Miss. Priscilla was a remarkable woman, a fully qualified doctor with a great medical reputation. Although she gave up her practice to join us, to me at this time, she seemed merely a harmless, slightly ridiculous old maid. She was forty-seven or so when she came to Beaumanoir, a wrinkled thin ungainly woman, who dressed very badly. She was very patient and submissive, and I treated her with the utmost disregard. I did not resent her presence in the house, as I did Helen's. I looked upon her as of no importance whatever.
The first time I had any doubt about her was a year later when I was ill with a cold: I was then between fourteen and fifteen, and Helen brought her to my bedroom. At first I would not allow her to examine my chest, but Helen threatened to tell my father of my refusal and to send for a doctor from London. That, for a special reason, I dreaded. I let Miss. Priscilla open my nightgown and I saw at once a flash of wonder cross her face. I flushed scarlet. I had a secret that I had always tried to conceal. My bosom was much too developed for a boy's and continuing to develop as I grew. I had not merely the nipples of a boy, but the white globes of a girl's breasts were threatening to become prominent.
Miss. Priscilla examined them carefully. Then she turned to Helen and exchanged with her a significant look. When she looked again at me, a slow smile of triumph was spreading over her face. It seemed to say: "I have got you," and when she went out of the room I remembered with some discomfort the impertinences that I had showered upon her in the past. However, I soon took courage. She could do me no harm, I thought. What a fool I was!
The next term at school, an episode occurred of which it is difficult for me to write. But I must refer to it because it affected my future tremendously. I was, as I have confessed, girlish to look at, although I took my part in the games of the school, and my appearance brought upon me a great deal of chaff and ridicule. It also brought upon me the attentions of the bigger boys in the Sixth Form, especially from Guy Repton, a youth of nineteen, who kept pestering me.
The episode that I am about to relate is a description of my sexual awakening, and the pivotal event that shaped the rest of my life.
As you can imagine, I had been wallowing in a state of some confusion as to the nature of my sexual orientation since the onset of my adolescence. I had been reluctant to leave my home, which had been veritably dominated by women since my father was a widower. Not only was my experience oriented toward the feminine world, but I was slowly developing a pair of budding breasts!
When I was sent away to school, I took great pains to hide my body from the other young chaps, but this did not mean that I didn't take the opportunity to steal long glances at my schoolmates. I quickly noted that I was not growing hair upon my body as some of my companions were, and that my muscles were not turning hard, but quite the opposite. I was becoming softer and more round with every passing month. This gave me a terribly ambivalent feeling, for deep within my heart, I could not help but admire the fantastic changes that were happening to my body. On the other hand, I was ashamed and stood up to much ridicule during my time at boarding school.
My interests were limited when it came to discussions that most of the other boys delighted in. In fact, even though I had grown to mistrust Helen and Miss. Priscilla, I severely missed their gentle company. I found their conversations so much more reassuring and civilized than those of my new companions. I was miserable and terribly out of place. I found that my one solace was daydreaming, and I took to staring out of my window, and the windows of the classrooms, remembering the womanly luxuries that I had once been surrounded with at Beaumanoir.
Many was the night that I lay alone in my bed, creating images of delight, picture fancies of the lovely gowns that Helen wore and all the accoutrements of her station and sex. I would worry, on such sleepless nights, about my future when I was to take over as master of the household. I felt that I should look forward to that day with much hunger, but in truth, I was not anticipating the day with gladness. In fact, I knew deep within my soul that I had no taste for the powers of my impending manhood, but I did not know how to escape my destiny. If I had only known at that time that my fate was already decided, I would have worried considerably fewer hours away.
But those hours during which I lay awake were not without their pleasurable moments. It was during the secret quiet of the night that I began to discover the pleasures my own body had to offer. Because I was not obliged to share a room with anyone else, I could spend hours lightly stroking my body and bringing myself to pleasure over and over as I massaged my cock and my extra-sensitive breasts. During these wonderful moments, I would always imagine myself to be dressed in the finest of women's clothing. I fantasized that my hands ran over my body encased in kid gloves, and that my breasts were softly caressed by the fine lingerie or the harsh lacing of a corset. These thoughts aroused my fancy almost more than the actual touch of my hand did. The potency that these fineries held for me is impossible to describe in detail. I can safely say that the deep hours of the night were among the only happy ones that I spent at that boarding school.
I devised elaborate passion plays in which Miss. Priscilla dominated me, while Helen enjoyed toying with my breasts, or even better still, I liked to imagine Helen's lovely full lips wrapped around my cock while Miss. Priscilla lightly abused my nipples with her fingers or her mouth. Of course, during these imaginary scenes, the two women would be dressed in the most exquisite of gowns, while I too was dressed in the dainty underclothes of a young lady. Oh, the hours of pleasure I afforded myself thinking these wickedly delicious thoughts.
I had yet to see a woman naked, so it was hard for me to imagine. But there was an instance that I liked to draw upon during my hours of fantasizing. One time, a few years previous to being sent to school, Helen and I were sent to the shore. I will never forget the moment when Helen bent over and gingerly removed her shoes and then her stockings, revealing the most beautiful pair of feet that I had ever seen. I watched with jealous hunger as she ran to and from the sneaking tide. Oh, how I wished that I were the sea, that it was I caressing her perfect white feet with my tongue, with my hands and fingers.
But I digress! I was to relate the story of the fateful evening in which a turn of events happened that shaped the entire course of my life.
It was a night like any other previous to it. I lay alone in my bed, lightly stroking my cock with one hand, my lovely little breast with the other. I was recalling an elegant evening dress of satin and tulle that Helen had worn at a spring party the season before. I was enjoying my solitary pleasure so greatly that I never heard the door of my bedroom creak open. As I was quietly moaning into my pillow, I felt a pair of cool hands stroke the soft flesh of my buttocks. I sat up instantly, quietly yelping in surprise when I was met with Guy Repton's hungry eyes. Guy Repton! Here was the boy who had taken such pleasure in tormenting me, and now he had caught me in nightly pleasures.
"Guy! What are you…"
"Shh!" he hissed, and covered my mouth with one hand, while the other began roving around my body freely.
I began to struggle, and he pushed me roughly against the pillows. My heart raced, half in fear and half in a new lust aroused.
"Guy, what do you think you're doing?" I whispered desperately as I thrashed weakly under his body, which was pinning me to the bed.
"I know what you've been doing in here, you nasty little thing," he said. He reached between my legs, and grasped my cock in his strong hand. "I came to join in your fun."
I felt my face flush painfully, especially because my erection showed no sign of quieting. Not only that, but I was painfully aware of my breasts and tried to cover them with my arms.