The Finishing School

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James teaches sex. His sister becomes one of his pupils.
8.6k words
4.34
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Part 1 of the 2 part series

Updated 06/09/2023
Created 03/26/2020
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chris99999
chris99999
3,974 Followers

"Thanks."

Then I tasted it. It was perfect, and I knew that it would be. Nobody makes a better hot chocolate than Jennifer.

After giving her a big smile, I said, "It's delicious."

"You always say that."

"That's because it's always delicious."

That made her laugh. Then, when she turned away from me to leave the room, I leant back in my chair, and put my feet up on the desk. As I sipped my drink, I couldn't help smiling. It wasn't just the hot chocolate that was perfect, my job was as well.

I'm twenty five years old, and I teach at 'The Willow Hall Institute'. It's a small, exclusive, and very expensive, Finishing School for young women, between the ages of eighteen and twenty one. The pay could be better, and I would like to work less hours, so why is it my ideal job? That's an easy one to answer, the girls!

Six months ago, I was working somewhere else. I was a teacher, earning extra money by working two evenings a week as a masseur. Massage was something I had always been interested in. I regarded myself as a talented amateur, so when there was a vacancy at the local Spa, I applied, and to my surprise, they took me on.

Life was good then, but it was about to get even better.

"Thank you James. I liked the massage," then she kissed me on the cheek, before whispering in my ear, "But I liked the sex even more."

She then picked up her coat, and started walking towards the door, but suddenly she stopped. When she turned back, I looked around the room to see what she had forgotten.

"Have you got ten minutes, I want to talk to you about something?"

"Yes, I don't have any more clients today."

"Is it true that you're a teacher?"

I hadn't expected that, and I was now trying to stay calm, but it was difficult. Was she going to report me to the school? They would not be happy when they found out that I had another job, and what that job was.

Then I got a nice smile from her, before she said, "Don't worry, you are not in trouble. But are you?"

I hesitated, and then I told her that I was. For the next few minutes she asked me lots of questions, all of them related to my teaching and my qualifications. I answered them truthfully. I was now intrigued, rather than concerned.

"I was right. You are just the man we are looking for. Would you like a new job?"

She then spent the next fifteen minutes telling me about it. After she had gone, I stayed in the room. I was sitting on the massage table, and in my hand was a card. I kept looking at it, and smiling. On it was a telephone number. I was to call it to arrange an interview.

The next day I did, and on Saturday morning I was at The Willow Hall Institute.

"Nice to meet you Mr. Gibson."

She then offered me her hand.

As I firmly shook it, I said, "Thanks for seeing me Headmistress."

She then gestured for me to sit.

"I understand that you talked with Angela Taylor about our forthcoming vacancy."

I nodded.

"Good, but I think it's best if I go over it as well, in case anything was missed."

For the next twenty minutes she talked about the school. I hoped that I appeared interested, but I was finding it difficult, because I had heard it all before. Then she got to the part that Angela had only hinted at. She hadn't said much, but it had been enough to excite me. It was why I was here now.

"We teach them all aspects of life. When they leave our institution, they will be confident, and able to do well in the world."

She then paused, giving me a nice smile, before continuing with, "One topic we regard as being very important is Sex Education."

She was now staring at me, looking for some reaction to what she had just said.

"I agree with that."

Even while I was saying it, I knew that it sounded a bit lame, but the stare had now gone, and she was smiling.

"Good, I am glad you said that. Just to be clear, you will not be teaching the girls sex from a book, you will be fucking them. Is that OK?"

Thinking about that interview was making me smile. I had been offered the job, and I had quickly accepted. I then drained my hot chocolate. It was time to get ready. Jennifer would be here soon, and it wasn't to bring me another drink. Five minutes later there was a knock on the door.

"Enter."

As soon as I saw her, I started to get hard. Her skirt was very short, and her blouse was at least two sizes too small, making her large tits look even more prominent. The tie was a nice touch. She was wearing a school uniform.

"I borrowed it from my younger Sister."

She then started playing with her pigtails. Earlier, when she had brought me my drink, her hair had been straight. I was impressed, she had certainly made an effort.

This was going to be our last time together. The girls are with us for six months, with the last two weeks being mostly Sex Education. I had enjoyed teaching her. She was pretty, with a nice body, and she was eager to learn. Today's lesson was on the art of seduction. I was going to resist, and she had to win me over. That was the plan, but now that I had seen her, I knew that I wouldn't be able to hold out for long.

"Sir, I have a problem."

"What is it?"

"My top buttons are stuck, will you undo them for me?"

She was now looking at me all coy, with big innocent eyes, but she would have to do better than that.

I gave her a nice smile, but I shook my head.

That got a sulky look from her, and she even put her bottom lip out. She then slowly unbuttoned the top one. She struggled with the next one, and I almost believed that she really needed my help.

"It's stuck," then she thrust her chest out.

I was supposed to be looking at the button, but my eyes were drawn towards her large tits. When I thought about the juicy nipples, that I knew she had, I almost gave in.

"It's hot in here."

She then started running her hands over her tits. I had to briefly look away so that I could compose myself.

"Please will you try?"

I did, and I took my time doing it. When I had finished, I stepped back. I could see the disappointment on her face, she had wanted me to undo all of them.

"I have another problem."

She then sat down in the armchair before continuing.

"I have this strange feeling, but I don't know what it is."

When she opened her legs, and put her hands on her thighs, I knew what she was hinting at, but I was going to make her say it.

"Where is this strange feeling?"

She then gave a girly giggle, that sent a shiver down my spine, before opening her legs even wider

"It's between my legs."

I could now see her mound, covered by tight white knickers. I was just about in control, but my cock wasn't. It was rock hard, and trying its best to rip a hole in my trousers.

"It's a sort of itch," then she looked at me wide-eyed, before adding, "Will you scratch it for me."

"No."

"Then I suppose I will have to do it myself."

Her hand was now between her legs, and she was rubbing on her knickers. When she closed her eyes, and started moving her fingers quicker, I realised that she was going to settle for a climax from her own hand, rather than from me fucking her. I was surprised, and disappointed. She was supposed to seduce me. Then she stopped, but only so that she could take her knickers off.

She was now fingering herself, and I moved closer so that I could get a better view. Then she stopped again, removing her hand, but leaving her legs wide open. My eyes were fixed on her open cunt, then I realised that she was beckoning me to come towards her. When she put a sticky finger to my lips, I couldn't resist. I greedily sucked on it. She had won. I wasn't going to stop now until I had fucked her.

"Finger me."

I didn't need asking twice. She was hot and wet. Two fingers slid in easily, and I pushed them in up to the knuckles.

"That's nice, but your cock is better."

The build-up had been slow, but the fucking was going to be frantic. All that teasing had made us both very excited, and all we wanted now was a quick relief.

I don't have a monster cock. It's not a foot long and as thick as a coke can, but it is a decent size. It's seven inches, and I am proud of it. It's always rock hard, and it has never let me down.

There are lots of things I like about Jennifer. She has a face that turns heads, and a firm body. Her tits are big, but not excessively so, and her nipples are a thing of beauty. Her clit is also very responsive, and she climaxes easily. And she makes hot chocolate that is perfect! However, what I like best is the tightness of her cunt. It touches my cock in all the right places, and when I climax inside her it always feels special.

Before pushing into her, I placed both her legs over the chair arms. Her legs could not be any wider. When I was fully in, she groaned.

"I'm going to miss your big cock."

It was always nice to be called big, but she was only saying it because her cunt was small, and she was inexperienced.

I was now fucking her hard. I was also groping her tits, but only through her blouse and bra. We didn't have time to stop to take them off. She was already breathing heavily, and I wasn't going to last much longer.

Surprisingly, we lasted another five minutes. She got there first, and as she orgasmed, her little cunt squeezed my cock. That took me over the edge. As her head rocked from side to side, and she made all sorts of noises, my cock twitched several times, and I flooded her cunt. When my cock started to go limp, I pulled out of her.

Looking up at me, she said, "Did I pass?"

I laughed. This hadn't been an actual test, with a pass or fail, but I was going to answer her.

"Yes you did," then I smiled, before adding, "With top marks."

Half an hour later, she was back again, but this time in her normal clothes.

"I made you this."

After placing the drink on my desk, she blew me a kiss, and then she left. I was going to miss her, then I smiled. She might be leaving, but I would soon be getting more girls to teach.

The Willow Hall Institute is a very exclusive Finishing School. It's expensive, and we cater for the Daughters of the rich and famous. Each month we have an intake of up to ten pupils, so in total, at any one time, we have a maximum of sixty girls boarding with us. We have twenty three members of staff, split almost equally between male and female. All of us teach multiple subjects, but only seven of the men, and two of the women, take part in the Sex Education. Tomorrow morning I am seeing the Headmistress, to find out who my next pupil will be.

I woke early, and with a smile on my face, but that quickly disappeared when I thought about what might happen. It was possible that two girls would be assigned to me, but it was also possible that I wouldn't get any. I took my time eating breakfast, then I had a long shower. At ten to eight I left my room. When I got to her office, I straightened my tie, and then I took a deep breath before knocking.

"Come in."

I was apprehensive as I entered.

"Morning Headmistress."

"Good morning James. Sit down."

She was seated behind a large desk, and I was now sitting in a small chair that was in front of it. She then picked up a single piece of paper, and she took her time reading it. When she had finished, she was frowning.

"James, we have a problem."

She had said 'we', but I had a feeling that the problem was going to be mine.

"It's your Sister."

Inwardly I groaned. What had she done now? When I had started working for The Willow Hall Institute, I had discovered that one of the benefits of being a teacher here, was that close relatives could attend for free. This was a place, that under normal circumstances, my family could not afford. It was too good an opportunity to miss. After a month, when my probationary period ended, Amy enrolled in the school. My parents and I had hoped that Kate, her twin Sister, would have done the same.

"There is no way I am going there. It's for sad losers. I have better things to do."

She had then stormed out of the room. Mother kept trying to persuade her, but after a week she realised that Kate was never going to change her mind. However, Kate's loss was my Niece's gain. The Headmistress agreed to take her instead. Helen was only seventeen at the time, so she had to wait, but she was now also at the school.

"Did you hear me?"

I quickly nodded, then I gave her my full attention.

"I have had a talk with her about the Sex Education course."

That was so that she could be assigned to a suitable teacher. I have heard that the Headmistress is very good at this. The pupils are questioned about their sexuality, and their likes and dislikes. The conversation is open and candid. The aim is to pair the pupil with a teacher that they are attracted to, one that they will be able to learn from.

"She has picked a teacher, and she refuses to consider any of the others."

I should have expected that. She may only be nineteen, but she knows her own mind. What she wants, she generally gets.

"So this teacher is unsuitable. You would rather she was with somebody else?"

"No, she has picked the right one."

I was confused.

"So what's the problem?"

"She wants you."

I was now back in my room, with a mug of coffee in my hand. I was drinking it, but not really tasting it. I was too busy thinking about what had just happened. She had persuaded me to say yes, but I was now having second thoughts. She had talked about the right of a woman to choose, to have what they wanted. That we were consenting adults over the age of eighteen, and what we did together behind closed doors was nobody else's business. At the time I had agreed with her, but now it felt as if I had been bullied. For all her fancy words, what she was asking me to do was to fuck my Sister. Wasn't that wrong?

An hour later I was a lot calmer. I wasn't completely happy, but I was going to try and make it work. Then I smiled when I remembered what else the Headmistress had said.

"This time you will also be getting another girl. It's Felicity."

We both knew that it was a bribe, but nothing was said. That might have been what finally made me say yes, because she was offering me somebody that I longed to have, but I thought I would never get.

Two days later, it was time for the first lessons. I was going to start with Amy in the morning, then Felicity in the afternoon. I was now in my room, waiting for my Sister to arrive. She was fifteen minutes late, and I was beginning to think that she wasn't coming, that she must have changed her mind. There was then a knock on the door.

I shouted, "Enter."

Amy breezed into the room, as if she hadn't a care in the world.

"Hi Bro."

She had a big smile on her face.

"Do I just take all my clothes off, and then you ravish me?"

I shook my head vigorously, and she laughed.

"Just joking."

Normally it's the girls that are nervous, but this time it was me. I had done this lots of times before, but never with my Sister. I took a deep breath, and then I tried to compose myself. The only way to deal with this was to think of her as just another girl.

"Sit down, we need to talk first."

She was now sitting in the armchair, and I was on the sofa opposite it.

"I need to know how sexually experienced you are."

With some girls this is an awkward time. They find it embarrassing, and I have to tease it out of them, but I had a feeling that my Sister was not going to be like that.

"Tits played with lots of times. I like my nipples sucked. I have lost count of how many fingers have been up my pussy," then she laughed, before saying, "And not just my own."

I kept a straight face, as I waited for her to carry on.

"I have only been fucked a few times," then her smile disappeared, as she added," But none have given me a climax."

So, despite all her self-confidence, there was something I could teach her.

"When you are fingered, do you climax?"

"Always if I do it myself, but only sometimes with others."

"How often do you masturbate?"

"Once a day, sometimes twice."

Good, she had a high sex drive

"Have you done it today?"

"No, I wanted to, but I thought I should wait."

I nodded. I now had all the information that I needed.

"Please sit next to me."

She then did, with her legs touching mine, but she wasn't looking at me. I kissed her on the cheek, and she then turned her head. I then kissed her gently on the lips. I had to kiss her again before she responded. For a while, that's all we did. Experience has taught me to take it slowly, especially when it's the first time.

Amy is a pretty girl, with short blonde hair. I can never decide if it's her face that is her best feature, or if it's her tits. They are not massive, but they are prominent, and they are a nice shape. I have often wondered what her nipples were like, I was about to find out.

When I squeezed one of her tits, she gave a low moan. It felt firm, and I was eager to get her top off, but I resisted. However, it wasn't long before I was unbuttoning her blouse. When I had finished with all the buttons, I didn't take it off, instead I just parted it, and then I pushed her bra up, so that I could get to her nipples. They were everything I had hoped they would be. Chunky is the best way to describe them. Perfect for sucking on.

I was now doing that, and it was getting her, and me, very excited.

"I need your fingers in my pussy."

My hand was now quickly going up her skirt, and she was parting her legs. When I cupped her mound with my hand, I could feel the heat from her cunt. I tried to get a finger inside her knickers, but they were too tight.

"Take your knickers off."

She stood up to do that. When they were off, she got back onto the sofa, but this time lying down, with her legs wide open. My fingers were quickly inside her. At first she got two, then I added another. It was a tight fit, but she was very wet, so I was able to fuck her with them.

I now also had a finger, from my other hand, on her clit.

"Lower."

I moved it, and she gasped.

"That's the spot. Now rub it until I come."

Initially, I had been apprehensive because she was my Sister, but now I was desperate to get my cock inside her. Should I try, or should I just give her what she has asked for? Reluctantly, I decided that it was best to continue. I was going to be her teacher for the next two weeks, so no need to rush.

Her clit was now getting my full attention, and she was slowly coming to the boil. I might not be able to fuck her, but I could make sure that she had a nice climax.

"This is so good."

She was almost purring when she had said it. I puffed my chest out, proud that I was doing a good job. I was enjoying it as well, even though my cock wasn't getting any attention.

"Finish me off."

I was tempted to ignore her, perhaps to even tease her by slowing down, but I knew that she would not be happy if I did that. It was time to make her come.

My finger was now frantically rubbing her clit. It was almost a blur. She wasn't going to last much longer, and she didn't. When she climaxed, it was a big one. I was impressed. Her head went back, and her body went rigid. The look on her face was pure pleasure. I only took my fingers out of her when her orgasm was over.

Five minutes later, she left the room, and I then sat down on the chair. I had a lot to think about. I had just fingered my Sister to a climax. She had obviously enjoyed it, and I had as well, so why was I now feeling uncomfortable? Half an hour later I had managed to put it out of my mind, and I was now thinking about Felicity. Her first session was at four o'clock, and I was definitely going to fuck her.

At three thirty, one of the new intake brought me a hot chocolate, and a note. The drink was disappointing, but then it got worse when I read the note.

chris99999
chris99999
3,974 Followers