Jeremy's Punishment

Dear Diary,


My second day here in the S*** home, and it certainly was an eventful one! I rose early this morning; I wanted the opportunity to observe Jeremy before he left for classes, mainly to see if our discussion last night had any effect on him at all. As I expected, the potential for discipline had no effect at all.


I joined Nathaniel and Louise in the dining room for breakfast. Breakfast and dinner are served directly from the kitchen, while lunch is a do-it-yourself meal, unless there are guests planned for a luncheon. Breakfast is served promptly at 7:00 AM and dinner is served promptly at 7:00 PM. Nathaniel and Louise told me that Jeremy is persistently late for both meals, causing great inconvenience in the kitchen, where food has to be heated up or remade in order to accomodate him. I told them that this practice is to stop immediately; if Jeremy is late, he doesn't eat, and his tardiness is duly noted and discussed during our disciplinary meetings. They have given me free reign to discipline Jeremy in whatever way I feel necessary, and have agreed to stop catering to his petty demands. At 7:25, Jeremy chose to join us for breakfast.

"Sorry I'm late, gramps...just couldn't get my shit together this morning. Oh, and good morning granny and K!" He was starting off today in a very testing frame of mind. I made a few notes in my book, then looked at him.


"It is a pity you chose to be late this morning, Jeremy. Breakfast is over. I suggest you plan to be on time for dinner."


Suddenly, a loud car horn honked repeatedly in the driveway. "That's Bob, gotta run!!!" Jeremy dashed out of the house and headed off to class. I reassured Nathaniel and Louise that the next morning would be much calmer.


I spent the rest of the day getting to know the staff and exploring the house. I visited Jeremy's room, and was appalled, absolutely appalled, at the condition he leaves his room in. I summoned Betty, the maid, in order to question her about Jeremy's habits. 


"Betty, is Jeremy's room always like this?" I asked, taking a good look at Betty while she considered the room and her answer. She is an attractive young lady, probably 25, and is very good at her job. She may be a bit cheeky, and she wears skirts that may be a little short for her position, but I have never heard her be disrespectful in any way...which is a pity, because those short skirts show me the promise of a very enjoyable spanking session!


"Yes Ma'am" she replied. "I clean it every other day, in fact, it is on my schedule for today."


"You won't be cleaning it today, Betty, and hopefully you won't be cleaning it anymore at all" I informed her. "Jeremy is a grown man and can care for his own room and his own things." I noticed a towel lying in the middle of his bed, and when I picked it up, it was obvious what it had been used for.  "You mean you even have to clean up this kind of thing?"


"Yes Ma'am" she giggled. "I think he does it on purpose, trying to show off or something."


"Well, no matter...you will not be dealing with this any longer, and if Jeremy says anything to you about it, complains to you in any way, you are to report to me, understood?"


"Yes, Ma'am!" She is definitely an excellent employee...if only she wasn't quite so good ~sigh~

Late in the afternoon, I took the time to compile my notes from the day, made sure all appropriate entries had been made into the Infraction Book, had a wonderful, relaxing bubble bath and prepared for the evening. I heard Jeremy come home from school, and heard him yell for Betty from his bedroom door.

"Yes Jeremy?" I stood near my door so I could listen to the conversation.


"You didn't clean my room today!" He sounded, not really angry, but more worried.


"No, Miss Kiley instructed me that I am to no longer clean your room, and I am supposed to take any instruction from her as if it were from your grandparents." I might have to spank Betty just for being SO good!


"Damn!! I was worried this would happen...ok, thanks Betty." I then heard a loud SMACK!! and a "Oh Jeremy!" from Betty as she walked past my room...perhaps there was hope for her yet !

Jeremy appeared on time for dinner, which amazed us all. He was polite, attentive and made excellent conversation throughout the meal. After dinner, I reminded him that I expected him in my room at 9:00 PM sharp, and he assured me he would be there.

His knock on my door was hesitant. "Come in, Jeremy" I called, and he entered and closed the door behind him. I had positioned my spanking chair so it was near the bed. As I put him over my knee, I wanted him to be able to rest his upper body on the bed...we were going to be at this a while, and I didn't want him to be too uncomfortable.


"Jeremy, your behavior today, in the brief time I saw you, has been reprehensible. I am surprised that, even after our discussion last night, and your awareness of the punishments that would be in store for you, you still chose to start today off on the completely wrong foot!"


"I guess it is just habit, Miss Kiley, I'm sorry" He looked everywhere but at me, his hands behind his back and his embarrassment quite obvious. 


"Well, Jeremy, telling me you're sorry is quite nice, but it doesn't change your punishment at all. Come here and stand in front of me."


"But...but, Miss Kiley, I really tried, and it won't happen again...I was on time for dinner! I promise, I won't be late for breakfast again!" 


"No buts, Jeremy, come over here and stand in front of me!!" He stood motionless, staring at the carpet. "Jeremy! NOW!" He, very reluctantly, came to stand in front of me. "Tonight will be, barring any future issues, the most severe punishment you will receive from me. I understand you have been here in your grandparent's house for 6 months, and your bad behavior started about 5 months ago. Therefore, we have five months of correction to catch up on." "but...but...5 months??? That's not fair!!" "Jeremy, do NOT interrupt me! Your behavior has been reprehensible and you must suffer the consequences. I have talked with all the members of the household and have made a list of all the things you will be punished for. Please review the list, and we can discuss anything you feel is incorrect. I may or may not remove an item from the list but, unless there is a very good reason why I should do so, as far as I am concerned the list is complete." I handed him the Infraction Book and he began to read, muttering to himself "yes...oh I remember that...dang, I didn't think they noticed that...did I? Oh right, I did...shit" He handed the book back. "I take it everything appears correct?" "Yes, Miss Kiley" He gave every appearance of embarrassment and discomfort,  but again, I noticed the growing bulge in his pants...his body gives away his excitement, and I plan to use that to my advantage.


"Good...drop your pants"


"Wh-wh-what??" he exclaimed.


"You don't think I am going to spank you over your pants, do you? Drop Your Pants !!" With that, I reached out and unbuckled his belt. He stood there, seeming rather surprised at my demand. "Fine! If you are not going to do it, I will do it for you!" I stood, removed his belt, unbuttoned and unzipped his pants, and yanked them down around his ankles, leaving him standing in his t-shirt and boxers. He was not only greatly aroused, he was also greatly embarrassed, which made his arousal even more apparent. I must admit to my own arousal, he is a fine, strapping young man and preparing to take him over my knee was very intoxicating. 


I sat back down on the chair and spread my legs slightly. "Come stand between my legs, face the bed, and lay across my knee." He positioned himself over my knee, and I could feel his erection pressing against the inside of my thigh. I locked his near leg beneath mine and took up my hairbrush. "You will take 5 strokes with the hairbrush for each week that you have been in this house and have backtalked either your grandparents or the staff. That is 100 strokes. They will be swift and hard, but not so hard that you are not able to take more...ready?"


He squirmed in my lap "Please, Miss Kiley, not 100 strokes, please!! I promise, no more back talk, no more cursing, please not 100 strokes!!"


"100 strokes, Jeremy, is very fair...don't worry, relax and it will be over before you know it."


I started slowly, covering his bottom thoroughly with the first ten strokes. Oh how I love having a squirming young man across my lap, the sound of the hairbrush as it smacks his bottom, the heat I can feel as his ass begins to warm to my ministrations. Each time he squirmed, I could feel him rubbing his erection against my thigh, and I purposely squeezed my thigh harder against him. I gave him ten more strokes with the hairbrush
then pulled down his boxer shorts.


"Wh-what are you doing?" "Pulling down your underwear, of course...you don't expect me to continue to spank your covered bottom, do you? A bare bottom spanking will be the norm for you after tonight." I softly stroked his bare bottom with my hand, feeling the slight warmth from the spanking, knowing it would only get hotter and better.


Twenty more strokes and he was begging "Please Miss Kiley, please, no more, I promise, I will be a perfect angel, please, don't spank me anymore, I will be good!!" He squirmed harder, and his cock was so hard it felt as if it might burst as he pressed it ever harder against my thigh. "Jeremy, you still have sixty more strokes to go...I will be quick with them, then we will take a break." Twenty more strokes, fast and hard, during which he tried to put one hand beneath himself...I know he wanted to masturbate, so I grabbed his arm and held it behind his back as I swiftly administered the final forty strokes. 


I pulled his boxer shorts back up. "Stand up, and take a break." He stood, torn between covering his erection and rubbing his behind. "Starting now, there will be no more back talk from you, young man. When you are told to do something, you will do it, without question. Although you are an adult, you are not the authority in this house, and I expect you to respect your elders. Do you understand?" "Yes, Ma'am" he whispered, then he cleared his throat and said loudly "Yes, Ma'am, I will respect those in authority over me."


"Very good...now, take of your shorts, and bend over the edge of the bed." 


"T-t-t-take them off???"


"Of course, take them off or I will take them off for you." He quickly removed his boxers and bent over the edge of the bed. I picked up the belt. "You will now receive two belt strokes for each week you have been late for meals, late for class or missed a meal or class completely. That is forty strokes with the belt...are you ready?" "Oh Miss Kiley, please, not forty strokes...can it be one stroke for each week? Twenty strokes? Please, Miss Kiley, I promise it won't happen again...I was on time for dinner tonight, and I will be on time from now on, and I won't cut classes, or be late to class, or be late with homework ever, I promise, please, not forty strokes!" "Forty strokes, Jeremy...it's not that much, I promise." I made quick work with the first twenty strokes, then stopped and carressed his bottom, flaming red from the hairbrush and the belt. Stroking his bottom gently, I allowed my hand to slide briefly between his thighs, and he moaned softly as I brushed against his balls, tight against his body. Although he protested the spanking quite vigorously, his excitement was apparent and I knew that the end of our session would insure his future obedience. I rapidly finished the final twenty belt strokes, then sat on the bed next to him, stroking his hair as I told him "Well done, Jeremy, you are taking your punishment very well. I am extremely pleased with you...you are going to be very well behaved from now on, aren't you my boy?" "Yes, Ma'am...I am going to be so good...you don't even need to spank me anymore tonite, I have learned my lesson, and I won't ever misbehave again!" "Oh Jeremy, we are almost done...just one more thing to do. If you like, you may climb up on the bed, on your knees." He moved onto the bed, trying to keep one hand under himself. I pulled his hand out from under him, brushing my own hand against his cock as I did so, purposely, of course, I wanted to keep him on edge. 


I picked up the cane. "You will now receive one stroke with the cane for every week you have been in this house and have been disrespectful to your grandparents and the staff. You must learn to address your grandparents properly; you must learn that your poor personal habits show a lack of respect for those who work here, especially Diane and Betty. Your room is a disgrace and that you expect Betty to clean up after you is disgusting. Diane will not longer wait on you when you are late for meals or miss a meal, and Betty will no longer clean up after you. Your friend Bob, who picked you up this morning, is incredibly disrespectful to this house, and you are to be waiting for him every morning so there will be no more horn honking that early in the morning. Do you understand?"  "Yes Miss Kiley...so that is twenty strokes with the cane?" "Yes, Jeremy, twenty strokes with the cane and we are done...ready?"  His "Yes Ma'am" came very reluctantly. 


I took some small pity on him, and eased off on the cane just a bit, but it still made its mark on him, and after the twenty strokes, he was trembling, trying not to cry. I sat on the bed, and pulled him onto my lap, stroking his hair and telling him "That's all, Jeremy, we are all done now. You have been very, very good, taking your punishment as I would expect a fine young man to. You have learned some very important lessons tonight, and from now on, it won't be this bad." Continuing to speak quietly to him, I began to stroke his shoulders and his chest lightly, feeling him relax against me. His cock, however, was fully erect...I knew one touch would be all he would need, and at the same time, one touch would be all I needed as well. "Jeremy, why don't you step into the bathroom and take care of yourself, then clean up." He went into the bathroom, and I watched in the mirror above my dresser as he examined his behind in the bathrrom mirror, furiously stroking his cock as he felt the welts that had formed. I matched my own furious strokes to his, and orgasmed as he came, quickly composing myself before he came out of the bathroom.

I helped him get dressed, hugged him and watched him as he went down the hall to his own room. "Good night, Jeremy. Tomorrow is a brand new day, with a brand new attitude!" "May I have until the weekend to clean my room?" "Of course you may...sleep well, and I will see you at breakfast!"

Only an hour, dear diary, but sometimes it feels like a marathon. I am off to bed, and we will see what tomorrow brings !!


K