The Diary (Parts 1 and 2)

Chapter Twenty One: The Diary (Part One)

A long time had passed since I searched dad’s office and I hadn’t thought too much about my grandfather’s diary. I stashed it on the top shelf in my closet and had almost forgotten about it. Tonight I just felt as if I wanted to be alone in my room. So to kill some time, I brought old book down and began to peruse its pages.

The first entry was dated over fifty years ago, Jan. 1st. 1950. As I scanned the first few lines I was surprised to discover that my grandfather, Steve Bradley Sr., was a teacher at the Bolton Girl’s School. Dad rarely spoke about his parents. They both passed away before I was born. Dad told me that his father was a school teacher, but didn’t mention very much more. I found it very interesting that grandfather taught at the same private girl’s school that Amber now attended and so I continued reading the first entry.

I found out that my grandfather originally started his career at the prestigious Cartwright Girl’s Academy in New England. Apparently he got into some trouble involving one of the students and was forced to resign.

The next entry was dated Jan. 7th 1950.

When I interviewed for this position, I expected the headmistress to be some shriveled up old lady. But Miss Eileen Watkins is an attractive woman whom I would guess is in her early forties. I’m sure she didn’t completely buy my story about professional differences precipitating my resignation from Cartwright, but for the chance to get a qualified instructor at a bargain basement salary, I think she was willing to let things slide. Miss Watkins is tall and big built, but very nicely proportioned. She has a large rounded bottom that I would definitely like to get much better acquainted with and her breasts are sizeable too. I’m sure each one would make a very nice hand full.

At this point I stopped reading. Those previous lines sounded exactly like my thoughts. It looked like my inherited taste for women’s and girl’s bottoms went back further than dad. I continued to read on.

I believe I’ve found a kindred spirit here. Fred Persey is a dumpy little balding man, but looks are very often deceiving. For one thing, Fred is by far one of the most intelligent people at Bolton and I’m absolutely convinced he’s been sampling the wares amongst the students. I don’t blame him; I’ve seen the picture of his wife on his desk. Anyway I don’t know why I’m so sure about Fred’s extracurricular activities. He just has the look about him. I wonder if I have it too. Anyway I intend to walk carefully around the edges of the subject with Fred. If my suspicions are correct, he could save me a lot of time getting the lay of the land.

Jan. 10th 1950

There is a very attractive girl in my senior class. Her name is Susan Harding and she has that look about her. She’s just about as pretty as they come. I’ve noticed her watching me very intently since day one.

I’ve tried a little experiment with Susan. I returned her intent stare on two occasions, just to let her know that I’m aware of her. That little minx stared right back and didn’t as much as blink an eye. She’s a bold one alright. I’ve taken particular note of her body language and there’s sensuality to spare. She’s telegraphing her signals with a heavy hand on the key. She stretches and thrusts her breasts forward, crosses and uncrosses her legs at least a dozen times during the period, showing more and more thigh each time. She’s also good at the slow tongue over the lips with her sweet little mouth partially open. If it wasn’t for my recent setback, I guess I would have taken a few first steps with her already.

After reading this last entry, I knew grandfather’s diary was a find on par with dad’s videos. I knew it was going to be a fascinating read and I decided to pace myself. I resolved to read only a few entries at a time to make it last. I closed the book and replaced it on the closet shelf.

Chapter Twenty Three: The Diary (Part Two)

Late Sunday evening following our return from Aunt Vanessa’s, I spent a very long time in my room thinking about my sexual encounters; going all the way back to Jennifer. There was one recurring theme. None of my relationships seemed to get very far. Something always came up to spoil things for me. I told myself to stop the melodramatics. Since I couldn’t seem to get to sleep, I thought I might as well get out grandfather’s diary and do a little bedtime reading.

I picked up the narrative with the Jan. 24th 1950 entry.

I have managed to put the last two weeks to very good use. First I’ve rented comfortable living quarters in one of those large older homes that have been divided up into apartments. My new residence is within walking distance of the Bolton School.

One of my big accomplishments concerns Fred Persey. He and I hit it off immediately. In fact, my apartment is in a home owned by one of Fred’s acquaintances and I believe he had a hand in my getting it at a very reasonable rent. We’ve gone out to lunch together several times and our conversations were very interesting. Fred moves in some very high social circles. The explanation for this became clear the third time we went out to lunch. As we walked through the faculty parking lot Fred pointed to a brand new Cadillac and said, “Hop in Steve.”

As we cruised out of the lot I asked, “Do you mind telling me how you can afford a car like this on a teacher’s salary; especially the kind of teacher’s salary provided at Bolton?”

“Steve there’s one thing you should know about me. I’m the type of man who enjoys the good things in life. I need my luxuries. The best of everything is just about right for me. Now if you’re a very intelligent person and you need lots of money, there are several options. I chose the one best suited to me. I married it. Mary Ellen Sherwin was a very plain rich girl, who wanted a husband and I wanted money. Therefore, problem solved.”

“Now you may wonder why a very rich young woman would marry me, even if she’s not very attractive. One would conclude that there would be any number of tall, dark and hansoms, like you for example, who would be after homely little Mary Ellen’s money. The answer is simple my boy. There were a lot of others in the field; but I had the right equipment. To be very blunt Steve, I may be small and a bit plump; but I’m hung like a horse and believe it or not, Mary Ellen is hot as they come. Now there is one female who can’t get enough. I recognized that the first time I met her. It was at a Bolton fund raiser about seven years ago. There was a lot of false flattery flying around that evening and I could tell she saw through it all. So I tried the direct approach, got a date, had her panties off and the salami in on the first evening. The rest is history.”

Following this narrative I said, “I have to admire you Fred. You sound like a man who got his cake and is eating it too.

Fred chuckled and said, “I may be overweight; but that doesn’t mean I’m very fond of cake. There are too many other delicacies to tempt me. They can be nibbled on and eaten but they’re not necessarily food. These are the kinds of things that I sometimes run across in the class rooms at dear old Bolton and best of all, there’s always a fresh supply to choose from.”

Now we were getting into the area that interested me and I replied, “They do say forbidden fruit is the sweetest. It sounds like a man would be going pretty far out on a limb to pick the kind I think you’re referring to. I’ve had some experience in that orchard and I know if you take a fall the consequences can be serious.”

“Well Steve I suspected something of that nature in your circumstances. Obviously you’re right and I don’t need to tell you that the secret is in selecting just the right fruit to pick. A mistake in judgment could result in serious repercussions. But you had a soft landing. You’re still a free man and back in another orchar
d. I’m convinced that there’s a safety net and unless I miss my guess, it has to do with bad p
ublicity. The last thing any institution like Cartwright or even Bolton wants is even the hint of scandal. Since I believe we see eye to eye on the subject, I can tell you that for me the rewards have outweighed the risks.”

Feb. 6th 1950

Today I began moving on my plans for Susan. I assigned the class a theme on the Revolutionary War. Some were quite good and there were a few others that were just mediocre. Susan’s theme fell into the latter category. I asked her to come to my office during the lunch period to discuss her work.

Two hours later the door of my office opened and Susan came in, she was dressed in the Bolton regulation uniform, a dark blue pleated skirt, white blouse, black flats and white anklets. Although the skirt was full, it still showed off the enticing curve of Susan’s shapely bottom. Susan had black hair and big green eyes. Her complexion was somewhat pale but it contrasted very well with her hair and eye coloring. Her lips were full and red. Her face was small and nicely shaped. Susan was short for her age but she had an exceptionally well developed figure. She had an air of sensuality about her that was well beyond her years.

Susan strode across the room and sat in the chair facing my desk. She made it a point to cross her legs and even though her skirt wasn’t short, she somehow managed to show an expanse of thigh as she sat across from me. Then she made a production of stretching and yawning as she asked, “What did you want to talk about Mr. Bradley?”

I had made it a point to seem to ignore all of Susan’s actions and I continued my charade by pretending to be absorbed in examining her theme paper. Then I said, “Susan your work on this assignment was below the standard I expect. I hope you won’t be upset, but you must understand; I tell you this for your own good. I want you to succeed in your course of study here at Bolton and therefore I expect much better from you.”

Susan replied, “Maybe you just haven’t found the right type of assignment for me Mr. Bradley. I’m sure there are things I might be able to do that would exceed your expectations.”

I asked, “What types of things are referring to?”

Susan replied, “Oh I don’t know. I guess I would have to leave that up to your imagination.”

I said, “I get the impression that you aren’t interested in improving your grade by additional work on this assignment. If that’s the case, I suppose I could propose and alternate method for you to earn additional credit. Is that something you would be willing to agree to?”

“I suppose so Mr. Bradley. It might depend on what you had in mind.”

“Well Susan I had intended for you to rewrite this them. Judging from your attitude, I guess that you would consider that a punishment. Is that correct?”

Susan said, “You’ve got that right.”

“Then in lieu of one punishment, I suggest substituting another. Rather than rewriting this theme you can submit to a spanking, which I will administer here and now,” I said.

Susan looked at me with a puzzled expression and asked, “What kind of spanking?”

I said, “The most common kind Susan. An over the knee bare bottom butt warming.”

In spite of her previous bold demeanor, I think Susan was taken a little aback and I noticed just the slightest hint of a blush as she said, “You mean you want me to get across your knees with my panties down and let you spank me?”

I said, “Not exactly. You get over my knees and I’ll take your panties down. However I think I detect some hesitation on your part. I get the impression that you’re not quite ready for the other things that would exceed my expectations. I believe there’s more talk than action involved in your claims and that’s understandable. I suggest you take this theme paper and revise it as I originally suggested.” Watching Susan’s expression, I could tell my veiled taunts were having the desired effect. I could see that she had resolved to show me that she wasn’t just a typical school girl.

Susan looked me in the eyes and said, “I didn’t say no. I just wanted to be sure what you had in mind. I don’t have a problem with the spanking. If that’s what turns you on, then so be it.”

I said, “Very well Susan, but I’m afraid that last disrespectful comment is going to cost you a few extra hard swats. Now would you please go lock the office door? I don’t think we want any uninvited spectators.”

As Susan went to lock the door, I scooted the old straight backed chair away from the desk. Then I took my little wooden paddle from the bottom drawer and laid it in a convenient spot.

When Susan turned around I said, “Come over here behind the desk.”

She came over and stood by the chair. I could tell from her body language that she was more than a little nervous and trying valiantly to hide it. I also saw her glance down at the paddle and I could detect a little fear in her expression. I said, “As we have already agreed, this is to be a bare bottom spanking and that rather voluminous skirt you’re wearing will be a hindrance to the business at hand. So you will remove it. You can lay it on the desk so it won’t get mussed.”

I saw Susan’s fingers move to the fastening at the side of the skirt and then hesitate. I believe she was almost ready to back out, but apparently she mustered her resolve and continued. She unfastened the skirt, slid it down and stepped out of it. She then took her time folding it neatly and laying it on the desk. I had to give her credit, she wasn’t about to let me know that she was in any way embarrassed for me to see her standing there in her panties, blouse and shoes.

With the skirt laid aside I glanced up at Susan and patted my lap. She turned to the side and draped herself over my lap, positioning her bottom right in the center. The standard uniform issue panties at Cartwright had been plain white cotton and I saw that Bolton was the same. I had noted on previous occasions that these particular garments usually had a disappointing amount of room in the seat and therefore didn’t always fit snugly. I now observed that this was not the case with Susan. Her amply curved bottom filled the panties to taut perfection. The outline of her lushly mounded bottom cheeks were clearly visible straining at the plain white material.

As I gently ran my hand over the lush curve of Susan’s bottom through the tightly stretched seat of her panties, I said, “You have a very nicely fleshed bottom Susan.”

Susan looked up at me over her shoulder and said, “I hope it meets your expectations.”

I replied, “I’ll need a better look at it to make that judgment.” Then I began to slide Susan’s panties down over her ample hips. I took my time in this operation; slowly revealing Susan’s sexy posterior. I drew her panties down to her knees and I thought they looked very sexy dangling there. Then I turned my attention to her bare bottom. It was one of the sexiest butts I had had across my knees in a long time. As I landed a few light swats to each of Susan’s perfectly mounded and resilient bottom cheeks, I realized how much I had been missing this pleasure since leaving Cartwright.

I said, ‘Susan your bottom definitely meets my expectations. I believe it’s absolutely perfect for spanking.” Having said this, I picked up the paddle and brought it down with considerable force right into the middle of Susan’s bare butt. It made a delightful CRACK as it landed. Susan let out a shriek and her legs jerked up as she tried to squirm off my lap. I tightened my grip around her waist and brought the paddle down into her ample bottom again. Susan cried out again and started kicking her legs.

I said in a stern tone, “Susan this just won’t do! You must hold still and be a little quieter. You’ll have someone at the door if you keep this up. This is nothing more than a little butt warming and you’re taking on like I’m killing you. Now this sexy butt of yours has plenty of padding you’r
e not being hurt nearly as much as your actions seem to indicate.”

Susan said, “It stings like fire. Please don
‘t do anymore.”

I said, “I’m afraid it’s too late to have second thoughts now. So stop acting like a baby so I can get on with this. You’re going to have to do much better than this to meet my expectations.”

At this point I began to apply a series of moderate force swats to each of Susan’s bottom cheeks; alternating from one to the other. Their bounce was beautiful as the paddle continued to crack down. Susan didn’t cry out again, but occasionally she would come out with an, “Ouch!” as the paddle connected with her butt. After a couple of minutes I paused and said, “Now you have those hard swats coming for being disrespectful.”

Susan said, “No please Mr. Bradley. I didn’t mean it. My butt’s on fire now. You’ve done enough.”

I didn’t reply. I raised my knee to elevate Susan’s bottom to a more convenient position and came down with three more very forceful swats right to the middle of her butt. The paddle cracked loudly each time it connected and Susan let out a little squeal on each swat. I laid the paddle aside and lifted Susan off my lap. When standing by the chair again, her hands flew behind her back to rub her bottom. At the same time I was getting a good look at the dark bush of hair between her legs. Susan’s pussy was quite attractive. I knew that I had to get more familiar with this part of her anatomy, but now was not the time nor was my office the place for the activities I had in mind.

I said, “Susan quit rubbing your bottom now and turn around.” Susan turned around and I saw that her bottom cheeks were very nicely warmed from the spanking. I slowly ran my hand over her beautifully curved bottom as I said, “I believe you do meet my expectations in this area.” I stood up and turned Susan back to face me. I put my arms around her, bent down and kissed her. Susan’s response was immediate and enthusiastic. As we continued to kiss I moved my hands down and gently cupped her bottom cheeks.

The entry concluded at this point and I decided it was time for bed. I wanted to think about what I had just read as I drifted off to sleep.