An Evening in the Headmaster’s Office

By Miss Em

This is the fifth of several stand-alone stories about a strict, yet caring headmaster, Eric Davenport, and the girls at his school.

After dinner, I returned to my office to get ready for Helen Archer and Leslie Carlton to arrive for their canings. While waiting, I busied myself with some paper work and the planning of Saturday’s detention.

About 8pm, I brought a straight back chair over near my desk for the girls to lean over while I dealt with their bottoms. I placed two canes on my desk and the punishment book. Then I returned to my paper work.

At 8:15, there was a soft knock on the office door. I walked to the door and let two very concerned-looking young ladies in and asked them to stand facing the wall until I finished filling out the punishment book. Both complied without a word, so I returned to my desk.

“Come stand in front of my desk, please ladies,” I commanded after about fifteen minutes. Helen and Leslie slowly approached my desk. Helen, the more confident young woman, stared at the canes, while Leslie burst into tears.

“Oh, Headmaster Davenport,” Leslie began. “Please don’t do this. I am so, so, so sorry, and I will never EVER leave campus again without permission.”

“Oh, stop whining and pleading, Leslie! I told you, we are going to get caned and there is no way out of it,” Helen chastised her friend, before addressing me. “Look, Sir, if you don’t mind let’s get this over with, I still need to complete my Algebra homework.”

“You’ll have plenty of time for homework in my detention session tomorrow. But you’re right, we need to get on with this. I’ve instructed your dorm mother to see that you are both in bed before ten.”

“TEN! Really, Davenport, do we look like nine year olds that need extra hours of sleep?”

“Miss Archer, I have had enough of your attitude,” I said firmly. “Suppose you show Miss Carlton the correct position for a caning. And if you would stand over here please, Leslie,” I directed pointing her to the front of the chair so she could view the caning without seeing the after-effects.

Rolling her eyes, Helen took her place behind the chair. “Do I have to take my trousers down, Davenport, dearie?”

“Yes ma’am, and if I don’t get an apology for that insolence and a change in your attitude, you can have the eight strokes on your bare bottom.”

“But Sir,” she started. I put up my hand for her to stop.

“It will take less than three minute for Mrs Jordan to get here,” I started picking up the telephone receiver. “Now I suggest you think carefully before you speak.”

Helen lowered her head. “I’m sorry Headmaster; I was out of line. I’ll be more careful. I didn’t mean to be disrespectful. Please, don’t call Mrs Jordan.” Helen begged looking into my eyes.

“Very well. Get those trousers down and bend over that chair,” I demanded as I picked up the slightly larger, but none-the-less flexible, cane. “Now, reach on over and grab the front legs. I don’t want you interfering or getting up before I tell you it’s all right to do so. Understand?”

“Yes Sir,” she said, before following my directions.

I placed the cane directly across the middle of her see-through panty-covered bottom. I drew back and swiftly applied the first and second strokes, leaving about ten seconds between them. I did this because it is very hard to place more than six strokes evenly across a young woman’s bottom without some over-lap or crossing. By doing this, the two almost immediately together, the two stokes meshed and formed one welt. Helen moaned ever so softly.

I placed the next two strokes above those middle stripes. I spaced them evenly and about 15 seconds apart. SWISH! CRACK! “YEOW!” A short wait and again: SWISH! CRACK! “YEOW!”

Helen wiggled her legs, causing her bottom to sway side to side. “Be still, Miss Archer,” I directed. “We’re only half way.”

“Yes, Sir, I’ll try but my bottom is really stinging.”

“Then I must be getting my message across, Miss Archer?”

“Yes, Sir.” As she responded I placed the fifth and sixth strokes on the lower half of her bottom. Again I spaced them and allowed about twenty seconds between each. “Ooooooh! Siirrr! Pppleeease! No more, I won’t ever leave campus again! I promise! Plea-ease!” Helen started to reach back and cover her panty covered bottom.”

But her hands quickly returned to the chair when I sternly asked: “Do you want extra stokes, Miss Archer?”

“NO! NO, not extra! I’m sorry,” she cried as her weight collapsed into the chair. “I’m sorry. I’m sorry.”

I looked at Leslie Carlton who had been looking on too petrified to move or speak. “Miss Carlton, come hold your friend’s hands.” I directed. She stood still as if she didn’t hear me. “Miss Carlton!” I shouted; Leslie looked my way. “Come; hold Miss Archer’s hands.”

Leslie knelt on the floor in front of the chair. “I’m sorry, Helen,” she whispered as she took hold of Helen’s hands.” Helen just nodded.

I placed the cane against the lowest part of her bottom, drew the cane back, and let go a full force stroke. “Aaaarrggg!” Helen moaned. I saw an angry red welt start to form across Helen’s bottom as her panties offered little protection to this area. Leslie brush tears from her friends face.

“Last one, Miss Archer. Remember to stay in position until I give you leave to stand.” I placed the cane just below the last welt. I planned on the last stroke landing on the tender area where her bottom met her legs. I intended for Helen to remember this correction every time she sat for at least a week. I swung the cane; it was a full force strike to that tender sit spot.

“Eeeeeeeooooooooouuuch!” Helen’s scream was loud and long. The cane did its job and placed a welt across the bare pale skin of her upper thighs.

I had her stay in position for a minute before letting her rise. “All right, Miss Archer, you may get up and fix your clothes. I need you to hold Miss Carlton in place.”

“Yes, Sir,” came her soft, tearful reply.

While Helen struggled with her trousers, I took a moment to speak to Leslie. “Do you understand what I expect from you, Miss Carlton?”

She nodded and brushed away tears. “Sir, I don’t think I can take six strokes of the cane.”

“You can and you will. I’m going to ask Miss Archer to help you stay in place, so you don’t earn extra strokes. However, if you are ever in my office again for discipline, I expect you to take your punishment bravely. I do not want to cause you pain or discomfort, but that is the consequence for bad judgment and misbehavior. Do you understand, Miss Carlton?”

“Yes, sir, I understand. I’m really sorry, Headmaster. I won’t leave campus again.”

“I appreciate your apology, but it doesn’t prevent the punishment. Now, prepare yourself and get over the back of that chair. Miss Archer, if you would come help Leslie stay in position, please.”

Helen was gently kneading her own sore bottom. “Yes, Sir,” she said before turning to her friend. “Come on Leslie, get it over with.” Leslie nodded her head, lowered her navy trousers, leaned over the back of the chair, and showed her non-regulation light blue bikini briefs. Helen took hold of both of Leslie’s hands.

I picked up the lighter cane and approached Leslie’s left side. Swishing the cane a couple of times I saw her tense and wiggle her bottom in nervous anticipation of what was to come. I did not make her wait long. remembering corporal punishment was new for her. “There will be a short wait between strokes, Miss Carlton; I need you to remain in position until I tell you to get up. Do you understand?”

“Yes, sir,” came her tearful reply.

I immediately placed the first stroke across the middle of her bottom.

“EEEEEEEEooooooooouuuuuucchh!” Came Leslie’s scream of pain.

I could see a red tramline forming from the first stroke. I waited only about ten seconds before laying a second above the first.

“OOOOOOOOOOHHHHHHHHH!” Came another shriek.

I didn’t wait long before placing a third stoke between the first and second.

“YEEEEEEEEOOOOOOOOOW!!” Leslie wailed, before she managed to break loose from Helen’s grip. She started to stand and reached for her bottom. “Please, no more! Headmaster, please I’m so, so, sooo sorry, I won’t ever cut classes again.”

Before I responded, Helen was pulling her friend back over the chair and scolding her. “Are you crazy, Leslie? Do you want extra strokes? Stay over the chair.”

“I can’t take any more, Helen, I can’t.”

“You have to! Now be still!” Leslie struggled against her friend’s hold, but this time Helen held on tightly. “I’m sorry, Sir, it was my fault she got up. Please don’t give her extra strokes.” Helen frantically explained. “I’ll take them if you have to give extra.”

“Just hold her down for the last three,” I demanded. Then I applied a firm quick stroke below the first. Leslie wailed and collapsed in a torrent of tears. In doing so, she presented the lower portion of her bottom in a higher, better position for striking. “Keep her in this position, Miss Archer. Two more, Miss Carlton.”

Leslie moaned, almost whimpered, as I drew back to administer the fifth stroke of my cane. This one landed right on the junction of her buttock and thigh. There was very little protection from her panties at this point. I waited only a few seconds before delivering the last stroke a little lower and on her upper thigh. No protection; she would remember this every time she sat down for the next week.

“YEOW! OOOOuuuch! OOW! Oooooo!” Leslie bawled as I replaced my cane and took a seat behind my desk.

“You may get up and fix your clothes, Miss Carlton,” I suggested, hoping to start her calming down process. “Perhaps you could help her a bit, Miss Archer.”

“Yes, Sir.” Helen replied. She helped Leslie stand and gently pulled her trousers over her hips. Leslie winced and whimpered. “I’m sorry, Leslie, I know it hurts.”

“Girls, if I could have you both here at my desk please. We will finish this and get you off to bed.” Helen took Leslie’s arm and helped her walk to my desk. “I hope you have both learned your lesson here tonight and we will not have to repeat this. You are both very capable students, but you must be in your classes to demonstrate your abilities.”

“Yes, Sir,” came two soft, tearful replies.

“Very well. Go by the infirmary and see the duty nurse. She will have some cream to apply to your bottoms. Then off to your dorm rooms and go to bed. I expect to see you here at 9.00 am, after breakfast and room checks. Bring your books, paper and pens. And don’t be late!”

“Sir, sometimes our dorm mother is late checking. Should we stay for the room check or come here?” Helen nervously asked.

“I’ll make sure Mrs Toby checks out your rooms early enough for you to be here on time. Okay?”

“Yes, Sir, thank you.”

As the girls turned to walk away, I felt uneasy because I knew they were both frightened. I called them back. “Ladies, wait a moment, please.”

I saw them look nervously at each other as they turned to face me again. I stood and walked toward them. Leslie was still trying to control her tears. “Is there something else, Headmaster? I mean did we forget something?” Helen asked.

“No, Helen, you didn’t forget anything. I just wanted to tell you that I’m proud of the way you took your punishment. I know it is difficult to take a caning. And Leslie, you did exceptionally well, considering you have never received corporal punishment before today. Let’s hope this will be the last time, for both of you.”

“Yes, sir,” they both replied quietly.

“Well, you best be off to see the nurse and then get some sleep. Tomorrow will be a very busy day for you.”

I opened the office door to let them out and saw my adopted daughter, Rebecca Shaw, and a police officer. Both Helen and Leslie stared at Rebecca and the officer, so I scolded gently: “Girls, I believe you have somewhere you need to be.”

“Oh! Uh, yes, sir.”

“Sorry, sir. We’ll see you in the morning.” They left heading towards the infirmary.

“Yes. Goodnight, ladies.” Then I turned to Rebecca, who was obviously upset and shaken about something. “Becca, what is this about?”

She immediately broke into tears and an apology. “Oh, Daddy, I’m sorry. Please don’t let him take me to jail. I’m so sorry.” She buried her head in my chest and continued to cry.

“Jail?” I looked at the officer. “Could you please explain what is going on? Why did you escort my daughter home this evening?”

“Are you Eric Davenport, Sir?” Asked the officer.

“I am. I’m Rebecca’s legal guardian and Headmaster of this school. Is Rebecca in trouble?”

The male officer, who was about 40 years old, spoke. “I’m afraid so, sir. She was caught shoplifting and the young man who was with her managed to get out of the store with over $500 of jewelry. Your daughter had a fifty dollar bracelet on and was following him out the door when the store clerk stopped her.”

I took Becca by her shoulders and held her at arm’s length. “You were with that young man from St. AndrewsAcademy, weren’t you?”

“Yes, sir; I was with Jeff, Jeff Coles.”

“Officer…?” I paused and waited for a name.

“Sorry, Sir; I’m Officer Timothy O’Conner.”

“Well, Officer O’Conner, I appreciate you bringing Rebecca back this evening. Is she under arrest or do I need to pay for the jewelry?”

“No, sir, I talked to the store manager and since the bracelet was recovered without damage, he didn’t want to press charges for a $50 item. But he did want the young man arrested and the young lady punished by the school or her parents.”

“Oh, I assure you, she will be dealt with as soon as you leave. She has an appointment with my tawse.” I glanced at my adopted daughter, who was now sobbing and wiping tears from her eyes.

“That might present a problem, sir,” the officer said. “You see sir, the store owner said he wanted to witness the punishment tomorrow.”

“That is just not possible, Officer. I have responsibilities here and students to supervise tomorrow. I also try not to postpone punishments for my students or my daughter. Let me give this store manager a call, see if I can work something out.”

The Officer O’Conner gave me a business card and I called the store. Mr Holmes, the manager, said he was shocked that one of my girls was involved in this robbery. He was co-operative, but wanted to know the name of the young man. I told him I would give the young man’s name to the police officer, but that I was sure the headmaster at the boy’s school would see that merchandise was returned and that the boy was punished. I also explained that the young lady involved was my daughter and that she would be receiving two punishments; a severe spanking from me as her father and then another paddling tomorrow at the end of detention for embarrassing the school. I also assured him that Rebecca would work off the cost of the bracelet and I would have her donate the money to a charity of his choice. This seemed to appease him and I suggested that he join Rebecca and me the next evening for dinner, so she could offer an appropriate apology. Mr Holmes agreed.

“Officer O’Conner, Mr Holmes and I have come to an agreement.” I walked to my desk. “The young man my daughter was with is Jeff Coles. He is a student at St. Andrews Academy. I’ll be glad to call the Headmaster, Paul Michaels, and let him know what has happened, if you’d like?”

“Thank you, Sir, but no; I think this is something I should discuss with him in person.”

“Well, here is the student’s name,” I said offering him a piece of paper. “If necessary tell Paul, Headmaster Michaels, to call me for information.”

“Yes, Sir, thank you. Well, I’ll leave you to talk with your daughter.”

“I promise you, it will be more than a talk.” I looked at Rebecca, who nodded in understanding. I walked the officer to the main entrance and said goodnight. Then I returned to my office.

Becca had placed the tawse on top of my desk. “I figured I’d save you some time.”

“Can you tell me why you took the bracelet?” I inquired.

“I didn’t take it. I tried it on and I didn’t mean to wear it out of the store; I was trying to catch Jeff. I didn’t want him to leave me there.”

“Did the two of you plan to steal from the store before you went in?”

“Oh, no, Dad, no! I didn’t know Jeff had taken anything until after the lady at the store stopped me. I had put the bracelet on and just forgot about it when I ran after Jeff. Oh, Daddy, please believe me. I wasn’t trying to take it.”

“You are very lucky the store manager is willing to let me deal with you and not press charges for stealing or shop-lifting.” I reprimanded.

“Yes, sir, I know. But I wasn’t going to take anything!”

“How did the clerk or store manager know that? Especially when your boyfriend walked out with $500 worth of jewelry? And you walked out after him with a $50 bracelet on your wrist?” Rebecca just hung her head and wiped away more tears. I continued to admonish. “Do you realize you could be in jail right now?”

Tears fell freely and Rebecca collapsed into my arms. “I’m sorry. I’m so, so, sorry, Uncle Eric. Please don’t hate me!”

“Whoa! I could never hate you and what’s this Uncle Eric? I thought I was your Dad now.”

Becca turned away. “I figured you wouldn’t want to be my Dad anymore, since I’m so bad.”

I pulled the scared girl back into my arms. “You are my daughter and I’m your Dad; that is not going to change. And you are not bad,” I scolded. “What you did was wrong and I promised the store manager that you would be punished. But Becca, Sweetie, I love you and nothing you do will change that.”

“I love you, too. And I am sorry, I was really stupid.”

“You’re not stupid, but you weren’t thinking. You left the store wearing a bracelet. I promised Mr Holmes you would be properly punished. I think we need to take care of that now.”

Rebecca pulled away. “Do you want me across the desk or over the chair?” She asked as she unsnapped her denim jeans.

“The chair will work; this won’t take long,” I said, picking up the tawse as she took her place at the back of the chair.

“Panties too?”

“No. Just lower your jeans.” She slowly slid them down past her thighs. “Down to your knees, Rebecca.”

“No, Daddy, please,” she begged, knowing her legs were about to be striped.

“Now!” I ordered.

She whimpered, but pushed the jeans slightly below her knees. Then, without my saying anything, she placed herself over the chair, her hips perfectly placed to raise her bottom for discipline and her long legs at a 45-degree angle.

“There will be six stokes on your bottom and six to your thighs. Be as still as you can and I’ll do this quickly.” She nodded and I proceeded.

This tawse was a little longer than the standard school tawse and, since it was split, it was like being struck twice with a belt. I did not have to use a lot of force to cause pain. In less than 20 seconds Rebecca’s bottom was red. I placed two stokes on the tender sit-spot and the last four strokes across her upper thighs. I knew she would feel these every time she sat down for the next few days.

I rubbed her back a moment then helped her stand. “Come on, Sweetie. You’ll be okay in a few minutes.”

“Daddy, that really hurt! I think that it’s worse than the cane,” she cried and buried her head in my shirt.

“I’m sorry, Baby, you’re going to hurt for a few days, but you’ll be okay. Now fix your clothes. It’s getting late and we both have to be up early. Detention starts at 9.00. I expect you to join my group.”

“Yes, sir. Guess I’m grounded for a while too?”

“We’ll start with two weeks. If you can work off the fifty dollars in that time, I’ll lift the restriction.” She sniffled and nodded. “Here, blow your nose,” I said offering her a tissue, before we left my office.

“It’s going to hurt to sit tomorrow, isn’t it?” She asked as we walked back down the hall, and into the night air heading for our campus apartment.

“Yes, it is meant to be a reminder of your misdeed,” I explained.

She slipped her hand in mine. “Are you angry with me?”

“No, Sweetie, you know I don’t administer any form of punishment if I’m angry. I was disappointed, and if I see that young man of yours I may have a few angry words for him.”

She giggled. “Oh, Daddy.”

“What do you find so funny, young lady?”

“You wouldn’t get upset with Jeff, would you?”

“Oh, I am upset with him, taking you to a store, stealing, leaving you to take the blame. I’ll be talking with Headmaster Michaels before I go to bed. I don’t think you realize how close you were to having a criminal record, young lady.”

I unlocked the apartment and ushered Rebecca into the living room. “Sit down a minute.”

“Am I still in trouble?”

“Sit down.”

“Oooo,” Becca eased her hands under her legs and tried to ease her discomfort. “Oh, gosh! If this couch hurts now, I don’t want to think about how those wooden desks are going to feel tomorrow!”

I reframed from laughing at her. “I told you, you will be uncomfortable for a few days. Rebecca, you need to understand your punishment is not over.”

“I know. Grounded for two weeks and detention tomorrow.”

“What happens at the end of a Saturday detention?” I inquired.

Her face went pale, as she remembered our school policy. “Nooooo! Dad, please. You can’t paddled me, too. Please, no.”

“The whipping tonight was from me, your dad. Tomorrow, as headmaster, you’ll receive a paddling, as I’m required to do. You are fortunate no-one from the school saw you; there would have to be a school wide viewing of your punishment.”

“That would be so embarrassing, but… I guess that’s the point, huh?”

“Yes ma’am; the embarrassment of a public spanking hopefully would prevent you from repeating the offense.”

“Oh, Dad, I won’t ever shoplift; I promise! Tonight really was an accident. I didn’t mean to wear the bracelet out of the store.” Rebecca got up from the couch and rubbed her bottom as she explained.

“I’m sure you won’t,” I concurred. I followed her and gave her a kiss on her forehead. “Why don’t you go get ready for bed and I’ll fixed some of my famous cinnamon hot cocoa.”

“Sounds good, Daddy,” she replied softly before throwing her arms around my neck. “I love you and I’m glad you’re my Dad.”

“I am too. Now, go get into your PJs.”

After hot chocolate, Becca went to bed without argument. Spankings tended to leave her exhausted. After an assurance from Paul Michaels that Mr Jeff Coles was about to be suspended and go before a judge, I turned my thoughts to Saturday’s detention. While I waited for sleep to come, I thought about how I would approach the upcoming detention day with Rebecca, Leslie Carlton and Helen Archer (who had skipped classes), Chelsea Hunter and Beth Schwartz (who had plagiarized), and Margo Tuttle and Janet Linn ( who had started a lunchroom fight). My job would be to make the detention so memorable that none of these girls would want to return.

The End

In the future, I will tell you about Saturday Detention for Girls from The Brandon Academy.