The following story is fiction about a youth getting to discipline the big boss, his son and his secretary at the office and elsewhere initially by chance but then on request.  The story contains scenes of spanking and strapping.  If these subjects are offensive, uninteresting or if you are a minor (i.e., child) please leave now.

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Strapping the Boss

By

YLeeCoyote@juno.com

Preseason

I was on the final sweep of the day when I heard the noise from Manager Terrence Ackerman's office.  It was unusual that anyone was still about since it was after normal office hours and the cleaners were not due for another hour.  I had to collect all the outbound mail, make sure it was properly stamped and get it to the post office on time.  If I was late my immediate supervisor, Mr. Riefer, would rip up my ass just like my dad had (and, I'm sorry to say, still does even though I'm sixteen).

I would have loved to hang about to listen and hopefully get a peek at the action but I had to keep to my schedule and route.  I did listen very carefully for it was the all too familiar sound of a hand spanking a naked butt.  I had been hearing that sound since I was a little kid and although I had graduated to the strap, my kid brother still got spanked by hand.

Compared to what I was used to the spanks sounded a bit wimpy and I wondered about that.  The spankee, with a low masculine voice, was promising to be good.  I lingered a little bit longer (while carefully watching the time) and then I heard: "That's all, you naughty little boy.  Now, pull up your pants and finish your work.  I have to go."

That was a big surprise for the latter was the voice of a woman, certainly not Mr. Ackerman's voice.  It could only have been Mrs. Deroy, his secretary, who was a petite woman in her thirties.  The image I got made me laugh for Mr. Ackerman was a big man and it was ludicrous that he was being spanked by the little lady.  That was reinforced when I heard him say: "Yes, Ma'am.  Thank you, Ma'am."  I rushed to move on before I was seen and accused of spying or even worse, spanked.© YLeeCoyote

That night I dreamt of Mr. Ackerman.  In my dream he was only a boy of ten although of adult size.  He was dressed not in his usual three-piece suit but a sailor suit with short pants – a little boys' outfit – and I was in charge of him.  I heard my dream-self lecturing him that he was a naughty little boy for hitting a girl, getting muddy and earning a spanking.

"Please don't spank me, Daddy.  Please.  I'll be a good boy.  I promise." he whined.  But that did not do him any good whatsoever for I just stripped him completely and took him over my lap.  A few hard spanks turned his little bottom bright red and stopped his struggling.  He kept whining and promising and even started to cry as I continued to spank him.  The sobs turned to cries and then to full fledged blubbering for I had turned his little bottom a hot fiery red.  When I let him up, he just hugged me and continued to cry.  He was now a well-chastened lad.

Oh, how I desired that it had been real although it was very exciting even just in my dream, proven by the crusty deposits on my pj's in the morning.  How I wished that I could spank Mr. Ackerman for real.

First Game

It was Sunday afternoon and I was heading home after a day biking with my buddies.  I had separated from them because they lived on the other side of town and this was a quicker route for me.  I liked the route because there was very little traffic and I could feel free.  I was near the middle of a stretch through the woods when I saw a car stopped in the middle of the road.  A man was by the car waving as he was obviously stuck for this was not a place to ambush anyone.  Of course, I stopped.

The first surprise was that the man was Mr. Ackerman.  He had run out of gas.  He recognized me also as one of his employees.  Of course, I had to help him.  He was positive that the car was OK and he even had a can for gas so if I could just get that filled and return it would be great.  I went back the way I had come and found a gas station.  I called my folks to let them know that I was delayed because I was helping Mr. Ackerman so if my friends called before I returned they would not be worried.

The gas station guy insisted that he couldn't put the gas in a plastic container and that he would drive me back in his service truck with a proper gas container.  Once there, the empty tank was quickly refilled and the car checked.  Mr. Ackerman was delighted for the car started right away and he paid the gas man who drove off. He also gave me a couple of bills in appreciation and offered to drive me home.  As we stowed my bike in the trunk, I said something that I immediately thought was very stupid.  "It's a good thing Mrs. Deroy isn't here.  She would surely have spanked you for being negligent and careless for running out of gas."  I immediately realized how indiscrete I had been.  I tried to think of something to say but Mr. Ackerman beat me to it.

"I'm afraid so." he said before he realized that he was admitting anything.

"I won't tell her, Sir." I said.  The devil then kicked me in the butt so I added: "If we take care of it now – mano a mano.  Waiting is awful."

«Oh fuck! What have I said?» I thought, «He's going to fire me on the spot.»  I was just about to apologize when we locked eyes.  I was frozen like I was in stasis.  Mr. Ackerman was processing for his expression was changing.

Then, suddenly he spoke, shattering the stasis field.  I was dumfounded for he agreed.  Well, I certainly was not going to argue with my boss's boss who signs my paycheck so I silently thanked the little critter with the triangular pointed tail smirking on my shoulder and waving his pitchfork triumphantly.

"Please give me your belt, Sir.  Then drop your pants and bend over the hood." I said.  Well, he did and I got into position to strap him.  A dozen times I raised up the belt and brought it down on his upturned ass with a loud WHACK!  This was nothing like those namby-pamdy feminine love taps he got from Mrs. Deroy but proper punishment for a man.  These were hard man cuts from a heavy belt which left him red and knowing that he had been well spanked.  Just like I knew I had been punished after either Dad or my boss ripped up my sorry tail. He took a few minutes to recover and then pulled up his pants.  I gave him back his belt and we drove off in silence.  When we got to my house, he helped me get my bike.  I thanked him for the ride and the money.

"It is nothing.  Thank you for what you did.  I needed that – badly."

I knew I was going to have another great wet dream that night as I walked my bike to the garage.

Minor League

For the next week two things were foremost on my mind.  Mr. Ackerman's bright red butt after I had strapped it.  Every night I jerked off to that red hot image and thinking of swinging a belt at it over and over.  It was most exciting to say the least.  The other thing was my situation at work.  Mr. Ackerman certainly could have had me fired without any difficulty at all.  Of course, I was extra careful when I was near his office as well as listening carefully for the sound of another spanking.  Well, I was relieved that the former never happened and regretted that the latter hadn't happened.

It was Mrs. Ackerman that I heard from early one evening.  She told me that her husband was away and she needed help with a man's job.  She did want to get into details on the phone but she knew that I was well qualified because she had discussed it with Mr. Ackerman.  As I biked over I had wild ideas that she wanted sex with me.  I had seen her at the office and she was not a bad looker but not for me.  I how could I tell her that I was not interested.  I was completely off the mark on that score.

She took me into the family room, offered me appropriate refreshments and explained.  Junior was the problem.  The barely teen had, with his dad away, gotten out of control and desperately needed a man's firm, hard and forceful hand to adjust his attitude.  She had called me, rather than let their friends and neighbors know.  "Would I spank the lad for her?" she asked.

I agreed and got all the details from her.  Part of the problem was that the lad felt that an OTK spanking by his mother with her hairbrush was inappropriate at his age.  I thought about the options and went to see Junior in his room.  I certainly was not surprised that he did not want to deal with me and thought that he was too old for a spanking anyway.  Little did he know that his father was still spanked.  "You are NEVER too old for a spanking, young man," I told him definitively, "not even when you're a grown man with kids."

He scoffed at that but I told him: "You are getting a spanking regardless.  We can do this the easy way with you acting like a young man and accepting your punishment or the hard way with you acting like a baby brat.  It's entirely up to you, Junior."

He refused reason so I just grabbed him and sat on his bed.  He struggled a bit but I quickly got him under control with his legs pinned between mine and twisting one of his arms up his back so he could not move.  "The longer you struggle, the longer your spanking will be, Junior." I said as calmly as I could with my guts raging.  As he struggled, I used my other hand to unbutton his shorts.  I then taught him an important lesson why sagging style is not good by easily yanking his shorts down and then his fancy boxers and even his basic briefs.  He had the cutest buns which I joyfully rubbed prior to spanking him.

He had potty mouth for he was yelling the most nasty things about me and my tastes but one hard SPANK shocked him into silence except for a howl of surprise and pain.  I admired my hand print on his butt check so much that I made a duplicate print on the other cheek and paused before continuing.  I then proceeded to spank him long and hard.  Hard enough that I was worried about how my hand was hurting.  Fortunately for me, Junior gave in by going limp and crying.  I was sure he was ashamed to be acting like a baby but it was good for me.

I stood him up and frog-marched him into his bathroom where I grabbed a washcloth.  It was easy to get it wet and to squirt some soap onto it.  I surprised him by shoving it into his mouth.  He did not like that at all.  "Little boys who run off their potty mouths get them washed out with soap like this."  Junior did not want the washcloth in his mouth at all but I kept my hand over his mouth to be sure it did its job.  Then I removed it and let him spit.  That did not remove the nasty taste.  I did not let him rinse out as I wanted it to persist.

I dragged him back to the bedroom.  He was a different lad now that he had a red hot tail, a sickening taste in his mouth and surely knew that I had zero tolerance for any of his antics.  "Now were we?" I asked rhetorically.  "Oh, yes, we were just about to decide how you're to be spanked for your intolerable misbehavior and upsetting your mother."

"You just spanked me!  Nothing more to talk about." he exclaimed rubbing his painful butt obviously upset by the experience.

"I spanked you for your insolence and disrespect with me.  Your potty mouth required a good washing for what you said.  Now there is still the matter your mother charged me to take care of.  Understand?"  He nodded just a little bit.  "I understand that you feel that you are too big to be taken OTK and spanked like a little boy.  I'll agree if you are willing to act like a big boy and bend over for a proper whacking."

Junior looked very wary but nodded agreement.  "I think a dozen with this should be about right." I said holding up a flip-flop.

"But I'm sore already." he whined. "True, but that your own fault.  Nevertheless, I'll give you a choice.  Just ten whacks now considering your tender state or fourteen tomorrow."  I then told him to go rinse out his mouth and that he had ten minutes to decide.

"What will it be, Junior?" I asked when the time was up.

Junior choose to get the ten immediately.  He handed me a flip-flop when I asked for it and assumed the position after dropping his pants.  Since he behaved properly, so did I and gave him the ten whacks alternating cheeks.  He was brave and kept in position without screaming through it all.  I praised him for that and left him to think about his behavior.

I let his mother know some of the details and she paid me as promised.  This was definitely a fun job.  My wet dreams increased and my worries about losing my job abated.

Double Header in the Office

I was despairing of getting to discipline either of the Ackermans again after a couple of weeks.  I knew that Terrence was around so that he would deal with his son and what was the chance like catching the old man in a transgression where I could act.  He surely wasn't going to run out of gas a second time.

I was surprised one afternoon when I finished the last pickup round that Mr. Riefer, my boss, told me that Mrs. Deroy had called and I was wanted in Ackerman's office ASAP.  He said he would deal with the mail and to clock out when Ackerman dismissed me.  I hot footed it there not knowing what awaited me.

Mrs. Deroy asked me to have a seat and then explained that Mrs. Ackerman had told her of my special skills with naughty boys.  She went on to say that there was a naughty boy waiting in the corner in there (indicating her boss's office) for me.  His offence was to have delayed doing a mess of paper work which required her and others to have to work overtime.  I couldn't help but to smile as I said: "Yes, I understand what is needed."  She explained that she would remain at her desk to assure that we were not disturbed but to lock the door anyway.

My heart was racing as I went into his private office.  I did a double take for Manager Mr. Terrence Ackerman, Senior was literally standing in the corner like a naughty little boy with his hands on his head and his pants down awaiting his father.  I took a while to adjust to this new reality.  On the desk was a paddle.  Since there were some Greek letters on it, I guessed that it was a fraternity paddle.  It was clear why it was there and what it was for.  This was definitely on-the-job-training.

"Procrastination and costing the firm money is very naughty, young man." I said sharply.  I could see Ackerman stiffen as he heard my voice.  Perhaps he had expected another namby-pamdy spanking from Mrs. Deroy but he certainly knew that was not in the cards anymore.  I'm sure that he remembered the strapping I had given him – a spanking that was appropriate for a grown man.  "Get your naughty butt over here and bend over the desk, boy." I barked and pushed the papers out of the way.  He obeyed silently, shuffling over because he was hobbled by his pants.

I raised and swung the paddle at the proffered target using moderate force for I was not sure how effective the paddle was.  It made a resounding whack and the naughty boy yelped.  It was a more effective weapon than the belt I had used the time I strapped him.  Almost immediately I could see the target turning red.  I repeated the operation and the effects were the same – more of the target turned red and Ackerman was gripping the desk so tightly that his knuckles were already white.  This was definitely a potent weapon to use to roast a naughty butt.

I got up to eight when he really showed signs of pain and yelled.  I kept at it until I had delivered ten whacks.  "That's it.  Get up, boy."  I said,  "I hope that you have learnt your lesson."  Of course, I was thinking that there must be lots of lessons I could teach him."  While he got up, I adjusted myself inside my jeans having already decided that I'd jerk off in the john as soon as I could.  "Back into the corner, boy." I ordered.

I was revved up.  I wanted to keep going but certainly Ackerman had been sufficiently punished, however, Mrs. Deroy was certainly far too smug and surely had failed to assure her boss kept to the schedule.  It was time for her to also get her comeuppance.

"Mrs. Deroy, come in please." I said opening the door.  Once she was in the office, I gave her a short lecture about how she had failed also.  She was quite surprised.  I moved a side chair to the middle and ordered her to stand next to it.

"Please remove your panties or knickers or whatever you are wearing so I can properly spank you."  Her surprise increased and she stood frozen.  I reached under her skirt, grabbed the garment and quickly yanked it down.  Then before she could object, I pulled her across my lap just like I had with Junior and lifted up her skirt to expose her wide woman's derriere.  (Incidentally, also getting a peek at her hairy sex.)

I raised my hand and brought it down just like she had on Ackerman's butt albeit a bit more forcefully.  She howled in pain and I continued spanking until she was crying and her tail was bright red.

I stood her up and called Ackerman from the corner.  "I trust that you both will tend to your jobs more diligently in the future." and with that I left.

I rushed to the privacy of the lavatory and basted my first shot in only a couple of minutes.  Then I repeated the operation more leisurely reliving the spankings I had just giving those two very naughty adults before heading home.  I sacked out early knowing I would have great dreams.

Double Header at Home

"I've got two naughty boys that need spankings!  Can you come over at seven today?" said Mrs. Ackerman on the phone at right after I got home from school today.  I told her certainly and biked over right after dinner.  I figured that Mr. Ackerman must have been away for the day and Junior and a friend, or more likely a cousin, were in dire need of male correction.  I must confess that my cock was full from the anticipation as I peddled over to the Ackerman's fancy place.  I was in for a real big surprise.

When she showed me into the family room I was not surprised to see two corners occupied by two male Ackermans with their hands on their heads.  One was Junior, just as I expected, but the other – the senior Mr. Ackerman – was a surprise.  Junior was there because he had been spotted fishing that morning rather than being in school.  He had insisted that he should not be punished and especially not by his dad because he was just following his sire's example.  For years he had heard his dad boasting that he had played hooky on the opening day of fishing season and that his grandfather had just laughed.

"Like father; like son." I said.  "But that does not make it right at all."

"Exactly, Drew," she said, "they both need to be spanked.  There is no statue of limitation on juvenile delinquency."  My questioning look led her to add: "And Junior should see that his father gets his just comeuppance – even after three decades – for his misconduct so that he does not do this again."  After a few more comments, she left us to tend to the unpleasant male business.  I did not tell her that it was not unpleasant for me as she did not need to know that.

I asked Junior if what his mother had told me was the whole truth and if he had anything to add.  He said that it was so I knew that I could proceed.  I ordered Junior to stay in the corner but now facing out and I called Mr. Ackerman from the corner.  "It is quite a disgrace that you boasted to Junior about how you were a very naughty boy thus leading him astray.  Playing hooking – even on the first day of fishing season – is unacceptable and your father should have taught you that.  The fish will still be there two days later when school is out.  Getting a proper education is most important." I preached.  Of course, although the lecture was formally directed to the Senior it was also meant for the Junior Ackerman.

The man was hanging his head in shame by the time I had finished.  (I was getting good at this and it was a lot more fun than when my dad lectured me.)  As Mr. Ackerman stood there with his son watching, I proceeded to undress him.  I unbuttoned his shirt and pulled it off him.  I extracted his belt and draped it over my neck before opening his pants which fell to his ankles and then pushed his underwear down.  "Take your shoes off and step out of your pants." I ordered sharply which he did silently.  Junior's eyes were huge as he watched his father being disciplined like a boy; like he was.  I'm certain that he surely knew that he would never be too old to be spanked.

"Over the end of the couch." I ordered and he got into position.  I folded the belt knowing just how effective it was and got into position.  I swung the belt hard knowing that Junior had to be impressed that a long ago crime was being paid for.  Over and over I swung that heavy belt and the target turned cherry red just as it had the first time.  Ackerman held tightly onto the cushions surely afraid of disgracing himself in front of his son by jumping up.

"That's all, boy.  I trust that you'll never play hooky again."

"Yes, sir.  Never.  I promise." he said rubbing his red hot tail.  I pointed to his corner and he returned.  He faced out copying his son's position.

I waited a minute and then turned to Junior.  He looked pale perhaps fearing that he was about to get strapped hard like his father just had been.  "Your turn, Junior." I said.

With trepidation, he walked over to me.  I striped him as I lectured him like I had his father.  After he had stepped out of his clothes, I told him to go fetch the flip-flop for his spanking.  Apparently relieved that I was not going to strap him, he rushed out and returned quickly.  I put out my hand for the flip-flop and he hesitated.  Then I was the one who was surprised.  Junior walked over to his dad, proffered the flip-flop and said softly: "Father, I was very naughty just like Mother said, for I played hooky.  I'm ready for you to spank me."

Mr. Ackerman looked at me.  The implied question was obvious so I just nodded indicating that he should go ahead.  I saw no reason to interfere between a man and his son, so I just watched.

"Yes, my son, your mother was right.  It was very naughty to play hooky."  Mr. Ackerman sat on the couch and Junior lay over his lap without another word.  I'm sorry that I mislead you.  He dropped the flip-flop and grasped his son tightly about the waist.  After a couple of rubs and gentle pats, he began to spank his son with his hand.  The spanks were hard and Junior yelled as his butt turned flaming red like his father's.

By the time Junior was lifted up, he was sobbing.  Mr. Ackerman held his son tightly as he sobbed on his shoulder.  "I'm sorry, Daddy, I promise never to play hooky again."

I saw that it was time for me to go as the two renewed their father/son bond.  "We'll go fishing this weekend" I heard him tell Junior, "when school's out."

The End

© Copyright A.I.L. February 11, 2013

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