to see blood gushing from the cock cage tube, thinking the metal screw points were an inch deep into my dick, but only sweat dripped from the end of the cock tube, no blood.  Another diabolical torment courtesy of Sir.  “Safe and sane,” yes, but also genuine torture.  I hadn’t minded the earlier cock cage, other than the remote zapper.  It was bigger and you almost forgot you were wearing it.  This friggin’ one was very tight, very nasty, and would serve as a constant reminder that I was in training to become a slave to Sir.  And part of that painful training was elongating my nips, which added to the aches.   

I had a brief pity party, but then bucked up to the situation.  I could take it, I was strong.  A little voice inside me replied:  “You’re an idiot.  He’s going to win, you know that.  It’s just a matter of time, pain, and humiliation!”

I guess I had to agree with the little voice.  The recorded mantra came back to me:  “Obey, comply, submit, let go.”  WTF was I going to do?   

NEXT: CH 36, Testing One, Two

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