Tutored

I had been worried that getting a tutor would make me seem different to the other boys, but as we sat together in the midday sun in our matching petticoats I knew that I had been worried about nothing at all. Today was a Saturday and there was nothing to learn. Still we sat outside together. She would show me flowers and tell me their latin names. With her delicate fingers she wove them together into an elegant crown. As she slipped it onto my head I could feel her soft hands against my cheek and it sent an excited shiver down my spine. She noticed and gently guided me into her lap. Above me i could see the sky wide open and clear. I closed my eyes as I felt her hands glide their way down my body, gently grazing against my new breasts and exploring down my navel towards where my clit was happily straining against my cage. In a few days father would be home and this beautiful summer would have to end.

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There were no schools left for me to be kicked out of. That was how I had ended up sitting at one end of our dining table staring across its length at the woman that called herself Miss Jean. She was dressed in an old fashioned brown peacoat embroidered with small blue flowers. Her hair was short and set in tight curls. Easily, her most striking feature was her lips. They were drawn in a bright red, with a sharply defined cupid's bow. It gave Jamie the uneasy feeling that he was always doing something that was disappointing her.

Jamie's father was explaining that he was leaving for a while, for work. It was the same speech every year. Usually Jamie was abandoned in some god awful boarding school in the middle of a massive empty field. His father had thought he was doing well at St Jude's. He had lasted two years there. That was until his clandestine girlfriend from the small hamlet six miles away broke into the schools Christmas service to tell the whole congregation about Jamie's affair with the maths teacher Mr Karidge-Phip. Jamie watched as his father's mouth continued to move and noises continued to emanate from his mouth. Jamie watched as his father's hands lingered on Miss Jean's shoulders for just a little too long. She did not seem to notice. Miss Jean would not break her gaze from Jamie. She stared at him like some distant mountain she would one day summit. Then his father was gone. He used to hug Jamie before he left. The last few years he had gotten a handshake.

They stood and watched as his car made its long way down the drive. Miss Jean looked at him kindly for a second before promptly informing him that lessons would begin tomorrow at 7am sharp. With that she left. There was a faint floral scent in the air behind her.

The first thing Jamie did was look for his car. It was gone. There were no buses and the nearest town was miles away. There was no leaving unless he wanted to walk for about a day and a half through cow muck.

The first stop in the house was his father's wine cellar. He was extremely proud of his collection and would always insist that guests stare at the racks of bottles with obscure French names. Jamie pulled out the oldest dustiest bottle he could find. Taking the cork out with his teeth he started exploring the house taking deep swigs from the bottle. What had once been his playroom had been converted into a classroom. It had one desk at each end. The childish wallpaper gave the room a slightly sinister air. Miss Jean was sitting reading a small paperback. She looked at Jamie, noting the bottle in his hand and then turned the page and continued reading

.

By the time he had reached the third floor he was already onto his second bottle. He knew what he was heading for. It was the same every time he came home. Making his way through his father's room into the large walk in closet at the back. He started to tear away at his father's suits, throwing them to the ground. There, buried at the back were three white boxes, untouched since the last time he had been home.

An hour later and the contents were neatly arranged across the bed. There was the beautiful emerald necklace and earring set which shimmered in the disappearing sun. Emeralds had always been his mother's favourite. Her dresses were laid out next to each other, silk and velvet. He ran his hands over them. He kept his favourite item for last. His mother's fur coat used to swamp him. Now the warm fabric sat heavy and delicate on his shoulders. He could still smell her perfume on the coat. It might just be his memory.

--

Jamie was woken at seven in the morning when Miss Jean threw open his curtains. The bright morning light shot across the floor and into Jamie's skull, splitting it in two.

Miss Jean was sitting at the edge of his bed. She was wearing a tight purple pencil skirt. Even in Jamie's reduced state he couldn't help but stare at her legs. She was wearing an elegant pair of stockings with a seam guiding his gaze up the back of her legs

It was only after his eyes adjusted to the light that he realised he was still wearing the fur coat. As far as he could tell he was wearing nothing but the coat. If he wasn't quite so hungover he'd feel embarrassed. But miss Jean didn't seem upset or even surprised. She was smiling at him in a way that was somehow simultaneously sympathetic and patronising.

"Class starts at 8. Now get in the shower, quick. No time to waste. Make it a cold shower" She told him.

If Jamie had the mental agility to work out where he was he might have been embarrassed. He was skinny and scrawny, looking like he was held together largely by bits of string and his own stubbornness. However, stings of sordid affairs with men and women, girls and boys in most of England's most elite private schools had given him a somewhat underserved swagger.

He got up, swaying a little as he went. Miss Jean was holding out a hanger and he hung the coat, careful not to crease it, his hands delicately tracing its folds. Miss Jean watched, seeming completely unphased sharing this space with her naked hungover 18 year old student. She took the hanger and with the same care and attention hung it up in the closet.

The cold water started to revive and wake Jamie. He could feel his headache growing in magnitude, the cold water barely containing it. As he stood, cold water running over his body, he started to really consider Miss Jean for the first time. The two had said maybe three sentences to each other. He was sure she was the largest stooge his father had lined up to attempt to control his behavior. He would probably fuck her or she would quit after a week. It would be interesting to find out which. There was something attractive about her in an archaic way. He started thinking about her hair, set in neat, carefully arranged ringlets. Her lips, the only remarkable thing about her face. She painted them in bright red. It was hard to tell what her body was like. Today she was wearing some kind of dark purple suit with a skirt that went down beyond her knees. There was something so old fashioned about her, not just the way she dressed, but her mannerisms, the entire way she held herself looked like she was trying to retroactively insert herself into an Austen novel.

Despite the cold water Jamie could feel his cock began to rise. He started to stroke himself slowly, tilting his head back so the cool water ran over his nipples. The cold water running over the head of his cock sent electric shivers through his body. He closed his eyes, imagining Miss Jeans red lips wrapping around his cock. He imagined grabbing her head and shoving his cock deep down her throat. He imagined wiping that smug grin off her face.

Jamie heard a small cough and opening his eyes, he saw Miss Jean standing in front of him. She was smiling politely and holding out a towel. Jamie's hand shot away from his cock, embarrassed to be caught. He could feel himself turning red. His cock was still hard, pointing accusingly at her. He felt his cock twitch desperate to be touched again.

"That's enough Jamie. We'll eat breakfast and then it's time for class." She told him.

She sat in the room while he dressed, pulling out the same battered paperback. She paid no attention as he dressed, only turning a page occasionally. She escorted him downstairs to the kitchen. Jamie could only assume that his father had told her to keep a close eye on him. That would only last so long. Once they were there downstairs she told him to make her breakfast, a sliced peach and thickly buttered toast. This was not the way Jamie was used to being treated.

Once they had eaten Jamie was told it was time to start classes. There was no reason for him to listen to her. If he wanted to he could get blackout drunk again. He could run away. But there was something strangely authoritative about her. It seemed only fair to humor her for the day at least.

"Harrow, Eton, Elmsbrorough. You certainly have quite the reputation." Miss Jean was sitting behind a desk, scanning a piece of paper. "Good grades, largely, maths and economics are a bit of a blip. Your father made you take those?"

Jamie didn't say anything.

"What does your father do Jamie?"

Jamie said nothing.

"He runs a hedge fund. Is that right Jamie? Do you know why he hired me Jamie?"

Jamie thought again of his father's hand lingering on her shoulder yesterday. She was just another in a long line of people hired to do exactly what his father told them to do.

" Jamie, your father hired me because he can get away with paying me less. Also, because he likes having power over women."

Jamie was stunned. He had never heard anyone talk about his father this way. Especially not someone on his payroll.

"Jamie, I think this is an important and underserved facet of your education. I think it's important for you to understand what it means to be a woman. What it means to really be a woman."

By the time the lesson finished the sun had set. Jamie barely noticed. They had talked the whole time. She had listened carefully to what he had to say, correcting and making suggestions where appropriate. In return he had paid close attention to what she had to say. They had talked about the role of women in history and the history of the household. They had talked about what it meant to be a woman. They talked about femininity not as a shadow or a mirror of masculinity but as its own unique historical project. .Now the lesson was over Jamie couldn't stop looking at Miss Jean. There was something in her closeness, her distance that seemed to draw him in.

Jamie walked up to her desk. She was scratching a few notes in pencil. This wasn't the first time he had tried to make a move on a teacher, but, for some reason this time he was tense, his heart was going wild in his chest. He could feel his cock starting to harden, still desperate for him to finish off what he had started this morning.

"Hey Miss Jean, there's not much to do around here. What with being stranded in the middle of nowhere. So, do you think you would-"

"-Jamie, I'm very disappointed. I really thought you were doing so well. Jamie I'm going to ask you a question. When you were masturbating this morning, were you thinking about me?" Her tone was not accusatory but it wasn't particularly encouraging either.

Jamie was stunned. He was not expecting this. What was he going to tell her? That he was imagining fucking her face. Imagining how her red lips would feel wrapped around his manhood.

He tried to keep his composure. "Yes miss, I was thinking about you." He was not entirely successful. Jamie could feel the colour rushing into his cheeks and a vague desperate twitching in his cock.

Jamie was trying his best. He was leaning over her desk. He was sure his hair was falling over his eyes in that way that everyone else seemed to find so irresistible. He was employing every element of charm that he had at his disposal . Yet, Miss Jean was still sitting there at the desk, barely noticing him. She was frowning at a piece of paper. If it weren't for the way she had her pencil delicately pressed between her lips and the most delicate blush entering her cheek he would have thought he was having no effect on her whatsoever.

She sharply underlined a line on her page before standing up and commanding that jamie follow her.

"Jamie, I'm very disappointed. I thought we were making great progress today." They were making their way through the vast house, back up the stairs towards Jamie's room. " The work we are doing here is designed to teach you that there are those who experience the world differently to the way you do. I wanted you to be able to see the world the same way I do. I wanted you to see the world the same way a woman does. While you have done some excellent work today, and that intellectually you are starting to grasp what we are working towards..." she took a long pause here, as they approached his room. " I think the curriculum needs to change to allow you to empathise in a meaningful way with what I am trying to communicate. Now, strip."

Jamie thought he had misheard her for a second. They were alone together in his room. Perhaps his advances had not been the absolute failure that he was expecting. Gleefully he threw the clothes he was wearing to the ground. Now he was standing before her, fully naked. He could see the lines of his own delicate musculature and he could see his cock was hard and starting to get a little wet with all of this sudden excitement. He suddenly started to feel a little embarrassment, his brashness rushing out of him as he came to the realisation that she had noticed none of these things.

She left the room, leaving him standing uncomfortably naked and alone in his room. He could hear the sound of her heels disappearing down the hallway. Was she trying to teach him something right now? Was she just trying to embarrass him? He stood like this, half in shock, half in humiliation until she returned a minute later, wheeling a bright pink suitcase behind her.

The suitcase was placed upon the bed and thrown open. It was full of women's clothing. As Miss Jean 'silently removed it from the suitcase and started hanging it in his wardrobe Jamie looked on with utter confusion. He saw white blouses and plaid skirts, what could only be a school uniform. But, in amongst these were more delicate items. There were soft satin negligee, delicate lacy bras, a multitude of tights in every colour imaginable as well as leggings and deep woolly jumpers.

As she started to collect his clothing and neatly fold it, placing it back into the case, she talked to him. "Now Jamie, your father has told me to do whatever is necessary to get your behavior under control. To do that I designed this curriculum. I was hopeful after today's lesson that I wouldn't need to take a step this drastic, but I can see that you are out of control. You have no sense of decorum or decency. Can you not imagine the kind of pressure that you were putting on me by hitting on me like that? It was completely inappropriate. That is why I am implementing these..." She paused, clearly taking great pains to choose the right words. "special measures. You will wear these clothes from now on. On school days you will wear your uniform, on the weekends, you will be free to choose from whatever you like. If you find something is missing or you would like me to purchase something for you, I can make pocket money available to you. I am afraid for the time being I must insist you wear these at all times. I think it will be an important lesson in... humility.".

With that she produced a small pair of black high heeled black leather shoes. The heel must not have been more than an inch and a half but to Jamie it looked like an impossible task.

Jamie had listened, still nude, to everything she had told him. In that time he had moved through surprise into confusion through anger and finally had come to rest in incredulity. He could feel his cock deflating in front of him.

"This is ridiculous." He told her. "I'm not going to wear any of this shit. My father would never allow any of this. When he hears about what's going on-"

"-then tell him." Miss Jean had interrupted him. She was holding out a mobile phone with his father's number on it.

It took Jamie a long minute of thought, staring at the phone, before he slipped his feet into the high heeled shoes on the floor in front of him. What the hell. This is the first exciting thing that had happened to him in months.

"Good boy. I will see you for class tomorrow morning." with that Miss Jean left.

Jamie was left standing alone in his room, unsteady in his new shoes. There were a lot of emotions to process, a lot to think about. It was tough but Jamie did have to accept, this was the most fun he had had in months.

He turned to face himself in the mirror. He liked the way the shoes made his legs look. He moved his hand softly down his thigh, feeling the texture of his calf before touching the soft leather of the shoe. He could feel his cock starting to harden. He realised before he started to even think about the predicament he had found himself in, he would have to deal with the problem at hand.

With one hand he started opening his drawers , looking at his piles of new clothes. All of his old clothes were gone. He didn't miss them. His other hand was gently playing with himself. He found that he was gently stroking his soft mound of pubic hair, teasing the base of his cock. His movements were somehow more feminine already. He was enjoying himself. He found a pair of tightfitting boy shorts and slipped them on. He loved the way they felt against his skin. He found himself grinding against the soft fabric. A soft moan escaped his mouth. He was moving unsteadily around the room, the heels still a challenge. Next he slipped a black strappy bra around himself. After struggling for a minute he fixed the clasp and gasped as he saw the effect in the mirror. Jami could see himself, towering in the heels, his hands eagerly playing with himself through the fabric. His cock was getting wetter and wetter through the fabric. The dark stain on the front of his underwear was spreading as his hands moved ever more feverishly. He was staring at himself in the mirror, moaning at the sight of himself. He could feel his pleasure washing over himself as he sunk down to his knees, overcome with pleasure. Still playing with himself, gasping and wide eyed he looked at himself in the mirror. His body started to buck and contort itself as he could feel his orgasm building. Gasping he looked at himself, looking like a desperate slut, wide eyed and open mouthed as he came in his underwear, his body shuddering with the force of his orgasm.

On the other side, Miss Jean stood pressing her ear against the door, straining to hear Jamie's desperate moans. Her skirt was pulled up around her as her fingers rhythmically rubbed at her clit. She had a lot to do before tomorrow. It was going to be another busy day at school.