“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

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

Chapter 29

Dickie-boy Gets Gut Punched

Well, I was wrong.  I thought my physical torture had ended and Sir was going for the psychological torture of humiliation and abuse.  Seems Sir still wanted to hear more screams of pain.

By this time my shoulders and wrists were hurting bad from all the crazy pulling and thrashing I had been doing in the frame bondage.  When you’re spread eagled, it’s usually your arms and shoulders that get punished, not your hips or legs.  I was surprised when Sir removed the bit gag from my mouth.  Drool was still dripping out.    

My terror meter hit the red zone when I saw Sir pick up the heavy club which ended in the large, hard rubber ball.  It was the one He had used on Terry the other night, brutalizing his torso.  OK, so that was next up for me now. 

I found it mildly amusing that Sir couldn’t punch, that He had to use a club, like this was some sort of weakness or deficiency.  It wasn’t.  The large ball at the end of the club was every bit as vicious as a man’s fist, maybe even more since you could get more momentum swinging a club.  The only plus here was that Terry had survived his gut work the other night, so maybe I would too.  Once it started, I had my doubts. 

Sir stood off to my left.  He grinned at me as He positioned the hard ball against my navel.  I started to say:  “I’m sorry, Sir, for displeasing . . .” but then He swung the club against my stomach.  After the low whoosh, the club’s ball made a thudding sound as it tore into my gut.  The thud was followed by an earthquake inside me, as the ball crashed into my tensed ab muscles and pounded them hard.  I yelled out from the pain.  It wasn’t the mind-bending sting of the cane, but a wider, deeper pain, like my insides were getting rearranged. 

Then He hit me harder, same spot.  This one upped the pain ante quite a bit and I screamed louder.  Oh God, a different pain but getting into agony.  Bam, another hit, just as hard but a tad lower on my abs.  Another scream.   Sir kept going lower on my abdomen, brutalizing my muscles, hurting my innards, inflaming my skin.  Each thud peaked in torment, a literally gut-wrenching pain, spreading outward and inward. 

Then Sir decided to move back and forth, hitting off center, same areas, abs below my navel.  The ball felt like a pile driver, hammering into my abs.  Each thud splashed sweat away in droplets.  I could take this kind of punishment.  This was a manly torture, right in my ridged ab muscles.  It hurt to tense them, but I had to, sort of a natural way to protect my gut. 

OK, my lower abs were now turned to mush, time to move up.  Sir swung the club against my upper abs, just below my ribs.  I thought if this fucker hits my ribs, that hard ball’s going to crack bone.  He carefully did not let that happen, but that didn’t stop Him from tearing into the musculature below my rib cage, which He fid with a vengeance.  Just as brutal as a full uppercut.  My diaphragm was getting brutalized also, making it hard to breathe without deep, inner pain. 

The blows kept coming, now randomized all over my fuckin’ torso.  Then the inevitable:  my diaphragm and stomach started to spaze out, prepping for an upchuck.  As Sir did with Terry, He spotted the telltale signs and reached for the plastic bucket.  He held it under my chin as I lost my dogfood dinner.  Wave after wave of contractions until I hit the dry heaves.  He held the bucket in place until the whole spastic event was over.  Then He handed the bucket to Terry who emptied it in the corner sink and washed it out. 

I thought Sir was going to resume the beating, but He put the club away.  I sagged in the bondage and moaned:  “Sir, thank You, Sir.  Sir, thank You, Sir,” over and over like a puppet.  That’s sort of how I felt, like a programmed puppet.  Torture it and it thanks you for the pain.  What was I becoming?  A punching bag piece of slave meat?  I didn’t know what was next.

Then Sir told me:  “Get ready, boy.  I need to get My rocks off and you’re on the receiving end!”

OK, here comes another Master Fuck.  Fuck!   

NEXT: Ch 30, Dickie-boy Gets Plowed Proper

______________________

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

Chapter 28

The Cane

I guess I was lucky growing up that my step dad never discovered the cane.  We had abundant trees on the farm and a few were willows which, I’m told, make for good switches.  I heard guys talk about getting punished with thorn bush branches, nettles, even rose bush stems.  Caning is actually worse than a lashing with a whip, depending on the type of cane.  Instead of a branch, however, a real cane is the worse.  Branches are supple and can bend to absorb some of the force.  A stiff cane cannot.  The full force is delivered to your skin.  And the thinner the cane, the worse it can be ‘cause a thin cane concentrates the force in a narrow strip of skin.  Sir had the worst cane of all:  a thin, clear plastic rod about three feet long.  The rod had a black plastic handle.  And that’s what Sir was going to use on me tonight.

He held it up in front of me, saying nothing.  I almost threw up my dogfood in fear as my stomach knotted tightly.  My body gave an involuntary shudder when went behind me and started to tap the rod on my ass.  My ass cheeks were super-sensitized from the whip.  I imagined them criss-cross with red welts.  And this was going to be the target of the freakin’ cane. 

He kept tapping my ass, varying the pressure and the timing.  I knew the second He stopped tapping, the real caning would start.  And I was right.

The rod sliced through the air and Sir actually grunted as it hit my ass.  The pain was blinding, like a flash of lightning right in front of you., blood red lightning.  I have never felt that level of pain before; that’s the unique power of the cane, especially when wielded by a Master.  My throat hurt when I screamed the loudest in my poor life and I braced like a nutcase against the chains.

Getting whacked with a paddle produces a wide-spread pain.  It peaks but quickly fades.  A belt behaves the same.  A whip with multiple tails hurts even more as each tail cuts into your skin, but the pain is still spread out.  A single-tail, like Sir had just used on me, really focuses the energy and the pain.  But, like I said, the rod-type cane is absolutely the worst.  Maybe getting branded is worse, but Sir promised that would never happen, so the cane was going to be the ultimate discipline tool for my foreseeable future.

The cane pain peaks like Mount Everest and takes its good ol’ time ramping down to a raw sting.  Tears were streaming from my eyes as my body tried to handle the insane level of torment.  Drool was dripping from my open mouth and I think some snot hung from my nose.  OMG, my ears could have bled for all I knew.  I was panting from lack of air.

Then Sir started the tapping again, and again I shuddered without even willing it.  The tapping was psychological torture leading up to the real thing.  He tapped and tapped and I was going insane with anxiety and fear.  Then He struck.  Another stab of blinding pain from my ass.  I simultaneously screamed and flexed every muscle.  The level of punishment was insane.  I started to wonder if I’d survive.  Sir knew exactly what He was doing and had perfect control over the level of force He was using.  He took me to the peak of agony, but not enough to make me pass out.  That was the diabolical nature of His punishments.  He was a very experienced torturer. 

More tapping.  Did I start to cry?  I’m not sure.  I know I was pleading and begging Him to stop in between screams and gasps for air.  “No, no more, Sir!  Please!  Stop, please, Sir!  I can’t take any more, Sir!” alternated with “:A-a-gh!  AAAAAAGH!” when the cane struck again.  The gag garbled my begging, but not the screams.   

Terry told me later I got six strokes.  I hurt like it was six dozen.  My ass stung like hornets had attacked it, deep, throbbing sting of fire.  It decidedly did NOT ramp down, at least not right away.  The residual pain from a caning is unique; it lasts and lasts. 

Again Sir stood in front of me:  “I think that shook you up a bit, b oy,” He said, again lifting my head up and locking eyes with me.  “Most guys have no idea of what the cane can do.  Now you do,” He added.  “Just so you know, I’ll use the whips and belts a lot.  We’ll save the cane for when you do something really bad.  And I can see from your eyes that you are still willful, still have that little voice in your head that thinks you’ll win this tug of war we are in.  You won’t, I assure you.  I always win.”

He let His words sink in, and then He and Terry headed for the stairs.  He turned to me:  “When I come back, I think you know what’s next,” He leered as they went up the stairs.

I was confused for a few minutes.  My mind was still shattered by the pain.  Then I knew.  another Master fuck.  My shredded ass was going to be abused once again. 

NEXT: Ch 29, Dickie-boy Gets Gut Punched

“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

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

Chapter 26

Yeah, More Pain

OK, so. The evening drill was the same:  strip, self-collar, drop to slave A and wait.  I screwed up again.  When Sir came to us in the changing room, I looked over at Him to see what He was wearing.  Bad move.  That brought me two slashes with His whip across my back and a loud yell from me.

“Keep it up, dickie-boy,” Sir said to me crunching down on the back of my head with his heavy boot.  “Every time you screw up, you will get punished.  Even a dumb slave like you will eventually learn.  But if not, you can expect more of my whip.  As of now, I am doubling the whip lashes.  You will go from two to four, so feel free to disobey.  I do enjoy whipping that muscular back of yours.”

I remained silent, my eyes glued to the floor, afraid to move a muscle.  My back stung from the whip.  Being in the presence of Sir was going to require all my concentration and focus.  The slightest mishap and – whoosh! – I’d get lashed with his friggin’ whip.  Four times, no less.  ‘Houston to Dickie-boy, Houston to Dickie-boy:  Wake the fuck up!’

Sir continued to upbraid me:   “You have put me in a foul mood, boy.  There’s only one cure for that.  I need to hear you scream your guts outs and that’s exactly what we shall do right after dinner.  I will eat upstairs.  Terry-boy will bring you your dog food shortly.  Then you will get into slave A and ABSOLUTELY hold it until I return.  Do you fuckin’ understand, boy?” He yelled at me.

“Sir, yes, Sir!!” I shouted back.  “Sir, thank You, Sir!” I added, trying to be a good boy. 

He said nothing in return but stormed out of the changing room.  Terry motioned for me to get up.

“Go downstairs and I’ll bring you dinner,” he said.  “For God’s sake, after you’re done, get into slave A and hold it for dear life.  He might calm down.  I can’t promise anything.  Just do it.”

“Got it, Terry.  Thanks,” I said as we left the room.  I went down into the dungeon and Terry came down with my “dinner” a few minutes later. 

I ate the dogfood and lapped up the water.  I was afraid to lift the water bowl and drink from it.  Sir was surely watching on the video system and the last thing I wanted to do was rile Him up any further.  I got into slave A and held it like a statue.  After a while I was going out of my mind with boredom but I was at the same time terrified of moving a muscle lest Sir see it and get mad at me. 

He and Terry came down an hour later.  I could tell from the tone of His voice that He was a few notches down from His previous anger.  Whew! I thought.  Saved my bacon.  As usual, I was wrong. 

He ordered me over to the frame in the center of the dungeon, put me into a spread eagle stance, and then manacled my wrists and ankles to the cuffs on chains bolted to the frame.  OK, I thought, this was going to be bad.  He then gagged me with a bit gag.  I could tell as he pulled the strap in He was not happy. 

A bit gag is like a horse bit.  It’s a solid bar, in this case a metal bar covered with hard rubber.  When the straps are pulled in tight, it goes way back, stretching your cheeks.  Obviously it garbles any speech.  All you hear are weird vowels.  Like a ball gag, however, it does not stifle screams.  They come out full-throated and loud.  It also has an embarrassing side effect:  you drool like a baby.  It screws up swallowing, so the  normal saliva production trickles out of the sides of your mouth, down your chin and neck, and makes rivulets on your chest.  That’s part of the abuse and humiliation side of His training program.  Your basic bodily functions become embarrassing. 

“So, tonight, the program consists of a gut punching lesson with the club and I also want to show you the delicious impact of a caning on your ass and back.  You saw Terry-boy last night get a gut punch with the club.  Now it’s your turn.  As for the caning, I want you to experience one of the worst disciplines in the world, so you can file it away in your little brain and remember it later if you are tempted to disobey.  The gut punching and the caning will hurt a lot.  Feel free to scream.”

It’s always that last statement that scares me.  He didn’t say ‘groan’ or ‘grunt.’  It was scream.  I almost pissed myself in fear.    

“Terry-boy,” Sir said to his #1 slave:  “Get me the gut punching club and the plastic cane.”

“Sir, yes, Sir,” came the reply as Terry walked over to the equipment wall and retrieved the items which were on the menu for torturing me.  Thanks, Terry.  But, then again, you have no choice.  Just like me.

“Terry-boy will bring your dog food,” Sir said as they both left the dungeon.    

NEXT: Ch 27, A Vicious Night

__________________

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

Chapter 25

Fun and Games in the Closet

The morning routine for me was the same as yesterday:  startled awake, power washed, change into work clothes sans briefs.  At least I got clean clothes.  The jeans were maybe a size too small; they fit like a second skin.  I got another dress shirt, also a tad tight.  I knew I’d get stares and snickers at the office.  My metal cock cage sure made a tempting bulge.  We had a silent drive to work.  This time, however, Sir told me to be available at 10 for a special project. 

“Sir, yes, Sir,” came my reply.  Guess I was learning. 

I fiddled around answering emails until the designated time and then went to His office ten minutes early.  Terry nodded to me as I came into the outer room.

“Sir left orders for you to go to the janitor closet at the end of the east corridor.  You are to strip off all your clothes and stay there for a half hour.  That’s all He said, Dick,” Terry told me.

“Well, OK, I guess I’d, like, better get to it,” was all I could think to say.  I was stumped as to what this was all about. 

I went to the end of the east corridor, which is kind of deserted.  All the offices in that wing were unoccupied and even the corridor lights had been turned off.  Light came through from some of the offices which had open doors and there was a window at the very end of the corridor.  As Sir had indicated, there was a janitorial closet there.  It was small and smelled of musty mops.  I tried the light switch, but all the power was disconnected when this wing was shut down.  When I closed the door, it was almost totally dark except for a slight crack under the door.  I shucked my boots, jeans, and shirt, but retrieved my phone from my jeans pocket.  I checked the time; it was 10 on the dot.  A text message suddenly popped up:  “Feel free to scream.”

OK, then I realized Sir was going to play some nasty game with me, probably using the remote controller on my cock and ass shocking metal cage on my junk.  That split second of realization was followed by a strong electrical shock.  I screamed from the suddenness and intensity of the pain.  “A-g-h!” hurt my own ears in the small closet and I doubled over from the pain.  There was barely enough room for this in the small closet and my head lightly scraped the wall. 

Another shock.  Another loud scream.  This one dropped me to my knees.  Sir must have notched up the shock level.  I knocked over a bucket as I went down.  The metal clank was lost in my screams.  I had both hands on my crotch, gripping the cock cage, as if that could bring me relief  The pain continued for a good ten seconds, which, of course, seemed much longer.  When it stopped, I was gasping for breath and groaning from the residual pain in my crotch. 

Nothing happened for several minutes, but I was in an agony of anticipation and fear.  This waiting, knowing you have no idea when the next shock is coming, is truly diabolical.  Your stomach is in one constant knot of fear and you almost throw up from the anxiety.  I was naked and felt completely vulnerable, hopelessly tortured by a metal cage locked on my cock and balls and a large metal ball rammed up my ass.  There was no way I could get the device off.  You usually don’t find bolt cutters in a janitor’s closet.  Even then, Sir had said the device would react to any attempt at removal.  Probably send me insane from the pain. 

The waiting dragged on.  My head was totally mixed up between dread, anxiety, defiance, determination not to be broken, and a deep, sexual gratification from the punishment.  That’s what sex slaves need:  pain, discipline, punishment, abuse, humiliation.  I was getting a dose of this in spades. 

Then the wait was over, another devastating shock.  I screamed and doubled over until my head hit the floor.  “AGH!  A-A-A-HH!”  My own screams were deafening in the tiny closet.  My cock, balls, and ass were on fire from the electricity.  I knew I would be permanently damaged, ruined for life, if this kept up.  It stopped, leaving me almost crying from relief.

My skin was covered in sweat and I was still doubled up on my knees, forehead to the floor.  If felt like slave A except this time my position was not voluntary.  It was a instinct, an automatic reaction to intense crotch pain.  Think of getting kicked in the balls.  That’s the kind of pain the device could produce. 

My thoughts were shattered as another jolt of electricity had me screaming again.  I fell over against the door and wound up in a fetal position, just like being in the hole.  There was no escape!  All I could do is cord my muscles and scream.  And scream.  This one went on and on, I don’t know for how long.  I completely collapsed when it finally shut down. 

I happen to glance over at my cell phone, which had fallen to the floor in my agony.  There’s was another message on it:  “Several other Masters have joined in on the fun.  You have twenty minutes to go until We’re done with you.” 

I knew Others at the company also had remote controllers for Their own slaves and for any other slave within range.  What I didn’t know was the result of multiple remotes going off totally at random.  The shocks came very fast this time, no pattern, .  Shock/scream/spaze.  Shock/scream/spaze, over and over.  I laid on the floor, knees to my chest.  My whole body shook with each shock, each scream.  All my muscles were cramping from being flexed so hard.  My throat was getting sore and my mind was getting fuzzy.  The torture just went on and on.

But, like I said earlier, all tortures eventually come to an end.  They have to so the next torture can take place.  I couldn’t believe it when the wave of shocks seemed to end.  I kept waiting for the next one, but there wasn’t any.  Guess they were done with me.  Or, at least for now.  I tried to relax.  I mean, the fetal position is sort of comforting, if a little embarrassing.  Then I realized I had to piss – and there was no pad like I had in the hole.

Then I realized the torture was truly over, my half hour of agony was done.  I laid on the floor until the urge to piss got too strong to ignore.  I grunted as I slowly got up from the closet floor.  My skin was still sweaty but I had to get dressed so I could hit the men’s room.  I felt like a proverbial wet dish rag.  All my joints and muscles hurt, plus I was shredded from the screaming and struggling. 

I hit the men’s room, the only pleasure I got all day other than lunch with Terry.  He told me he know what was going to happen to me when he conveyed Sir’s orders. 

“So far that week at least three other slaves had been ‘sent to the closet,’” he said.  “I remember my own sessions there.  Sir doesn’t send me there anymore, thank God.  I guess I’ve graduated from basic training.  You’ll see, Dick.  Sir has a program and I’m afraid you’re trapped in it.  I’m not allowed to tell you more.  Sir insists you be surprised at each step.”

“Well,” I replied.  “Guess you’re right.  Pain, pain, and then more pain.”

“Yup,” Terry said.  “That’s the program.  From what I’ve seen so far, Dick, I know you can take it.”

All I could do was sigh.  That’s my life, now.  Terry nailed it:  pain, pain, and more pain.

I got a big taste of that later that day when we returned to Sir’s mansion dungeon. 

NEXT: Ch 26, Yeah, More Pain

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

Chapter 24

Master Fuck

He moved in close behind me and teased me by running His cockhead up and down my crack.  It stung when he crossed a welt and I groaned at the renewed pain.  Then He centered his dick over my asshole and applied gentle pressure, another tease.  I tried to move away, but the bondage stretch in the frame was so tight I couldn’t budge an inch.  My ass was trapped for His total abuse.

Then the push in.  I did scream at that one.  His cock stretched me wide and I was mortified to have a cock breaching my body under these circumstances.  This was not fun in the showers.  This was a brutal rape and I was in hard  bondage. 

Then the plunge.  Another scream as his hips grazed my highly bruised ass cheeks, stinging the skin, smearing blood and sweat into the welts.  He made this worse by moving his hips in small circles, churning my gut in an obscene way. 

Sir started the in and out, playing with the speed, keeping me off balance.  Sometimes He thrust like a jackhammer, pounding my ass.  Other times He was slow, almost sensual, or, at least sensual for Him.  All I could do was struggle in the bondage and groan at the pain of the invasion.  My own cock was struggling to get hard but the damned cock cage prevented it and my cock and balls ached for release. 

Then He picked up and I realized He was getting close to His cum.  This didn’t take long.  Guessed He was primed from the beating He had given me.  He started to shout from pleasure and I was screaming from the pain in my gut and my ass cheeks.  “Yes!  Ya!” from Sir mixed with “A-a-gh!  A-a-h!” from me in a frenzy of sexual fulfillment.

I could feel Sir’s warm splooge spurting inside me, completing the rape and humiliation.  I was truly just slave meat, a muscular ass to be used and abused.  I once heard the phrase ‘cum dump.’  Well, that’s what I was, a piece of sex meat for Sir’s perverted pleasure.  Let me tell you, this knocks you down a few notches. 

Sir pulled out with a plopping sound.  Then He boasted of His satisfaction:  “Ahh!  Nothing like plowing a whipped ass!”

I heard Terry chime in:  “Sir, yes, Sir!” 

Of course, I knew he had gone through this many times over his two years with Sir. 

I wondered what my fate was going to be after three abusive projects.  Didn’t take long for me to find out.  Sir unfastened my wrist and ankle shackles, while Terry helped me stay standing.  Sir then used some kind of spray on my back and ass.  It stung at first but then seemed to soothe the welts. 

“This is a special medication I use on my slaves.  It will hasten the healing of your welts so I can whip you again without getting blood all over the place,” Sir said.

I managed a “Sir, thank You, Sir,” but the gag garbled it.  I guess He got the message. 

“Terry-boy will fix you out in chains and then it’s off to the hole.  I promised you at least another night there.”

Another garbled “Sir, thank You, Sir!”

Sir left the dungeon and Terry eased the ball gag from my mouth.  My jaws hurt from the hyperextension of the ball, but that was the least of my concerns.  He decked me out in the heavy chain harness bondage, helped me over to the floor cell, and then hoisted me into it.  I slowly curled up on the floor, very happy to be over the torment and humiliation.  All I had to do now was survive another nightmare night in the punishment hole. 

Everything hurt as I curled up in the fetal position.  I didn’t bother to take inventory.  I just coasted in the temporary respite from agony and abuse.  I was back in my rabbit hole for another night of cramped muscles, sore joints, wetting the bed, and now with the added attractions of a stinging back and a sore ass.  OK, so maybe I took inventory. 

NEXT: Ch 25, Fun and Games In the Closet

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

Chapter 23

The Cat-O-Nine Tails

He was in a terrible mood.  “You stupid fuckhead!  Don’t you remember anything?!  My orders were to get into slave A IMMEDIATELY after you finished eating.  What did you do?  You wondered around the dungeon like a fuckin’ tourist!  Don’t you remember the dungeon has total video surveillance?!  Didn’t you learn anything?!  Well, that’s going to change and change right tonight!  Get over onto the platform and stand in the frame!  Now!!” He barked.

I jumped up from the floor and scampered over to the raised platform in the center of the room.  Then I stood in the center of the heavy wooden frame bolted to the platform.

“Raise your hands up and out,” He ordered.

“Sir, yes, Sir” I immediately complied and He shackled my wrists into leather cuffs already on the frame on short chains.  He didn’t have to lock the buckles; there was no way I could reach them. 

Then he kicked my right leg:  “Spread your feet wide apart, right against the frame!” came the order.     

Another “Sir, yes, Sir,” trying to placate him by perfect obedience.  It didn’t work.  As I spread my legs, my body dropped an inch or so and extra strain was put on my wrists and shoulders.  The wide stance was uncomfortable, but I’ve had my legs split farther in wrestling bouts. 

“Terry-boy, get the cat and a large ball gag,” came the order.

“Sir, yes, Sir!” came the required reply.  He walked over to the equipment wall and brought back the items. 

Continue reading

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

Chapter 22

Two Projects

We drove in silence to the office and I went to my cubicle, hitting the men’s room on my way.  I had to take a crap real bad.  Sitting in my workstation chair with no briefs on was sexy, but again I couldn’t enjoy the situation due to the tight cock cage – and the potential of a remote zap at any moment.  That kept me on edge most of the time.  Occasionally I got lost in my project work, which provided me the only peace in my new life.  I had lunch by myself; Terry was busy.  Without breakfast I was famished.    

I still wondered who else in the company had been to the “retreats,” fitted out with remote zappers, and enslaved to an executive.  Some of the guys looked like they had over-sized bulges, like a cock cage or something, but the maddening thing was that nobody said anything about “it.”  Kind of like Fight Club.  I did find out a few names, but that was much later in this story.

At five we met at Sir’s office and the three of us went back to Sir’s mansion.  Terry and I rapidly stripped and got into slave A awaiting the Master.  I had learned not to say a word during this time, but I slipped up when Sir came into the room:  I looked over at Him to see what He was wearing.  Today he had high rubber boots, hip waders, actually, and a tight-fitting rubber T shirt, which showed off his good build.  He had a rubber jock on also.  Big oops.

Slash!  Slash!  Slash!  I got three lashes from his single tail in rapid succession.  I yelled out from the searing pain.  Slaves were permitted to yell, at least, without asking permission.  The initial blistering ramped down to a bad stinging so I could stop yelling.  Sir waited until this step.

“I can see you are going to be a problem slave,” He said walking over to me. He put his rubber-booted foot on my neck and pressed down hard.  I struggled to hold my head rigid, but I grunted from the pain and humiliation. 

“That calls for some special training,” He continued.  “Tonight there are two projects for you.  The first is a severe whipping to try to convince you that the rules, all the rules, must be followed exactly or there’s more heavy pain in your future.  The second concerns dinner.  You will have supper, but not with us.  I am going to begin your dog training by feeding you delicious dog food along with a bowl of water.  Your hands will be bound behind your back, so you will have to find some way to eat and drink.  Terry will provide you with that very shortly.  The beating will be later, after our supper,”  Then they both left the room.  I stayed there in slave A.

Terry returned within a few minutes.  “You are permitted to get up now,” he said and I jumped up to the at-attention stance. 

“No need for that with me,” he laughed.  “Follow me downstairs.”

We went down to the dungeon.  At the foot of the stairs there were two dog bowls.  One had brown stuff in it and the other was clear.  There was a distinct odor of meat. 

“First, I have to put these on you,” Terry said, brandishing a set of handcuffs.  “Put your hands behind your back,” he ordered. 

I felt the metal cuffs close down on my wrists and heard the locks click shut.  It hurt to crunch my back which still stung from the most recent lashes.

“Sorry for that, but that’s what Sir wants.  Sir wants you to have your supper here and then get into slave A when you’re done.  We will have our dinner upstairs.  I guess we’ll be back in an hour or so.  Don’t forget:  slave A when you’re done eating.”

“Thanks, Terry,” I said.  “I guess,” I added smiling at him. 

“It’s actually not all that bad.  I know it’s degrading, but that’s part of Sir’s program,” he replied.  “Just do it.  That’s how you survive around here.”  Then he went back upstairs and I knelt down to have my doggy feast. 

As Terry had said, it wasn’t all that bad once you got over the idea of eating like a dog.  The mush had a strange taste, but vaguely resembled beef.  At least that’s what it smelled like.  The water tasted good, washing away the dog food taste.

I finished up my “meal,” and then decided to take a closer look at the toys Sir had on the equipment wall.  The assortment of paddles and whips and canes was extensive.  I twitched a bit imagining what they would feel like.  There were a few hoods, all of them elaborate with straps and metal studs.  Collars ranged from a huge one designed to immobilize a guy’s head to small chain links connected by a key lock.  Then there were the tools to torment a guy’s cock and balls:  plastic presses, odd metal and leather harnesses, a variety of long, thin rods, some with beads along them, clearly designed to go painfully up a guy’s dick,  Ouch on those!  There were loops of chains, coils of rope, leather thongs, and a small assortment of wrist and ankle cuffs, all with locks on the buckles.  My familiar heavy chain harness was there, hanging from its enormous metal collar.  Man, I hated that thing. 

Then I sauntered back to the base of the steps and got down into slave A the best I could with my hands behind my back.  All my forward weight was on my forehead, so I did slouch down a bit to rest on my legs.  I stiffened up into the proper posiion when I heard the door to the kitchen open.  Sir was coming back.

Let the tortures begin!

NEXT: Ch 23, The Cat-O-Nine Tails

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

Chapter 21

Eventually Morning

All tortures come to an end, if only to get you ready for the next one.  My second night in the hole came to an end.  I was humming to myself again when I heard metallic clanking on the cell’s door.  Someone was fiddling with the lock.  Yeah!  Then the sound of the latch sliding over and – FINALLY – the door above me was slowly opened.  Room light flooded my cell and I squinted from the brightness.

When I could finally focus, I saw Sir standing over me, dressed in a suit and tie for work.  Terry was off to the side, naked, of course, except for his collar, cock cage, and boots.  Sir ordered me to stand up.  Terry got down on his knees and reached down into the cell to help me.  At least the angry redness on his torso had vanished overnight.  He still winced a bit when he moved. 

I groaned from the pain as all my joints and muscles protested.  They were stiff from the hours in the cramped position.  The full weight of that damned collar was once again on my shoulders and I had to watch my balance as I painfully stood up. 

Terry inserted the lifting fork under my arms and attached it to the hoist hook.  I was slowly lifted out of that damned cell.  When my feet cleared the opening, he grabbed me by the chain between the collar and waist, pulled me off to the side, and then lowered me to the floor.  I was very unsteady finally standing.  He unhooked the lifting fork and sent the hoist hook to the ceiling with the lift button on the control box.   Then he removed the fork from under my shoulders.  That felt good. 

Sir stood there watching all this until Terry was finished.  “You stink, boy.  Looks like our little slave boy wet the bed!  How naughty!  Terry-boy, hose him down and finish up here.  Then both of you get into Slave A until I’m ready to leave.”

“Sir, yes, Sir” Terry said. 

I missed my cue.  Sir unhitched his whip, went behind me, and delivered two more slashes on my back.  I yelled from the flash of pain and was a little confused as to why I was whipped.

“When I give an order, you will answer properly.  Now, do it!” He said.  “You were told to get into slave A after getting cleaned up.  Will you never learn?”

OK, OK, I thought.  That was my fault.  I presumed his question was rhetorical and didn’t answer.  It wasn’t.

He hit me twice again and I yelled again.  Then I stammered:  “Yes, Sir, I’ll learn, Sir.”

“Not right” He yelled.  “Good God, you’re slow.  I don’t know how you do your job.”

I realized I had left off the first ‘Sir.’  This Guy was really touchy.  “Sir, yes, Sir!  Sir, I will learn, Sir!” I said loudly, trying to placate Him.

“That’s better, boy,” He replied, hitching the whip back to his chaps belt.  He turned and abruptly left.

“Come on,” Terry said.  “We don’t have too much time.”

I followed him through a door I hadn’t noticed before off in another corner of the dungeon.  It led to a room with a tiled area on the far wall. 

“Stand on the tiles while I hose you down,” Terry told me as he uncoiled a garden hose from a bracket on the wall.  He turned on the cold water and sprayed it all over me.  It felt good at first to rinse the dried sweat and urine off, but then the stream stung when I turned around and he hosed my welted back.  He worked as quickly as he could.

“OK, sport, now the chains come off,” he said.  “Sir has loaned me the key.”

It was the greatest relief in the word to be out of the chains and have that ridiculously heavy collar off my shoulders.  “Oh, man,” I said to him.  “That feels wonderful.”

“Good, good.  I have to tell you that Sir is furious with you over your cursing him out last night.” He added.  “That’s why Sir activated your remote shocker.  He laughed when you screamed from the pain.”

“I sort of thought so and I certainly regretted it as soon as it happened,” I replied.  “Is that why He’s in such a touch mood?”

“His moods are unpredictable.  You have to get used to that.  Look, we have to hurry and get dressed for work,” he said with urgency in his voice. 

I followed him upstairs, still dripping wet.  We went into the small changing room we had first visited yesterday and put on the same clothes we had worn then, although Terry instructed me to go commando today. 

Then we went back to the foyer and got into slave A on the floor as we waited for Sir.

NEXT: Ch 22, Two Projects

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