Anonymous - Miss High-heels:the story of a rich but girlish young gentleman under the control of his pretty step-sister and her aunt

The headmistress looked me over disparagingly as Helen explained everything to her, and after Helen concluded she paused for a long moment before she answered.

"Well, Miss. Deverel," she said, at last prying her eyes from my bosom and my girlish hands and feet, "I am certain that we shall be able to remodel your charge into a refined young lady of society. I must only ask if he is willing to undergo these changes, for if he is here entirely against his wishes, our task will be next to impossible."

Helen turned to me and said, "Denise, answer the headmistress."

I lowered my eyes in shame and said quietly, "I wish to be here, Madam. Please accept me as Miss. Denise Beryl."

"Very well," said the headmistress. "You shall stay. You really do look more a girl that a man. You know that, don't you?"

I kept my eyes lowered and nodded yes. I was hiding a smile, for I felt that she had just complimented me, and my feelings confused me, for I knew any other young man would have been outraged. I was inwardly exploding with joy. In truth, the events that had started as a consequence of the episode with Guy Repton, the impending punishments, and imprisonment among the lovely young ladies of the school were the greatest and happiest events of my life. But I did not completely understand that at the time.

"She shall have her own room so that the maids can help him dress, and attend to the special regimen that I have constructed for her," said Miss. Priscilla. "She will be needing massages and special care in order to keep her appearances as feminine as possible."

"Yes, and we have had sent a wardrobe befitting a girl of her rank. I do hope this arrangement will be to your satisfaction, Madam," said Helen to the headmistress.

The headmistress nodded, and then instructed us to say our farewells, for I had a lot of adjusting to do as a new pupil in her school.

My eyes met Helen's as we said good-bye, and within our gaze a mutual agreement was passed. I would acquiesce to her power. She understood me more than I understood myself at that moment. Power became her, and her lovely dark eyes gleamed with an unnatural glow.

"Good-bye dear Dennis. We shan't be seeing each other for quite a while. Be a good girl, Denise, and mind what the mistress says." She kissed me lightly on the lips, and left the room, Miss. Priscilla following her out.

Soon the headmistress returned to the parlour, and her stern presence frightened and excited me. This was supposed to be a punishment, and I did not want to betray the exquisite sensation of happiness that was beginning to flood my being. I was afraid that if the women who were controlling me knew what a great coup this was for me, they would retract and redesign their plan for me. I kept my face as expressionless as possible and my shining eyes cast to the floor.

"Now," said the headmistress sternly, "we shall design some rules for you. You are to obey them stringently or you shall be severely punished. As much as you look and behave like a young lady, the truth of your sex remains. You are not to reveal to anyone,with the exception of the maids and myself, your true gender. If you do, you shall be unconditionally expelled. You are to behave in a modest fashion at all times, and I expect nothing more than perfect submission to all the ordinances that apply to all the other girls here. Is that understood, Denise?"

When she called me Denise, I shuddered with excellent joy. "Yes, Ma'am," I stammered, not venturing to look at her.

The headmistress rang a pretty little bell, and a lovely young maid entered the room. Her golden red hair was tied up in an elaborate braid, and she had striking green eyes and the fairest skin I had ever seen. It was unbelievable to me that this magical creature was a maid. She was beautiful, and I could not help but staring at her enviously.

She curtsied in front of Miss. Priscilla, and said, "How can I help you, Ma'am?"

"Nellie, take Miss. Denise to the suite upstairs. Her maids will be arriving shortly with her trunks. While you are waiting for their arrival, draw a bath for Miss. Denise, and see that she is well groomed for supper." And with that, the headmistress dismissed both myself and my lovely, lovely Nellie.

As we walked up the stairs, I could not take my eyes off the perfect form of her buttocks, which rubbed against the black fabric of her skirt as she walked.

"Where are all the other girls?" I asked.

"They are all on a picnic for the afternoon, Miss.," Nellie replied.

I couldn't wrest my eyes from her perfect complexion, or the unusual fullness of her pert breasts, which strained at the fabric of her apron. She had dainty, small feet that were enclosed in a simple pair of black boots with many grommets for the high lacings. She had tiny hands, uncharacteristic of a maid. Her general beauty and manner seemed much more refined than any maid that I had ever known. I was falling hopelessly in love with her.

"You are such a pretty thing," said Nellie as she went about preparing my lovely new room. "I do hope you like it here at the school. Most of the young ladies are such nice girls. I think you will be very pleased here, Miss." Nellie approached me as she paused, and took a lock of my hair and twirled it on her finger. "You are a pretty thing," she repeated.

So I passed for a girl. I was shocked and pleased. I was equally surprised by Nellie's forward behaviour as a servant, but then I realized that I was unfamiliar with the ways and manners at a girls' school. In a sudden rush of impulsive affection, I reached out and drew Nellie to my breast.

"Thank you for saying so, Nellie. I think you are lovely too. I am so happy to be here!" I gushed. I felt the warmth of her large breasts against my own, and felt her arms encircle my waist. My heart sang. Her hair smelled sweet and clean, and her skin was as soft as butter.

"You are so lucky that you will be in a room of your own, Miss.," said Nellie as she pulled away from my embrace. Her face was suddenly flushed and probably as red as my own.

"Nellie, don't be ashamed of being kind to me. I think you are a wonderful creature, and I do hope we will be friends," I said, stroking her hot cheek.

"Oh yes, Miss. Denise. I would like that ever so much," she cried as she smiled.

I could scarcely believe my fate! I was the happiest youth in the world. The possibilities of the next two years unravel as a delicious fantasy within my mind's eye. My dreaming was interrupted by the thrilling, shocking sensation of Nellie's delicate fingers pinching my nipples.

"Nellie!" I cried, but did not move away. She meant to draw her hand away from my bosom, but I grabbed her wrist and guided it back to my breast.

"You like that, Miss.? I overheard the headmistress say that you will be getting special massages, and I just wanted to please you, Miss." Nellie's face was still quite red, but there was a mischievous gleam in her eye.

"What else did you "overhear" the headmistress and my cousin Helen discuss!" I asked, continuing to keep her hand pressed to my tittie.

"Nothing, Miss.," Nellie insisted.

"Are you certain that you didn't mistakenly hear something you shouldn't have?" I pressed. I felt certain that she knew my true identity and that she was simply toying with me. I realized that she had wanted to touch my breast to see if it were in fact a woman's breast.

"Yes, Miss. Denise. I didn't hear anything. Nothing that I shouldn't have heard, that is," she retorted with growing confidence.

Ah, so she was going to blackmail me. How absurd the thought is in retrospect, but at the time, I was terrified of being discovered and expelled from the school; a place I desperately wanted to stay.

"You would like to see my titties, wouldn't you?" I said suddenly.

"Oh, Miss.! I-I…," she could not finish her sentence.