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Last Wills and Testaments - Two

Kim's caning is repeatedly interrupted by the headmaster's secretary and phone calls

Preston and his wife Gail sat fidgeting in front of the massive desk of Janet Johnson, Attorney at Law.  Would the woman stop with the small talk and get down to business.  To the business of reading the Last Will and Testament of Preston’s now-deceased father, Irwin T. Lakehurst Jr.?  Finally she got down to the nitty gritty.

“I appoint my faithful attorney Janet Johnson, Esq. to be Executrix of this my Last Will and Testament and Trustee of the Irwin T. Lakehurst Jr. Testamentary Trust.”

Preston and Gail looked at each other.  “You?  Why you?  Is this normal?”

“Who’s to say what’s normal, Preston.”

“Well go on.”

“I bequeath one hundred thousand dollars to the Greystone Academy.”

“That much?  I know he was sent there himself as a teen, but.”

“The Academy is where your father formed his morals and guiding light through life.  He discussed that at length to me.”

“And his strictness.  Had it not been for that frigging academy he wouldn’t have used the belt on my rump at every opportunity.”

“Now dear.  Let’s not bring that up now.”

“My son Preston having not had the strength nor fortitude to handle the rigors of the academy, and having disgraced me by dropping out, I can only hope and pray that his son and my grandson Kim attend and matriculate at the academy.  To that end the trust is to pay all tuition cost and all other expenses for Kim to attend the academy.  It is my fervent prayer that my grandchild Kim shall reinstate the family honor by graduating.  In the event that he should be suspended or expelled then Preston shall have one year to whip him into shape and have him reinstated.”

“In the event that my grandson should not graduate before attaining the age of twenty then I leave that one hundred thousand dollars to my son Preston instead and the balance of my estate to the academy.”

Preston, the heir apparent, looked stunned.  He turned to look at his wife Gail for help.

“Miss Johnson, what if the academy goes defunct?”

“Highly unlikely.”


“Yes, Preston?”

“Won’t the academy have the incentive to see that Kim fails so that it can take my inheritance?”

“Possibly if it knew the terms of the will and trust.  But there is no reason now for them to know more than that all tuition and boarding costs will be paid.  Paid for four years, no less.”

“It’s a very strict school.  They believe in corporal discipline.  At least when I was there.”

“Preston here was a wimp back then, Mrs. Johnson.  That’s why he quit.  No backbone.  And that has cost us to this very day.”

“That was then.  Now is now with Kim.  Is Kim also a wimp?”

The lady lawyer didn’t need a voiced response.  The looks the two Lakehurst gave each other said it all.  Apparently Kim had inherited his father’s trait of wimpiness.  Or his parents had instilled it.


“Yes, Gail.”

“He does have a nickname.”

“That being?”



“Yes.  I’ve told Preston a thousand times that he needed to deal with Kim’s prissiness.  To use the belt.  But no.  No backbone, I’m afraid.  And now we are paying the price.”

“I don’t believe in child abuse, Mrs. Johnson.”

“Who said anything about child abuse?”

“They use the strap at Greystone.  Did you know that?”

“Not so.”

“Not so?  Well that’s a relief.”

“They now use the cane.  The rattan cane.”

“Good,” said Gail.

“Good grief,” said Preston.

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Archibald Yorkstone looked at sixteen year-old standing in front of his desk.  The diminutive nerd was looking around the headmaster’s large, handsomely appointed office for it was the first time he had been there.  Unsurprisingly the kid’s eyes had landed on the wall rack on which six rattan canes of various sizes and shapes and hues were rested.  The kid’s eyes behind those oversized horn rim glasses of his were squinted in trying to block out the image, but without success.

“Welcome to Greystone, Kim.”

“Thank you, Headmaster.”

“Did you find your room satisfactory?  I see that you share it with three others.” 

“Yes sir.”

“Did you manage to snare a lower bunk?”

“No sir.  They were already taken.”

“Well you’ll find that the upper bunks sleep just as well.  Right?”

“I was short-sheeted.”

“Oh my.  How did you handle that?  Did you give the rascals a piece of your mind?”

“They are all bigger than me, sir.”

“Did they hide your other sheet when you went to remake your bunk?  They often do that to extend their laughter.”

“I don’t know.”

“You don’t know?”

“I haven’t made it up yet.”

“Do you mean to say that you slept the whole night short-sheeted?  Slept in the curled-up fetal position?”

“Fetal position?  Oh. I guess that’s what you would call it.  Are you going to cane them sir?”

“Cane them?  That little prank is hardly an offense that warrants the cane.”

“Oh.  Good, for they would know that I tattled.  I hope that tattling is not an offense.  It isn’t is it?”

“Tattling is not an offense for we need informants.  But humbly submitting like you did is.  I can’t believe that you slept the entire night curled up in the fetal position out of fear.  That shows a total like of backbone.  While it is true that you are smaller than the norm for first termers that is more reason for you to develop backbone.  Wimps do not last long here at Greystone.”

“Yes sir.  I.  I.  I understand.”

“It grieves me that I must introduce you to the cane on your very first visit to my office.  This was supposed to be a welcome call.”

“I’m sorry to have you grieve over me, sir.  I apologize.” 

“Accepted.  Since this is your first visit to my office I shall show leniency.”

“No cane today?”

“Leniency by having you fetch the smallest cane from the rack over there.  The one at the bottom which I refer to as Baby Cane.”

“Ugh.  Ugh.  Thank you, Headmaster. That is most kind of you.”  Oh God.

 “In view of your being of short statue you can also fetch that foot stand there.  We’ll need to get your rump up.”

Archibald watched as the sixteen year-old nerd walked to the rack and took hold of the Baby Cane as if it were a serpent.  He watched as the newbie took up the small foot stand that had a ten inch platform from which four corner legs depended.

“Where does the stand go, Headmaster?”

“In front of the desk, lad.”

Archibald felt himself already getting aroused as he watched the kid place the foot stand down and promptly mount it still dressed out in his Sunday best with starched white shirt and bowtie and jacket while holding the Baby Cane.

“Here is your cane sir,” said Kim as he offered it to the still seated Archibald Yorkstone, Headmaster.

“Thank you, Kim.”

A silence came over the large, wood paneled office as Kim stood elevated a bit in front of the massive desk.

“Shall I hold the back of my jacket up for you sir?  You know, so that you.”

“I know.  Rather than that I want you to hang it up on the clothes rack over there.”

“Yes sir.”

As Archibald watched the kid walk towards the rack while taking off his jacket he spoke again.

“Along with your trousers and undershorts, son.”

The words stung like an arrow had pierced his back.  He paused in his walk and searched for words.  His search proved fruitless.  He resumed his walk.

As the sixteen year-old unbuckled his pants he felt the first of tears begin to form.  Oh lord.  What if the man saw this?  He would surely know that I’m a sissy.  But when he felt the cool room air envelope his legs as he hung up his trousers fear seemed to bring the tearing to an end.  At least for now.  Still he had to wipe away those that had formed which of course had caught the eye of the aroused headmaster.  Caning was such a labor of love for the man.

Back came Kim with his hands shielding his privates to the foot stand.  Once more he mounted it with his hands still over his privates.  He looked down to see the headmaster fidgeting with the Baby Cane as his eyes scanned the boy up and down.  Up and down.

“Bend over and put your forearms flush down upon the desk and take hold of the desk edge.”  Just as the kid was complying came a new voice spoke behind him.

“Excuse me, sir.”

“Yes, Mrs. Thorne?”

Kim turned his head back to see the headmaster’s secretary enter the room holding some papers.

“Sorry to interrupt but these really must get signed and sent over to the postman.” 

“No problem.”

Kim watched in amazement as the woman placed the papers down on the desk between his outstretched arms as if he wasn’t even there.  So routine it appeared.  It almost seemed that she was oblivious to his presence.  

With his forearms flush down upon the desk straddling the papers Archibald scanned them one by one before signing where indicated.  When he was done he simply thanked the woman and handed them back to her.  In turning to leave the office she walked by Kim who was still standing on the little foot stool bent over with his forearms on the desk.  She paused by his side and tucked the papers under her arm before taking hold of the kid’s shirttails and folding them neatly over his back.  She pressed them down neatly on his shoulders which left his butt totally exposed.  She was a slave to tidiness. 

“There we are.”

When Kim remained silent the Headmaster spoke.

“Aren’t you going to say something, Kim?”

“Me say something?  Oh.  Oh yes.  Thank you, ma’am.”

“You’re welcome.  Nice ass you have,” she said as she gave each ass cheek a friendly little love-pat.

“Thank you ma’am.”

When his secretary resumed her way out the headmaster pushed his leather chair back from the desk and stood with the rattan cane tucked under one arm.  A shutter ran up the boy’s spine as Archibald started swishing the room air with the Baby Cane.  But then he felt the Head’s hand gently and lovingly slide over his butt which was the highest point of his body.  “She was right.  You have a fine young ass, my boy.”

“Thank you, sir.”

“Fine for a girl’s, that is.  Do people tell you that you have a rather feminine bun, Kim?”

“Not really, sir.”

Swish. Thwick!

A line of pain formed across the center of his elevated ass.  Good God Almighty.

A silence fell throughout the office as the sixteen year-old struggled to absorb the pain.  This was what the Baby Cane did?  Imagine what the others would do.

“I must apologize, Kim.  I neglected to tell you what to say after each cut. You are to say in a forceful and distinct manner Thank you, sir.  That was one.”

No response.


“Oh.  Thank you, sir.  That was one.”

“Very well.”

The kid felt the length of the cane line up on his butt just below the line of fire that was growing from the first cut.

Swish. Thwick!

Kim’s hands gripped the desk edge so hard that his knuckled protruded and took on a light color.  A dirty white tint.



“Sir.  Yes, sir.  Thank you, sir.  That was one.”


“Isn’t that what you told me to say?”

“Good grief.  Use your head.  Think!”

“Oh.  Oh I see.  That was two.  Two, sir.”

“Of course it was.”

Kim felt the cane line up along a line just beneath the now two festering tramline welts.  Oh God.  Oh God no.  Wrong.

Swish. Thwick!

“Thank you.” His voice was interrupted.

“Mister Yorkstone.”  It was the voice of that secretary again.  The voice of Mrs. Thorne.

“Pardon the interruption again but you didn’t say whether you wanted to send the papers by Express Mail.  And there was one that you overlooked and didn’t sign.”

“Is the postman still waiting?”

“Yes, sir.”

“Put them back down on the desk.”

As tears welled up in the boy’s eyes behind his oversized black horn rim glasses Kim saw the papers as they were placed by the woman back down on the massive desk between his two extended forearms.  He watched as the man gently laid down the cane on the desk beside one of his two forearms and retook his seat in his leather chair.

Mrs. Thorne waited patiently as she watched her boss scan the papers again.  Then suddenly she spoke.

“Oh my.  Oh my.”

Archibald looked up to see her hurriedly taking a tissue from a box of tissues on the desk.  He looked to see that a droplet of tears had formed on the bottom of the horn rim of one of the kid’s oversized eyeglasses.  Fortunately she was able to dab it away just before it was about to fall down upon one of the papers.

“Good grief the boy is crying.  Crying after just three mild introductory cuts with Baby Cane.  You had better thoroughly dab his eyes, Mrs. Thorne.”

“Don’t you realize?  What’s the name?  Oh yes, Kim.  Don’t you realized that you were about to wet the documents and smear them.”

“I’m sorry ma’am.  It’s my first time, you know.”

“Don’t you realize that I would have had to print out a replacement sheet?”

“I’m sorry ma’am.  I’m sorry, Mister Headmaster.”

“That I’m sure we can all agree on.  Here are the papers back, Mrs. Thorne.  Let’s hope that he doesn’t go and nervously piss on them.  He-he.”

After giving the distraught sixteen year-old a few disapproving shakes of her head in disgust she took the papers and started to exit the office.  But something caught her eye right off.  The cute little butt of the wimpy boy with the three tramline welts in their staggered state of early growth and festering.

“If I may say so this is excellent work, Headmaster.”

Kim heard her words as he felt her feminine fingers go to sliding lovingly along each of the three fiery welts.

“Why thank you, Mrs. Thorne.  How gracious of you to say so,” said the man as he rose and took up the cane again.   “This one never tires of complements.”

“Well it’s true and the truth never hurts.”

“So true even if you are trying to butter up your boss.  Don’t you agree, Kim?”

“It never.”  He was cut off in mid-sentence as the woman went to giving his blistering welts mild spanks with her free hand.

“That hurts!”

“Nonsense,” said Archibald.  ”Those are just little love spanks of hers.”

“Well I must get back to the postman.  Excuse me.”

And with that she was off with the papers in hand but not before pausing when she heard the swishing sound of Baby Cane as it sliced through the room air and with a Thwick! strike boy ass meat for the fourth time.

Kim’s right arm collapsed as his right shoulder went down onto the desk.  His right face cheek followed.  

Archibald walked around to the back of his desk and leaned over until his own check was almost on the desk.  He looked into the large black rim glasses to see that Kim’s eyes were closed as he sobbed.  “Kim?”


“Is there a problem?”

“My butt.  It’s on fire.”

“Oh, is that all?  You had me worried there for a moment.  Now then, back up.  We’re trying to develop your backbone.  To give you backbone and fortitude.”

“Yes sir.  I’m sorry, sir.”

“Sorry that you neglected to finish your last call-out?”

“Oh that.  Yes, thank you sir.  That was four.”

“What about three?”

“Oh thank you too for number three.”

Archibald watched as the nerd pulled on the desk edge and righted himself.  He straightened the kid’s horn rim glasses which had cocked when his face cheek had fell onto the desktop.  He then straightened the boy’s bowtie which had also cocked to one side.

Swish. Thwick!

The sixteen year-old’s knuckles turned almost white as he gave the rear edge of the massive desk a death grip and gasp for air.

“Oh God, I thank you.  Thank you for number five.”

“There.  That’s better.  I believe you’re getting the hang of it.  But please don’t be calling me God.  I’m merely the Lord’s faithful servant.”

Swish    Thwick!

The boy’s arms and shoulders shuttered as his head swung from side to side.  Still he managed to keep his forearms down flush upon the desktop and to grip the desk edge.

“Thank you.”

Ring. Ring. Ring. Ring. Now it was the telephone on the headmaster’s desk.

“Excuse me.  Don’t go away.  He-he.”

“Hello.  Bob?  Interrupting?  No, not at all.  I was just welcoming a new boy.”

“What?  No problem.  You have a tee time?  Good.  Seven fifty?  Bad.”

Kim couldn’t believe this.  Here he was still standing on the footstool bent over with his starched white shirt draped over his back and his ass on fire and the headmaster was chatting away about some golf game.  When he took one hand off the desk edge to wipe his eyes Archibald casually slid the box of tissues over to him to use.

“Thank you, sir.  Oh, and that was number six.  Six, I think.”

As the phone conversation continued Archibald swiveled his chair and propped his feet up on the credenza that was behind him.  He laid the cane down on his lap and leaned back as Kim dabbed his tears away.  Oh how he yearned to reach for his blistered bare butt but didn’t dare.

“That hilarious, Bob.  Really?  You’ve got to be kidding.  Right there in the sand trap?  Unbelievable.  What a guy.”

Kim heard the door open behind him.  It was that Mrs. Thorne again.  In she came ignoring the bent-over new boy standing atop the footstool.  She took a position beside his and looked down at her boss as he continued to chat away with his feet propped up on the credenza.  Finally she gave a little cough to get his attention.

“Hold on a moment, Bob.  Yes?”

“Mr. English won’t be able to attend a three o’clock meeting.  Could we make it at four instead?”

“Four o’clock would be fine.  What?  Oh no.  I didn’t mean you, Bob.  I was talking to my secretary.  No.  The tee time is a bit early for me but I’ll make it.  Bye now.  Got to go.”


“Yes; back to welcoming our new boy here.”

Without taking his feet down off the cadenza he looked at the nerd of a new boy whose head was bouncing about with his mouth grimacing.  Mrs. Thorne had again paused on her way back out of the office to see how the kid’s ass was coming along.  She was taking quite an interest in it as she slid her fingers along the tramline welts.  That was the cause of his grimacing.  She was scaring the crap out of him for he well remembered her little friendly little spanks the last time she had visited his butt.  That was several cuts back.

“What do you think?” inquired the headmaster in soliciting another compliment from the woman.

“There is still some room.”

“Room?  Room for improvement?”

“Oh no.  Some untouched room still waiting.”

“Well good lord woman.  Don’t you think I know that?”

Poor Kim felt devastated.  The man wasn’t finished with him.  Oh God.

The sixteen year-old watched as the man stood with the cane in hand and walked around him.  Now two adult heads were bent down and hovering over his welted ass.

“See.  Down low here and here.”

“Precisely.  Since this area is the most sensitive I wanted to save it for last to give the boy some time to adjust to being caned.”

“I see.  Well of course.  That does make sense.  My you do do such good work.  I’ll tell them that four o’clock will be fine.”

Spank. Spank.




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