Private Lessons - Cover

Private Lessons

Copyright© 2022 by Master Jonathan

Chapter 1

Erotica Sex Story: Chapter 1 - Timothy Stewart is the principal of a private high school and he has in his school, a particularly wayward student Allison Walker. When she has come to his office once too many times, he takes her aside for some special instruction on how to succeed in his school!

Caution: This Erotica Sex Story contains strong sexual content, including Ma/ft   Reluctant   Heterosexual   Fiction   School   Workplace   Anal Sex   Masturbation   Oral Sex   Teacher/Student  

My name is Timothy Stewart and I am the principal of one of the biggest private schools in Southern California. Being a private school of some standing, I am pretty lucky – I don’t have to deal with the same sort of drama and chaos that the public schools have to deal with. Drug busts, gang wars, bullying and other street troubles are not a part of Bancroft Academy.

Now that doesn’t mean that B.A. is free from all troubles. We do have our share of drama, but it’s usually limited to dealing with spoiled kids whose parents were too busy or too lazy to raise their kids with rules and consequences.

We have bullying too, but it’s more along the lines of demeaning and shaming the other kid instead of physical fighting. You know, making the kid feel like he can’t compete with the rest of his or her classmates, or that he/she doesn’t fit in with the crowd.

Being the principal and the last word on whether an errant student remains in school or is expelled has brought a lot of unique opportunities my way over the years. I have had a number of very attractive mother’s flirt with me, and some even straight out offer me sex, to not expel their child. And I have had many very pretty teenage girls offer themselves to me to avoid suspension or expulsion, to not call the police when it was that serious a matter, or even flirt and play with me during in school detention classes.

I had always resisted these temptations and I prided myself in being above that sort of thing. I had a reputation and a good standing in the school and with the school district and I didn’t want to risk besmirching it with some ill-conceived and foolish scandal.

However, after suffering through a divorce I didn’t see coming, a long dry spell afterwards, and problems with funding and school board rule changes, I no longer held my willpower to such high standards. To be completely truthful, I had quit caring so much about the school and my job as principal and my moral compass. My once lofty position which I took such pride in had become a regular job ... something I did to pay the bills.

So I suppose it was really not all that surprising that when the opportunity arose the next time, I wouldn’t have such a high wall built around myself to protect me from my natural urges. And like Humpty Dumpty in the nursery rhyme, I sat on my wall and had a great fall ... with similar results too, I’m afraid.

That day started out like any other; I got up, showered shaved, had breakfast and made it to work in plenty of time. I got to school and went into my office setting up for another school day. Things went smoothly until just after lunchtime, and that’s when I began my fall from grace.

“Sir, Miss Walker, Miss Taylor, and Miss Davis are here to see you,” Mrs. Humbolt, my secretary said.

“Oh?” I asked, “What about?”

“Sir, the girls were caught skipping school and wandering around the Ravenwood Mall. One of the mall security guards spotted them and called our security who brought them in. All three girls are sitting here in the waiting room,” Mrs. Humbolt said.

“Okay, thank you. Give me a couple minutes to pull up their files and I will call them in one at a time,” I said. I knew all three of these girls ... I’d had them all in my office before. I pulled their files and gave each of them a quick look over. Then I called each girl in singly starting with Miss Davis. After a few minutes talking with her, I called in Miss Taylor. I talked with her a little as well. Then it was time for Miss Walker.

I knew Allison Walker to be the ringleader and primary instigator of these three. Actually, there were two other girls in their little band of troublemakers, but apparently they weren’t in on this scheme.

“Come in Miss Walker, have a seat,” I said.

Allison walked into my office and closed the door. She walked to her chair with a sexy wiggle, one I’m sure she had used many times in the past to get her out of trouble. Sitting down, she made sure she showed off her long lean legs. I smiled to myself; if I had my way, she would soon be showing a lot more than that.

Allison Walker was a very attractive 18 year old senior who was looking forward to graduating from high school in a few short months. That is, if she could get her act together and not be expelled before then!

Allison came in and took a seat while I looked over her file. I intentionally took awhile to do it too – looking over the top of the file from time to time to see her fidgeting and squirming in her chair. I hid my smile behind the file paperwork ... letting her sit and stew on her predicament was exactly what I wanted her to do!

Finally, I snapped the file closed and set in on the desk in front of me. “Miss Walker, you have become quite the regular here in my office haven’t you? This the third time this school year that we have had to have a little visit,” I said.

“Yes Sir,” she said.

“You know the policy of this school – no one is to leave the school grounds during school hours unless on an approved school function such as a field trip or sporting event. You are supposed to be in class getting your education instead of at the mall getting in trouble!

“Yes Sir,” she repeated like a parrot.

“Then why would you risk getting caught off school grounds by going to the Ravenwood Mall? Don’t you know that’s one of the first places we look when looking for truants!” I told her.

Allison started to cry, but fifteen years of this job had taught me when the tears were real or a devious teen girls’ I-can-cry-on-cue-to-get-out-of-trouble tears.

Allison finally stammered, “I-I am so sorry Mr. Stewart, it was a real stupid thing to do.”

Ignoring the crying girl, I explained, “You understand if this goes on your record, you can kiss graduation goodbye.”

“W-what?” she asked shocked at this news.

“That’s right Allison. According to your file, this is the third time this year we have had to discuss your behavior. And looking back, you have come to see me quite a few times over the years. You have quite a record here at B.A.! And you can stop with the waterworks, they may have worked for you with your parents or other people, but it won’t cut it with me.”

The tears stopped almost as quickly as they began. “Yes, Sir,” a now distressed and fearful Allison said. I don’t think she realized that she was this close to losing everything.

“I may be able to look past this latest lapse in judgement, young lady, if I could only understand how you thought you could get away with it,” I said, curiosity getting the better of me.

Allison looked down and explained, “Janet told me to meet her in the first floor girls bathroom in the east wing at lunchtime. I thought she was kidding and wasn’t going to go, but...”

“But, you had to go just to check it out, right?” I finished her sentence.

“Yes. And when I got there, Janet and Cathy were already there. The next thing I knew, we were leaving the school grounds and headed to the mall. I knew we weren’t supposed and I tried to tell them but...”

“Stop!” I said, cutting her off in mid-sentence, “Stop right there, Allison. I have already talked to both of your cohorts individually. And both of them have independently pointed you out as the ringleader in this escapade. So your version of what happened and your claim of ignorance and innocence isn’t holding up. You weren’t ‘just along for the ride’, you were the driver!”

Allison was caught dead to rights and she knew it. Not only was she caught by the security guard at the mall, but her two confederates had rolled over on her, pointing her out as the one who came up with the idea of cutting class and the one who drove them all to the mall. She knew she couldn’t cry her way out of this one and her cute tits and ass weren’t working for her either!

She sat there quietly for a couple moments trying to figure out how to handle this situation. I’m sure that in the past she had been able to manipulate her parents or whoever was in charge of her at the time. She seemed pretty sure that her tactics would work on me too when she first came in my office. But now she was learning that she had underestimated me greatly. And the cocky, confident Jezebel was worried now. Very worried.

I had long ago learned that when negotiating with someone, for whatever reason, more often than not the one who spoke first lost in the deal. So I sat there behind my big imposing desk (one I had gotten for that very reason) while my rival in this negotiation sat across from me fidgeting and squirming in her chair. I sat there, studying her and waiting for her to make a move. This was a chess game and I had her in ‘check’ ... her next move would determine her fate.

Finally she caved. “I am very sorry I cut class Mr. Stewart. And I’m sorry I got Janet and Cathy in trouble too,” she said. “I won’t do it again, I promise.”

“As much as I would like to believe that, Allison, your record here in my file shows differently. You have a long record of breaking the rules and disciplinary problems and apparently the I’m sorry, it won’t happen again, thing hasn’t worked very well for you.

Realizing she was up against the wall she tried another tactic ... bargaining. “I know, Sir. But I’m supposed to graduate in June. There must be something you can do, Sir.”

I shrugged, “Oh, there is lots of things I can do, Allison.”

Catching the innuendo, she smiled letting me know she understood. Using her sexual wiles, her voice dripped with seduction, “There must be something I can do to change your mind, Mr. Stewart.”

“Tell you what, Allison. You seem to be a nice girl and I would hate for you to lose out on graduation after having come so far. Can you keep a secret?”

“Yes Sir,” she replied, the glimmer of hope shining eagerly.

I stood up, startling her, and moved around my desk to stand in front of her, leaning back on my desk. “I will overlook this matter, Allison, but you will have to do something for me in return,” I said.

“I will do anything you want, Mr. Stewart,” she smiled, assuming I was going to make her give me a blowjob or maybe fuck her.

“Be careful, Allison, the word ‘anything’ is a very dangerous word. What I am going to ask of you may be more than you are willing to agree to,” I warned, standing in front of her and looking down.

She repeated, unable even to begin to comprehend what I had in mind, “I will do anything, Mr. Stewart.” Confident her sexual charms were irresistible, she stood up from her chair and moved closer to me. Her hand went to the large bulge in my pants and feeling my hard eight-inch cock, she purred, “Hmmmm, very impressive, Mr Stewart.”

“So I have been told,” I smugly retorted.

“So is there anything I can do for you, Mr. Stewart?” she said in a soft lusty whisper.

As much as I would have liked to take this tender young morsel right then and there, I had my job to think about. “Not now, Allison. I don’t have the time for this right now and it’s too dangerous. Too many people around. Come by my office this afternoon after school and we will discuss ‘anything’ then,” I said. Make sure you show up too, young lady ... you are already in enough trouble. And remember, this is between you and I,” I said.

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